Welcome to Messy Work: a newsletter about the messy work of creating a life that feels like yours.

The following post is an expanded version of an email I sent to my private mailing list a few weeks ago. I kept on working it because, in a world of increasingly unrealistic expectations and representations, it’s important to me to lift the lid on what it really looks like to pivot careers and run your own business—not the “I quit my job 2 weeks ago now I make 6 figures” version. So here goes…

A few years ago, I went through a phase of being obsessed with designer handbags.

When I say “designer”, we’re talking Hereu, not Hermès. The objects of my desire were two or three mid-tier labels that spoke of artisanship, had cult (read: relatively mainstream) Instagram followings and transmitted chic, without straying too far from the boundaries of what I could just about afford (if I spent every spare minute trawling sales and secondhand marketplaces).

The bags were lovely—and before we proceed, I want to make it known that I have nothing against enjoying beautiful things (I’m a Libra; I live to enjoy beautiful things). I’m also conscious that conversations around “de-centering money” can fall prey to all sorts of hypocrisy and that’s-easy-for-you-to-say-itis, as well as shame around wanting money.

But it doesn’t take a psychotherapist to point out that the bags weren’t an unadulterated manifestation of my personal style. They were a status symbol—an expression of the person I thought I wanted to be at that particular point in my life.

The Bag was something to clutch to my chest on the tube, as I commuted into my women-only members club and coworking space just off of Regent Street. The Bag was a prop to place carefully on the chair next to me, as I eavesdropped on the Zoom calls of CEOs and consultants who used phrases like “out to tender”, while I tried not to feel inferior and Googled “out to tender”. The Bag was something to coo over with friends who arrived at brunch, toting their own transmissions of chic.

You see, back then, I had made it. Only a year into waving goodbye to my startup marketing job and going freelance as a copywriter, I was fully booked with clients. I was earning way more than I ever had in a full-time job. And I was blessed with the flexibility and freedom of being my own boss.

Only, I didn’t feel very free.

If she could see me now

Fast-forward to today, and you’re much more likely to see me leaving the house with a tattered tote, an unintentionally gorp-core rucksack or, for special occasions, one of my thrifted Silly Little Bags™️, than my Hereu, which is currently gathering dust in the back of my wardrobe.

I left London for Bristol, where I walk to my new coworking space (all genders) up and down inclines that require sturdy shoes and ergonomic accessories. The average passerby is much more likely to be impressed by my tie-dyed tracksuit than a designer handbag (I once walked back from the swimming pool wearing said tracksuit and have never received so many compliments). I’m now merely semi-booked and earning less than I have in years.

Less than I was in a full-time job. Much less than the peak of my freelance copywriting career.

Oh, how the chic have fallen.

But the thing is, most of this (bar ChatGPT coming along and causing a rumpus / general economic decline) was completely by choice. Around 18 months ago, in an act of blind faith/sheer insanity, I let go of all but one of my copywriting retainers to give my burgeoning coaching practice a fighting chance. If I’m being real, to give myself a fighting chance. Because while I’m really proud of my copywriting career (and continue to do this work), all I was doing as a freelancer was replicating the same unhealthy, productivity-worshipping patterns I was trying to escape from in my last job.

Without descending into a self-conscious spiral of caveats about my privilege or going into the details (the main one being that I lost a parent), I am fortunate to have enough of a safety net, at least for now, that I don’t actually need to earn what I used to. Nevertheless, it has shocked me just how destabilising it has been to exist without a steady income. To stand tall in my own brand, not hide behind other people’s. To dispense with the trappings of my former, girlboss-coded life.

And sometimes, as a human living in a capitalist society, my lack of designer handbags gets me down.

A peer blithely mentions last month’s revenue and I cringe at the thought of them seeing my QuickBooks. I fret that everyone else knows some magic secret that I don’t about sales pipelines. I worry that I am not working hard enough. That I am not successful enough. That I am not good enough. I wonder if ultimately, I have just gone utterly mad and poured my entire career down the drain to do this delusional “self-authoring” thing. Get real!!! says the voice in my head.

It feels vulnerable—slightly vulgar even—to admit all of that. We aren’t motivated by money! says another voice in my head, while yet another worries that sharing this will discredit me as a “respectable professional” whom people will want to hire as their coach.

But honesty, in a world of BS business advice, LinkedIn humblebrags, and the dizzying Coaches Coaching Coaches economy, is important to me.

I am in the business of being a certified, accredited transformative coach. Not an influencer selling a lifestyle. That means I am trained in a set of professional skills (approved by regulatory bodies) that help clients find their own answers, rather than me prescribing them.

I am sometimes a few steps ahead of my clients. But more often than not, I am right there beside them, navigating the exact same challenges.

And the truth is, there is always a cost to following your dreams. The messy work is figuring out what price you’re willing to pay.

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The meaning vs stability tightrope

Something that’s felt very alive for me recently is the tension between meaning and stability. Purpose and pragmatism, vitality and safety, starving artists and corporate drones—call it what you will.

It’s a balancing act (which Satya Doyle Byock presents in her book Quarterlife) that can be sticky, seasonal, and steeped in a quagmire of social, cultural and familial conditioning.

It’s the pulse of most my clients’ coaching inquiries: is it possible to find work that brings me meaning, without sacrificing stability? To what extent do I actually need my work to bring me meaning, if I create it elsewhere? Can I have both?!

I won’t pretend it’s easy to find the answers, which look different for everyone. I recently held a journaling workshop and discussion circle for a small group of women doing the messy work of grappling with this tension (fill in this form if you’re interested in joining a future cohort). We were all coming at it from different angles and chapters, but we were united by the shared experience that it’s really bloody hard.

We found that what lifts us up in moments of doubt is a good, healthy dose of perspective. The acknowledgement that we are all on our own timelines, which usually take much longer than we anticipate. Reflecting what we all saw in each other—brave, bold moves and beautiful lives—but can struggle to see in ourselves. And, importantly, the tentative belief that maybe, just maybe, we can allow ourselves to have what society, or our families, tell us is impossible. The artist who doesn’t starve. The corporate employee who doesn’t have to drown.

And so when I find myself lamenting my lack of handbags, I zoom out. I remind all those voices that we chose to deprioritise money, status, and shiny vanity metrics as the KPIs for our livelihood, wellbeing, and happiness.

Which isn’t to say that financial security, independence and freedom, and the emotional safety they provide, aren’t important. Obviously, they are, and I am actively working towards increasing mine.

But it is okay to take the slightly longer route to get there. After all, it’s true that I could work harder—if long hours, stress, and compromising my health weren’t exactly what I walked away from.

My clients have walked away from something too. They are deconstructing the old definition of success and writing a new one that’s fully their own. When we come to the end of our work together and I ask them what they’re leaving with, they say:

“I’m proud of putting myself first and making the decision to leave.”

“I trust that the bigger picture will emerge. I’m exactly where I need to be.”

“I know I’ve got the answers. I’ve always had the answers.”

“I’m listening to myself differently.”

“I’ve grown.”

“I’m ending with courage.”

“I trust myself.”

I can’t turn these words into a carousel of hard-nosed case studies illustrating how everyone I work with goes on to secure their dream job / a Ted Talk / an extra 100K followers / a seven-figure salary. But I’m not that kind of career or business coach, and my clients experience a different kind of ROI.

A different kind of rich

I was recently invited to speak about career pivots at Paulina Zapotoczna’s Deep Reset half-day retreat. At one point, Paulina asked me a question. I think it was: looking back over your career pivots, is there something you’d never change, even if it was really hard?

What came from my answer was the reflection that, even if I have less financial stability than I used to (i.e. a regular, predictable income), my work and my life are full to the brim with meaning. And the spaciousness and autonomy I’m afforded by being my own boss create stable conditions for me to grow from (when I look back on my career, there’s an inverse relationship between my financial and emotional stability).

Every decision and sacrifice I have made—every time I have said no to money, status, and designer handbags—has brought me here.

To a career where I do work, both coaching and writing, that brings me a huge amount of purpose and the joy of using my gifts.

To a calendar that’s on my terms, and a lifestyle that aligns with my values: integrity, balance, connection, creativity, growth, and love.

To the place I now call home. A city that got under my skin the minute I set foot here fifteen years ago, where every wall is an artist’s canvas, where everyone really f***ing cares, and you’re as likely to see a seventeen-year-old as a seventy-year-old at a rave.

To a community that holds me: my coworking space, my neighbours (after years of living in London this is a real novelty), the new friends, and the old friends who have watched over me through all of it.

These are the real riches. Anything else is a bonus.

And that client who can finally trust themselves? They make it all worth it.

So if you’re also walking the meaning vs stability tightrope, I see you. And I wonder, while the six-figure salary takes its sweet time to appear: what riches are you already reaping?

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If you enjoyed this you might also like…

• Why I quit London

• Can you break free from hustle culture and stay ambitious?

• An anti-girlboss approach to working for yourself

• What it really takes to self-author your career

• Are you having a career identity crisis?

• This guide to the meaning vs. stability theory from Quarterlife by Messy Club member

Working towards a different kind of rich?

I coach recovering high achievers and independent spirits doing the messy work of self-authoring their careers. Whether you’re stuck at a career crossroads or need a sounding board for the “self” bit of self-employment, I’m here to help you find clarity on your direction, work through psychological blockers, and bridge the gap between intention and action. If that sounds like you, I’d love to chat! Book a call here.

A few months ago, in a moment of weakness, I upgraded to LinkedIn Premium. I know.

I imagine that, as per my last post, there is a “bulletproof” 50-step sales plan somewhere online that I have failed to utilise. But alas, LinkedIn Premium made virtually no difference to my business. (Cue: a man in the comments telling me what I have been doing wrong)

However, there was one thing about LinkedIn Premium that intrigued me.

I had full, unfettered, premium access to the ‘Requests’ inbox. It’s a bit like a B2B version of lonely hearts, where people submit their requests for the professional support they are seeking, and you can send back a proposal.

Because I am a career coach, a lot of the requests I saw went something like this: I want help finding a new role, improving my networking skills, preparing for job interviews, etc.

And technically, this is work I could do with my clients. It’s just often not the real work that needs to be done.

Where’s the option for ‘spiralling’?

I’d put good money on the suspicion that these neat, preset responses were masking a deeper, messier problem: these people weren’t just “open to work” (the nonchalance!!!), but having a full-scale career identity crisis.

If only we could stick that on our little green banners, hey?

We’ve all seen the headlines about big tech companies axing staff to pave the way for “lean” new organisational structures. Recently, a copywriter whose work I have long admired—and envied—shared that after two redundancies, burnout, and the emotional whiplash that is the current job market, she was taking a break. I am speaking to seasoned specialists who are on the verge of giving up.

Meanwhile, I follow ex-CEOs on Instagram who are supposedly making six figures from "courses” and “content”. Lots of self-employed people I know are genuinely smashing it. And we have a whole new lexicon for the way we work: the choice is no longer full-time or freelance, but fractional, portfolio, solopreneur, squiggly.

All of this change can be liberating and exhilarating. It can also be confusing and frightening. As individuals, I think we are all trying to find our place in it.

Over the past two years, I have coached around one hundred people on a range of professional goals and challenges—from career crossroads, to the rollercoaster ride of self-employment, to the pressures of working in startups.

My clients come from diverse countries and backgrounds, they hold their own unique set of hopes and aspirations, and the intricacies of each beautiful personality mean they struggle with different things. But what unites them all is the complex question of who they are becoming in relationship to the work they do.

Where is their place in the job market, the organisation, the world? Which values, beliefs and talents must their career represent—and what are they no longer willing to compromise? And (the big one) is there such thing as a career that provides them with both meaning and stability?

From these rich, fascinating conversations, I’ve started to notice some patterns emerge, which are also reflected in conversations with friends, relatives, and peers in my age group (I’m a millennial, largely coaching Gen Z and millennials).

Allow me to introduce the seven types of career identity crisis. Which flavour are you having?

The 7 types of career identity crisis

1. Dazed and Confused: Minimum of one burnout under their belt, slowly waking up to the possibility that this is not it.

Let’s start at the beginning. If you fall into this category, you’re likely working in a secure, full-time job a lot of people in your line of work would kill for. Except you’re questioning if it’s really worth all the hoop-jumping it took to get you here.

You’re stressed, burnt out, or jaded. You are slowly lowering the bottle of Kool-Aid.

You dial into the All Hands and watch with incredulity as two colleagues battle it out in a passive aggressive, spiritually violent display of corporate jargon. You’re finding it harder and harder to wrestle with the competing truths and complexities of your role: do you hit the KPIs? Or do you be a good human?

You are wondering, with increasing urgency: how much longer can I keep this up? And: what will I do instead?

Right now, you may be too deep in the soup to think clearly or take action. But soon, you will have no choice but to confront the fork in the road. Do you suck it up and stay, or do you go? Enter…

2. Disillusioned and De-centering: Done with climbing the ladder, wants to chill out on the middle rungs.

So, you decided to suck it up—a very valid choice that many of us who have real, financial needs are required to make. Now, the work is finding new ways of being in the same role.

The Kool-Aid bottle is in the bin and frankly, you couldn’t give two hoots about Tim and Amelia’s emoji-laden Slack feud over how to format a spreadsheet. But where once you would have vented like a steam train gathering speed to anyone who made the mistake of asking how work was going, consumed blue light long into the night, and done everything short of sleeping in the office to impress your boss, you’re learning to treat your job with the warm-but-slightly-removed friendliness you might reserve for an overstimulating neighbour you can only tolerate in small doses.

You placidly agree or calmly push back. You take lunch breaks and finish no later than 6pm. You rise above the drama. You set boundaries. You do your job well, get paid, and go home. What you definitely don’t want is more responsibility. The odd pay rise might be nice, but when it comes to status and power, you’re fine right where you are.

You have achieved the admirable feat of de-centering work, disentangling your identity from your job title, and making room for other things in life—hobbies, health, relationships, rest. This is less “quiet quitting”, and more conscientious objecting. And actually, it doesn’t need to be a crisis. Unless…it all starts to feel a bit empty.

3. The In-betweener: Going through their second puberty.

In-betweeners are a mixed bunch. Perhaps the emptiness got to you and you made a big decision, like quitting your job or retraining in something new. Or you had a big decision made for you, and now find yourself wondering what the proverbial you are going to do now.

For others still, there may be no big decision or action. You are being pulled by nothing more than your own intuition, or perspective has slapped you round the face—and maybe, this inflection point has opened up a new purpose or passion. In my own case, losing my lovely dad made me question what on earth I was doing with this one precious life.

Whatever the catalyst for your crossroads, you are aware of a new destination—and the vast distance between you and that destination.

The scaffolding of beliefs that held the old you together is crumbling, and you are building new foundations brick by brick. Like existential Jenga, it’s a case of one brick forward, ten tumbling to the ground. Some days you feel alive and assured, full of conviction and courage on a deep, soul level. Others, you feel shaky and porous. That conviction seems laughable, the destination impossible, and you revert to old habits, clinging to what is familiar and cosplaying as the old you.

If this is your flavour, I have a free journaling practice for you 👉 here 👈.

But like a sponge, you are soaking up all the change; like a sponge, you will bounce back.

4. The Frazzled Freelancer: Jumped off the ladder, but still circling it.

You did it! You quit the toxic job. Said adios to Tim and Amelia. Struck out on your own and stuck it to your old boss—because who’s laughing now, Miss Fully Booked and earning twice your old salary?

Only, wait…didn’t you quit the job to stop working all these long hours? Didn’t you vow you’d make working with arsehole bosses a thing of the past? Didn’t you say you were over hustle culture? Are you now your own arsehole boss?

The thing is, the freelancing fantasy (four-day weeks, meaningful work, a happier you) doesn’t always match reality. And that’s perfectly normal. Because most of us were only ever taught one way to work—by our schools, by our workplaces, by society.

Our subconscious beliefs, day-to-day behaviours and identity markers are still rooted in the very systems we were trying to escape by working for ourselves. So we default to workaholism, people pleasing, vanity metrics, or whatever your particular poison. The work is to become aware of these factory settings, and begin to rewire them.

5. The Patchworker: Toggling between multi-faceted and majorly fragmented.

I shouldn’t have favourites, but…for me, this is one of the most interesting developments in the world of ever-changing career identities.

Our parents had one job, for most of their lives. Today, I meet people who have as many as four different income streams, which they can dial up or down to meet their shifting priorities.

There are people like me, who do a blend of freelancing (usually related to phase one of our careers) and starting a new venture. In the early days or perhaps forever, the former finances the latter.

But I’m also seeing a pattern emerge whereby people want to gradually decrease the time they spend at a desk and take on more low-stress, low-stakes forms of employment that give them a steady income. For example, working one or two days a week in retail or hospitality.

(My friend wrote a really interesting piece about the secret lives of freelancers here)

The major advantage of this type of “portfolio” career is that it recognises your identity, your interests, your skills, and your needs as multi-faceted and flexible. The disadvantage is that your energy can feel stretched and your identity fragmented. You need to hold firm boundaries and have a lot of clarity on where your focus goes. And occupying these different identities can start to feel like a performance if your heart lies with one more than the other.

6. The More-To-Lifer: Pulled towards something more, but constrained by pragmatism.

This is probably the most “mature” form of career identity crisis, in that if you’re a more-to-lifer, you may have experienced all five former crises (lucky you!).

You’ve already committed to a lane and been fairly successful in it, whether that’s working a dream job or running your own business. So you’re not necessarily running away from something, or unhappy with your lot.

But something in you is restless. Part of you yearns for more. Maybe it’s evolving your business into the next phase. Maybe it’s bringing more of yourself to your work.

And it can be a really exciting, fruitful place to be, as you’re creating more meaning from a place of stability.

Only, the stability piece is also what gets in the way. You know you have it good and you don’t want to blow your life up. But to let a little more of the light in, you’ve got to crack open the window and be prepared for the breeze to reshuffle things.

The other side to this is that it’s important to get honest about what is actually driving the more-to-life feeling (as I wrote about here). Because maybe, the work is learning to be content with what you already have. What if contentment is so unfamiliar, that it doesn’t yet feel safe?

7. The Trash Talker: Everything is rubbish! I’m rubbish! I’m throwing it all in the bin!

And now, we meet the latest arrival to our very chaotic, faintly hysterical dinner party. Our final career identity crisis type hails from the absolute sh*t-show (see, I’m a trash talker too) that is the creative industries right now. And I describe it thus not to be whingey or fatalistic, but to be realistic; to acknowledge that actually, sometimes we are the victims of forces beyond our control (which isn’t to say that we can’t also rewrite this victimhood).

Picture this: you went to uni, did a humanities or arts degree, fell into the world of advertising, marketing or branding, and did really well in it. You’ve got solid job titles under your belt, impressive names in your portfolio, and maybe once upon a time you were a Frazzled Freelancer.

But then the work started drying up. Clients started asking you to deliver briefs yesterday for approximately ten pence. You can no longer perform the simple act of applying for a job and getting it; you are now one of thousands scratching their heads over whether writing your own application will help you stand out, or put you in the Reject pile where cover letters without AI-optimised keywords go to die.

And speaking of rejection: it sucks. Your confidence is in tatters. You can’t remember the last time you enjoyed your work. The craft you honed for decades is now being done very badly—or even worse, very averagely—by an sycophantic “agent”. You are asking the very same sycophantic agent what jobs you can do instead of the one it has taken.

You alternate between fierce, productive rage and feeling utterly demoralised. You are 👌 this close 👌 to selling feet pics.

The work is accepting that it isn’t personal; that you are a grain of sand in a revolution historians (or ChatGPT) will write about in centuries to come. The work is acknowledging that it’s really bloody personal; it’s railing against the revolution and holding on to your brilliant, original, creative spirit as an act of defiance. It’s finding the joy again.

Because if there is one thing I have learned from coaching clients through all seven types of career identity crisis—and living some of them myself—it’s that we all have far more resourcefulness, resilience, and maybe even radicalism, than we think.

Which type are you?

And there we have it: the seven different types of career identity crisis. Jung would be proud.

So which one are you? And are there any you’d add to the list?

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The bit where I give you my $99 career identity system

I doubt I’m the first person on Substack to write about the concept of a career identity crisis. Right now, my feed is awash with “corporate dropouts”, “messy middlers” and “coaches” (emphasis on the quotation marks for some of them) who are using their writing to grapple with their own truths, and act as a guiding light for anyone in a similar boat. Which is really quite beautiful—a sprawling, communal self-help book, if you like.

The perspective I do want to offer is that all of this is, well, a lot. A lot more than our parents had to deal with. A lot more than school prepared us for. A lot more than our peers who aren’t questioning this stuff (is anyone not questioning this stuff, really??) understand. I do not want to dress it up in a cute, Instagrammable bow; condense it into a carousel; simplify, optimise and monetise it in an app. I do not even want to repurpose it into a series of too-perfectly formatted Substack notes that will gain me subscribers.

Really, the work I want to do is behind closed doors. In the nooks and crannies of conversations with my coaching clients, where I do more listening than talking, and which tend to plant the seeds for realisations that sprout up outside of our sessions. In the monthly thinking space I’m starting for anyone doing the messy work of self-authoring their career. In the workshops I facilitate. In the small, incremental steps of experimental thinking, courageous action, and integrated experience.

Curious about that work? Here’s how to learn more:

• If you’re Dazed and Confused, Disillusioned and De-centering, an In-betweener or a More-To-Lifer: check out Crossroads, my 1:1 pathway for transitional times

• If you’re a Frazzled Freelancer, a Patchworker, or a Trash Talker: check out Sounding Board, my 1:1 pathway for the “self” bit of self-employment

As I come to the end of this post, I’m thinking of that saying: it’s not a breakup but a breakthrough.

Right now, a lot of us feel like we are breaking up with or being dumped by our careers—whether we’re taking decisive action, or worrying about being replaced by You Know What. You might be thinking “Have I just lost years of my life?”, “How do I build a future without them?” or “Will I ever find The One?”

It takes me back to my twenties, when my crises were of the romantic kind. And how asking those questions led me to do a lot of deep inner work, break anxious-avoidant attachment cycles, and finally find a loving, committed relationship after a decade of heartache.

I don’t need to spell out the analogies. But it gives me a lot of hope—that perhaps we are all on the brink of an exciting new chapter in how we relate to work.

Book a no-strings chat if you’re curious about 1:1 coaching* for career identity crises—zero prescriptions or “platforms”, just dedicated thinking space, psychology-based methods, and deep conversations.

*I am a certified, EMCC-accredited and trauma-informed coach who works across the levels of identity, beliefs, behaviours and somatics to bring about real, lasting change. If you are looking to work with a life or career coach, I recommend checking for these certifications and accreditations. It’s wild out there!

If you enjoyed this, you might also like:

• The shadows of startup culture

• What it really takes to self-author your career

• Should you follow the feeling there’s more to life, or fully inhabit the one you’ve got?

• An anti-girlboss approach to working for yourself

• Can you break free from hustle culture and stay ambitious?

• Everything I know about the messy middle

You don’t have to do the messy work alone

Hi, I’m Lucia! A transformative coach and freelance writer living in Bristol. I know that creating a life that feels like yours isn’t easy. So I write personal essays, share loose guides and chat to ideas people who are also doing the messy work.

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It is a warm week in July and I don’t have any work. My days are either spent in a haze of frenzied productivity—updating my portfolio, editing my CV to meet various and unrealistic JDs, firing off emails that don’t sound desperate, hitting the refresh button to check the likes on my latest LinkedIn post—or listlessly lying in the park, trying to “make the most of the downtime”.

Rewind to a busy month in March and I have so much on my plate that I want to hurl it at the wall. The client I work for on Tuesdays is asking to move our weekly catch up to Wednesdays, which is my day with another client. The scope of a project I was initially excited by has crept to the point of surly, begrudging resentment. I am “fully booked”, which means days bleed into evenings and evenings into weekends. Everything else—social plans, life admin, business development, my writing, my health—is on hold.

Fast-forward to November and I am watching on Zoom as a client (whose dubious romantic exploits, I subsequently learn, were publicly aired in the Daily Mail in the nineties) bullies his marketing assistant, insisting that he never asked her to do the task she has meticulously and excellently delivered. I silently screenshare and pull up the email where he asked her to do the task. He criticises the jumper she is wearing. The next day, I fire him.

Welcome aboard the emotional and existential rollercoaster of working for yourself

The above are excerpts from the last five years of my career. I have been out of work. I have been booked and busy. I have been stressed. I have been jubilant. I have lamented that I didn’t graduate from uni and go and get a “real job”, instead of accidentally falling into the fickle, amorphous world of brand-building, where no one really has any formal qualifications and the ability to wing it is your bread and butter.

I have been supremely grateful that I get paid to do this. I have entered flow states. I have laughed in the face of last-minute client requests. I have bent over backwards. I have undercharged. I have over-committed. I have doubted myself. I have backed myself. I have worked from coffee shops, gardens, Thailand, Spain, and once, when it was the coolest room in a heatwave, my bathroom. I have figured it out as I have gone along.

In other words, I have been self-employed.

I started working for myself full-time in 2022. Partly to recover from burnout, and partly to pick a thing. For me, this meant honing my craft as a writer after many years in generalist marketing roles, where it felt like my creativity was drowning in a sea of spreadsheets and office politics. Then in 2023, I re-trained as a transformative coach (a formal qualification, at last!).

These days, I still do freelance writing and consulting for brands alongside running my coaching practice; a collage or “portfolio” career of multiple interests and skill sets, which I have built from scratch and which no one ever really prepared me for.

I am one of an increasing number of people who are self-authoring their careers. Who are diverging from the conventional path to design work around our own values and visions. Who seek to build livelihoods that feel as intentional and purposeful as possible. Who are taking ownership of our own narratives and timelines, rather than measuring ourselves against somebody else’s/society’s blueprint.

“[Self-authorship is] an ideology, an internal personal identity, that can coordinate, integrate, act upon, or invent values, beliefs, convictions, generalizations, ideals, abstractions, interpersonal loyalties, and intrapersonal states. It is no longer authored by them, it authors them and thereby achieves a personal authority." - Robert Kegan

These are also the people I coach: freelancers, business owners and founders, who are often juggling multiple clients, ideas, and income streams in the quest to be a new kind of “self-made”.

From the middle of the Venn diagram, I have a unique vantage point. I get to peek behind the curtain and witness what it takes to architect a less traditional career. I have a deep, lived insight into the kind of support self-employed people really need.

Because the thing is, there’s an awful lot of it out there.

Smoke and mirrors

Statistically speaking, the number of self-employed people in the UK is plateauing. Pre-pandemic, it was steadily climbing, and since then it has been spiking and petering. I struggle to read even the most simple of graphs and therefore have no authority to speak on this, but I wonder if this means the rates are sort of stabilising, i.e. those of us that are in it are here to stay (assuming AI doesn’t come for us all, which is a post for another day).

Making up 13.1% of the population (16.5% in London), and potentially more if we take into account that not everyone declares their side hustles, what we have done over the past few decades is prove that this way of life can work. But that’s not to say that it’s easy.

Yes, a lot of us wouldn’t have it any other way: the freedom, flexibility, creativity, variety, and sense of purpose we find in our work and lifestyle.

At the same time, working for yourself is really f***ing hard.

Outsiders think this is because we have to do taxes. Speaking from my own and my clients’ experiences, HMRC pales in comparison to the other challenges of self-employment (and if you have ever had to log into the self-assessment portal on Government Gateway, this is really saying something).

The reality is that on a near daily basis, we navigate financial (and potentially existential) uncertainty, strategic complexity, managing multiple relationships and team dynamics, displaying strong leadership skills, juggling competing roles and demands on our time, adapting to new technologies, mediating stakeholder disputes (oh, to work with co-founders), and being The Face of the company, not to mention delivering the actual work. All of which reads like the JD for a CEO of a multi-million-pound company, rather than a humble solopreneur.

And as we know from the world of multi-million-pound companies, whenever there is complexity, inefficiency or uncertainty…there is always money to be made.

As more and more people have chosen or fallen into self-employment, a huge new industry is booming: one that proffers support. Some of this is genuine, valid support. We need to pick up new skills, share essential knowledge, save time, build networks, cultivate community, and feel inspired by those who have gone before us.

However, this “support” can also manifest as endless courses, clubs, “communities” and “gurus” that promise to launch your business in five easy steps (lol) / 100x your social following with this simple hack / join the elite inner circle of Successful People™️ who will open doors you can’t even imagine / teach you the secret to unwavering confidence and negotiating the kinds of deals that would make Roger Sterling order another round of martinis.

The message behind the madness? Usually that:

• You are not doing enough (“supercharge your productivity with my X system”)

• There is something everyone else knows that you don’t (or something BARELY ANYONE knows that you soon will…along with hundreds of other people who will sign up to the same course)

• Or that you are, in fact, not being enough. Assertive. Authoritative. Strategic. Smart. Fun enough to make TikToks.

Ironically, the carrots that the purveyors of these promises dangle—7 figures, huge audiences, global stages, book deals, brand sponsorships—are predicated on achieving levels of stardom that are actually pretty irrelevant if you just want to design nice packaging for drinks companies and pay your mortgage.

Yet the fear-, scarcity- or guilt-based marketing tactics they use are compelling. The illusion they sell is intoxicating: namely, control and certainty, i.e. the very things that self-employment cannot guarantee.

Take, for example, a webinar I joined the other day for research purposes, which was about building a sales pipeline.

The webinar was led by a couple who teach freelancers how to get their dream clients and make more money. As always, the cynic in me couldn’t help but wonder: if you’re so good at getting clients, then why are you not so busy with those clients that you don’t have time to teach other people how to get clients? Alas, one of the great mysteries of this entrepreneurial age.

Anyway, they started the webinar by addressing the elephant in the room: the economy, general state of affairs in the world, etc. They acknowledged that it was a really tough time for freelancers, with businesses cutting back, rates plummeting, AI replacing us, etc.

However, none of this would be a problem if we just nailed our positioning, dressed up our processes as a unique “methodology” (you don’t just hop on a kickoff call, you facilitate a holistic and transformative deep-dive into objectives, challenges, and deliverables) and then paid $199/month to access their trademarked sales pipeline system.

(All of this, I should add, was set against the incongruous backdrop of a romantic photoshoot featuring the two of them sipping cocktails and holding hands by a swimming pool)

Now, I did take away some genuinely useful ideas, so it wasn’t all bad. But the notes I took during the call pretty much sum it up:

Tbh, all of this is selling the illusion of control by attempting to wrestle the inherently uncertain, unpredictable nature of self-employment into neat “frameworks”. Rinse and repeat strategies do not always hold up against the complex, ever-evolving world of business / complex, ever-evolving people. While there is some truth and value to what is being shared, it glosses over the fact that some things are just beyond our control. And anyway, if you want a straightforward business model with replicable sales, a service-based business probably isn’t your best bet.

My sanctimoniousness aside, I do believe that practical steps can only take us so far in self-employment. Steering the ship of your livelihood, honing your craft, creating work you are proud of—it is a huge emotional journey and a major evolution of your identity. It’s reductive to imply that it’s merely a lack of technical skills, insider knowledge, or bulletproof systems that’s holding you back. And naive to think that there will be a one-and-done solution to changing an innate part of your personality or humanity.

In reality, the real blockers are often psychological. And the “solutions” take constant practice.

The real, messy work of self-authoring your career

I’m talking about learning to exist in the confusing, uncomfortable toggle between uncertainty and autonomy, which scrambles our nervous systems.

On the one hand, independence gives us agency, and thus a sense of control. This makes us feel safe on a primal level, self-actualised on a higher one. On the other hand, our nervous systems register a rejected proposal or a quiet week as though a hungry tiger has just landed on our laptops, licking its lips. Cue a cognitive bias towards pessimism and compulsive thinking as your brain hunts for causal explanations (”I must be terrible at my job”) and projects negative, rather melodramatic outcomes (”I’ll never work again!!!”) in order to manufacture its own, perverse sense of certainty.

I’m talking about unlearning the behaviours and beliefs that keep you trapped.

Part of the problem with the bulk of business advice out there is that it can end up replicating the same tired systems or reinforcing the same old habits that most of us were trying to escape by leaving full-time employment: rigid schedules, codependent relationships, deferring to someone else’s authority. A client once described this as the “girlboss residue” she couldn’t shake.

This is why very normal aspects of freelancing can feel so destabilising:

• Hearing feedback on your work feels like an attack on your performance - maybe in your previous workplace, feedback always meant criticism

• Saying no to a demanding client feels impossible - something in you always yields, and you don’t know why

• Working out how to fill a quiet day sends you spiralling - if you’re not productive, then are you successful?

• A low income month feels like a sign that you’re not cut out for this - you are used to seeing an annual salary as the measure of your success/worth

I’m talking about developing the courage and resilience to keep putting yourself out there, when rejection is inevitable and success can be random.

Understanding the deeper personal narratives and also very universal ones that may make it feel unsafe to be seen: why is it that the prospect of someone you went to school with seeing your Substack makes you want to crawl into a hole, but you’re fine with a stranger in Milwaukee reading it? Thinking really carefully about staying rooted to your integrity and detaching from the whims of the algorithm, so that you don’t accidentally spend an entire day in the Edits app rather than focusing on tasks that actually build your business—or just refill your cup.

I’m talking about the emotional labour of working for yourself.

Picking yourself back up, without a colleague take you out for coffee. Trusting in your own ideas, without a boss to sign them off. Finding ways to celebrate and communicate your ups and downs, so that you feel seen by your loved ones, not invisible or inferior next to their “real” jobs.

Because ultimately, you are your business. Your energy, self-awareness, emotional intelligence, and self-leadership are your most valuable assets. From coaching my clients and carving out my own career, I know that these things impact outcomes far more effectively than the content marketing video course you still haven’t opened.

These capacities are not fluffy nice-to-haves: they are the difference between you doing the thing you say you want to do and living the life you say you want to have, or sitting in fear, indecision, and inaction. They are the human capacities that will prevail in the face of a technological revolution that is happening—and could perhaps rewrite our careers even more dramatically—whether we like it or not.

I coach a client on her visibility wounds. I see her publish a LinkedIn post the next day, a Substack the next week. I coach another on his “procrastination”; he realises that actually, the thing he’s been putting off isn’t at all aligned with his values and vision, and focuses his attention on something that ends up being much more fruitful for his bottom line. Another on setting boundaries; once we get to the real root of why they feel so hard, the fog lifts, she emails the client, they immediately accept her new rates.

I need coaching on all of these things myself; my role is not to be the teacher, mentor or adviser whose life or personality traits you emulate, or who tells you what to do (a misconception perpetuated by many a business “coach”) . What I do have is the training, skills and psychological insights to help people think deeply and independently about what’s bothering them or what they are yearning for, move forwards, and trust themselves.*

This inner work breeds strategic clarity and tangible, financial business outcomes—not to mention helping the messy, tough process of self-authoring your career feel a whole lot better.

In her book Time To Think, Nancy Kline writes: “The quality of everything we do depends on the quality of the thinking we do first.” And also: “The quality of your attention determines the quality of other people’s thinking.”

This process doesn’t necessarily warrant a trip down memory lane on the therapist’s sofa. And it’s probably a waste of money to download an e-course by a man in Bali who speaks with aggressive and unnatural intonation, and insists that when it comes to happiness/healing/obscene wealth, he’s cracked it.

It needs, as Nancy Kline puts it, time to think. Maybe this is through working with a certified and accredited coach: someone to listen, ask the right (and often the unexpected) questions, and offer insight that might unlock ideas, without seeking to advise, influence or lead you. I would love to live in a world where coaching is a widespread and well-understood recourse for transitions, working towards professional and personal goals, and ongoing emotional maintenance—not just because I am a coach, but because being coached has genuinely changed my life.

But I know that 1:1 coaching isn’t accessible to everyone and I also believe we need more safe, collective spaces to feel seen, heard, and supported. Which is why I am shaping a journaling club for recovering high achievers and independent spirits doing the brilliant, messy work of self-authoring their careers.

And why I’m committed to keep building an alternative narrative to the one that prevails in the traditional business coaching industry: one that says you are already enough, just as you are, and makes space for the “self” bit of self-employment, rather than denying it.

I’ll be writing about that here. And if you’re curious about joining the journaling club, you can share your ideas and register interest here.

“Your prompts certainly got me thinking in ways that I never have before. Also love how you combine psychology with coaching. I’ve worked with coaches before that have been great in my business, but when it came to tackling mindset stuff and getting that little bit deeper they lacked.” - Feedback on one of my journaling workshops

In the meantime…keep on doing the messy work!

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*For a guide to the type of ICF-regulated coaching I practice, check out this article on freelance coaching, which I reviewed for the Life Coach Directory.

If you enjoyed this, you might also like…

• An anti-girlboss approach to working for yourself

• Should I go freelance?

• The Freelance Downturn™️ Part 1 and Part 2

About Messy Work

Messy Work is a space for anyone grappling with the feeling that there’s more to life. Featuring personal essays, coaching field notes, and conversations with ideas people who followed the feeling.

To learn more about how coaching could support you, book in a call or check out my website.

This morning, I walked along the river where I grew up in leafy, cosseted Surrey. It’s a route I discovered in lockdown, my footsteps tracing it back and forth as I began to live with the loss of my dad. I sought refuge in the cool shade of the trees, the air woody and damp even on the hottest of days. The sounds of the river were soothing.

It was around that time that I started questioning if there was more to life than the one I was living.

My story, other than the surreal experience of losing my father to covid, is not unusual. A career I was “successful” in, a job that burnt me out. A rented flat in London, where I’d fill my days with claustrophobic fitness studios and tense meetings; my nights with overpriced small plates and ill-fated dates. A creative, curious spirit that increasingly grumbled and groaned as it was put to use flogging consumer goods and filing spreadsheets. A pandemic that put things into perspective.

I know it’s not unusual because I’ve now made a career of talking to people whose stories follow a similar arc.

They, like me, are the high achievers: the ones who did well in school and largely complied with what their families, schools, cultures, or society expected of them. Life was a series of preset hoops to jump through. Yearly exams training them for GCSEs and A-Levels, then university. Grad schemes, corporates, or—if, also like me, you itched for a bit more “impact” (selling sustainable consumer goods)—startups that schooled them in professional jargon and the aggressively linear trajectories of promotions and pay rises.

But somewhere along the way, things started to fall apart. We realised that adult life is not as clear cut as our parents and institutions made out—particularly when the world also started to fall apart.

The million-dollar question

The big, daunting questions of what to do with one’s life and—to borrow a tired catchphrase—how to live one’s best life are nothing new.

Seneca was scratching his head over it in 49 AD, writing to his father-in-law, “It takes the whole of life to learn how to live, and—what will perhaps make you wonder more—it takes the whole of life to learn how to die.”

Simone de Beauvoir was plagued by FOMO: “I am awfully greedy; I want everything from life. I want to be a woman and to be a man, to have many friends and to have loneliness, to work much and write good books, to travel and enjoy myself, to be selfish and to be unselfish…You see, it is difficult to get all which I want. And then when I do not succeed I get mad with anger.”

Kierkegaard was a pessimist: “I see it all perfectly; there are two possible situations—one can either do this or that. My honest opinion and my friendly advice is this: do it or do not do it—you will regret both.” Lennon a pragmatist: “Life is what happens when you’re busy making other plans.”

But I think my generation of millennials, and the Gen Z-ers who follow, find themselves at a particular kind of crossroads, faced as we are with an increasingly uncertain future (and present).

More than half of Gen Zs (55%) and millennials (52%) say they are delaying major life decisions, such as marriage, starting a family or business, or furthering education, due to their financial situation. - Deloitte

For some of us, the choices feel frustratingly limited—whether we are shackled by golden handcuffs that protect us from the cost of living crisis, making do with whatever pays the bills in a desperate job market, or victims of unexpected layoffs that rob us of stability, freedom, and agency.

At the same time, the options can feel overwhelming. The linear career path our parents dutifully adhered to is a thing of the past; splintering, branching, and sidestepping into squiggles, portfolios, and lateral moves. We live Under The Influence, privy to how other people are living their lives every single second of every single day. Should we stick it out and be a corporate girlie with a FIRE lifestyle? Or follow our hearts, like that influencer who moved to Cornwall and started a seaside sauna business?

Beneath it all, that constant refrain: is this it, or is there more?

Whether we are shopping for a new job or a new face, it’s the million-dollar question of our generation.

What if there is more?

I meet people at these wobbly, indecisive crossroads; when something about the path they’re on feels off, but they don’t know which one to take instead.

These crossroads are destabilising. Because basically, the illusion of control and certainty we have trusted up until this point is fading. It is a denouement in the most literal sense: an unravelling. But unlike the books and movies, the final resolution or clarification doesn’t immediately reveal itself.

And also, these crossroads can be exhilarating. I witness people put down the weights they’ve been carrying, take off the mask they were wearing, and reconnect with who they truly are. The interests and talents that used to be integral to their identity, but have somehow been eclipsed by more “realistic” or socially-sanctioned pursuits. The values they betrayed in favour of the growth-at-all-costs productivity and “ambition” dictated by their workplaces. The dreams that start to emerge, hazy at first, which often aren’t anything grand or superhuman, but simply a vision for how they want to potter about their day.

Maybe they start to experiment: a conversation with someone in a field that’s calling them, an evening life drawing class, a radical prioritisation of rest. And it turns out, there is more to life—and more to themselves than meets the eye.

Sometimes, following this feeling leads to a big life change. I have clients who finally quit the job, retrained, moved cities, ended relationships.

But sometimes, it’s about fully inhabiting the life they already have. Which is why we need to talk about the curse of the more-to-lifer.

Or, what if there isn’t?

The other night, I was struck by an urge to look up my birth chart.

Astrology is something I dabble in: 50% cynic, 50% zealot. The psychology-trained coach in me eyes it warily, cautioning that astrology can be a useful practice for self-reflection if approached with a pinch of salt, but that any form of personality typing can be restrictive at best, bullshit at worst.

Side note: I implore you to listen to this podcast episode on the origins of Myers-Briggs if you have ever waxed lyrical about being an INFJ (same).

Meanwhile, the meaning-making mystic in me points to eerily accurate descriptions of her personality and has a fondness for arguing with men who scoff at star signs, but believe in capitalism.

Anyway, once I’d plugged in my time, date and place of birth, the coach and the mystic read a line that shook them both to their core:

“Librans are always looking for the “best” way or the “right” way to live. Harmony is the ultimate goal, but their idealism and high expectations can mean plenty of discontent. If Libra doesn’t learn to live in the moment, at least some of the time, she’ll be in a constant state of unrest.”

A constant state of unrest. Bleak, isn’t it?

I am disappointed to learn that Simone de Beauvoir was not a Libra. But, as astrology naysayers would smugly point out, this passage could serve to encapsulate the modern human condition in a world that is obsessed with always-optimising—and it certainly hits on the central tension of being a more-to-lifer.

If you identify as someone who is always wondering if there’s more to life—a seeker, a dreamer, a maximiser—it is likely that you are highly curious, adventurous, creative, and principled. Someone who is full of ideas, fights for what you believe in, and committed to enjoying your short time on earth as much as possible. All the more reason to follow the feeling that there is more, and not waste a minute—your messy work might be figuring out the what and the how.

But equally, there’s a shadow to this strength. Always chasing the “more” can distract us from, can make us discontented with (“mad with anger”), the beautiful life we’ve already got. The messy work is learning to interrogate the why, so we can tame our yearnings and enjoy what’s right in front of us, eyes wide open and feet firmly planted on the ground.

There is nothing wrong with wanting to squeeze everything out of this one life; but we also need to drink the juice.

The more-to-life dilemma

The more-to-life feeling can be a vital, truthful sign that we need to make changes and honour who we really are—an intuition we can absolutely trust. But it can also be perfectionism, avoidance, escapism, boredom, or even just exhaustion in disguise.

I think of myself, and many of the people I coach, as “recovering high achievers”: people who have woken up to the falsehood of always striving and are recalibrating their definitions of success and a life well lived. The problem is that even when we choose a different path, we still carry the residue of the one before, like stubborn mud that cakes our boots.

This can show up as a dreadful sense of unease when our days are not as busy and “productive” as they used to be—even though we are intentionally slowing down, part of us finds the slowness unbearable. It’s doubting or shaming ourselves because the salary we’re now earning is nowhere near what we used to earn or what our friends are earning. It’s going freelance, then giving ourselves the same harsh treatment we were trying to escape when we left the job with the toxic boss.

We start to fret that we chose the wrong more. Or we think that it’s still out there, somewhere. We keep itching, yearning, chasing: a constant state of unrest.

If we are living yesterday’s dream (imagine five-years-ago you seeing you now!), why are we still dissatisfied, still pushing to accomplish more? Are we seeking and building in the name of expansive growth and natural evolution, or perfectionism, restlessness, and those well-worn high-achieving tendencies?

For the more-to-lifer, these are the living inquiries we must learn to co-exist with.

Why do we feel so torn?

Critics of astrology say that it tells us what we want to hear. A beguiling hall of mirrors that bends and distorts, so that we may always see someone that resembles us, but the reflection remains vague and evasive, refusing to commit to anything fixed.

I would agree with this; and also argue that’s why astrology can be so useful. Horoscopes are just words on a page. Like any other story, we interpret them through the lens of our own experiences, and imbue those words with our own meanings.

Similarly, the more-to-life dilemma has many layers. By sifting through them, we begin to distinguish truth from trickery.

What I see as a coach is that the drivers beneath that grass-is-greener instinct can broadly be categorised into:

1. The stories we hold.

We inherit beliefs from our parents, political systems, pop songs, Disney films, fairytales, Instagram posts—the list goes on.

Some narratives and archetypes (parables, myths, folklore) are buried deep within our psyches, and their wisdom is worth listening to. I think of Clarissa Pinkola Estés telling stories of women trapped in cages in Women Who Run With The Wolves; their soul’s journey is to listen to their intuition and honour their feminine instincts for freedom, beauty, and self-expression.

Others, like the hamster wheel of consumerism that keeps us in constant pursuit of a materialistic version of more, are like parasites that spread from host to host, sinking their teeth in until we shake them off. Whether these stories are systemic or specific (a childhood teacher, a Tik Tok, or dinner with a particularly judgmental friend) we can only discover what we truly want by choosing which stories to own.

2. The animal that lives inside us.

Our nervous systems, stress responses, and basic instincts for survival (food, shelter, belonging, etc) have not evolved much from when we were hiding from saber-toothed tigers.

This means our primal wiring to survive often clashes with the cognitive, evolved desire to self-actualise, producing a gap (sometimes a chasm) between what we rationally know and what we physically or emotionally feel.

Psychotherapist Satya Doyle Byock has a really useful paradigm that describes the tug-of-war, acute in what she coins “quarterlife” (early adulthood), between Stability and Meaning. On the one hand we have needs—for safety, security, consistency—and on the other we have wants—for purpose, intensity, joy.

Hence why the well-paid corporate girlie is reluctant to leave her unfulfilling job and follow her heart’s calling. Or the purpose-led freelancer struggles to adapt to the inherent unpredictability of self-employment, losing faith in the path they’ve chosen.

Perhaps the search for contentment can be found in a healthy balance of stability and meaning, where we identify and respect both our needs and our wants.

3. The parts we are composed of.

Ultimately, the reason I find the astrological birth chart compelling and resonant is that (contrary to the myth that star signs casts us as singular types) it draws a parallel with the main school of thinking that informs my coaching practice: Internal Family Systems, or “parts work”.

Astrological birth charts acknowledge us as multi-faceted creatures, composed of different signs (Sun, Moon, Rising, etc.) and complex in our strengths and shadows. For example, as a Libra I am supposedly balanced and open-minded, good at seeing things from multiple perspectives. But the cost of this can be indecisiveness, people pleasing, and fence-sitting.

In the Internal Family Systems model, our personalities are composed of different “parts”, each with their own strengths and shadows. Often, our parts are at war with each other (for example, the side of you that values stability vs the side of you that values artistic expression), which is why we might find it hard to make a decision, or feel one thing one day, and the complete opposite the next.

And it’s no good ignoring or demonising our parts—if we do, they will usually saddle us with more of what we don’t want. Like the dreamer part who wants to escape your current reality, but is so head-in-the-clouds that it sabotages any efforts to make those dreams happen. Or the perfectionist part who is so wired to achieve and averse to failure, that it endlessly deliberates, holding you back from ever realising your true potential.

When it comes to the more-to-life dilemma, it’s likely that our committee of parts will each have something valuable to offer; the work is to listen to them, but ultimately discern the right course from a place of Self (our “wise adult” or true essence).

How to know what you want and need

This intersection of beliefs (the stories), behaviours and responses (the animal) and identity (the parts) is where the more-to-life tension lives—and what coaching is designed to support.

I came to coaching by following my own more-to-life feeling. First it was a process that helped me sift through all of the above. Then I became so fascinated by the practice that I trained as a coach myself.

Today, the question of whether we should give ourselves permission to want more and do something about it, or shift our perspective and fully inhabit the life we have, only seems to grow more pertinent the more complex the world becomes, and the more clients I meet—which is why I called my practice More To Life.

I won’t pretend there are always straightforward answers and quick fixes or that the process is easy. The transformative style of coaching I practice is less about “achieving your goals” and more about knowing yourself and becoming your own authority, which takes time (or if we take Seneca’s word for it, a lifetime).

But this is how you become the judge of whether your intuition is telling you something, or your perfectionism is leading you astray. The voice of truth when you are distracted by society’s illusions or other people’s projections. The calm, courageous decision-maker at each crossroads (there will be more than one).

And, perhaps overlooked in favour of the knotty challenges, how you remember to celebrate and appreciate when things are going just fine—the more to life moments that aren’t about pulverising the fruit, but slowing down to sip the wine.

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Do you identify as a more-to-lifer?

Meet me in the comments. I’d love to hear what you’re wrestling with and how you know when to listen, or when to say “Not today, perfectionism”.

Work with me

I am an EMCC-accredited transformative coach who works with:

1. Recovering high achievers seeking direction at a career or life crossroads

2. Independent spirits who need a sounding board for the “self” bit of self-employment

If something in this essay spoke to you, I’d love to chat. Book in a call here, or check out my website.

If you enjoyed this, you might also like…

• Everything I know about the messy middle

• Ideas People: an interview series with people who followed their more-to-life feeling

• My loose guide to parts work (Internal Family Systems)

About Messy Work

Messy Work is a space for anyone grappling with the feeling that there’s more to life. Featuring personal essays, coaching field notes and conversations with fellow ideas people.

First came the hustle and the girlboss. Then came quiet quitting and slow living. Now, it seems we are in the era of the messy middle.

I can’t pinpoint exactly when this became A Thing. As a transformative coach, my work sits in the realm of uncertainty: career crossroads, life transitions, identity shifts, and the inherently unpredictable nature of self-employment. So perhaps it’s an occupational hazard that every time I open Substack or Instagram, I’m served content about this weird, liminal vortex that so many of us find ourselves in.

There was, I’ll confess, a period of naiveté when I thought I’d coined the “messy middle” (this Substack is called Messy Work, after all). Then all of a sudden, it was everywhere—in autobiographical carousels, soul-baring reels, members-only communities, and neatly packaged (oh, the irony) video courses. Had I inadvertently stolen the phrase from someone else?!

The truth probably lies somewhere between the Baader–Meinhof phenomenon, synchronicity, and zeitgeist. Because there’s no doubt that the messy middle has sprung up, like a scattering of wildflowers, at a time of radical uncertainty.

Our individual existential crises are nothing new. Humans have long been obsessed with the idea of metamorphosis (as I’ll get into below). Our cultural shorthands are themselves always shape-shifting to accommodate the set of concerns that defines the times—from the bildungsroman, to the Don-Draper-esque mid-life crisis (affairs, fast cars, and spiritual bypassing). Really, change is one of life’s only constants. It’s hard—but very normal—to outgrow the job, relationship, or home that once lit you up.

Perhaps the phrase “messy middle” is merely the latest buzzword. An honest, yet non-threatening way to name that raw, uncomfortable period when something is crumbling, but we are not quite sure what will be built in its place.

But I also think it speaks to something much bigger: the huge, collective crises we are going through. Globally, politically, economically, environmentally, culturally—we’re living through a time where the future feels unusually, and frighteningly, difficult to predict. As the “old order” collapses and a new one is yet to emerge, it can feel like the whole damn world is in a messy middle.

And when you look at it this way, “messy middle” feels like an understatement.

But I’m fascinated by how it’s entered our lexicon, and what it signifies. On the one hand, it feels liberating to release the pressure to be perfect, and get honest with each other about the process of change. At the same time, I am wary of packaging all of this uncertainty and vulnerability into a cute, alliterative trend. And I’m curious: has the messy middle, like its forbears of girlbossery et al, become something to aspire to? Is it embarrassing to have it all figured out now?

Perhaps that’s one I’ll leave for a hopefully viral column (Vogue, you know where I am), but the truth I want to acknowledge here—which I think the pastel-coloured carousels are in danger of glossing over—is that the messy middle isn’t something we can optimise our way out of. What is far more pressing, and useful, is learning to live inside it.

The bit we don’t talk about: the in-between

Of course, the huge merit of the messy middle becoming such A Thing is that we’re not always good at talking about the in-between.

Whether it’s saying “Fine, thanks!” when a successful friend asks how we are, or LinkedIn’s fragile veneer of announcements and congratulations (which belie the desperate job seeking and crippling comparisonitis beneath), we are conditioned to share only our highlights, achievements, and outcomes, not the confusing, uncomfortable stretch it took to get there. Even if we are honest about this, it’s usually with the benefit of hindsight (some retrospective reflections on what a deeply traumatic personal tragedy can teach us about B2B sales, for example).

Now, I’m being deliberately cynical in service of my point. This is not to say we all need to start “writing from the wound” on LinkedIn, and there are many of us who are comfortable being real and vulnerable. But broadly speaking, we live in a society that values the finished product: whether it’s record labels pressuring artists to pump out new music, or perfectly made-up, surgically enhanced, photo-shopped faces that make the rest of us believe we are flawed.

In actual fact, the behind-the-scenes of creating something—whether it’s a piece of art, a business, or change itself—can look like pure chaos. When you’re:

• Feeling pulled towards something new, different, or more meaningful, but you don’t have the faintest proverbial what it is

• Reeling from an expected blow—a redundancy, a breakup, a loss, an opportunity that didn’t turn out as expected—that’s sent a wrecking ball through carefully-laid plans

• Performing an identity that belongs to a past you; like wearing an ill-fitting, itchy coat

• Careening between moments of complete clarity…followed by spirals of self-doubt

• Wondering whether something you’ve spent months, years, or maybe even your whole life building is actually not what you want after all

• Wise to what you want and the path to get there, but the distance between the starting point and the destination feels enormous.

Whatever the case, certainty, confidence, and control can feel wildly out of reach. Cue self-improvement culture trying to sell them to us.

In our always-optimising, efficiency-obsessed world, the in-between is treated like a problem to solve. Quickly. And so we get:

Five steps to find your purpose. Three months to land your dream job. Ten tips and tricks to be more confident. A guaranteed framework to unlock your “next-level self.”

As someone who has found their purpose, their dream job, a little more confidence, and the courage to be more me…I can tell you it took a lot longer than five steps, three months, and some “tips and tricks”. And the work is ongoing.

Because the in-between is not something we can rush. In fact, in both my personal and professional experience, the more we try to force change or clarity, the more elusive they become. I’m going to unpack the psychological perspective behind this shortly, but before we do that, I want to acknowledge another reason why change feels so damn hard…

What stories do we bring to times of change?

Whenever we enter a sticky, murky in-between phase of life, we don’t arrive empty-handed. We bring stories with us.

Stories about what change should look like. How long it should take. What the end result should be. Because for as long as humans have been telling stories, transformation has fascinated us.

In Greek mythology, metamorphosis is everywhere. It’s a punishment from the gods, who turn their rivals’ hair into serpents, or peeping toms into stags. It’s a reminder that nature, identity and reality are always in flux.

Meanwhile, fairytales grapple with the concept of “true nature”: appearances deceive, humans are trapped in the bodies of beasts and frogs, and change comes after trials, rites of passage, or redemption arcs—only once you’ve proven yourself “worthy” of becoming who you’re meant to be.

Today, we have our own modern myths. Reality TV contestants bargaining away their privacy and dignity for wealth and status. Rags-to-riches founders. Corporate exiles who quit the pension-bearing palace to seek out their destiny.

These stories contain both truth and trickery. They give us a set of expectations, fears, and assumptions that can shape how we experience change.

Maybe we’re frustrated that the “2.0 version” of ourselves hasn’t materialised yet.

Maybe we’re waiting for external permission or guidance. Where’s that fairy godmother when you need her?

Or maybe we expect change to deliver us into a completely new reality, only to discover that beneath the shiny new job title or big life decision, the same old insecurities are still very much intact.

Part of the work of navigating the in-between is gently questioning these myths. What if transformation isn’t a dramatic before-and-after? What if it’s slower, stranger, and more subtle than that?

The myth of self-improvement culture

Here’s something that might sound slightly controversial coming from a life and career coach: the self-improvement industry also sells us myths that make the messy middle harder than it needs to be.

When you’re looking for answers, it’s tempting to read all the self-help books, fill your brain with theory, implement rigid routines, or hope that reformer pilates will catapult you into self-actualisation. But what if this approach is the very thing keeping you stuck?

There’s a perspective I learned from a coach called Steve March called the Self-Improvement Paradigm. The idea is that self-improvement (also capitalist and consumerist) culture has conditioned us to approach personal growth like a video game: a series of missions, challenges, and milestones we must complete to unlock the next level of success or fulfilment.

And there’s nothing wrong with learning new skills, seeking support, or experimenting with different perspectives and practices. This is not about settling.

But when we approach growth from a place of lack—from the belief that there is always something to fix, something wrong, or something missing in ourselves—we reinforce the very feeling we’re trying to escape: the feeling that we are not enough.

There’s no end to the ways in which we can “elevate” or “level up”, and so this mindset can be exhausting and usually makes deeper, lasting change impossible. Something that the Paradoxical Theory of Change, from Gestalt Psychotherapy, speaks to:

“Change happens when a person becomes what they are, not when they try to become what they are not.”

So, an alternative perspective: what if you are already enough, just as you are?

What if personal growth isn’t about completing more missions, but about learning how to relate to yourself, and change itself, differently? And what if the messy middle isn’t a failure, but a necessary part of becoming?

My own messy middles

Part of the reason I care so much about this topic (and have made a profession out of it!) is that I’ve been through several messy middles of my own.

1. I graduated from uni with an English Literature degree. Perhaps unsurprisingly, I couldn’t get a job. So instead of heading to London on a grad scheme like many of my peers, I spent a summer volunteering on organic farms in Italy. Then I moved back to Bristol, where I’d studied, and worked four jobs: as a magazine events editor, a clothing boutique assistant, a vegan sous chef, and a marketing intern. It was chaotic, but honestly one of the most fun periods of my career, and it taught me a valuable lesson about variety—which I’ve now come back to in my portfolio career as a coach and writer.

2. The internship eventually turned into a full-time job, and so began my career in startup marketing. A few years in, I wanted to transition into a new industry. To get a foot in the door, I had to take a more junior position, which came with less clout and responsibility. But within a couple of years, I was back on the leadership team again. The lesson: progress does not have to be linear.

3. And then there were the more seismic shifts. In 2020, I lost my lovely dad to covid. I was navigating my own grief at the same time as the whole world was in the most surreal in-between any of us had ever experienced. I think most of us are still suffering or processing this time more than we realise, and death is not something you can extract a “lesson” from. But grief is a teacher: it threw my priorities into sharp relief and I started to reassess how I wanted to live my life, honour my dad’s legacy, and do work I was proud of.

4. I had some coaching as a workplace perk and it opened up my eyes to how stress was ruling my life. I realised I’d fallen out of love with startup marketing, so I went freelance to get back to the thing that had got me into it in the first place: writing (and I can’t tell you how much of the work in my Crossroads coaching pathway is about reconnecting to the interests and strengths we’ve held all along).

5. Through experiencing coaching myself, I became curious about the profession. That led me to train as a coach. I found my calling, but it wasn’t a single lightbulb moment. Coaching training was a huge inner journey that has totally changed how I see myself, other people, and the world.

Today I run my coaching practice, More To Life, alongside my freelance writing work. And while I have so much more clarity than I once did, in many ways I’m still in transition. I’m building a life in a new city. I’m growing my business—and being self-employed requires us to coexist with uncertainty all the time.

The real skill we need

If there’s one thing I’ve learned from my own life, and from coaching clients through their messy middles, it’s this:

The most valuable capacities we can develop are not bulletproof confidence, or absolute certainty and control.

What is far more useful is being able to:

1. Understand and regulate your nervous system when everything feels up in the air.

2. Gain perspective, without forcing clarity; discerning what is within your control and letting go of what isn’t.

3. Maintain faith in the unknown, and in yourself, when certainty isn’t available.

4. Have the courage to take small, intentional steps forward—even when the path ahead is foggy.

In other words: to learn the art of in-betweening.

A practice for the messy middle

When you’re navigating a transition, coaching can provide you with clarity, a path forwards, actions, and accountability. And this is usually what my clients initially seek. But when I ask what they’re ending with after we’ve worked together, these things become secondary to the deeper shifts. Instead, they say:

I’m ending with hope.

I’m ending with self-trust.

I’m proud of myself for showing up.

I now feel permission, not pressure.

I can befriend myself, instead of fighting myself.

I have conviction that it will all work out—that the journey is the point of it all.

It’s a huge privilege to bear witness to these moments. But I know one-to-one coaching isn’t accessible to everyone (and a lot of people don’t really know what coaching is!).

So to offer some support to anyone the messy middle, and give you a taste of what coaching is like, I created IN-BETWEENING: a free guided journalling practice for moments when life feels uncertain, or you find yourself in flux.

It’s not about forcing answers or fixing yourself. It’s about slowing down, reflecting, and learning how to be with change.

Inside the practice, I share some of the coaching insights that have helped me and my clients navigate these seasons, along with prompts designed to help you:

• Ground yourself when everything feels wobbly

• Gain perspective on what’s changing in your life

• Build the self-trust to move forward at your own pace

All you need is something to write with (or record with—voice notes are a great way to journal) and an hour to yourself.

If you’re currently in the messy middle—between jobs, identities, chapters, or possibilities—you’re very welcome to try it and I’d love to hear how you get on.

Sign up to get IN-BETWEENING in your inbox here

A final note to anyone in the in-between

If you’re in a messy middle right now, I know it might feel like this phase will never end. It’s wobbly and confusing and vulnerable. You’re probably wishing there was a fast-forward button.

But sometimes we spend so much time yearning for the future that we forget how far we’ve already come—the lessons we’ve learned, the skins we’ve shed, the brave decisions that blasted out the old and made space for the true.

We spend so much energy trying to rush the process, when there’s so much beauty in it. And it might feel hard to believe right now, but I can promise that one day you’ll look back on this time with, if not fondness, then appreciation. For where it brought you and what it taught you.

Until then, be gentle with yourself. You’re not lost. You’re in-between!

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What resonated with you? What challenged you?

I’d love to hear how these reflections landed with you.

Leave a comment

Further reading for in-betweeners

• Why the more you try to change, the more you stay the same

• When slow living becomes another form of self-improvement

• What if we need to anti-optimise?

• Can you break free from hustle culture and stay ambitious?

• Writing (and living) without a plan

About me & Messy Work

I’m Lucia, an accredited life and career coach, freelance writer, and work-in-progress based in Bristol, UK. Messy Work is a newsletter about being human and creating a life that feels like yours.

Learn more about 1:1 coaching for career crossroads and the “self” bit of self-employment here

Jamiel Thompson is the co-founder of home swapping platform Twin City and a freelance creative strategist working at the intersection of brand, travel, and culture. With members in 60+ locations all over the world—from Margate to Mexico—Twin City lets creatives and travellers ditch hotel and Airbnb costs, and experience cities like a local. In his freelance work, Jamiel has worked with brands like Offspring, Nike, Converse, Spotify, Footlocker, Wray and Nephew, Guinness, Youtube, and more.

A good friend (the kind who has fingers in all the coolest pies and gets credit for introducing me to 99% of the most interesting brands and people I follow) sent me a link to Twin City a couple of years ago.

The concept, a private home swapping community for creatives and travellers, made total sense to me. And it didn’t hurt that the thoughtfully curated aesthetic—all lush landscapes, sunset moped rides, and low-slung, mid-century sofas—made me want to book a plane ticket.

I’ve spent most of my career working remote jobs or freelancing, and I’ve always been drawn to the idea of cashing in my freedom to “work from anywhere”. But I’ve never wanted to make a permanent move or had the cash to pay rent/mortgage on a base in the UK and accommodation elsewhere. The premise of Twin City—swapping homes with trusted hosts who share the same conundrum—is the perfect solution to that tension.

I’m yet to do a home swap myself (a combination of moving house loads and living with a partner whose work is less flexible), but I’ve been avidly following Twin City’s growth over the years, as well as the journey of its Co-Founder and Creative Director, Jamiel Thompson.

When I started this series, I wasn’t interested in replicating the same “success stories” we’ve seen time and time again: VC-backed tech bros who get paid millions to launch yet another app we don’t really need (often from positions of privilege). I wanted to speak to people building businesses or services that felt genuinely needed, or who simply stood for a different way of thinking, being, and living.

Jamiel is someone who embodies both of those things. Because Twin City isn’t just a “platform”; it’s a vision for a way of life that values slow, connected travel; feeds creative inspiration and cultural exchange; and builds genuine community. And Jamiel Thompson isn’t another tech bro; he’s a freelance creative himself, from a working-class immigrant family, who decided to make space for himself when the corporate 9-5 didn’t.

This was a theme that really spoke to me from this conversation: that as industries buckle, “traditional” trajectories fail us, and structural barriers prevail, more of us are questioning how our lives, careers, and identities intersect, and creating new ecosystems that serve all three.

I also really appreciated Jamiel’s candour about the emotional realities of being a founder—the isolation, the regrets, the headlong collision with one’s own, fragile self-worth (can relate)—which are a big part of my work as a coach for the “self” bit of self-employment. And I loved his permission slip to ignore the marketing “gurus”, forget the rule book, and fuck up as many times as it takes for something to fall into place.

My takeaway: Creating something new requires deep devotion, trying and failing, and really getting to know yourself. And even though Jamiel can’t yet say if it’s all been worth the risk…reading about his journey and hearing his words of wisdom? Something tells me it has been.

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Where did the idea for Twin City come from? What made it important to you?

I was born in Jamaica, and I moved to London at a young age. A lot of my family members, especially older ones that have more of a connection back home, would always travel back [to Jamaica]. So for a while, I’ve been trying to find a way to live a life that allows me that flexibility.

Twin City also came from me really understanding that if you’re going into an office, you’re swapping your time for money—and I didn’t want to do that. I felt like the workplace environment wasn’t for me. As a working class, immigrant, black guy, it’s assumed you’re aggressive if you state your point strongly. Then if you don’t say anything at all, you’re assumed to be moody. I wasn’t able to really show up as my authentic self and I didn’t really see a space for me in white collar office work. There’s all these nuances around class that really didn’t appeal to me, and I didn’t want to play that game.

So those were the seeds that started the idea for Twin City.

“The idea with Twin City was: if we’re all in the same position, why don’t we all come together? Surely if there’s this many people with the same problem, we could help each other out.”

When did you know you had to do something about it?

Where it got interesting was during the pandemic. I had already been freelancing for some years, and I had noticed that the part of the industry I was working in (which was largely for cool youth brands like the Nikes, the Jordans, the Vestiaire Collectives, the Jimmy Choos of the world) didn’t really have budget anymore.

It felt like this massive shift where [in the past] I’d get a budget of upwards of £200k to do an activation in one city, sometimes just for one event or influencer campaign. Then it seemed as though the budgets were getting stretched, which for me, was the canary in the coal mine of where we are now, with the industry being on its knees. I was wanting to get out anyway—I didn’t want to work on Gen Z stuff and had outgrown the category.

At the same time, the world was changing, and we were told that everything was going to be different: we don’t have to go back into the office. All of a sudden, my dream since I was a child, of being able to live bi-coastally and not have to go through the London winters anymore, felt like a reality because I could just work remotely. It became a socially accepted thing and it felt as though there needed to be new businesses, types of working, ways of living, in order to support this paradigm shift.

It obviously didn’t last very long, because they wanted us back in the office! Also, a lot of my friends who had the means and the flexibility weren’t travelling. And that’s when I recognised that the hospitality and hotel industry had lost a lot of money during COVID, and they were trying to make it back up. So even though we had the freedom of travel, because we could work from anywhere, there was also this massive barrier in that accommodation prices had gone up 40% since the pandemic, because Airbnb and hotels were trying to make their money back.

So the idea with Twin City was: if we’re all in the same position, why don’t we all come together? Surely if there’s this many people with the same problem, we could help each other out. That was the premise of it.

“That was a bit crazy…running a fairly successful business that’s gaining momentum, with your mum hoovering in the background when you’ve got an investor meeting.”

What allowed you to do something about it?

I had some money from the freelance work that I’ve been doing, so that really helped. What also helped was that I was living with my co-founder at the time, who was looking to do something else, and he had a job that gave him quite a bit of cash as well. So it didn’t feel like that much of a risk at the time.

But to be honest, we didn’t even Google “home swapping” or check if it was a real thing. So it would have been blind faith, really. And because I’d been working for myself since the pandemic, I didn’t feel like it was impossible to come up with a new way to do that.

How exactly did you make your idea happen? What sacrifices or compromises did you have to make?

We didn’t really prepare. We didn’t really save any money, so it meant that we had to make a lot of sacrifices. Within the first year, both my co-founder and myself had to move back home into our parents’ house, which was absolutely mad. If you have immigrant parents, you’ll know what it’s like—it’s like you’re a child, even though you’re a grown adult. So that was a bit crazy, having to navigate that—running a fairly successful business that’s gaining momentum, with your mum hoovering in the background when you’ve got an investor meeting.

There’s also what that meant in terms of things like dating and feeling like you’re an adult. If there’s no money, you’re living back at mum’s, and you’re single, it’s super stressful. Ultimately, that stress led to my co-founder leaving the business. I had the freelance work still coming in at this point, whereas he’d already quit his job, so he went straight into working at pubs and doing odd jobs. And there’s only so long that you can do that, especially when you’re getting to the age where you want to start a family and you want your potential partner to see you as stable and serious.

“Being a founder forces you to deal with a lot of the ego. It forces you to look at yourself and say, I’m worthy of love without being successful or without achieving the end goal.”

Then there were all the sleepless nights, all the birthday parties missed, and all the social engagements that you wish you could have made, because you’re at home working on a deck that didn’t end up doing anything—you pitched it and it flopped.

It can feel really isolating being a founder, and it’s something I’m still working on right now. If you look at it more holistically, the reason why I believe a lot of people found businesses and are overachievers is probably because of some childhood trauma type shit. You’re trying to find fulfilment. I think that’s, like, 99% of child actors and 99% of founders. They’re one and the same, and I definitely fall into that category.

Being a founder forces you to deal with a lot of the ego. It forces you to look at yourself and say, I’m worthy of love without being successful or without achieving the end goal. Learning to love yourself during that process, learning to still show up for friends and for family during that process, decentering the business or idea or ego—I think that’s a big part of the process for me.

Where are you with your idea now?

We’re in 60 cities, all the big metropolitan European capitals that you can think of—London, Amsterdam—also across APAC: Singapore, Tokyo, South Africa, South America, Bahia, Sao Paulo, Cape Town.

It’s in a place where it’s starting to generate some real income, which is nice. The work that we’ve put in over the years is only now really starting to feel like it’s compounding, and things are getting a bit easier.

I think we’ve only really understood the problem that we’re solving in the last six months. Not from a theoretical level, but having tested so much shit, and so much stuff not working, and finally understanding why things work and the weird idiosyncrasies of human psychology that work within your particular niche.

I get frustrated, as we all do, with these internet gurus who are saying stuff about marketing or whatever the new buzzword is that week. Ultimately, you have to just fuck up enough times.

“All this stuff that you read online—about having your proof points, having this, having that, make sure there’s testimonials, or whatever—I’m not saying it doesn’t work, but for us, mystique is way more powerful.”

What have you learned?

From a business perspective, I’ve learned that operating in a luxury or premium space, the rules don’t apply.

We didn’t actually start out as a members club. We started out as this free, cool way of travelling, and we felt like we cracked the matrix—if everybody did this thing, nobody would have to pay for Airbnb again. That was the sort of bright idea enthusiasm that we went into it with. But surprisingly, even if you come up with a really good solution for a problem, you still have to convince people to use it, even if it’s free.

We didn’t want to charge people at first, we weren’t really even interested in monetising it in that way. And people were like: “Yeah, right. There’s no way this is gonna work”. We weren’t sending the right social signals to make people trust us.

One day, me and my co-founder were at the British Library in Kings Cross. We had very different approaches to design and communication; there wasn’t really a language built around the business. We didn’t really know how to articulate that shared vision. We got frustrated, wiped our website, and just put “Twin City, members only”, and we listed the cities that were in that time (which was maybe 20 cities). Our conversion rate went up 30%.

It was then that we really realised that all this stuff that you read online—about having your proof points, having this, having that, make sure there’s testimonials, or whatever—I’m not saying it doesn’t work, but for us, mystique is way more powerful.

I was actually talking to a VC today, and we were discussing a study called the snob effect. You know, why do people queue up around corners for street wear drops? Why do people sign up to a waiting list after they’ve bought tens of thousands of luxury items to get a Birkin bag? And basically, the premise of the snob effect is that the more friction that you put between your product or service and the consumer, the more people want it.

I think that’s really true, and something that I don’t really see discussed a lot, but it’s these real nuances that I think I learned, especially coming from working with global brands with millions of pounds of budget, the legacy, the brand trust. The stuff that we would do for Nike or Johnny Walker Blue Label just wouldn’t work for us. Some of the strategies did work, but a lot of them just didn’t. And when you’re operating at scale, at each version of your business, you need to employ different strategies.

Was it worth the risk?

Honestly, I think I’ve definitely changed and grown a lot as a person. But you can’t get back the moments. You can’t get back the time that you spent. Can’t get back the money. So I guess ask me again in a couple of years! That’s my best answer to that right now. I’m not completely sure. I’m not completely convinced. I feel like it’s a very, very slow, uphill battle, and then it gets a little bit easier, year on year. You don’t just wake up and you’re rich with a Porsche parked outside.

“Make sure the idea feeds you back. The idea is going to work on you as much as you’re going to work on it.”

What advice would you give to fellow ideas people?

Ideas aren’t enough. That’s the first thing I would say.

Good ideas are really brilliant. But you need to ask yourself how and not why. You’re not the only person to have an idea—I know other people have said this, but I genuinely think ideas exist in the ether, kind of floating around. You can grab it by acting on it—by acting on the how. I think ideas people are very much why-driven. But what actually helps me is when I think how, and I think more practically.

I saw somewhere, probably on Instagram, that you think starting a business is one good idea, and it’s not. It’s one good idea followed by another good idea, followed by another good idea, followed by another 1000 good ideas. So if you’re going to invest your time into an idea, you need to naturally be excited about it, and it needs to feed you back.

The relationship between you and your ideas is an interesting one. It can often be a mirror, I think, pointing at our own flaws, misconceptions, and understanding of the world. Which is beautiful, right? Because everyone has such a unique perspective. And that’s what makes interesting ideas. That’s why neurodivergent people contribute so much to the idea ecosystem: because they think differently.

So make sure the idea feeds you back. The idea is going to work on you as much as you’re going to work on it.

Big thanks to Jamiel for sharing! Here’s where to follow him and Twin City

• Follow Jamiel on Instagram

• Follow Twin City on Instagram

• Apply for Twin City membership here

What’s the big idea that feeds you?

The one that keeps you up at night? The vision you’ve had all your life? The dream that you’re willing to stay devoted to, even if the “results” don’t materialise right away? Jamiel and I would love to hear what resonated with you in the comments.

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Fancy being my next Ideas Person?

I’m always looking for guests who took a risk to act on their big, bright, burning idea—whether it was starting a new movement like Jamiel, moving to a country you’ve never set foot in before like Mary Alice, going back to art school like Kasturi, housesitting around the world like Hannah, or queering your career like Katrina. Drop me a message to tell me your story.

About Messy Work

A Substack for deep thinkers, big feelers, and more-to-lifers

I’m Lucia, a writer and EMCC-accredited life & career coach based in Bristol, UK. I work with recovering high achievers and independent spirits who can’t shake the feeling that there’s more to life. And I write about the messy (but beautiful!) work of figuring it all out.

Since I launched this Substack in 2024 (wild), I’ve played with a few different approaches to publishing—from religiously posting every other week, to monthly “magazine” issues, to not really posting at all. But the heart of Messy Work has always remained the same: to write about the messy work of being human, and creating a life that feels like yours. This year, I’ll still be writing Messy Essays, Loose Guides, and Ideas People (my interview series), but I’m returning to a more flexible publishing schedule. Part of me worries this makes me look inconstant—but then again, what is digital content if not experimentation?! So thanks for being here along the way—and letting me play! And on that note of self-consciousness, let’s dive into today’s post on the curious paradox of being seen…

This is uncomfortable to admit, but I really want you to like this. I don’t mean in your head, before you drift over to the next tab or app. I want you to actually click the button. To scroll to the end of the post and turn the little empty heart red.

And while you’re there, why don’t you leave a comment? Tell me if you agree or disagree. If you see yourself in my ramblings. If are we less alone than we think.

Better yet (oh, be still, that little red heart), tell me I’m a good writer by telling other people that you think I’m a good writer. That my words matter. Go on, press the taunting, cyclical arrows and get this seen in all the right places. Prove to the algorithm gods that I am worth a millisecond of people’s eroding attention spans.

Yet at the same time…

I’m mortified you just read that. Go away. Stop looking at me. Please refrain from smelling my desperation.

If we know each other in “real” life, let us vow to never speak of this. At most, you may ask me how’s the writing stuff going? But then carry on, as you are, liking my pictures of artfully strewn burrata on “small” plates (which are actually quite big considering it’s just a burrata), politely turning your head whenever I stoop so low as to bare my soul (not my pretentious taste in restaurants) on the internet.

In other words, I want you to see me. But I’m also scared of you seeing me. And I’m embarrassed that I care either way.

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Welcome to the age of visibility (it’s weird here)

We live in the age of visibility. Divulging everything from our morning runs, to the insides of our homes, to our live locations online. We share on autopilot—ne’er a pretty sunset goes by without our thumbs swiping to camera mode and ‘add to story’.

This impulse, though habitual, can be painfully self-conscious. That pretty sunset may conceal a calculated move, designed to prove not to the world, but to one person in particular, that we are doing just fine without them. The rules of engagement are always changing (didn’t you hear, boyfriends are embarrassing now?), and we try (as nonchalantly as we can) to keep up.

Yet however much energy we pour into curating our digital selves, anticipating how we might be seen by others, we are bizarrely terrible at really seeing each other. We scroll past video clips of someone crying. We respond with a laughing emoji when a friend jokes about the martinis they’re mainlining after a shit day. The same friends that are the first to like our thirst traps have never supported our businesses, liked our essays, or shared our art.

As someone who is, by choice and necessity, visible online, last year I found myself spiralling deeper and deeper into a state of perplexity. In the past couple of years, (like every other millennial with a minimum of one existential crises behind them) I’ve started a Substack and a coaching business. And honestly? I had no idea it would feel so hard to “put myself out there”. Especially because for most of my career, I’ve created stuff for the internet. But I guess it was always for other people (or I was simply younger, braver, and bolder).

However, this essay isn’t a strop about people not liking my Substack posts (it’s fine guys, really). My own, very specific example—which I recognise may not be relatable to those who have the good fortune of not needing to promote themselves online—got me thinking about the wider implications of this paradox: our simultaneous longing for, and deep-seated fear of, being seen.

Visibility neuroses

We want to be seen on LinkedIn. Just not by people we went to school with.

We want to be seen as an attractive, captivating lover. But only for the first three dates. The moment we lay our cards on the table, or let someone see our face without makeup, it all starts to feel a bit too real. Easier to nip it in the bud now, rather than risk them rejecting us later.

We know our partner loves and understands us. But every now and then, we throw in some protest behaviour—testing their commitment by adopting a sassy, angry mask, rather than being honest about our insecurities.

We’re desperate for validation at work. Thrilled when we get the promotion. But then we have to rise to the occasion. We assume people will think we are frauds. We watch colleagues ahead of us get pushed off their pedestals and worry that we’ll be next.

We sing at home, in the shower, imagining the joy of joining our voices with others, the thrill of performing on stage. But when we get to the door of the local choir, we turn around.

And maybe, just maybe, we’ve got to where we want to be: the accolades, the social media likes, the fancy job title. Only our pursuit of external validation has cost us our authenticity and integrity. We find ourselves being seen for the wrong reasons: a mere impression of a person, not the real us.

This conflict is deeply human: a product of our wiring for social belonging pushing up against our instinctive need for self-preservation. The deep, tender heart of us vs. the over-sensitive vigilante, spying opportunities for judgment, rejection and shame at every corner.

When these parts are at loggerheads, the cost is often inaction. Safer to do nothing, and avoid getting hurt. Yet when we do nothing, nothing changes. We stay in the job we hate because it’s easier than chasing the dream—and potentially failing. We stay in the wrong relationship because without it, we fear our friends, family and society would pity us. We shush our intuition and temper our yearnings. We prioritise survival, at the expense of Self.

It’s all a bit bloody dramatic, isn’t it?

Well, yes. Because these two parts of us are playing with extremes, with the things that could change our lives at one end of the spectrum, and the lizard-brain fear that these very same things could end our lives (at least socially) at the other.

So how do we find a happy medium?

As I moved through excavating and healing my own visibility wounds towards the end of last year, I learned that as much as this conundrum is universal, it’s also deeply personal.

Yes, I think this paradox is exacerbated by social media, where we fear both being seen and not being seen. Whether it’s business, relationships, or a haircut, we live out so much of our lives online, hyperaware of how the choices we make will be perceived by others. Culturally, we are inventing new stories about the consequences of putting yourself out there—saying/doing the wrong thing can get you “cancelled” as if you were a streaming subscription, not a human being. And so which is worse: all eyes on you, or radio silence?

But we also carry specific, personal stories about what it means to be seen. A relative, a teacher, or a group of nasty schoolchildren who took us down a peg when we dared to put our head too far above the parapet. A family value of modesty (it’s rude to brag). A friendship group that loves to bitch and critique. Unwanted attention on bodies we cannot control.

I’ve needed to mine my own narratives to find clarity on exactly what it is that can stop me being the truest version of myself (a woman who is still revealing herself to me). To meet those different parts of me—the one who yearns and the one who hides—hear them out, and give them the reassurance they need that it will be different this time around.

Because ultimately, we need to see ourselves in order to feel comfortable being seen by others—comfortable enough that we can risk the possibility of rejection, and know that we have a safe place to come back to.

Like many women of my age who are (perhaps dangerously) in need of some escapism, I have succumbed to the steamy, trope-laden world of Prythian in Sarah J. Maas’ ACOTAR series. As someone who hasn’t read romantasy since Twilight, I’m not quite sure how I got here—but I am loving it.

Anyway, there’s a scene in the third book where the protagonist, Feyre, has to retrieve a deadly mirror that’s driven previous victims mad with the horrors it’s revealed. After Feyre has mysteriously but successfully managed to retrieve it, we learn what she faced: herself.

“It’s a rare person to face who they truly are and not run from it - not be broken by it. That’s what the Ouroboros shows all who look into it: who they are, every despicable and unholy inch.” - A Court of Wings and Ruin, Sarah J. Maas

Unlike those before her, Feyre doesn’t try to turn away from her own, monstrous reflection. She stares it down, confronts her darkness, and lives to cultivate a sense of peace and forgiveness towards those ugly parts of her. Armed with this self-acceptance, Feyre emerges stronger and wiser—able to stand up and fight for what she believes in, empowered to do the hard things.

Back to my own hero’s journey aka the trials and tribulations of posting on LinkedIn

When it comes to self-promotion, there’s a lot of advice out there to “just do it”. To start small. To even tell ourselves, nobody cares. To an extent, this attitude can be useful and liberating.

But at the same time, it’s okay to admit that we want people to care. And ultimately, I think that care has to start within. We need to resource ourselves with, if not self-love, then enough self-acceptance that we can allow ourselves to be vulnerable. We need to see ourselves as we really are, so we can make sure we are being seen for the right things: our true values, voice, or talents, not those of someone who has lots of followers on TikTok.

We also need to practice discernment over when we choose to share and when we may need to retreat. Not to hide, but to take a beat if we’re feeling overexposed.

Perhaps above all, I’ve realised how important it is to give ourselves opportunities to feel seen beyond the like, comment, and restack button. Maybe that’s joining the writing circle and having your words read by beautiful, fallible humans sitting right in front of you. Going to the networking event and seeing someone react to your elevator pitch in real time. Telling a friend about the seedling of a creative idea over coffee. Or booking that session with a coach or therapist (some of the most powerful work I’ve done as a coach is simply witnessing people).

I recently had a profound experience of feeling deeply seen as part of a women’s circle, led by the wonderful Becky Symes. For eight weeks, eight of us met for two hours on a Tuesday night, showing up as our rawest and most vulnerable selves. Both seeing and being seen by these women—being held by them and by Becky—was ultimately what produced the biggest shift in my own relationship to visibility.

Finally, we might ask ourselves how we make our loved ones, or strangers we admire, feel seen, understood, and valued. Sending the text. Restacking the post. Crafting the compliment. Celebrating all the things they’re working hard on, not just the birthdays, engagements, and fancy holidays. I think we’re all guilty of getting so wrapped up in our own fears, that we forget to appreciate what’s right in front of us.

And if you can’t see someone else, how the hell are you going to see yourself?

What did this post bring up for you?

Validating vanity metrics aside, I would love to hear about your relationship to visibility and feeling seen. Have you had to move through any visibility wounds or neuroses to feel comfortable putting yourself out there? And what do you make of existing in the age of visibility? Feel free to share in the comments, or drop me a message.

About me & Messy Work

I’m Lucia, an accredited life & career coach, freelance writer, and work-in-progress based in Bristol, UK. Messy Work is my newsletter for recovering high achievers, independent spirits, deep thinkers, and big feelers who are always wondering if there’s more to life…

Learn more about 1:1 coaching for career crossroads and the “self” bit of self-employment here.

Hello and Happy 2026! I’m writing to you, as I usually do at this time of year, as a kind of New Year scrooge—primed to caution you on the perils and psychology of goal-setting and remind you that you don’t need to be a “new” you. But first, allow me to tell you a little story…

It is a bright, bitter day during the existential vortex that is Betwixtmas. I am marching through Bristol in search of a warm, atmospheric café in which to read and write, craving the clarity of solitude after several weeks of joyful but intense socialising.

As I approach the harbour, I hesitate, toying with a couple of familiar faces—establishments where you can count on decent coffee, but where the patrons will certainly count the minutes you drag out your singular drink. £4.10 may buy you an oat flat white, but not time.

So I keep on walking. I realise that what I need is not just a café, but a third space to rest my weary social batteries. Onwards I march to the Arnolfini, Bristol’s stalwart supplier of free art, peaceful nooks and crannies, and harbourside ciders. There, I’ll get some natural light, a view of the water (framed by photogenic potted plants and piles of artsy magazines), and music loud enough to coax me into a flow state.

But the Arnolfini is closed—even though I’ve compulsively checked the opening times on Google Maps (such is a millennial’s relationship to certainty). I frown.

I try the café a few doors down, but find the lighting, seating options, and ambience unsuitable. I Maps other locations, but calculate that it won’t be worth walking all the way up Park Street and down again, because I’m due to meet my boyfriend at the cinema in an hour and a half. So I settle on the bar of the cinema itself, which does offer sufficient spaciousness, ambience, and a view.

Only once I get there, it’s disappointing. I am not satisfied with my table (I should have sat over there, but it feels silly to gather up all of my belongings again and move), nor my oat hot chocolate (too watery). The music isn’t loud enough to coax a flow state, but too loud to drown out with my headphones. To make matters even worse, the two men next to me are watching videos on their phones without headphones.

I try, I really do. But so often, in my pursuit to wring the most out of life, I am disappointed. And there we have it: the condition of a perpetual perfectionist, an eternal optimist, an indecisive Libra, and a recovering high achiever.

What’s all this got to do with New Year’s resolutions?

In Exhibit A: The Café Saga, we see one of my most recurrent patterns play out:

1. I have good intentions. My quest for the perfect café was born from self-awareness. I knew I needed to dedicate some time to myself; prioritise my creativity; do self-care; perhaps “romanticise my life”.

2. I have hope. I didn’t settle for the first café I came across. I believed in better.

3. I know what I want, and to some degree, myself. I wanted to cultivate just the right conditions for my creativity to thrive—I’m someone who is very sensitive to my environment, soaking up every incongruent sound/aesthetic/scent/emotion like a sponge.

4. The problem is, not everything is in my control. Alas, the Arnolfini was closed. People are obnoxious.

5. When reality fails to meet my expectations (rude), I am thrown off-course.

   My perfectionism breeds panic and decision paralysis. I let logic override my intuition. What would have happened if I’d let myself wander, instead of pressing my nose to Google Maps and reverse engineering the minutes on the clock? Why didn’t I just gather my belongings and move to a different table?

6. I feel disappointed. In reality, but also (perversely) in myself.

The reason I’m sharing this tragicomedy, other than my love of a bit of compassionate self-deprecation? It closely maps onto how I, as a recovering high achiever, am prone to approach goal-setting—and I see the exact same pattern play out for my coaching clients, too.

Take one of my goals from January 2025, which was to hit 1,000 subscribers on Substack by the end of 2026—an objective I wilfully set, despite having written about the dangers of rigid, quantitative goal-setting for recovering high achievers (do as I say, not as I do, etc.).

I had the good intentions: committing to a writing practice, sharing my insights as a coach, and helping more people feel less alone in the messy work of being human.

I had hope: I was steadily growing my audience.

I knew what I wanted: to work towards my dream of one day publishing a book.

But my goal was being influenced by outside noise: capitalism’s fixation on growth at all costs, social media’s arbitrary measures of “success”, all the other writers and coaches who had more subscribers than me.

There were also several factors outside of my control, like a reader’s choice to subscribe, and how the Substack algorithm distributes content.

When my growth plateaued, I hesitated and changed course—trying a “slow publishing” model to cut through the noise (update: the Substack algorithm did not like this).

I let my rational brain take over, either disciplining me to write to a precise schedule, or cautioning me against it altogether. Rather than writing when inspiration struck, or finding the courage to keep going.

Things started to feel forced and uncomfortable. So I took a break from posting. At the end of the year, I had not hit my target.

Luckily, I don’t feel disappointed. Along the way, I realised that this number wasn’t actually that important to me. What really matters is that a) I show up consistently to my writing and b) my writing resonates with my audience, even if it’s just one person.

And with my coaching hat on, I know exactly where I went wrong.

The curious crisis of being a recovering high achiever at the start of a new year

If you’re someone who values personal growth, but you’re also trying to carve out a new model of “success”, the New Year can trigger a perplexing tension. On the one hand, it’s healthy and enriching to value growth or crave a deeper sense of purpose. It’s beautiful to let yourself dream.

On the other hand, following the call that there might be more to life can lead us astray when we confuse it with chasing yet more “achievements”.

Because while there’s nothing wrong with wanting to grow—to learn new skills, deepen commitments, and experiment with different ways of being—the problems start when we approach our goals from a place of self-lack or inauthenticity, with an all-or-nothing mindset.

We are not [fill in the blank] enough, so we must become someone who runs every single morning/has 1,000 social media followers/is fluent in Spanish.

We see our peers earning six figures, running marathons, or throwing lavish weddings, and so we assume that’s what we should want too.

When we attempt change through this paradigm, we usually set ourselves up to fail. Or we achieve the goal…only to realise it doesn’t actually bring us what we were looking for in the first place.

But when we approach change with self-trust, authenticity, curiosity, and acceptance of who we already are (whole and enough), it tends to flow more easily, and run deeper (see: this Loose Guide on the Paradoxical Theory of Change).

And so this year, I am proceeding with caution. I can’t quite resist the winds of change, but I’m trying to keep my feet firmly planted on the ground. As I spend the next few weeks processing 2025 and looking to the year ahead (reminder: January 1st is another arbitrary number and you can take your time with that vision board!), I’m sitting with the following questions.

If you relate to any of the above (please comment if you can also spin the simple act of choosing a café into a huge ordeal), perhaps they’ll be useful for you to think about too…

Leave a comment

Questions to ask yourself before setting New Year’s resolutions

In no particular order…

• Does this goal serve my growth, or my ego?

• What deeper emotional need lies beneath this goal? (e.g. feeling seen, loved, safe, supported) And are there other ways I can (or already do) experience that?

• Does this goal come from me, or someone/somewhere else?

• To what extent is this outcome really in my control?

• When do discipline and structure serve my growth? And when do they limit me?

• Instead of focusing on the outputs, what if I focused on my inputs?

• What might change if I treated my goals as experiments, not measures of worth or success?

• How can my intentions honour who I am now, rather than asking me to become someone else?

• What would it look like to shift from striving and achieving to accepting and appreciating?

• Instead of focusing on self-improvement, what could it look like to think about world-improvement?

Happy New Year, everyone! ✨

P.S. I’ll be sharing more soon on what I’ve got planned for Messy Work in 2026…

In the meantime, if you enjoyed this post you might like…

• Messy Essay: Radical unsubscribing

• Loose Guide: Why the more you try to change, the more you stay the same

• Messy Essay: When slow living becomes another form of self-improvement

• Loose Guide: An antidote to self-improvement culture (and the dodgy world of personality testing)

• Messy Essay: Can you break free from hustle culture and stay ambitious?

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About me & Messy Work

I’m Lucia, an accredited life & career coach, freelance writer, and work-in-progress based in Bristol, UK. Messy Work is my newsletter for recovering high achievers, independent spirits, deep thinkers, and big feelers who are always wondering if there’s more to life…

Learn more about 1:1 coaching for career crossroads and the “self” bit of self-employment here.

*I always wonder if people who share photos/videos of themselves crying during their rock bottom pause mid-sob and remember to document it, such do we live in a state of anticipated memory, or if they re-stage it afterwards. And which is worse?

Welcome to Messy Work: Start here!

If we haven’t met before, I’m Lucia and I write about the messy work of being human, and creating a life that feels like yours.

Before we dive in…

It always strikes me as funny that we use the word “slop” to describe inauthentic-feeling content that’s obviously generated by AI. When in fact, it’s actually the unnatural slickness—the bland, smooth edges and regurgitated genericness—that’s the dead giveaway (NOT the em dash!!).

Human writing, on the other hand, is gorgeous because of its rough edges.

I’ve been reading Dead and Alive, the latest collection of essays from the inimitable Zadie Smith—inimitable precisely because of her meandering digressions, her refusal to commit to an unambiguous, logically-stacked conclusion, and her occasional, endearing use of “like” (the filler word) in her prose.

The effect is, of course, warm and conversational. But this isn’t Cosmo-esque chit-chat; Smith is one of the greatest thinkers of our time. And what a privilege for us, her readers, that she lets her brain spill out onto the page. She invites us to participate in that curious, funny, razor sharp, and relentlessly grappling mind of hers—which, in her own words, is “very messy and chaotic”.

When I started Messy Work, it was with the intention of liberating my writing from the shackles of contentification, after many years of working in marketing. I wanted a place to confront the frustrating contradictions, mind-bending paradoxes, and yes, inevitable sloppiness of being human. And to document the deep, messy work of trying to build a life that feels like yours—not the sham, Müller Light version of it. This feels even more important as GPT drivel floods the feed at an increasingly alarming rate.

(speaking of Müller Light, check out my good friend Emma’s post on ultra-processed content and messy, organic intelligence)

While looking back on everything I’ve written sometimes induces a little cringe (or worse: the realisation that I’ve effed up my SPaG), I’m proud that I’ve shown up in all my glorious humanness. If not spilling my brain onto the page as expertly as Zadie does (a writer can dream), then at least, my heart.

And with that (almost Smithean?!) digression, let’s dust off the digital spines and delve into the Messy Work archives.

Whether you’re new here, or you’ve been around since the beginning (s/o to my mum, boyfriend, and best friend), I’ve put together a little compendium of posts to (re)acquaint you with the mess.

How to use this archive

I write about all sorts—from transactional analysis psychology to my simultaneous relief and regret that I may never ask the DJ to play Drake again. So to help you find what tickles your fancy, I’ve categorised every post according to different themes.

As I always say to my coaching clients, follow your curiosity! If you’d like some recs, the ones marked with a ⭐️ are popular with other Messy Work readers.

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The Messy Work archive

What’s this all about then?

To learn what Messy Work is all about, why I started a Substack, and how my thinking about writing on the internet has evolved along the way, check out:

• About Messy Work (and I guess, me!)

• Are we ready to try again? (Messy’s first ever post!)

• ⭐️ Writing (and living) without a plan

• ⭐️ How to be a good writer

• ⭐️ I don’t want to write content anymore. So I’m changing my Substack.

Self/personal

The heart- and gut-spilling stuff, for which my biggest hope is to help someone think “Oh, so it’s not just me!”:

• Do we really need to learn to be alone?

• The limitations of self-awareness

• ⭐️ Why can’t I just love my body?

• How am I supposed to age in a society that’s de-ageing?

• ⭐️ 31 lessons I’m learning in my thirties

• ⭐️ ⭐️⭐️ Why I quit London (my most popular post ever!)

• ⭐️ The second arrow: when self-abandonment cuts the deepest

• ⭐️ I got stranded on a train for 12 hours in the Spanish blackout. Here’s what it taught me.

• It’s cool to be an introvert. So why is it painful to be shy?

Career

This section and the next one are what you might call my bread and butter! I coach recovering high achievers at a crossroads in their life and career…

• ⭐️ Is it normal to change your mind about your career?

• ⭐️ What to do when you hate your job

• ⭐️ Can you break free from hustle culture and stay ambitious?

• The shadows of startup culture

Self-employment

…and I also coach independent spirits who need a sounding board as they navigate the ups and downs of self-employment.

• ⭐️ Should I go freelance?

• ⭐️ An anti-girlboss approach to working for yourself

• End-of-year journalling prompts for the anti-girlboss

• ⭐️ The Freelance Downturn Pt 1: Is this the worst time ever to be self-employed?

• ⭐️ The Freelance Downturn Pt 2: Perspectives to help you ride out The Ebb™️

Creativity

As a writer, I identify as being a “creative”. But I don’t always feel like one—and society, with its insistence on productivity, efficiency, and “growth”, doesn’t always help…

• There’s no such thing as not being creative

• How to be more creative: ideas and practices that actually work

• Do you really have writer’s block, or do you just hate the internet?

Coaching psychology

My personal mission is to put coaching on the map as something that’s as normal and accessible as having therapy—and therapy isn’t even there yet. So I often use my Substack as a place to share perspectives, tools, and frameworks that I’ve learned and use with my clients.

Imagine if they taught us this stuff in school, instead of faffing around with algebra, eh?

• How to make decisions

• ⭐️ Rebuilding the courage to take risks in your thirties (check out part one: How do you feel about taking risks?)

• An antidote to self-improvement culture (and the dodgy world of personality testing)

• Why the more you try to change, the more you stay the same

• How to think differently (no cringey positive affirmations necessary)

• Why your boss is so “toxic” (I can’t believed I missed the opportunity for a Britney GIF here)

Anti-optimising

I seem to bang on about this a lot…

• What if we need to anti-optimise?

• Deathbed screen time

• Your reminder to just be

• Can you be too productive?

• How to make 2025 #anti-goals

• When slow living becomes another form of self-improvement

• Radical unsubscribing

Navigating difficult emotions

One of the best ways for me to process big feelings and complex experiences—from grief, to euphoria—is to write about them.

• On navigating transitional times

• Are you done crying yet?

• How often do you get high?

• Are you asking for too much?

• Stop being so sensitive

• ⭐️ Nobody wants to talk about the pandemic

Interviews

And last but not least, this Substack is no longer just about me finding my voice. Ideas People is my interview series with people who’ve had a big, scary or unusual idea and taken a risk to make it happen, designed to give fellow visionaries some encouragement to bridge the gap between dreaming and doing…

• Introducing Ideas People

• Hannah Wilkinson on finding the faith to follow the fire within you

• Kasturi Kiritharan on following her childhood dream to be an artist

• Mary Alice Duff on why confidence comes after the leap

• Katrina Fairhurst on queering the way we work

Phew, that’s a wrap! Which posts did you like best?

Do you also find yourself nostalgic for winged eyeliner and the “embarrassing stories” section of Mizz magazine? Have you got Thoughts on Society™️? And where are you wondering if there’s more to life?

One of my favourite things about writing this Substack is hearing what resonates with you.

Leave a comment

Subscribe for monthly issues

Once a month, I publish:

• A Messy Essay: documenting my latest musings/existential crisis

• A Loose Guide: (strictly non-prescriptive) insights from the world of coaching psychology aka stuff I think they should teach us in school

• Ideas People: inspiring, honest conversations with more-to-lifers who had a big idea and took a risk to make it happen

If that sounds like your cuppa, consider subscribing to show your support—it gives me the faith to keep on writing.

You can also join Messy Club, my free subscriber chat, for bi-weekly journalling prompts to get you thinking.

Welcome to the mess!

Where else to follow my work

• 1:1 coaching: peruse the More To Life website

• More To Life Instagram

• Talking about coaching + copywriting on LinkedIn

Drop me a message if you fancy a chat 🙂

Ideas People #4: Designing a career that honours every part of you with Katrina Fairhurst

Katrina Fairhurst is a freelance copywriter and self-professed word slut. Her business Satisifed Kat Copy works with business owners in the sex tech and pleasure industries to create their brand tone of voice, website copy, and SEO optimisation. Since her first article during her Master’s—an interview with the London-based feminist sex shop Sh!—she knew that sex tech was the world she wanted to be a part of. When she isn’t writing about sex, you can find her swinging around a pole!

Many moons ago, I worked for a period care company—my entry point into the wonderful, weird, world of female and sexual health. I say “weird” because so much of this work is fighting taboos: normalising experiences that are so normal, they happen to half the world’s population.

From periods, to erectile dysfunction, to menopause, to sexual exploration, I’ve had the pleasure (pardon the pun) of working with several amazing brands since then, and it’s taught me so much about speaking the unspoken. Something this month’s guest, Kat Fairhurst, embodies to her core: whether it’s finding the voice she lost to vaginismus, shouting loudly and proudly about the sex work industry, refusing to conform to working cultures that don’t support her PMDD and AuDHD, or the delightful realness and candour she brings to our Zoom catchups.

If you’re someone who holds a similar “f*** that” attitude to the shame and stigmas society imposes on us, then I have a feeling you’ll like this conversation. Kat talks about:

• Not holding on too tightly to the plan: allowing our ideas to change and evolve as we do

• Designing a career that honours every part of her: health, sexuality, gender identity, neurodiversity, “failures” and all

• Embracing being a work in progress: recognising when she’s falling into a full-time mindset (a common trap for freelancers), but also not punishing herself for it

• Shifting from working with brands to individuals: the connection, creativity, and freedom this brings her (something I really relate to)

• Queering the way we work: expanding the conversation about “feminine” ways of working to encompass the full spectrum of our gender identities—and the power this holds

• Lessons from the sex work and sex tech industries: from business resilience, to communication and community

My takeaway: perhaps we need to invert the concept of “bringing our whole selves to work”. It’s not about wearing a slightly jazzy T-shirt on Fridays; but, for those of us with the freedom to design our careers, making our work reflective of our whole selves…

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What was your idea or dream?

Originally, my dream was to become one of the go-to freelance copywriters for sex tech brands and see my byline everywhere. But as I went through major shifts in my life and health, so did that idea.

While I absolutely love my job and the business I’ve created, the dream is now designing a career that honours all the different parts of me. My health, my values, and my personality.

It’s not just about slow living, but honouring myself and my happiness: working on things that make me happy, having money to feel secure and independent, having time for my family and friends, and watching my garden grow. Freelancing and working in this industry is just part of how I’m doing that.

“As freelancers, I think we need to recognise that our own life experience shapes who we are and what we want to offer to people.”

What made it important to you?

As freelancers, I think we need to recognise that our own life experience shapes who we are and what we want to offer to people. I feel like I’ve restarted therapy, asking myself “who am I?” as I try to break the habits of being a people pleaser, reflect on my journey with vaginismus, and explore how to work with AuDHD and PMDD.

When I first started freelancing and was taking on too much, my mum said, “You didn’t go freelance to do things you don’t enjoy”. I have to keep reminding myself of that now as I think about what I actually want to do, and set boundaries around the work I accept.

Having vaginismus means I’ve gone through a huge journey with my health, which kick-started my entire interest in sex tech and sex positivity in the first place. Vaginismus is such an isolating thing; for years, I felt like it just robbed me of my voice. First from not having the actual language to advocate for myself. Then even when I did and started getting help for it, I saw the ways that it impacted my ability to connect with others, due to the constant fear that it would be triggered or I would be judged. Going through it alone forced me to learn how to find my voice, but also learn how to advocate and be outspoken around the topic. This learning curve has bled into my services and how I want to work.

Add in PMDD and AuDHD, and this year has honestly felt like I have had to relearn not just how to work productively, but how to be a person. We spend so much time at work that finding ways to do this while recognising and honouring the ebbs and flows of my moods, energy, and headspace throughout the month—cyclical working—has become crucial.

I think that’s why my business goals have changed from not just wanting to work with these amazing brands around sex-positivity, but also offering 1:1 membership and mentorship. I want to give everyone a space to have their own voice heard, especially in professions where that support can be lacking—whether it’s writing website copy for erotic service providers, or mentoring new copywriters who are just starting out.

“I made this huge jump and have been putting on my parachute and learning to navigate as I go. Does that mean I have had a few snags? Yes. Have I made mistakes and gone off course? Definitely. But isn’t that the fun part of learning how to run a business and learn what you want to do?”

When did you know you had to do something about it?

I went freelance on a whim. It was the last few months of COVID, when we were ushered back into the office, and my boss at the time had told me that I couldn’t have more writing opportunities because I “didn’t have enough knowledge”.

I was was in Ann Summers with some friends, ranting about this and the fact there are no g-spot vibrators for those with vaginismus. My friends joked that if I needed to know what I was writing about, then I should just start writing about orgasms and sex toys, as that’s my real passion. It was very much a light bulb moment.

So I went away over Christmas, got a few clients together, handed in my notice, and started working for myself completely that February. No savings, no real plan, nothing.

My journey to now has been a kind of free-falling experience. I made this huge jump and have been putting on my parachute and learning to navigate as I go. Does that mean I have had a few snags? Yes. Have I made mistakes and gone off course? Definitely. But isn’t that the fun part of learning how to run a business and learn what you want to do?

After I went freelance, the dream changed from wanting to write blogs, to focusing on website copy and brand voice, and setting up mentorship and courses to help others. It’s been a slow dawning as I grew bored or frustrated with the work I was doing. I don’t like being bored and I love the idea of creating connection and helping people. I had quiet periods this year, which offered me the space think about launching The School of Satisfaction [Kat’s upcoming mentorship and course offering].

What allowed you to do something about it?

I think alongside blind faith in myself (or maybe just being pushed into a place where it’s sink or swim), the community and connections I have made this year have definitely inspired me and given me the confidence that what I am doing is the right path.

One of the things I love about both the copywriting and the sex tech/adult industry worlds is the sense of community. People want to talk and share experiences and ideas—hell, sometimes we just want to chat about the latest gossip and what is going on in the world of astrology. But it offers a warm space where you can go ‘Hey, I have this idea, can you let me know if it is stupid?’, and someone will listen.

Things got very quiet this year (as I think everyone can attest to), so I used that time to focus on networking with people I am inspired by, and it has been fantastic. Talking with others in the industry and hearing their insights or advice has helped my writing get better. And the trust they’ve had that I’m good at my work has reinstated my confidence.

Actually going out and making this happen has shown me just what I can do. I always knew I had a loud personality (I am definitely a professional yapper,) but seeing that reflected back to me by people who respond to my warmth or vibe has given me the self-belief to run courses and offer support to people.

How exactly have you made your idea happen?

For me, everything is still a work in progress. One of the issues I have had is trying to juggle all my ideas and work, and still falling into the old patterns that I had in full-time work.

This has left me burnt out, or taking on work I don’t enjoy. As this year has gone on, there have been lots of tears, lots of failures, and even falling out of love with things I once adored. These have been learning opportunities of what I want, how I can make that happen, and what honouring myself actually looks like.

I’ve started to make my business work for me in two main ways: firstly, I am slowly revising my services and actively getting rid of things that I have no passion or interest in anymore. Sadly, this means a few client relationships have ended, but I would rather do that and give them the chance to work with someone who can, than feel like I am dragging around a dead horse—and that showing in how I turn up for them.

Secondly, honouring myself in the day-to-day means understanding where in my cycle I am and working accordingly. My PMDD is really intense, and I have noticed that even when I take my ADHD medication, it is hard to concentrate. So I try to ensure that all deadlines are delivered before that week, so I can slow right down and focus on my health or admin tasks.

I have been playing around with my schedule, recognising that I have more energy/concentration in the mornings, so I am making sure I work from 7.30-15.30 and have a hard stop at 1700 so I can relax and settle down. It allows me to do a few hours on my own things in the morning and evening, and then throw the majority of my focus into getting client work done. Accounting for when my ADHD meds wear off and I crash in the afternoon.

Don’t get me wrong, it’s tough. Some days it doesn’t happen because of deadlines etc. But having a schedule helps to keep me on track.

“I would love to say I have everything under control…that’s bullshit.”

What sacrifices or compromises did you have to make?

In an ideal world, I would love to say I have everything under control, I never work past my end time, and I am juggling work and life balance amazingly…that’s bullshit.

Truthfully, I have had to find ways to balance my intention with the reality of working for multiple clients at one time. Sometimes that means working late or having meetings in the evenings because of time differences. And even taking work I don’t enjoy to pay the bills. For me, the biggest compromise I can make is to say if I do this now, it allows me to do what I want later. Which helps. But there have been many times I’ve cried about it.

In those times when I can’t keep my schedule and I have to work late, it can feel pretty overwhelming. Especially on days I have had to cancel date nights or plans with friends. Or when it has been an emotional day because of the PMDD. Giving yourself the grace to say it sucks and I am not happy about it is good, but you also need to know not to punish yourself. People have bad days; it doesn’t make you bad at work or a bad partner or friend. It’s about being able to communicate that you’re really sorry you’re unable to do X, but once this is done, I am able to do Y the day after.

Those weeks or times when everything gets a bit too much, I find having a weekend or just a Saturday or Sunday where you reconnect with your loved ones can be beneficial for your health and mental well-being. I journal, I paint, I turn my phone off and focus on the people and the world around me to realign myself again, and then start again on Monday.

“I know there is a lot of conversation around a ‘feminine’ way of working…Personally, I love the idea of queering the way we work and stepping into the power of gender fluidity.”

Where are you with your idea now?

This idea of connection and amplifying voices is a huge driving factor for me right now. I lost my voice for a long time through vaginismus, PMDD, and AuDHD. I am an out and proud lesbian who loves their woo-woo. I feel most like myself when I am supporting and helping others to advocate for themselves. And I feel like I have spent so much of my adult life trying to find it, that I don’t want to cut off parts of my identity anymore to fit in for work. So I am making a business that honours that.

I am currently going through a rebrand and expanding myself. Satisfied Kat Copy will be focused on delivering copywriting, courses and 1:1 mentorship for ‘heart, mind and soul’—working with erotic professionals (body), coaches and educators (mind), and life, astrology and human design coaches (soul). Working with clients that allow me to immerse myself in that is such an embodied and powerful feeling.

I know there is a lot of conversation around a ‘feminine’ way of working, especially when we talk about slowing down, working with cycles etc. Personally, I love the idea of queering the way we work and stepping into the power of gender fluidity. For me, that shows up in a few ways: from understanding the places where work and life intertwine (especially as a business owner or a freelancer), to choosing clients that are open-minded, and also not being afraid to be a little weird.

Queer culture and the community are so multifaceted, beautiful, and unapologetic about who they are. It’s open-minded af, colourful, loud, and a little messy at times, and that is beautiful. It’s a place to honour all sides of yourself, build connection and community, and be open. I know my personality and my openness is one of my greatest strengths, so why hide any part of myself? The people I want around me are those who want to do the same.

I think it’s also recognising that there is space for both types of energies in your work. The feminine: creative, slower, and more compassionate/community-focused. And the masculine: negotiating, setting strong boundaries, having a bit of a schedule, or focusing on building and expanding. When done right, they honour each other completely and allow us to be fully ourselves in our own businesses.

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“Not having a plan can be the plan.”

What have you learned?

There are so many things I have learnt, especially this year!!

Firstly, I think I have learnt that not having a plan can be the plan. Not having this rigid of idea of “I want to be here in 6 months, or a year, or even 5 years”, but having a more expansive, adaptable way of building a business has been a lifesaver. I have basically spent the past few years feeling it out as I go, which in turn has allowed me to make the pivots so much easier. Whether that’s expanding my client base, niching down on the type of copy I want to do, or deciding to start courses.

I have also learnt more about not just how I want to work, but who I want to work with. I have slowly transitioned from working with bigger brands to working with people: escorts, business owners, and solopreneurs with either a small or no team behind them. It has been liberating! I get to work with people who are so passionate and vibrant! And it’s usually a place of trial and error, so you get to be more creative and try new things. It also means that I can show up 100% as myself, which makes the day-to-day less exhausting, as I am not masking all the time.

Some of the best lessons I have learnt have come from working with sex workers. Whether you’re a career dominatrix or an OnlyFans creator, these people really know what it takes to run a business and market themselves. Talking with them has been a lesson in communication, power, business resilience, and boundaries. 2025 has been a huge year for sex worker rights, and legislation is trying to tighten the noose even more in the majority of my industry. Watching how these amazing people have figured out new ways to market themselves, stay safe, and pivot their content has been eye-opening.

As I have been making a community for myself, I am also learning that the system is changing. It feels very much like we are all building this new economy that isn’t based on knocking others down. We all want to win, and we want to see each other win as well!! It doesn’t feel competitive at all, even when talking with other copywriters. We’re all specialists, willing to support and recommend each other.

Was it worth the risk?

Definitely! I have always called myself a ‘bad employee,’ and I think to an extent that is true—not because I am bad at my actual job, but because I don’t understand why I have to fit in these rigid boxes of what someone else has deemed as professional. It’s exhausting. I am now in a place where I can create a business that allows me to honour myself, my health, and work around the ebbs and flows.

I love my industry as well. Early on in my vaginismus journey, I started pole dancing. The school I did it at introduced me to an amazing community of sex workers, who taught me so much about the industry and how to set up a business, supported my wins at the pole, and taught me that being confident doesn’t mean putting others down. In many ways, I don’t think I would be the person I am today if I hadn’t gotten to know that community. Because of that, I have developed a bit of a protectiveness for those within it.

This industry is a place of expansion, creativity, and change. For every legislative push back we get, we say fuck that and keep creating amazing products and services that promote self-love, pleasure, and empowerment. However, I am seeing a divide between sex tech and the adult industry. Sex tech is focused on products and sex education, which are starting to be accepted by mainstream culture. While this is very important, sex workers and adult content creators are still being silenced. In my opinion, we need both for the world of sex and pleasure to be fully accepted. This is why I made the point of offering my services to people in the adult entertainment, creating, and professional services areas. They deserve to have their work be respected just as much as everyone else.

So, yes! I do think it was very much worth the risks. It has been worth every mistake, pivot, and learning opportunity I have had, I think. I get to do work that I genuinely love, working with clients I am inspired by—what could be better than that?

“Take everything you have failed at and make it a learning experience for others.”

What advice would you give to fellow Ideas People?

Don’t rush the process. And take everything you have failed at and make it a learning experience for others. No matter how long it takes, if it resonates with you, believe that it will happen.

Don’t get me wrong, it can be frustrating to see others get ahead or do things you also wish to do, but sometimes you need to slow it all down. Look at where you have come from, what you have achieved, and what you want from your career, and then make a plan to get it.

Where to follow Kat’s work

A big thanks to Kat for sharing so beautifully! Go find her on…

• Her Website

• LinkedIn

• Instagram: @satisifedkatcopy

What does this conversation bring up for you?

How does the concept of queering the way we work land with you? Which “failures” could you alchemise to help others? And what would it look like to design a career that honours every part of you? Kat and I would love to hear what resonated in the comments.

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About Messy Work

A monthly ‘magazine’ for deep thinkers, big feelers, and more-to-lifers.

I’m Lucia, a writer and coach based in Bristol, UK. I work with recovering high achievers and independent spirits who can’t shake the feeling that there’s more to life. And I write about the messy (but beautiful!) work of figuring it all out.

Once a month, I pop by with a Messy Essay, a Loose Guide, and Ideas People. The rest of the month, I’ll leave you and your inbox alone.

Put your hand up if you’ve ever hated your boss.

Now, put your hand up if you’ve secretly (or even quite publicly) loved to hate them.

You know what I mean—they’re basically your favourite topic of conversation. Your go-to when friends and family ask about work, the first thing you tell your partner when they ask about your day.

You have a work WhatsApp group that exists as a dumping ground for others who feel the same way—you record their latest crimes, you keep a furtive running commentary during Zoom meetings. Yet despite how freely and gleefully you will badmouth your boss behind closed doors, few of you would dare confront them. Understandable, given the power that they undoubtably hold over you. But also, part of you feels a bit sorry for them.

Because this boss is changeable. One day they’re full of praise, deferential even. The next they’re sullen and unfair. You never quite know where you stand. The workplace is a hotbed of gossip, scandal, and Oscar-winning theatrics.

You, my friend, are caught in a Drama Triangle.

Now, if the above sounds like a borderline abusive relationship, that’s because sometimes, it is. Unfortunately, work is not immune from the same problematic behaviour we more typically associate with romantic relationships: narcissism, anxious-avoidant attachment, gaslighting, love bombing, and so on.

These deep-rooted issues cannot be explained away or “solved” by the framework I’m about to share. If someone is engaging in bullying or harmful behaviour, it’s important to seek support and know your rights.

The Drama Triangle can, however, empower you to take action, if you are sufficiently resourced to do so. Because sometimes when you’re trapped in these situations—hating your boss, hating your job, but feeling like there’s no way out—it can feel hard to name what’s going on. Why they grind your gears so much, why you get sucked into the theatrics, why you continue to stay.

You might feel that there’s nothing you can do about it, other than resign yourself to your boss’s dickishness, and complain about them behind their back. And if you’re being honest, you might even get a bit of a thrill from it.

Of course, all this does is perpetuate the cycle…

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The Drama Triangle, explained

The Drama Triangle is a framework from Transactional Analysis (TA). TA is a type of psychotherapy that unpacks social interactions to understand why we humans behave in such weird ways, and hopefully improve our communication.

I won’t get too nerdy on you, but TA’s big idea is that we can communicate from different “ego states” (Parent, Adult and Child) in our social interactions. If you have ever chided your partner/left a passive aggressive post-it note for a housemate who hasn’t done the dishes, and they have responded with a massive sulk, you can probably imagine what this parent-child stuff looks like.

Anyway, from these ego states there are several different “games” we can act out in relationship dynamics, particularly conflict dynamics. These games describe interactions (or “transactions”) that have ulterior motives, i.e. one thing is happening on the surface, but there’s a lot going on beneath it.

One such game is Stephen Karpman’s Drama Triangle. It’s often really applicable to dynamics in teams and organisations where tensions and conflict run high—where there’s a lot of drama. But of course, it can play out in any relationship dynamic, from romantic relationships, to friendships, to families (and remember, a lot of our relationship dynamics are replicated from early years and what was modelled by our primary caregivers).

Word of warning: once you see the Drama Triangle, it’s hard to unsee it.

There are three primary roles in the Drama Triangle: the Victim, the Persecutor, and the Rescuer. From these names alone, you’ll probably get an idea of how this plays out, but here’s what tends to characterise each role:

The Drama Triangle in action

Let’s go back to your tricky boss. They’re unpredictable, volatile and demanding, which makes everyone’s life pretty stressful. You’re in a particularly sticky situation, as they’ve given some negative feedback on a presentation your direct report has been working on.

The direct report shows up to your weekly 1:1 in tears. They are the victim.

You fuss over them, assure them that you’ll take care of it, and drop not-so-diplomatic hints that you think the boss is a nightmare too. You are the rescuer.

And clearly, the boss is the persecutor. Needlessly terrorising this poor junior employee, and creating more work for you in the process.

These dynamics don’t really help anyone—they just reinforce your respective roles. Your direct report becomes reliant on you and struggles to feel confident doing the work independently. Either they get more criticism from the boss, or you have to pick up more slack. Everyone is increasingly alienated from the boss, who only grows more difficult.

And importantly, all the “players” may rotate through different roles. Your boss may think of themselves as the victim, and their employees as the persecutors, demanding more sympathy and support from them while they go through a stressful round of funding. The employees start to feel guilty, stepping in to rescue the boss. You may even start to resent the direct report, seeing them as the persecutor. And so on.

How to disrupt a Drama Triangle

Will learning about the Drama Triangle stop your boss from being a pain in the bum? Probably not—unless there’s a companywide intervention, where everyone opens their eyes and vows to change.

However, the point of opening our eyes to the Drama Triangle isn’t to change or control other people’s behaviour, which we can’t do. It’s to:

• Understand what is fuelling the drama (drama being something that carries more emotional charge or takes up more headspace than it really deserves)

• Acknowledge our own participation in the game and take responsibility for our role

• Exercise more control over our responses and agency in our actions

• And perhaps to cultivate a little more empathy, or at least objectivity, towards those who antagonise or frustrate us

Most of the time, and especially at work, we want to be operating from an Adult ego state (unless another is helpful e.g. actual parenting or tapping into our “free child” when we need to be creative). We are never going to be “perfect” at this, since these responses are so habitual and deeply ingrained—so human.

However, simply becoming aware of when you are in a Drama Triangle is the first step to disrupting it. Being able to name what’s going on, and humanising it, helps us create a little more distance between reality and our emotions. And once we recognise that we are taking on a role—a bit like kids playing a game of make-believe—we can choose to take off our costume, step into a different mindset, and experiment with new ways of being.

For example, instead of bitching about your boss, you could try to:

• Communicate some boundaries

• Report offensive or inappropriate behaviour to the relevant authority

• Seek therapy or coaching to support you

• Find a new role with the conditions you need to thrive

The point is that when we’re locked in a Drama Triangle, we struggle to see clearly. We lack self-awareness, feel baffled by others, and are blind to our options. We get wrapped up in the story, rather than confronting the facts.

This isn’t to say that you don’t deserve a better boss. But over the years, the Drama Triangle has helped me see things from their perspective too. For example, most founders and CEOs (particularly women) are under immense pressure and stress. They have taken risks to get to where they are, carry huge responsibilities on their shoulders, and often have no prior leadership experience to draw on. That’s not to say they didn’t choose this life, but think about it—what would you be like in their position?

As I mentioned earlier, the Drama Triangle isn’t restricted to the workplace. You might recognise these “games” at play in your friendship group. This cycle can even play out internally, among different “parts” of your personality (e.g. your inner critic as the Persecutor).

So, what does this framework bring up for you? And how does it impact how you see that dynamic?

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Shifting towards The Empowerment Dynamic

There’s a counterweight to the Drama Triangle that I really like, called the Empowerment Dynamic. The idea is that through reflection, we can shift into new roles: from Victim to Creator, from Rescuer to Coach, and from Persecutor to Challenger.

If you’re curious about how to make this shift, I’ll be sharing some reflective prompts in Messy Club (my free subscriber chat).

1:1 coaching

If you’d like deeper, personalised support exploring tools like this, I work with:

• Recovering high achievers at a Crossroads in their lives and careers

• Independent spirits who need a Sounding Board to navigate the rollercoaster ride of self-employment

Drop me a message or book a call if you’d like to chat.

About Messy Work

Messy Work is a monthly ‘magazine’ for deep thinkers, big feelers, and more-to-lifers. Once a month, I pop by with a Messy Essay, a Loose Guide, and Ideas People. The rest of the month, I’ll leave you and your inbox alone.

If I told you everything about my career working in early-stage startups, I’d have to kill you. Or at least break a few NDAs.

For some context, I spent the first eight years of my career working in brand and marketing roles at early-stage startups. After burning out in one job and losing another, I made the decision to go freelance in 2022. I always say I’ve never looked back. Working for myself has allowed me to focus on what I really love (writing) and find something else I love (coaching). It gives me flexibility, freedom, and a far greater sense of purpose and authenticity than I ever found in full-time work.

But also, for a long time I didn’t particularly want to look back. Not that all of it was bad. I loved the ideas, the creativity, the intimacy, the energy, the autonomy, the talent, and the impact of working in early-stage startups. I’ve had some truly lovely employers. Been part of launching revolutionary products. Learned how to build a brand from the ground up. And many of the people I met along the way are now cherished friends.

There were also times when I’d be one Slack message away from a nervous breakdown. Or pacifying a colleague who was one Slack message away from a nervous breakdown. Working in startups was a wild ride. One I’m grateful to have experienced, but which left me reeling.

Until now, I haven’t spoken much about my experience. And this post won’t be a tell-all, a trauma dump, or an exercise in finger-pointing.

But as I’ve done my own inner work in the years since I left full-time employment, and begun coaching clients whose careers have followed a similar arc, I’ve realised that there are certain patterns that characterise the experience of working in early-stage startups. And they can leave scars.

These are the patterns that cause startup employees to crash and burn, fall out of love with their careers, and in some cases, experience workplace trauma. Because those very same strengths I listed above—the ideas, the creativity, the intimacy, the energy, the autonomy, the talent, the impact—have their shadows.

I’m writing this post not to cancel startups or blame individual players, but to illuminate those shadows. After all, startups exist to find new ways of doing things; to fix broken systems. We can’t do that if the startup system itself is broken. And since we’re an entrepreneurial bunch, I think we can figure out how to do better.

So, let’s dive in…

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Eight patterns that can leave startup employees burnt out, confused & disillusioned with their careers

1. We are family.

When you first join a startup, everything seems amazing. There’s a mission that at least on paper (or in neon lights on the wall of an industrial-chic office) makes sense. A set of company values that sound great. A charismatic leader who’s lived nine lives by the age of 32. A branded tote bag, shiny new MacBook and Amazon-fresh copy of The Lean Startup.

More than anything, there’s a sense of belonging. You’re not walking into a vast, grey skyscraper of minions, but a tight-knit team of coworkers you will come to laugh, cry, and celebrate with.

That sense of belonging isn’t fake—it’s one of the things startups are really good at. But that early intimacy sets up expectations that are emotionally charged: we’re in this together, we care deeply, we’ll go above and beyond.

It’s all fun and games…until it isn’t. While these warm welcomes are certainly well-intentioned, they often set up unrealistic, and even unhealthy, expectations about what this job will mean to you. Boundaries become blurred. The same closeness that fuels creativity and collaboration can also make conflict or feedback feel personal. And it makes it harder to endure the dissonance down the line, when you realise that yes, we are like a family: dysfunctional.

2. Carrot-dangling.

Speaking of good intentions, startups are brilliant at inspiring people. And at times, that inspiration can spill into overpromising. Sometimes it’s free pizza. Sometimes it’s ping pong. Sometimes it’s “unlimited holiday”. And often, it’s equity: the dream of owning a slice of the pie you’re pouring your blood, sweat, and tears into.

Again, on paper, this sounds fair—you’re taking a risk by not working for a more stable corporate, so you get a stake (or a snack). But in practice, equity can be a way to pay lower salaries: job offers are tiered into different packages, with higher equity/lower salary deals, and vice versa.

This can sound enticing when you get the spiel about how “we’re going to be the Uber of Ayurvedic, biodegradable, self-charging toilet seats”. But in reality, it’s a way to manufacture loyalty and save cash, while dangling the dream of a lucrative exit down the line. Given 99% of startups fail and your shares could be minuscule by the time the company is in a position to sell or IPO, this rarely works out.

Carrot-dangling isn’t necessarily deceit—founders have got to believe in the vision they’re selling, and it’s a way to attract talent and build loyalty when budgets are tight. But it does take advantage of delayed gratification: securing your investment, without necessarily investing in you. It’s what keeps you working long hours, ploughing through crises, and telling yourself it will all pay off after the next fundraising round. Sometimes it does. Usually, it doesn’t. Because carrots don’t pay rent.

3. Unfettered/unfair progression.

In the world of startups, where brazenness reigns and bureaucracy goes to its death, promotions and pay rises can happen fast. Or, like, never.

The chosen ones will start out as baby in the corner, and end up as baby in the boardroom—because when career progression is that accelerated, you will often feel like you have no idea what you’re doing. One minute you’re making tea, the next you’re leading a team. There’s no playbook. No management training. And this can feel really, really good. Intoxicating, even, to have achieved so much. To wing it, and pull it off. To watch the numbers on your pay check rise.

But it can be lonely at the top, and at the bottom. In systems that prioritise speed, growth is rarely spread even. Where the lucky few are chosen, others get left behind.

Not having fair, structured progression plans in place can veer into dangerous territory: favouritism, systemic bias, performance, strained team dynamics, and talent drain. And if you do leave, it can be really confusing to know where to turn next, when you’re either over- or under-qualified for your current role.

4. Lack of management, mentorship and role models.

One of the top reasons my coaching clients cite for dissatisfaction in startup roles is a lack of management and mentorship.

Thanks to their small ‘n’ scrappy nature, it’s common for startups to have fluid hierarchies and one-person teams. There are advantages to this: you learn a lot, whether by figuring things out for yourself, or gaining exposure to colleagues with different skill sets. But at a certain point, people crave direction: a manager who can share their knowledge, teach technical skills, and guide progression. Even better, someone who can be a role model for healthy, strong leadership.

I’ve met so many young, talented professionals who feel let down by their employers for this very reason. Often, they either leave to work for themselves, or they seek out a role at a more established company instead. It’s a shame, because more often than not, they derive a lot of meaning, purpose and creativity from their work. But their employers aren’t fulfilling the necessary flip side to this: structure, support, and stability.

This is especially important (and yes, harder for employers to do) when so many of us have jobs that didn’t exist 20 years ago. Working in something like social media management, it’s easy for all of us to feel confused about what “good” looks like, but the result is startup employees who are under-confident in their abilities.

And in the absence of those positive role models for leadership, they can even begin to fear occupying positions of power—not wanting to be one of those CEOs we see in the Netflix documentaries.

5. Square pegs, round holes.

When funding rounds collapse or employees walk off into the sunset/their lawyer’s office, startups can find themselves with lots of gaps to fill. And if you happen to be a smart, competent individual, you’ll get plopped into one.

This can be both flattering and exciting. You’re given more responsibility, the chance to try on different hats, and it can be fun to throw spaghetti at the wall and see what sticks. Only, you got into marketing because you’re a writer. And now you’re not doing any writing, unless you count coding spreadsheets or harried emails to your team (true story).

Leadership aren’t doing this maliciously—they’re doing the best with what they have. But when we aren’t doing the work we signed up for, we can start to grow resentful. We begin to question the point of it all, and even worse, we can start to doubt ourselves. That’s why a key component of the work I do with my Crossroads clients is reconnecting with the core strengths, innate gifts, and very identities that can get lost in these environments: the essence of this work is reminding people who they are.

6. Flogging a dead unicorn.

Of course, when you’re an all-star unicorn (you’re a social media manager! A customer support agent! A PR expert! A videographer! An HR manager!), you end up working rather a lot.

In mission-driven startups that “feel like a family”, the line between life and work becomes increasingly blurred. This can show up in both obvious and more insidious ways. Yes, it’s early mornings, late nights, and weekends. But it’s also:

• “Fun ideas” (“No need to reply now, but have you seen this…?”) that don’t stop chiming in the work WhatsApp group

• Checking the likes on the company’s latest Instagram post while your date is in the loo

• The sound of the Slack notification sending chills down your spine

• Dropping everything to reply to emails from your boss straight away

• Letting office dramas dominate every conversation with your friends and family

It’s not just your time that your work infringes on; it’s your headspace. And when our identity becomes so conflated with work, it can be dangerous if the rug is pulled out from under us. Because the truth is, a job is always just a job, and business is business. No matter how devoted you are to the cause, a round of layoffs or fundraising failure could plunge you into unemployment at the drop of one of your many hats.

Even from the employer’s side, this level of enmeshment isn’t necessarily healthy. Not just because the risks of burnout, sick leave or quiet/loud quitting increase, but also because your employees can lose perspective—whether it’s on strategic priorities, or getting caught up in those office dramas…

7. Drama, drama, drama.

I don’t know why they bother dressing Claudia Winkleman up in some nice jumpers and renting out a whole castle in Scotland. If you want to see some real treachery, blind loyalty, suspicion, secrecy, and hysteria in action, just film an early-stage startup for a week.

And this is where I want to give a special shoutout (and a big hug) to the CEOs. Yes, even the “narcissistic” ones. Because while I don’t condone bad behaviour from those in power, it’s easy to blame founders and founders alone for the problems that plague startup culture.

In reality, they are usually the loneliest and unhappiest of all. And you know what they say about stress? It rolls downhill.

The reason startups must warn every unwitting candidate who stumbles across their JD that they are “fast-paced, high-pressure environments” is that most of them are predicated on the Emperor’s-New-Clothes-coded world of VC funding. Founders are under immense pressure to convince investors that their success is inevitable—and to keep doing it again and again.

It’s this, not one individual, that’s often the true source of toxicity. It sets up a Drama Triangle (more on this here), where everyone plays their part: the founder as villain, the team as victims (or the investors as villains, the founders as victims, and the team as rescuers). And the thing about drama is that it can become addictive; it can start to feel like safety.

8. Strategic ambiguity, shiny object syndrome, and nothing-to-show-for-it-itis.

It’s not just interpersonal dynamics or job descriptions that chop and change—the entire strategic direction of the company can “pivot” overnight.

Sometimes this is for a valid reason—and after all, adaptability is the first rule of entrepreneurship. Sometimes it comes from above (hello investors). But more often than not, it’s a reflection of the uncertainty that sits at the heart of startup life, which manifests in founders as what I fondly call shiny object syndrome.

Shiny Object Syndrome is when you’ve had multiple meetings about an idea, only for it to be squashed in a single Slack message. It’s when you’ve sacrificed precious time to hone your OKRs (I can’t believe I’ve made it this far without mentioning OKRs), and you’re just about to hit them—only for the founder to make up entirely new ones. Shiny object syndrome is when the company’s future (hell, your future) is at the mercy of the founder’s mate who’s started a home-brewed mead brand and wants to do a partnership (you sell sales software). Shiny object syndrome is the thoughtful, meticulously researched campaign that never was, thanks to your competitor’s sexy new TV ad.

Like I said, at first it can feel fun to adapt. But you reach a certain point where you think: exactly what is it that I’ve been doing all these years? And what have I got to show for it?

Although Shiny Object Syndrome is ultimately stress in disguise (the founder’s way of coping with macro uncertainty, and perhaps their own imposter feelings), for the people on the receiving end, it can feel like chaos. And this can hugely impact how we tell the story of our careers, as well as the stories we tell about ourselves.

The tip of the iceberg

I’m aware I’ve coated these observations in humour (you’ve gotta laugh, right?). But the intention behind them is a serious one.

What I’ve shared is only the tip of the iceberg: a high-level list of relatable experiences, rather than a thorough examination of their symptoms, root causes, and cures. But however laughable or innocuous these things seem—even like “first world problems”—I’ve seen how they can leave their mark. Often without us realising. These patterns can be the reason…

• You’re burnt out

• You struggle to write the story of your career

• You feel like you have nothing to show for months or years of work

• You’re confused about your seniority

• You’ve never had a manager/mentor figure

• You feel stressed and panicked by certain people or dynamics, but you’re not quite sure why

• You’ve trauma bonded with colleagues

• Your office drama takes over your life

• You feel disconnected from your ambition

• You’re disillusioned with the entire concept of work

I’m still unpicking the way my own experiences have shaped me; still dismantling beliefs, unlearning habits, and retraining my nervous system. And it’s an immense privilege to be helping others do the same.

So while I continue writing, I’d like us to continue talking: to stop brushing these big, burning parts of startup life under the carpet. To come out of the shadows. Because even if we can’t fix the entire system, we can start to heal ourselves.

Share your experiences

Some of you may hard-relate to all the patterns I’ve shared above. Others might firmly disagree. Whatever your opinion or experience, I’d love to hear from you.

I’m working on a project to dive deeper into the cultural and systemic challenges of working in startups, and offer perspectives and insights that can help individuals better navigate them. However, I’m aware that my own experience has its limits and biases. So my aim is to gather as many different perspectives as possible—on both the strengths and shadows of working in startups.

If you’d like to contribute your experiences or thoughts, I’d be hugely grateful.

👉 Just fill in this form (your responses can be 100% anonymous) or leave a comment if you’re happy to share publicly.

Leave a comment

P.S. If you’re feeling burnt out, confused or disillusioned with your career, I’m hosting an online journalling workshop on the theme of in-betweening: navigating that awkward, messy middle when you’ve left one version of yourself behind, but the new you hasn’t quite arrived. Get your free ticket here.

About Messy Work

Messy Work is a monthly ‘magazine’ for deep thinkers, big feelers, and more-to-lifers.

I’m Lucia, an ex-startup marketer turned writer and coach based in Bristol, UK. I work with recovering high achievers and independent spirits who can’t shake the feeling that there’s more to life. And I write about the messy (but beautiful!) work of figuring it all out.

Once a month, I pop by with a Messy Essay, a Loose Guide, and Ideas People. The rest of the month, I’ll leave you and your inbox alone.

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Hi everyone!

I know I’m breaking my rule of only posting once a month, but I hope you’ll forgive me on this one, very special occasion…

…because Messy Club is now open to subscribers and subscribers only!

What is Messy Club?

Messy Club is my new, subscribers-only Substack chat. I’m testing it out as a private, more intimate space for you to:

• Get coaching-led support to do your own messy work: expanding your self-awareness, gaining perspective, and building the clarity and courage to take action on things you want to change

• Chat to likeminded people: the deep thinkers, big feelers, more-to-lifers and ideas people who read this Substack

• Tell me what to write about! I’m really curious to know what’s going on in your lives so I can make Messy Work a place where you feel seen and supported.

How does it work?

Honestly? Let’s find out.

In a former life, I used to be a Community Manager. So I know that these spaces work best when they’re co-created.

My main idea is to share reflective journalling prompts every other week.

These will be focused on themes covered in my posts—and hopefully things we talk about in the chat! My prompts are inspired by coaching psychology, client stories, personal experience, and a healthy dose of intuition. And I’ll be on hand to answer any questions or respond to reflections you feel called to share in the chat.

What to expect

I’m an EMCC-accredited transformative coach working with recovering high achievers and independent spirits who can’t shake the feeling that there’s more to life—but need some help figuring out what that “more” is, and how to get there.

Learn more about More To Life

Here’s some feedback from some journalling workshops I’ve hosted in the past year:

“I’ve always found journaling tricky, but this hour let me slow down, reflect, and leave with steps to make work (and life) better.”

“Your prompts certainly got me thinking in ways that I never have before. Also love how you combine psychology with coaching. I’ve worked with coaches before that have been great in my business, but when it came to tackling mindset stuff and getting that little bit deeper they lacked. It’s something I’d love to learn more about!”

“Lucia has a rare gift for creating calm, thoughtful, grounding space. I came with a notebook, a pen, a cup of tea… and a lot of anxiety. I left with more presence, clarity, and a few very actionable insights. It was exactly what I needed. Lucia’s way of guiding the group helped me notice things I hadn’t slowed down enough to see. Proposed journaling prompts opened up questions I didn’t know I needed to ask. We listened to each other, and something about the way people shared made me feel more grounded in my own experience. It reminded me how valuable it is to have a sounding board - not for solutions, but just to be in the room with someone who listens with intention.”

See you in there!

I’ve been playing with this idea for a while, and wanted to launch it without putting pressure on it to be perfect. So if you’re happy to figure it out as we go, I’d love to welcome you to Messy Club 🤗

Join our first thread on the theme of radical unsubscribing here.

New chat threads won’t be sent sent via email, but you can download the Substack app and turn on push notifications if you want to stay in the loop (but on the theme of radical unsubscribing…do you? 😉). You can also access Messy Club on the web.

And if you’re not reading this via email, make sure you’re subscribed so you can join.

About Messy Work

Messy Work is a monthly ‘magazine’ for deep thinkers, big feelers, and more-to-lifers. Once a month, I pop by with a Messy Essay, a Loose Guide, and Ideas People. The rest of the month, I’ll leave you and your inbox alone.

Ideas People #3: Mary Alice Duff on the girlboss to slow living trajectory

Mary Alice Duff lives in the South of France with her husband, daughter, dog, and cat—a move they made sight unseen four years ago and never looked back. If she’s not travelling throughout southern Europe, or tucked into a good book, you’ll find her in the kitchen cooking, baking, or entertaining. Workwise, she’s a portfolio careerist: she partners with founders as a fractional COO and transformation partner, hosts workshops for aspiring expats, runs a coaching programme for new fractional operators, and writes about the messy, joyful reality of self-employment and small business. These days she tries to approach both work and life with a spirit of joie de vivre—curious, playful, and full of possibility.

Mary Alice reached out to me off the back of a LinkedIn post looking for guests for this series (if you’d like to be featured, hit me up!). We hopped on a call, chatted for half an hour, and quickly bonded over our mutual epiphany (learnt the hard way) that changing your environment can only go so far in changing your life.

As I wrote about in last month’s Messy Essay, the pursuit of the slow life isn’t always a walk in the park (iced matcha in hand). It takes a lot of trial and error, unlearning and relearning, one step forwards, and five steps back. Put simply, you can take the girl out of the hustle culture, but you can’t always take the hustle culture out of the girl.

Mary Alice has been on her own journey with this, so I knew she’d be a fantastic guest. Firstly, because she’s got a bloody great story: selling all her worldly possessions, packing in the girlboss badge, and moving her family to the South of France (a country she’d never set foot in before!!!). Secondly, because she really understood the premise of Ideas People: getting really honest and specific about what it actually takes to make our big ideas happen—from the mindset shifts, right through to the money bits.

What stayed with me from this conversation was how this huge, life-altering move started out as an unserious conversation between Mary Alice and her husband, one bleak evening during the pandemic.

In bed, working from their laptops, they mused about where they’d go if they could live anywhere. The idea that came from their half-joking musings? It turned out to have legs.

My takeaway: where could asking what if..? lead you?

What was your idea or dream?

It was really about slowing down life.

A couple of months into Covid, my husband and I were both suddenly working 100% remotely. At the time, I owned a clothing company with a small studio in Philadelphia, but once the pandemic hit, my whole team was sewing from their apartments.

We were sitting there in Philadelphia, where the weather sucks, and we just turned to each other like, Why do we live here? We asked ourselves, If we could live anywhere in the world, where would it be? And we both—kind of cheekily—said the South of France.

We’d never even been to France and had no connection to it, other than both of us once worked at the same French restaurant. But the idea stuck with me. I kept thinking about what it would be like to really slow down and live differently than we were: in a house we couldn’t afford, with a car payment we couldn’t afford, scraping by paycheck to paycheck, taking one measly vacation a year, which was usually just a couple of days at the Jersey Shore. I was running my own business, but barely making money.

So that was the dream—to work less, enjoy life more, have time for our little family and friends, build community, travel, and just explore.

What made it important to you?

I had been running my own business for about four years, and I was just absolutely exhausted and fried. I had bootstrapped a clothing company from my house, building it from scratch with no experience in the industry, no connections, no deep pockets.

I had burnt the candle on both ends for far, far, far too long. Mentally, physically, emotionally, my health was in absolute tatters. It was really clear we needed to make a massive change in our lives in order to actually start living.

It was important to both of us to say, Okay, we need to do something here. And I think during the pandemic, everybody was forced to change their lives. It makes you question everything: Why am I working so hard? Why is this important? It gave us the space to dream a bit and make the decision to change.

“It really started with that cheeky little conversation: If we could live anywhere, where would we go?”

When did you know you had to do something about it?

There wasn’t a specific incident where I was like, fuck this, we’re changing everything. It really started with that cheeky little conversation: If we could live anywhere, where would we go? We weren’t being serious about it, it was just a joke. But then I got curious. I found the visa I’m on now, and the more research I did, the more I realised, wait, this is really possible.

Also, I had never felt at home in the United States. It never aligned with my core values. My background is in social policy and community organising, and it was very obvious to me that the U.S. was never going to be a place of progressive values. I’ve always known that in my heart of hearts.

So part of my motivation was wanting to be somewhere fair: where universal health care exists, where my daughter could access higher education without taking on tens of thousands in loans, where we couldn’t be medically bankrupt, where there are consumer protections like rent control. Somewhere you feel more supported by the government you’re paying taxes into. France isn’t perfect, but there’s a more level playing field than what I experienced in the U.S.

What allowed you to do something about it?

I love how you ask this question, because it’s something that’s missing from so many of these conversations: what’s the actual financial piece that allowed you to do it? Everybody has a different story. Some people come from wealth, some have family money. That wasn’t my journey.

For us, it was our house. I went to grad school, graduated in the terrible economy in 2009, took a year off, went to Spain, then came back, got a job, and worked my way up the ladder really quick. I ended up in quite a well-paying job that allowed me to buy the house. It was a fixer-upper, and when the market went bananas during Covid, we realised selling it could fund our move. By summer 2020, my husband and I had quietly committed to moving to France. We spent the next seven or eight months fixing up the house, painting, repairing, decorating. Every spare minute went into it. We didn’t have money: I was running a business that didn’t pay me, and my husband was a public school teacher. But we got it ready, put it on the market, and it sold in two days. That sale became our nest egg.

The other part was curiosity. I just kept going down this rabbit hole of how to get the right visa and all that stuff. Once I found the entrepreneur visa, I just kept finding more and more information. I talked to as many people as I could on social media.

How exactly did you make it happen?

The house was the financial cushion so we could safely do this. Moving abroad is expensive. We didn’t even bring our stuff, just a couple of suitcases. We sold basically everything: our car, our house, the contents of our house.

Then there was the visa. France has what’s called the Entrepreneur/Profession Libérale Visa. It allows self-employed people, or people who would like to be self-employed, to set up a business in France. At the time, I had a clothing company and proposed bringing it abroad. Since I was already doing business with European manufacturers, suppliers, and pattern makers, it made a lot of sense.

That visa, combined with the funds from selling our house and just following the application instructions to the letter, is what allowed us to make it happen. It requires a tonne of paperwork and a tonne of tenacity (in typical French fashion, they love to tell you no first!) but if you keep going and provide whatever they ask for, it’s 100% doable.

Because my business was remote, we had funds in the bank, and I had a résumé that showed I could manage a company and make my own money, the visa was approved. My husband came over on a one-year visitor visa, then ultimately switched to the same entrepreneur visa. He had never been self-employed before, but now he runs his own business too.

I highly recommend this visa to anyone curious about living in France and willing to put in the work, because it is absolutely, totally, infinitely doable.

“I realised that France wasn’t going to force me to slow down. I had to force myself to slow down.”

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What sacrifices or compromises did you have to make?

We had to leave everything behind in the U.S., which honestly wasn’t the hardest thing. But our life looks really different now. We went from a big house to a tiny apartment. Nobody has a dryer here—you hang your clothes and wait. We don’t have a car; we ride electric bikes and use public transportation. There are conveniences I miss (like Target!) but are these really sacrifices? Not really.

The biggest shift was mental. When I first moved here, I thought France would force me to slow down. It didn’t. I brought my American work mentality with me. I still kept trying to make my business work. I still kept working seven days a week and burning the candle at both ends. And I realised that France wasn’t going to force me to slow down. I had to force myself to slow down.

Being in France is the perfect environment to do that, because it’s supported culturally. The cost of living where we came from was so much higher, and I felt incredible pressure to just keep going, going, going. Here I can access universal health care, and I don’t feel that same pressure. People just take things slower, and work plays a less important role in people’s lives—we don’t really talk about work with friends. It’s about enjoying life.

When I finally decided to slow down, that’s what forced me to change my business. I had structured it around my clothing company, but a year into living here I realised it did not support the life I wanted. It was too difficult, too exhausting, and it just wasn’t successful financially. I needed significant outside investment, and I wasn’t interested in that life anymore.

So I closed the business and pivoted into what I do now: working with bootstrapped small businesses and remote teams. I come in and I work across the entire business, from operations to people to marketing to sales to finance. And we figure out where the issues are, where we need more structure or more people, and we find ways to scale the business without driving the team crazy, burning anybody out and blowing through piles of cash.

Now I work 20–25 hours a week, earn a great living, and do it completely remotely—remote work is so important to me, and it’s changed my life. It’s the complete opposite of what I was doing when I came here—I call it “intentional life design”.

Where are you with your idea now?

I’ve lived here for four years. I love it. I have a long-term visa and am eligible for citizenship in a couple of years, which is so exciting. So as far as my idea to move to France and slow down, I am there.

There are still days when I have to remind myself that this is not a race and I don’t need to compete with anyone. If I feel like I have to be productive, I remind myself that’s cultural conditioning at work. Growing up in America, it’s so ingrained that your self-worth is tied to productivity. I’ve had to be conscientious and do a lot of self-coaching to divorce my self-worth from being productive.

I feel so lucky and fortunate to be here. I make intentional time for friends and read a tonne of books (juicy fiction, not nonfiction!). But slowing down is still a daily practice. I remind myself it’s okay for a day to be lazy or slow, not every waking minute has to be filled with something productive.

“Confidence comes after the leap.”

What have you learned?

When I tell people our story of how we moved here—we sold our house and everything we owned, we bought a one way ticket, our first day in France was the day we moved here, we did no scouting visit, we spoke no French, had no French connections, nothing—people are always like, wow, that’s insane. One client even said to me, you have huge balls.

We just believed it would work. And what I’ve learned is that we are braver than we realise. I was terrified when we moved, but once we did it, I was like, I can’t believe we did it. And then I learned French, and I’m like, I can’t believe I had that conversation. Confidence is a muscle. Taking the uncomfortable step comes first; confidence comes after. The more you push yourself, the more calculated risks you take, even just a little—send that DM, make that pitch, write that post—the more confidence compounds.

So I think that’s my biggest learning: confidence comes after the leap.

Was it worth the risk?

I mean, 100%. I can’t stress this further. The life we’re living now is just so radically different from the one that we lived in the United States. We work significantly less. We spend more time with our kid. We’re traveling way more. We can hop on a train and head down to Spain, or hop over to Italy, or take the train up to Paris, or grab a quick flight and go to Portugal. We drove to Basque country last summer.

We don’t earn as much as we did in our early American lives, but that’s okay. France is a completely different life, one that is secure and stable, that allows us to live and enjoy things and not stress about if someone gets sick. And not stress about how we’re going to afford our daughter’s higher education.

I would do it a million times over. When anyone expresses an interest in living abroad, I tell them over and over again, yes, it’s possible. Yes, you can do it. It’s absolutely worth taking the leap.

“Ideas are beautiful, but plans are 1,000 times better.”

What advice would you give to fellow Ideas People?

I work in operations, and I’m generally viewed as a founder’s right hand. I always joke that my greatest strength is getting the best ideas out of people’s heads and into the world.

Because humans are really, really good at coming up with ideas, but far fewer people are good at putting those ideas into action. So I would encourage folks, if you have an idea, start putting some meat around it. What does one step forward look like? Ten steps forward? Visualise it fully. Close your eyes and imagine it.

Then start laying out on paper the concrete steps to make it happen. Talk to people who’ve done what you want to do. Get curious about how they made it happen. Give yourself accountability and deadlines. I’m a big fan of telling people your idea, especially if you benefit from external accountability. When we decided to move to France, we didn’t tell anyone for six or seven months. Once we did, it was real.

And know that some ideas are probably shit. That’s okay—it’s a big part of what I do for work: helping founders figure out which ideas are worth pursuing. But if you have an idea you cannot let go of, start taking action, however imperfect or messy. Confidence comes after action. Take the idea, take some first steps, and your confidence will grow, inspiring more action. Ideas are beautiful, but plans are 1,000 times better.

Where to follow Mary Alice’s work:

• LinkedIn

• Newsletter: Ops & Other Opinions

What’s on your mind?

Have you made a big, bold move—only to realise that the real work starts within? What imperfect, messy action could you take to pursue your next big idea? Let us know what’s percolating in the comments.

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About Messy Work

A monthly ‘magazine’ for deep thinkers, big feelers, and more-to-lifers.

Hi there! I’m Lucia, a writer and coach based in Bristol, UK. When I’m not re-reading Pride and Prejudice for the 127th time, I work with recovering high achievers and independent spirits who can’t shake the feeling that there’s more to life. And I write about the messy (but beautiful!) work of figuring it all out.

Once a month, I pop by with a Messy Essay, a Loose Guide, and Ideas People. The rest of the month, I’ll leave you and your inbox alone.

When I started “slow publishing” Messy Work, I thought about setting an editorial theme for each monthly issue. I decided it would feel a bit too restrictive…and I realised that the idea was most likely influenced by false depictions of fashion magazines in the romcoms I watched growing up.

But as I’ve put each issue together, I’ve found that my three posts (a Messy Essay, a Loose Guide, and Ideas People) have a habit of speaking to each other.

This month, I wrote a personal essay about radical unsubscribing—something my guest on Ideas People, Mary Alice Duff, enacted when she quit her life in the U.S. to slow down in the South of France.

In it, I touch on the invisible, often inherited “subscriptions” we hold in our own minds: the outdated beliefs passed down to us through generations, the negative thoughts we cling to because their familiarity is more comfortable than challenging them (no matter how paradoxically uncomfortable they make us feel).

Now, the self-help world has made much of “rewiring your brain”, “adopting a different mindset”, or “thinking positive”. So I’ll caveat this guide by saying that we cannot simply press the eject button on all our undesired thought patterns, and play a new CD. In fact, I would question the very language we use to describe our thoughts through binaries like negative or positive.

As I’ve written about here, our thoughts come from different parts of us, all of which are (in admittedly perplexing ways) trying to protect us. Most of this is rooted in primal, neurobiological survival (it’s just that some of our instinctive responses have become a bit warped and unnecessary now we no longer have to contend with sabre tooth tigers).

But the good thing is that, precisely because of our neurobiology, we have the power to change our brains. Our capacity for neuroplasticity (got a ring to it, right?) means we can, over time, adapt our patterns of thinking and behaving, and even adopt new ones.

So, expanding on the theme of radical unsubscribing, I wanted to share an exercise from my coaching resource library (which you get access to when you work with me!).

I first learned about the NAT to PET ladder during my coaching training, and I still use it with clients to this day. The idea is to play with “unsubscribing” from our NATs (negative automatic thoughts) and replacing them with PETs (positive empowering thoughts). It comes from the evidence-based school of Cognitive Behavioural Therapy (CBT), which explores how our emotions, thoughts, and actions are connected, and seeks to develop alternative ways of thinking, behaving, or responding.

And yes, I cannot speak about it without thinking of natural wine.

Using the NAT to PET (or Pet Nat) ladder to shift the way you think

In CBT, NATs refer to all the pesky, worrisome and sometimes irrational thoughts that pop into your head when you’d really rather they didn’t. These can lead to difficult emotions or unhelpful patterns of behaviour, like triggering stress or self-doubt.

For example, let’s say you’re having a call with a new client, and they ask you a question you don’t know the answer to.

“They’ll think I’m stupid” squeaks the voice in your head. You start to feel stressed and deliver a somewhat garbled response (also known as blagging it), which fails to mask the indisputable fact that you do not know the answer.

It’s very difficult to stop a NAT in its tracks when we are in a high-stakes, pressurised situation. But if you experience the same pattern playing out again and again, it might be worth doing some deeper digging.

Enter: the three-step method that I like to call spot, plot and swap. Mainly because it sounds like a fun breakfast cereal.

You can try using it to reframe less helpful thoughts into kinder, more reasonable, and more productive ones.

Step 1: Spot the NAT

The first stage is to simply become aware of our negative automatic thoughts.

The act of noticing can hold enormous power in itself, since most of us are too busy to even be conscious of what’s driving our emotions and behaviours. When we slow down enough to hear our thoughts, it begins to create some distance and detachment from them. In other words, they don’t have to define us.

So if you repeatedly emerge from client meetings feeling flustered and frustrated, try taking a moment to reflect on what you where thinking during the conversation—without judgment, just noticing.

It might help to say the thoughts out loud or write them down. Hearing or seeing them can give you a bit of perspective on whether they are, in fact, true.

Step 2: Plot the NAT

Once you’ve starting spotting your NATs, you might notice that they follow similar messages and patterns:

What if they think I’m stupid?

I wish I’d come up with a better answer.

Everyone else is cleverer than me!

This is because our thoughts are rooted in our core beliefs.

A belief is a story we hold to be true. These stories come from messages we’ve internalised in the course of our lives. Some of them may be helpful and life-affirming. Others can be unhelpful or “limiting”.

A limiting belief is a story we hold to be true, which holds us back from what we really want.

In this case, the core belief might be I’m not clever enough (and they often do follow an “I’m not ___ enough” pattern). And it’s stopping you from building relationships with potential clients (and actually, you probably are still getting the clients—maybe you simply want to feel less stressed in those meetings).

We’re not aiming to get rid of these beliefs, as they’re often deeply ingrained in our psyches. But plotting your NATs against them can give you some useful extra context. And over time, that self-awareness can breed greater self-compassion.

Step 3: Swap the NAT

This is where we can let ourselves imagine what it would be like to rewrite the script. And don’t worry, I’m not going to suggest you recite positive affirmations in the mirror.

In fact, the reason positive affirmations can make us squirm is that they’re a bit too disconnected from how we see ourselves, and who we really are.

For example, jumping from “They’ll think I’m stupid” to “I am a genius, they WILL think I’m amazing!!!” might actually make you feel more stupid: a) because it’s what we imagine Trump might say to himself in the mirror each morning, and b) because of the Paradoxical Theory of Change, which we explored in last month’s Loose Guide:

Essentially, the idea is that the harder we try to force change—whether in ourselves or others—the less “successful” we will be.

Paradoxically, when we accept our present reality, and ourselves as we are, that’s when genuine change becomes possible.

Instead, the ladder technique helps us work towards progressively more positive, empowering thoughts (PETs) that feel believable and attainable.

Continuing with our example, let’s see how we could climb a few rungs up the thought ladder:

• Bottom of the ladder (NAT): “I don’t know the answer, they’ll think I’m stupid.”

• First rung: “It’s okay to not know the answer.”

• Second rung: “Not knowing the answer gives me an opportunity to show honesty and curiosity.”

• Third rung: “Admitting I don’t know the answer actually builds trust.”

• Top of the ladder (PET): “I don’t need to know every answer. What matters is how I respond.”

It takes time and practice to train your brain to travel up the ladder. And it’s okay if the NAT still pops up.

The idea is to slowly get better at spotting the negative thought before you spiral into stress. And practice swapping it for thoughts that can help you respond from a calmer place. So you could confidently say: “That’s a great question. Could you tell me more about XYZ to help me answer it?” or “I’d like to look into that and get back to you”.

A few extra tips to put this into practice:

• If you’re not sure where a NAT is coming from, a curious, non-judgmental chat with the part that’s piping up can help unearth the core belief (check out the 6 Fs exercise in this post for guidance).

• Make sure the PETs you’re swapping in feel believable and attainable. Thoughts you genuinely want to have, not thoughts you think you should have.

• Get curious about situations, environments or people that seem to trigger your NATs (e.g. meetings with a certain coworker, or scrolling on social media). What could you do to prepare for these moments? If healthy and realistic, could you remove yourself from certain dynamics or spaces?

Changing our thoughts can change how feel towards ourselves, and how we move through the world. And the more you change the input, the more likely it is that you’ll get a different outcome—helping you build up a body of evidence to challenge those core beliefs, and write new stories.

Let me know if you give it a try!

With thanks to the Animas Centre for Coaching for training materials that inspired this post.

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Ways to work with me:

1:1 coaching

If you’d like deeper, personalised support exploring tools like this, I work with:

• Recovering high achievers at a Crossroads in their lives and careers

• Independent spirits who need a Sounding Board to navigate the rollercoaster ride of self-employment

Drop me a message or book a call if you’d like to chat.

Messy Club

I started Loose Guides as a way to share all my nerdy coaching psychology study—because a) I wish I’d learned all of this stuff in school instead of piddling about with Bunsen burners, and b) I know not everyone can afford 1:1 coaching or therapy.

As I chat to more of you lovely subscribers, I’ve been thinking about how to provide a more intimate and regular level of support that’s still accessible. So this Sunday (5th October), I’m going to be opening the doors to the Messy Club subscriber chat.

I’ll be sharing coaching-led journalling prompts to help you do your own messy work. Our first batch will be on the theme of this month’s Messy Essay on radical unsubscribing.

If that sounds like something you’d value, stay tuned…

About Messy Work

Messy Work is a monthly ‘magazine’ for deep thinkers, big feelers, and more-to-lifers. Once a month, I pop by with a Messy Essay, a Loose Guide, and Ideas People. The rest of the month, I’ll leave you and your inbox alone.

It’s no secret that the world is collapsing in on itself. War. Hunger. Political polarisation. Plastic pollution. Plastic surgery. Sometimes, it can feel like everything is moving backwards.

Perhaps that’s why I felt so tired this summer. At 3pm, my eyes would glaze over. I’d leave my office early to fall asleep on the sofa (something I almost never do). There were days where I lay in parks, holding a book above my head until my arms ached. I stopped wringing out my evenings with workouts, chores, or more work, and did a better job of listening to my body. It helped.

Speaking of moving backwards, one of the books I read was about nostalgia. The history, the pathology, the politics. The pros and the cons.

And yes, it’s clear to see that nostalgia can be a force for bad. People who descend on the Costa Del Sol to eat fry-ups and drink Guinness get misty-eyed over the days of yore, wringing their sunburnt hands over the supposed erosion of “good British values”. Years of progress undone by one small, orange man who wants to “Make America Great Again”. And don’t think the Left aren’t guilty of digging their heels in—we can be just as stubborn in the face of change, and just as selective in our morals.

But briefed on its dangers, I wondered when nostalgia could also be a force for good. And so I indulged in some of my own by listening to a BBC 6 Music podcast about the noughties indie scene, narrated by Kate Nash (and fondly recalled my cousin and I affecting soft cockney accents to sing along to her debut, Made Of Bricks).

It’s funny to me that the music of my youth has come to be known as indie “sleaze”. Maybe because I was a 14-year-old who had barely tasted WKD, but it didn’t feel sleazy at the time. It felt…kind of pure?

We did our own makeup with shaky hands and patient friends, not YouTube tutorials and expensive products—the liquid eyeliner and dream matte mousse smeared all over our faces a testament to our innocence. We wore clothes (skinny jeans, owl necklaces, tea dresses, chunky boots) that proudly proclaimed the music we were into, not how much money we had. Most of the money we did have went on pilgrimages to Oxford Circus Topshop, or gigs at Brixton Academy.

Of course, looking back through my rose-tinted spectacles, I’m probably an unreliable narrator. My halcyon days co-existed with a deeply sexist music industry, creepy club photographers, the glamorisation of substance abuse and eating disorders, and a complete lack of awareness about this thing we now call “mental health”.

But if I practice some selective nostalgia, I can appreciate some of the good, inspiring things the indie scene stood for. It was a reaction to the perceived blandness of the mainstream music industry. An exercise in DIY. A product of the newly-birthed internet: a wild, wild west that relied on our parents’ dial-up connections and the kindness of strangers, not algorithms, ads, and vitriol.

Fans recorded sets at gigs and uploaded them to MySpace. Bands played on Camden rooftops, out the back of buses, and in the reception of the BBC (without permission, of course). You could talk to Pete Doherty on The Libertines’ message board.

What stood out to me from the podcast was how the indie scene had resisted the institutions and cultures that had so far shaped the music industry/our very identities, using evolving technologies to reclaim artistic agency and cultivate new tastes, systems, and communities. It was an inversion of power: where record labels had to beg artists to sign them, and fans called the shots on what we consumed. It was an act of what I like to call radical unsubscribing.

What is radical unsubscribing?

Radical unsubscribing is how I think of the process of becoming aware of the invisible, inherited “subscriptions” we hold; liberating ourselves from what doesn’t serve us; and rewriting (or re-rooting) how we live, create, and connect.

The word “radical” comes from the Latin radix, meaning “root”.

These “subscriptions” could be:

• A set of cultural or familial beliefs (e.g. “Resting is lazy”)

• Participation in unethical/unaligned systems or environments (e.g. buying fast fashion, working in toxic startups, churning out content to please the algorithm)

• Literal, paying subscriptions to media, devices, apps, or products that dysregulate our nervous systems or make us feel less-than (iPhones, social media, dating apps, expensive skincare serums)

By probing the forces that may be shaping our energy, emotions, relationships, and identities—often without us even realising—we can start refusing to passively consume, and instead think about how we actively engage. Reframing beliefs, removing ourselves from ill-fitting or ill-doing systems and environments, and creating new ways of living, working, being, and relating.

Back to Pete Doherty

Perhaps the fascination with indie “sleaze” of late is to do with the feeling that we’ve come full circle. That once again, it’s time to do it ourselves.

It’s an attitude that’s permeating our lives on macro and micro levels. We see it in whimsical “-cores” that butt heads with the beige-ification of fashion (in my day, the concept of “old money” would have been deeply uncool). The former “screenagers” ditching their phones to form Luddite Clubs in New York City. The mistrust in government from all angles.

More of us are testing out ways to upend the system, to reclaim some of our power. Of course, like nostalgia, there are dangers to the act of radical unsubscribing. As history has repeatedly shown us, rebellions and revolutions can often end in more tears. But as the wrong side of history embraces radicalism, it doesn’t seem wise to rest on our laurels. Like the messy-haired, sweaty-denim-clad bands of my youth, I’ve been feeling called to think deeply and imaginatively about how we rebuild the systems we exist in.

I have few answers for how to do this on a global, political scale. I’ll admit that I often occupy a state of mild oblivion, burying my head in novels rather than reading the news. I prefer studying the inner workings of the human mind than the convoluted establishments of men in power (although arguably, the world would be a better place if everyone knew how to emotionally regulate).

But sticking to my own wheelhouse, I’m having a lot of conversations (with myself and others) about what it means to be a creative, a coach, a freelancer, a woman, a person right now. Whether we are victims of a job market that no longer values us, a healthcare system that does a poor job of adequately supporting us, or workplaces that dehumanise us, we’re feeling increasingly called to a) unsubscribe from the status quo and b) create a new one.

One of these conversations took place at my coworking space, which welcomed a panel of speakers who are working to reconnect people to nature—whether it’s getting kids from global majority communities outdoors, or burnt-out adults away from their desks.

For the last question, each panelist shared their vision for what the future could look like. And it struck me that imagination is perhaps the most crucial component of radical unsubscribing; what prevents it from becoming a mere act of rejection (i.e. the closed-minded, simplistic political uprisings dominating our newsfeeds right now) and one of re-creation.

Because to meet problems with true creativity and resourcefulness, we must open our minds. We must have empathy and compassion for others. We must be courageous, not cowardly.

What radical unsubscribing looks like for me

For some people, radical unsubscribing may mean taking bold action—like the guests I’ve been speaking to for my interview series, Ideas People, who have quit jobs, sold possessions, moved countries, and gone all in on their dreams.

For others, it may simply start with some bold thinking: making a habit out of probing, unlearning, reframing, wondering, imagining. Take Mary Alice Duff, this month’s Ideas People guest, whose move from the U.S. to the South of France was prompted by an idle conversation—a half-joking thought experiment—with her husband.

As I said before, I am no Greta Thunberg. But I’m using the concept of radical unsubscribing to slowly explore and dismantle the constructs I may have unwittingly built my life around, and trust that small shifts lead to bigger changes. For me, this looks like:

• Questioning my relationship with (read: dependence on) technology: how do I wean my nervous system off of the dopamine rollercoaster?

• Slow publishing on Substack: deprioritising the algorithm, reprioritising my creative energy, and respecting my readers’ inboxes by publishing Messy Work as a monthly magazine.

• Railing against optimisation culture and expanding my definition of “wellness” to include rest, pleasure, and occasional hedonism.

• Greater emphasis on connection, collaboration and community; not transactions, individualism, and navel-gazing (as you may have gathered, a sport I excel in). This also includes challenging my slacktivism.

• Practicing self-attunement over self-improvement.

• Being inspired by random people I see on the street (mainly, 70+ women), not trends I see on social media.

• Working seasonally, adaptively and intuitively. Not forcing myself to work hours and schedules that don’t suit my body. Accepting that I don’t need to do the same thing, all the time, for the rest of my life—sometimes I will pursue meaning and purpose, other times I will pursue stability and security. And I never know where curiosity and serendipity will lead me next.

What does radical unsubscribing look like for you?

I’d love to know how the concept of radical unsubscribing resonates with you. What does it mean, in your personal definition? What could it look like in your life?

Leave a comment

And if you’d like to take this thought experiment one step further, this Sunday (5th October) I’m going to be opening the doors to the Messy Club.

Introducing Messy Club

I’ve alluded to this idea a few times now, and I’ll admit that my initial concept has gone through various iterations. But for now, I’ve landed on testing out Substack chat as a space to share journalling prompts. There are two reasons behind this:

1. I think it would be lovely to have a space where we can come together and share our experiences and ideas (and you can shape what I write about in Messy Work!)

2. As part of my personal mission to make coaching more popular and accessible, I’d love to offer some coaching-led guidance without the price tag.

I’ve hosted several journalling workshops in the past year, and find them really powerful way to give people time and space for themselves, introduce new tools and perspectives, and share questions that can support reflection and next steps.

It’s a taste of what coaching can offer, without needing to go the whole hog if you’re not in a position to commit OR you’d like some ongoing support after we’ve worked together 1:1.

For our first thread, I’ll be sharing some prompts on the theme of radical unsubscribing to support your reflection and continue the conversation. So if you’d like to swing by and see what it’s all about, just make sure you’re subscribed and you’ll receive a notification inviting you to join.

What people say about my journalling workshops:

“Your prompts got me thinking in ways that I never have before.”

“I’ve always found journaling tricky, but this hour let me slow down, reflect, and leave with steps to make work (and life) better.”

“I came with a notebook, a pen, a cup of tea… and a lot of anxiety. I left with more presence, clarity, and a few very actionable insights. It was exactly what I needed.”

Messy Club will be free for now, while I decide what this could look like long term. Hope to see you there 🙂

About Messy Work

Messy Work is a monthly ‘magazine’ for deep thinkers, big feelers, and more-to-lifers.

I’m Lucia, a writer and coach based in Bristol, UK. When I’m not performatively writing in artsy cafés, I work with recovering high achievers and independent spirits who can’t shake the feeling that there’s more to life. And I write about the messy (but beautiful!) work of figuring it all out.

Once a month, I pop by with a Messy Essay, a Loose Guide, and Ideas People. The rest of the month, I’ll leave you and your inbox alone.

Ideas People #2: Kasturi Kiritharan on defecting from the 9-5 to devote her life to her art

Kasturi Kiritharan is a painter based in London, transforming her encounters with the natural world into imagined visions in her work. A year on from completing a painting course in Edinburgh, she's now balancing creating art alongside part time work. Outside the studio you'll find her nose-deep in a good book, hunting for treasures at flea markets or collecting ideas for her Substack, .

Kasturi and I come from a background in marketing—a world we both have one foot in, and one foot firmly out. I think our paths must have crossed, or run in parallel, a few times, but it was this post on leaving London that properly got us talking.

Since then, we’ve had several conversations—over Zoom, WhatsApp, and salad boxes we fiercely guarded from Bristol’s greedy seagulls—that have spanned topics close to our hearts: writing, art, the concept of home, the importance of community, and how to build a life and career outside of the bounds of a full time job.

When I started this series, Kasturi was exactly the kind of “ideas person” I had in mind. Three years ago, she quit her job to study painting and live out a childhood dream to become an artist. These days, she still works part time in marketing, but devotes the rest of her week to the studio.

And I use that word devotes intentionally. Because Kasturi’s story isn’t just about taking one bold leap into the unknown—it’s about showing up to meet it every day. Committing to a sustained creative practice takes faith. It requires discipline, routine and ritual, as well as fluidity, openness, and ease—a recurring theme in this conversation, which stayed with me in the days and weeks that followed.

Something else that has stuck with me (and again, is why Kasturi was such a perfect guest for Ideas People) is that Kasturi didn’t become an artist to chase commercial success. She became an artist because that’s who she is, and has always been. As someone whose creative ambitions were also dampened by corporate life, I found this so reassuring.

My takeaway: If your current situation doesn’t light you up, your inner child knows what will—and it’s never too late to listen to them…

What was your idea or dream?

I've always had a vague sense of wanting to be an artist, simply because art was what I enjoyed doing. When I was younger, the dream was to do it full time. But because I was discouraged from going to art school, the dream didn’t go beyond that—it felt impossible to even study.

So the first iteration of the dream was to quit my job to go and enrol in a course [Kasturi studied at Leith School of Art], with the hope that eventually I could spend more time being an artist.

Now, having come out of the other end of studying, my dream is to continue committing to my art practice in a way that feels sustainable.

What made it important to you?

I'd always loved drawing as a child. I knew it was my happy place.

But as I grew older, I really neglected that part of myself. After a couple of years working in marketing, I realised that I needed to tend to my creativity again. In the end, I think that that uncomfortable contrast (between my drab marketing job and my quiet desire to be an artist) was helpful and important in getting me to be proactive about becoming an artist.

“I constantly questioned whether being an artist was something I actually wanted. I told myself, if you really wanted it, you would make time for it. But sometimes you just don't have the energy. It doesn't mean you want it any less, it just means you need to rearrange the music.”

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When did you know you had to do something about it?

When I was working full time, I found it very difficult to have any sort of creative practice. While some people have it in them to have a nine to five and then spend their evenings on their practice, I realised I wasn't that kind of person. I needed a lot of ease in my day to be able to be creative.

During that time, I constantly questioned whether being an artist was something I actually wanted. I told myself, "if you really wanted it, you would make time for it". But sometimes you just don't have the energy. It doesn't mean you want it any less, it just means you need to rearrange the music.

What allowed you to do something about it?

I started reading The Artist’s Way. It helped me reframe my mindset from this who I aspire to be, to this is who I already am. That emotional shift of telling myself I was already an artist helped massively.

I'm also quite financially anxious, so having financial safety was important. When I quit my job to go to art school, I was able to live at home with my family, and I had savings to fund the course. Then after studying, I did the same thing—being back home with my family now has given me more ease with sustaining a part-time studio practice.

But I think maybe the most important thing that allowed me to take the risk was my determination and belief in myself. I would like to think that even without that huge safety net, I would have eventually ended up building a similar sort of lifestyle.

How exactly did you make it happen?

I knew I needed some kind of mentorship, so spending time studying was the first step. I saved up, then found the art school I wanted to go to. I went to all the open days. I connected with the people there. I did any short courses they were running. I had loads of conversations with people who had already done what I wanted to do.

Post-study, I made sure I held onto the momentum of the course. I applied for studio spaces, connected with other artists, made sure that I made art a priority.

What sacrifices or compromises did you have to make?

Financially, I've taken a big cut. I have the privilege of living at home which has eased the burden, but this means I’ve had to exchange my independence. And my decision to move home has affected my relationship with my partner, who I now have to long-distance with.

But in the grand scheme of things, I feel so lucky that I get to do what I do. And I always remind myself that these decisions don’t have to be permanent, and whenever the compromise feels too big, you have the power to change that.

Where are you with your idea now?

Right now, I do half a week doing my “money” job, then spend half the week in my studio. I’m really just working on it becoming a routine, making time to (1) figure myself out artistically, (2) build connections with other people, and (3) put myself out there commercially. I'm being cautious about the balance of those three things, being sure to honour what I need at any given point in time—being careful not to stretch too far in one direction.

“Creativity requires…patience and listening.”

What have you learned?

To listen to my body! Most of that ease I’m always searching for comes from this.

My art tutors really encouraged it. If I was having a low energy day, they wouldn't tell me to push through it. Instead they would say, "okay, listen to your energy levels—do you need to go and sit in the library and read?" Creativity requires this kind of patience and listening.

Having peers, guides, mentors is also key! I share my studio with three other artists, which was an intentional decision I made when I was looking for studio spaces. If I’m stuck on something, I can just turn around and ask for advice. Again, this builds ease into my day so that I’m not just locked in, and I have space for my brain to breathe. And in the absence of my peers, I turn to the private notebooks, interviews, talks, and biographies of creatives I admire, absorbing their wisdom from afar.

Lastly, I remind myself that this is still early days. When you're in the very beginning stages of sprinting towards a dream, it feels like it's such a rush to get to the peak, and I have to constantly be like, you’re only three years in—calm down!

“Wherever doing something new feels impossible, ask what you can subtract from your life so that you can add the new thing in.”

Was it worth the risk?

Yes, of course! Living this lifestyle has been the best decision that I've made for myself.

Although I do have days where I have doubts—like, is this the right thing? Should I be focused more on stability?—my inner life just feels so much richer now, and I don't think that can be replaced. So I'm very grateful for that and I feel lucky that I can do this.

What advice would you give to fellow Ideas People?

Whenever doing something new feels impossible, ask what you can subtract from your life so that you can add the new thing in. Learning to spot those areas where I can make those healthy trade offs has been an important learning for me.

Find people you really admire, and channel their spirit in your work. Because if you're an ideas person and want to live a creative life, it often feels like a very scary, risky, unstable path. It's hard to find the confidence in yourself—there'll be days where you're really doubting if you're doing the right thing. So on those days where you can't find the strength in yourself, it's important to have your guides with you.

Where to follow Kasturi’s work

• Substack:

• Instagram: @shoesatthe_door

• Works available at Wondering People

What were your childhood dreams? Have you followed them, or are they still calling out for attention?

A big thank you to Kasturi for sharing so much wisdom, and for giving us a glimpse of her beautiful paintings. We’d love to hear what resonated with you in the comments.

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Stay tuned for more conversations about bridging the gap between dreaming and doing.

About Messy Work

A monthly ‘magazine’ for deep thinkers, big feelers, and more-to-lifers.

Hi there! I’m Lucia, a writer and coach based in Bristol, UK. When I’m not making Pinterest boards of Carrie Bradshaw’s best outfits, I work with recovering high achievers and independent spirits who can’t shake the feeling that there’s more to life. And I write about the messy (but beautiful!) work of figuring it all out.

Once a month, I pop by with a Messy Essay, a Loose Guide, and Ideas People. The rest of the month, I’ll leave you and your inbox alone.

Subscribe now

A few months ago, I gave away ten free coaching sessions to freelancers and business owners who were struggling with the uncertainty of self-employment.

Nearly all of them came to our session wanting to hear my opinions, experiences, and advice: on how to sign more clients, get more done, or be more confident.

I completely understood their curiosity; charting your own path can feel like shooting in the dark, and we need our guides and mentors. But…I didn’t give them what they wanted.

Firstly, because I’m a coach, not a mentor—I don’t advise, teach, or pretend I have all the answers. And secondly, because I knew from experience that deferring to my authority wasn’t what they needed.

Often, the real “secret” to self-employment is to stop chasing a reality where we have it all figured out, systems that are “bulletproof”, or a ballsier version of ourselves that does cold emails, viral LinkedIn posts, and TED Talks without so much as a shiver of self-doubt.

These are the dreams that entrepreneurship culture (which is really just a subcategory of self-improvement culture) sells us—whether it’s via a business course, a life coaching programme, or even a Substack. But if we subscribe too wholeheartedly to other people’s methods and instructions, it can be a form of spiritual bypassing: we learn the the cure, but we don’t necessarily heal the wound.

For example, imagine someone who feels directionless and burnt out, which is taking a toll on their business. Instead of sitting with those feelings, they sign up for a productivity course that promises to “10x their output”. It feels like progress—they’re doing something. But if the deeper issue is that they feel disconnected from their purpose, or they don’t believe they’re worthy of rest, a colour-coded calendar isn’t going to stop them from burning out—again, and again.

That’s why, rather than providing the answers, the crux of my work is to help my clients get to know themselves as they are, then start to see things differently: to confront what’s really getting in the way, to reframe a story that’s holding them back, to open up new perspectives.

Over time, this can lead to profound change. But I’ll let you in on a secret: we don’t get there by trying to change. And that funny little paradox not only underpins my coaching practice, but explains why self-improvement culture so often fails us…

Introducing the Paradoxical Theory of Change:

“Change occurs when we become what we are, not when we try to become what we are not.”*

*Paraphrased from gestalt.org.

The Paradoxical Theory of Change, coined by psychiatrist Arnold Beisser, comes from Gestalt Therapy—a psychotherapy approach that emphasises focusing on present experiences and taking responsibility for one’s feelings and actions.

From studying the work of Fritz Perls, who developed Gestalt alongside Paul Goodman and his wife Laura Perls (let us always remember the wives!!!), Beisser noticed a common thread running through nearly all Gestalt techniques.

He called it the Paradoxical Theory of Change because of its inherent irony. Essentially, the idea is that the harder we try to force change—whether in ourselves or others—the less “successful” we will be.

Paradoxically, when we accept our present reality, and ourselves as we are, that’s when genuine change becomes possible.

The Paradoxical Theory of Change in action

September is a good time to talk about the Paradoxical Theory of Change. Much like New Year, it has lots of us in a psychological chokehold—we get all nostalgic for new pencil cases and visits to Clarks, and decide ‘tis the season to become an entirely new person.

The thing is, 80% of us are said to abandon our New Year’s resolutions before we’ve even polished off the Christmas chocolates. Precisely because we are trying to become an entirely new person—and usually, this just isn’t realistic, healthy, or possible, especially in a short amount of time.

Let me use myself as an example. Back in my twenties, I was trying to find love. Only I never let anyone I was dating cotton onto that.

I had absorbed the cultural myth that dating is a game to be played; one where the winners don’t reply too quickly, put all of their eggs in one basket, or (god forbid) seem too keen. And so I played the role of the cool girl, keeping it easy and breezy so as not to startle anyone with my basic need for connection.

Unsurprisingly, this strategy royally backfired, time and time again. I could only keep up the cool girl facade for so long, then I would tentatively suggest that maybe we should talk about “where things were” seeing as we’d been spending four nights a week together for three months, gone on a romantic holiday, and met all of each other’s friends.

Aghast at my true colours, the men would pull back. I’d cling harder—both to the relationship, and the romcom-induced fantasy that all men are just a bit commitment-phobic and will get there eventually. It would all end in tears.

Now, there’s lots going on here: attachment styles, self-worth wounds, societal conditioning, etc. But I also think it’s a good example of the Paradoxical Theory of Change:

a) I was pretending to be someone I wasn’t, rather than embracing and expressing who I really am (a big, soppy, hopeful romantic).

b) I was also trying to force change on the people I was dating, even when they very clearly and categorically told me they did not want a relationship.

The harder I tried to change the both of us, the more stuck, even set back, I was. I’d go round and round in the same cycles of disappointment and heartache.

It was only when I truly faced myself (warts, anxious attachment style, and all), and fully owned who I was and what I wanted, that I finally met my partner. And the best thing about falling in love with him was that neither of us had to try—it just happened, beautifully and organically.

The key principles of the Paradoxical Theory of Change

OK, enough soppy romance. If you want the hard, psychological facts, here are three key principles of the Paradoxical Theory of Change, as I see it:

1. The “topdog vs. underdog” dynamic.

As I spoke about in last month’s Loose Guide, we tend to get stuck when we are experiencing inner conflict, i.e. different parts of us want different things.

In Gestalt Therapy, this is referred to as the “topdog/underdog” dichotomy:

• The topdog is the voice that tells us what we should be (a bit taller, a baller, etc.)

• The underdog is the part that feels pressured and resorts to stroppy, rebellious behaviour (“You can’t make me!”)

The more the topdog tries to force change on the underdog, the more the underdog resists—and so round and round we go.

This dynamic can exist internally, but also in therapy or coaching if the professional takes on the role of the expert who knows best (think: bearded psychoanalyst and his Freudian couch) and the client looks to them for authority and approval.

Practitioners like me don’t think this is the most effective way to bring about growth for our clients, as it can lead to codependency, superficial compliance (we may nod along to what our practitioner is saying, but not feel intrinsically motivated), and even shame.

Instead, we take a human-centred approach, where coach and client work together, as equals. And we don’t strive to change those inner parts—we give them attention and acceptance.

2. A working assumption of wholeness.

Much like Internal Family Systems therapy (which integrates a lot of concepts and techniques from Gestalt Therapy), the Paradoxical Theory of Change begins with the assumption that we are whole, not broken or lacking.

That’s not to say there’s anything wrong with valuing and seeking personal growth. We’re just not doing it from a place of believing we’re not good enough. Instead, we acknowledge that we are a real, complex person moving through life’s rich and varied experiences, not a machine that needs fixing.

3. Change as an unfolding process (without a fast-forward button!).

Finally, we recognise change as a process, not a one-and-done solution.

Gestalt Therapy says that in order to heal and grow, we must fully experience our struggles and blocks, rather than trying to skip to the good bit when we’re all shiny and new. This means really meeting ourselves in the present moment, and continuing to do so, because we are always changing and evolving.

For example, while my relationship has been (and continues to be) a very healing experience for me, it has not erased my anxious attachment style. Those parts, although softer, are still very much there. And I still bear scars from past heartbreaks. I need to keep meeting those parts and scars with compassion (especially when I find myself asking my boyfriend whether he’d still love me as a worm).

Change, for me, is an ongoing, unfolding process that I experience, rather than a destination I arrive at. Healing is a patchwork, not a straight line.

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Why does it matter?

It’s important to remember that none of this is in conflict with the desire to grow—it’s okay to feel like there’s more to life than what you’re currently experiencing, and want to do something about it.

Gestalt simply stresses the importance of self-awareness, and then self-acceptance, as the gateway to growth, rather than shaming ourselves for who we are—or more accurately, who we are not.

As if by osmosis, this is when the real change tends to unfold. Because when we deepen our self-awareness, we also recognise that we have choice: we don’t have to let our parts take over, we don’t have to let cultural narratives define our relationships, and we don’t have to try to control others.

Crucially, Beisser makes a case for the relevance of this theory in the modern world, pointing out that it took a long time for psychiatric and psychological establishments to accept Gestalt Therapy:

“What has happened in the past fifty years to make this change theory, implicit in Perls's work, acceptable, current, and valuable? Perls's assumptions have not changed, but society has. For the first time in the history of mankind, man finds himself in a position where, rather than needing to adapt himself to an existing order, he must be able to adapt himself to a series of changing orders. For the first time in the history of mankind, the length of the individual life span is greater than the length of time necessary for major social and cultural change to take place. Moreover, the rapidity with which this change occurs is accelerating.”

In other words, it’s futile to keep looking for solutions in a world that’s constantly changing; we’re better off becoming fluent in the process of change itself.

Taking it back to my self-employed clients, I could tell them all the ways I’ve won clients over the course of my freelance career. But because the landscape has changed so much since I started (AI, economic instability, increased competition), a lot of those tactics have become redundant.

Really, the best investment they can make isn’t in formulas or shortcuts—it’s in self-knowledge. The strongest insurance they can give themselves is the capacity to adapt.

It seems to me that those are pretty good lessons for life, too. And that’s the most “advice” you’ll get from me 😉

With thanks to The Gestalt Therapy Page for background material, and to the wonderful coaches at Famn, who first introduced me to this concept.

Work with me: 1:1 coaching

If you’ve identified with any of these challenges and are curious to explore these perspectives further, I’m an accredited coach who works with:

• Recovering high achievers at a Crossroads in their lives and careers

• Independent spirits who need a Sounding Board to navigate the rollercoaster ride of self-employment

Drop me a message or book a call if you’d like to chat.

Enjoying these insights?

I started Loose Guides as a way to share all my nerdy coaching psychology study—because a) I wish I’d learned all of this stuff in school instead of algebra, and b) I know not everyone can afford 1:1 coaching or therapy.

As I meet more of you lovely subscribers, I’ve been thinking about how to provide a more intimate and regular level of support that’s still accessible. So soon, I’m going to be opening the doors to the Messy Club subscriber chat.

Drawing from my experience as a coach, writer, and lifelong student, I’ll be providing fortnightly journalling prompts to help you do your own messy work.

If that sounds like something you’d value, watch this space—I’ll be sharing more soon.

About Messy Work

Messy Work is a monthly ‘magazine’ for deep thinkers, big feelers, and more-to-lifers. Once a month, I pop by with a Messy Essay, a Loose Guide, and Ideas People. The rest of the month, I’ll leave you and your inbox alone.

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It is 5.30am and my alarm trills through the darkness, rousing me from a fitful, wine-tinged sleep. I pull on my gym kit, grab my pre-packed holdall (work clothes, makeup bag, laptop) and march across London Bridge with the first wave of bleary-eyed commuters.

By 6.30am, I have descended into a small, strobe-lit studio, where I huff away on an exercise bike to the throbbing bass of Nicki Minaj vs Rihanna vs Ariana Grande. An hour later, I emerge sodden and exhilarated—high on endorphins, adrenaline, and the quiet fury I harbour towards the overly-enthusiastic spin instructor (really, it’s me vs her).

I queue for the showers, attempt to do my makeup while sweat still pours down my face, and pull on my second outfit of the day. Then I march onwards to Bermondsey, pick up a coffee en route, sit down at my desk, and whip out my tupperware of overnight oats, before firefighting my way through another working day.

By the time evening arrives, my nervous system is in tatters. But there’s no rest for a twenty-something desperate to prove herself. I will either be meeting friends to shovel down an overpriced plate of pasta and three glasses of wine before the restaurant turfs us out, or I’ll find myself in a dimly lit cocktail bar, willing my latest Hinge suitor to be The One so I can liberate my thumbs from all this swiping, and my heart from all this disappointment.

And to think that, thanks to my ClassPass subscription and occasional flirtation with matcha, I considered this “balance”.

It feels almost passé to talk about the pace of our lives pre-pandemic—perhaps because it’s a reckoning we’d rather brush off than fully integrate. But I still look back and marvel at how ruthlessly I pushed myself (and I know, it’s a pretty pathetic version of hedonism).

More than anything, I see a girl who didn’t yet know how to be her own authority. Who hadn’t yet learned to listen to herself—not not the status-chasing world of VC-backed startups, the wellness industry, or the existential crises of self-absorbed young men.

But slowly, she started to wake up.

Fast forward a few years, and grief has uprooted her life, rearranged her priorities, and cracked her heart wide open. She quits the toxic job to work for herself. She realises that, more than whirlwind romance and electric chemistry, she needs someone kind. She knows when to stop at one glass of wine.

But in so many ways, she’s still running.

The only way she knows how to “be her own boss” is to replicate the very patterns and behaviours she was so desperate to escape from. She’s still whizzing around on the Victoria line, commuting even though she doesn’t have to, saying yes to things she doesn’t want to go to. Even in the safety of a warm, loving relationship, there’s part of her that’s still anxious—sabotaging and protesting to test if this thing she’s always longed for is going to stick around.

Because the thing is, you can take the girl out of the startup, but not the startup out of the girl. And meeting The One may make you feel enormously happy, safe, and secure—but there are still parts of you frozen in the longing, not quite trusting that love is right here in front of you.

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Meanwhile, the tides of social media are turning. We’re moving away from HIIT classes, hustle culture and whitewashed girlbossery. A new aspiration, or at least aesthetic, starts to take shape: all artfully rumpled bedsheets, sunlight pouring through the windows, the book positioned just-so to get Matisse’s Icarus in the shot. Slow living was here; and I was here for it.

It seemed to represent everything I was working towards, driven by that feeling that there must be more to life than this constriction in my chest, this tension in my shoulders, this weight on my spirit.

I started to think more deeply about the kind of life I wanted for myself. In business, I learned to claw back my freedom, set boundaries, and embrace fluidity. As my partner and I looked around us, and really took in the secondhand stress and pollution we were unconsciously inhaling, we decided we needed a different place to thrive.

By October of last year, I’d given myself the slower life I’d been building for the past five years. And all those changes that I’ve made—going freelance, retraining as a coach, moving to Bristol, “settling down” with my partner—while not without their sacrifices, have been wonderful.

So why was my body screaming at me?

It started towards the end of last year, when the lower back pain I’d grown accustomed to living with (oh, to be a woman and have a distorted pain threshold) began radiating up my back and all the way down my right leg. Used to throwing all sorts of shapes in the yoga studio, I was shocked and shamed that I could no longer straighten it. At night, I would wake up with a searing pain in my hip and mid-back. There were some mornings where I woke up unable to turn my head properly.

I wondered if this was thirty. My physio informed me that no, it was just me. Stripping me down to my tights and standing me in front of the mirror, she showed me how the right side of my body was hitching upwards, as if an invisible puppeteer was pulling me with a string.

A decade of HIIT, spin, frighteningly-paced “yoga”, and god knows what other fitness crazes I’d made my body endure, had caused my QL muscle to seize up, making everything else a bit skew-whiff in the process. I needed to begin the slow journey of rehabbing my body, weaning myself off my 5x a week workouts in favour of sensible physio stretches and low impact movement, like swimming or walking. Oh, and I probably needed to stop hunching over a desk all the time.

It was then I realised that my relationship to slow living was conditional.

Sure, I wanted slow—but not this slow. I could pluck up the courage to amble over to my coworking space at the leisurely hour of 10am, but did I have the guts to sack off the squats, star jumps and chaturangas? I feared what would happen to my body without the discipline. I feared who I would become: lazy.

Fortunately, nothing really happened at all. I started doing strong, meditative lengths in my local swimming pool. Instead of bookending my days with sweaty studios and other people’s feet, I walked along the harbourside, stopping to simply sit and stare at the calm, rippling water, or the rowers gliding seamlessly across its surface.

As it turns out, doing my back in was actually pretty great for my (complicated) relationship with my body; it taught me the art of truly listening to it. Of trusting myself to know what it needs, not fitness influencers, sportswear companies, or even friends whose agendas I have taken on as my own.

But that’s not the end of the story—because the universe really wants me to learn a lesson. Last year, after much head-scratching amongst opticians and medical professionals, I was diagnosed with a mysterious condition called PIC (punctate inner choroidopathy, if you’re feeling fancy). It’s a rare, inflammatory disorder that can cause leaky blood vessels in the back of your eye, distorting your vision.

Naturally, it’s classed as an autoimmune condition that predominantly affects young, otherwise healthy women. Naturally, because it’s an autoimmune condition that affects women, no one seems to know anything very useful or reassuring about it.

While I don’t know what the future holds (PIC can sometimes fully resolve itself, and sometimes lead to permanent vision loss—a fun lottery!!), I do know that I want to do everything I can to avoid triggering a flare-up. And alas, we all know the relationship between autoimmune diseases and stress.

But the thing is, short of building myself a hermitage in the forest, hadn’t I already done enough to remove the stressors (namely, the self-absorbed men) from my life? How much slower could I get?

In last month’s Loose Guide, I mentioned the work of Steve March, who talks about something called the Self-Improvement Paradigm. The idea is that in modern, Western culture, we have started to view self-improvement like a video game to complete—only there never really is an endpoint.

We’ve grown accustomed to approaching self-improvement as a series of missions, challenges and accomplishments we must go through to unlock the next level of awareness, enlightenment or worthiness. That’s not to say that there’s anything wrong with learning new skills, exploring different perspectives and practices, or seeking support. But if we do all of this from a place of lack—of feeling like there is always something to improve about our career, our friendships, our love lives, and crucially ourselves—we are unlikely to ever feel fulfilled or truly worthy.

Paradoxically, all it does is reinforce the feeling that we are trying to escape or overcome: the feeling that we are not enough. Because no sooner have we mastered that yoga pose or splurged on another course, than we spot another area in which we are lacking; the road to living one’s best life is neverending.

Instead, March advocates for relating to ourselves from the premise that we already are enough. We don’t need to do self-improvement or “work on ourselves”. We just need to be with ourselves, and let more of who we already are unfold. And I think that’s where I was going wrong: trying to “achieve” slow living through the lens of the self-improvement paradigm.

I realised that slow living doesn’t just come from the big, bold moves—quitting the job, escaping the city. Slow living is in the mundane, micro choices. Lingering a little longer over lunch. Walking the scenic route to work. Not getting impatient in the falafel queue, when really I have nowhere to be. It’s choosing to let go of my ultimately pointless rage that the bed has not been made the way I would do it. It’s closing my laptop, staring at some paintings, and handwriting this from the free reading room of my local art gallery.

And most importantly, slow living is an inside job, not an aesthetic to consume. We don’t find it in performative gestures and self-conscious Instagram posts—shopping at the farmers market or visiting the boujie yoga studio. It’s in the deep seated beliefs, traumas (personal, collective, intergenerational), and physical tension we must face, rewrite and release. It’s learning that, for those of us who have the miraculous privilege of living in a peaceful society, life does not have to be a fight. We can choose ease. We can simply be.

About Messy Work

A monthly ‘magazine’ for deep thinkers, big feelers, and more-to-lifers.

Hi there! I’m Lucia, a writer and coach based in Bristol, UK. When I’m not refreshing Facebook Marketplace to find more mid-century hotties in my area, I work with recovering high achievers and independent spirits who can’t shake the feeling that there’s more to life. And I write about the messy (but beautiful!) work of figuring it all out.

Once a month, I pop by with a Messy Essay, a Loose Guide, and Ideas People. The rest of the month, I’ll leave you and your inbox alone.

Every month, we meet someone who had a persistent feeling that there was more to life, and made bold moves to follow their dreams and intuition. Expect brave and beautiful stories that reject limited definitions of success (there’s no such thing as a failed idea here). And honest conversations that don’t sugarcoat the messy work of building a life that truly feels like yours…

Ideas People #1: Hannah Wilkinson on quitting her job in marketing to become a full-time writer and house sitter

is a UK-based writer currently working on her debut book. When she’s not hammering words into her prehistoric Mac, you’ll find her on a yoga mat or tramping through the Scottish Highlands, and sharing stories on her Substack, .

I first came across Hannah through her Substack (this post on ditching self-help books, to be precise) and I was immediately taken—not just by her warm, funny and wise words (and dreamy pics of quaint British towns) but by her story.

After a decade working in luxury marketing, Hannah decided something needed to change. Drastically. So she packed up her life and packed in “normal”, ditching the 9-5 and London rent to explore a slower, more intentional way of living as a full-time house sitter. And, crucially, to do what she loves: writing.

As someone who also wants to write a book one day (emphasis on one day), Hannah’s story gives me a real sense of possibility. So many of us harbour these creative dreams, but feel trapped by the logistics and mundanities of our everyday lives; Hannah and her partner show us that there are other ways to live—which carry their own sacrifices, but can give us the freedom to commit to what’s really important to us.

My takeaway: perhaps we have more power than we know to create possibility, embrace uncertainty, and keep faith…

What was your idea or dream?

To become a full-time writer.

What made it important to you?

They say do something you love. I've always been a total bookworm, always written, and had things to say from a very young age. But I suppose, like many of us, I buried the idea of doing something with my passion and cracked on with a career that was a bit more "normal." If I could go back in time to my six-year-old self, after I'd written my first piece of genius (The Pig in the Wig), I'd tell her to bloomin' go for it [editor’s note: I would love to read The Pig in the Wig].

“My diagnosis sparked embers, and lockdown lit a raging fire within me.”

When did you know you had to do something about it?

In 2019, while moisturising my neck to stave off visible signs of ageing, I found a lump. I was living in London, had a great job, a whirlwind social life, and still had four years to make it onto the Forbes 30 Under 30 — everything was going to plan! So when my doctor told me that lump had a one in three chance of being thyroid cancer, I felt like the rug was completely pulled from under me. Multiple tests and one surgery later, I was given the all clear. The lump was benign. My diagnosis sparked embers, and lockdown lit a raging fire within me. By the year I turned thirty, I was yearning for a monumental change.

What allowed you to do something about it?

I had some savings, not a lot, but enough to keep me going for six months before I'd have to find work again. But if I'm being truthful, falling in love gave me the faith to do it. I know... so typical. I'd met someone who shared a similar dream, and finding each other was the final nudge we both needed to say f**k it! It was total kismet. And I feel very lucky to have someone in my life who can not only support me emotionally, but also understand exactly what I’m going through.

How exactly did you make it happen?

I put my life into a storage unit, quit my job and started housesitting as a way to avoid paying rent and give myself the financial freedom to write. We travelled around Australia for six months, Ireland for three, and have been gallivanting around the UK since last year. We've lived in 25 homes and looked after 40 pets, and although we're coming to the end of the journey now, it's hands down the best decision and adventure I've ever taken.

What sacrifices or compromises did you have to make?

The biggest sacrifice has been stability. Living in other people's homes, transporting my life around in a 2007 VW Polo, and not knowing when the next piece of freelance work would come along has been stressful. I've missed creature comforts and a "normal" routine, but for my partner and me, the benefits have outweighed the cons.

“Housesitting [was] the catalyst for a book I had no idea I’d need to write.”

Where are you with your idea now?

I’m in the throes of editing a book about the past two years, a memoir of the ups and downs of housesitting, and my search for a creative and more romantic life, and I hope to be pitching it out at the end of the summer. My original goal was to finish a fiction idea I’ve had for years, but housesitting has provided so much material and been the catalyst for a book I had no idea I’d need to write. It also landed me a full-page spread in The Telegraph, and thereafter, several bylines for titles like Stylist and Business Insider. I fill the gaps with freelance marketing work (my old career) and am still working towards funding a lifestyle entirely from writing, but I know I’ll get there!

What have you learned?

Make a plan, but be open to the unexpected. Embracing everything I hadn't planned for (and often the things that scared me most) has borne the brightest, juiciest fruit. I've become a lot more malleable and resilient in the face of defeat, which in practice isn't a fun skill to learn, but is tremendously important.

Was it worth the risk?

The alternative is never knowing, and I'm not sure I could live with that regret. For me, it was far riskier to stay in the comfortable life I had made for myself, than giving my big idea a go. Worst case scenario, I knew I could go back to my old life. I could get a job, get a flat, rebuild my savings. But tomorrow isn't promised to any of us. We get one shot. In my eyes, risking it is telling the universe you're ready for it. The hardest thing is making the jump, because no matter how long the fall — and so long as you believe it — a net will be there to catch you.

“On the days when everything is going wrong and nothing feels achievable (of which there are many), just keep chopping wood.”

What advice would you give to fellow Ideas People?

One of my favourite quotes is by E.L. Doctorow: "Writing is like driving at night in the fog. You can only see as far as your headlights, but you can make the whole trip that way." I apply this to everything in life. Break your idea down into bite-size chunks. Stay consistent. One percent a day can make all the difference. On the days when everything is going wrong and nothing feels achievable (of which there are many), just keep chopping wood. But most importantly, regularly remind yourself how brave and utterly fantastic you are for chasing your dream!

Where to follow Hannah’s work

• Substack: A Life Well Loved

• Instagram: @hannahxwilkinson

• Tik Tok: @hannahxwilkinson

• Website: https://www.hannah-wilkinson.com

• LinkedIn: Hannah Wilkinson

What did this conversation spark for you?

Are there embers that need tending to? Or is the fire already burning? Hannah and I would love to hear what resonated with you in the comments.

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Stay tuned for another gorgeous guest, coming next month 💌

About Messy Work

Messy Work is a monthly ‘magazine’ for deep thinkers, big feelers, and more-to-lifers—written by me, Lucia 👋

I’m a writer and coach based in Bristol, UK. When I’m not trawling vintage shops for impractical yet fabulous things I have no room for, I work with recovering high achievers and independent spirits who can’t shake the feeling that there’s more to life. And I write about the messy (but beautiful!) work of figuring it all out.

Once a month, I pop by with a personal essay (ft. my latest existential crisis), a loose guide (non-prescriptive insights from the world of coaching psychology), and Ideas People. The rest of the month, I’ll leave you and your inbox alone.

Subscribe now