Second Act Sunday #57

I have a friend, Aidan, who posts the same two messages on Facebook every year. On the 22nd of December, one day after the winter solstice, up it goes: “There’s a grand stretch in the evenings.” Then, on the 22nd of June, one day after the summer solstice, he’ll announce that “the evenings are really drawing in.”

There’s something magnificently Irish about it. We’re obsessed with the light, the rain, the temperature, the first longer evening you notice and the first evening you need a jacket. Beneath the joke, though, I feel those two dates quite differently; I think a lot of people do. The December one gives me a genuine lift because I know the darkest point has passed. The June one brings the opposite feeling because, however ridiculous it sounds, when it’s still bright late into the evening, I know we’ve tipped the other way.

I’ve never really liked the dark evenings and I dislike them more as I get older. I make the best of them, but I’d take long bright evenings every time. That’s probably why there’s a bit of melancholy for me at the end of August. Not sadness exactly. Summer is still here; there can still be warm days and bright evenings, but you can feel it beginning to move on. The light changes, the evenings shorten, and September starts to feel close.

My work follows a similar pattern every year. June and July are busy-ish, then August falls off a cliff. Coaching slows down, the calendar begins to fill up and the pace changes. By mid-September, things start moving again.

That’s what interests me about this last weekend in August. It’s a little gap between seasons. Summer hasn’t quite finished, and autumn hasn’t properly begun. Most of the time we move straight from one thing into the next, but this moment gives us a chance to notice what changed when life became a little quieter.

Maybe you had more brain space in July and August. Maybe you walked more, read more, saw more of someone, or just rushed around less. Maybe something disappeared from your routine for a few weeks, and you didn’t miss it nearly as much as you expected. None of that has to become a lesson or a new habit. It might just be useful information.

September has a way of putting things back. Work picks up, routines return, schools go back, calendars fill. Before long, normal life has reassembled itself around us. There’s nothing wrong with that, but maybe we don’t need to put every single thing back exactly where it was.

So before the noise starts again, I think there’s one useful question to ask: what do I not want to lose?

Some things belong to summer and are better left there. But some things may be worth carrying with us. A little more space. A person we’ve enjoyed seeing. A slower morning. Less urgency. Whatever it is, we can choose rather than simply let September swallow it up.

I know the dark evenings are coming. I’ll complain about them, make the best of them and wait for Aidan’s Facebook post on the 22nd of December. But we’re not here yet. For now, we’re in the middle bit, and maybe there’s no need to rush out of it.

This week’s journal prompt

What has been present in your life this summer that you would genuinely miss if it disappeared when the usual routines return?

This week’s gentle practice

Notice one thing that starts to return to your pre-summer routines . Before automatically making space for it again, pause and ask whether you still want it there.

Second Act Sunday #56

Wednesday, August 14th 1991. The day I got my Leaving Certificate results. I don’t have a photographic memory, I looked it up. The Leaving Cert is the equivalent of A-levels in the UK and, I suppose, SAT in the US.

I have no clue what my grades were but I do know that they weren’t good enough to directly get me into Computer Science in Dublin City University (DCU). I remember being disappointed but not really surprised. It just confirmed that my route into the course would have to be via a letter to the admissions department explaining why, as a disabled student, they should consider offering me a place on the course.

It worked and the following October, I started a four-year degree.

Fast forward to summer 1995 and the appointed time arrived to call Prof. T’s office to get my finals results. I will forever remember the feeling when he told me I’d failed and would have to repeat some exams in October. The shock, panic, embarrassment, shame, fear.

I’d been disappointed before but this was my first real experience of what I perceived to be crushing failure, something I couldn’t explain away or ignore.

I had to fix this and I was fortunate enough to have the opportunity the following September to repeat the failed exams.

What followed was a summer of study with my friend Eoin, who was in a similar spot.

Summer 1995 in Ireland was baking hot. We spent weeks inside, our heads stuck in notes. I suppose I could say it was brutally hard to be indoors when everyone else was enjoying the summer. It wasn’t. It was great fun studying with a good friend, stopping for lunch, chatting, arguing, just fun.

When the exams rolled around I was in a much better position than the previous June and completed them with cautious optimism.

Results day came and I wasn’t taking the risk of someone giving me that shock again over the phone. So myself and my Mum and Dad went up to the college. The results were due to be displayed on the faculty notice board that morning. I knew the sheet would have five columns. Firsts, 2.1, 2.2, Thirds and Pass.

My name wasn’t in the Pass column. I remember feeling a bit faint, this would mean I’d have to repeat the entire year. Beyond disastrous!

Then I spotted “Gary Allen” in the 2.2 column. The vivid memory of relief will never leave me. I can still feel it now as I type. I had a degree. I’d done it. This was probably the best feeling I’d ever had in my 22 years on planet earth thus far.

The funny thing is, it’s hardly crossed my mind in the last 31 years since that day. It was massive at the time, absolutely huge. My future. My identity. My sense of whether I was good enough. Whether I had made it. Whether I had failed.

But then life happened and it faded into the margins.

And that’s the point. I don’t remember what subjects I had to repeat. I don’t remember the Leaving Cert grades I got. I don’t remember the details of the result beyond seeing my name in that 2.2 column and the enormous wave of relief that followed.

What I remember is how much it meant at the time.

And yet, over the following 30 years, almost all of that detail disappeared. Life happened and it faded into the margins.

What felt like everything then barely registers now. It still flashes back for a moment every year when the Leaving Cert results come out. A brief reminder of how enormous things can feel at the time, and how completely their importance can change with the passing of years.

Thirty-one years on, it’s just one of those things that happened.

This Week’s Journal Prompt

What’s a failure you still carry as evidence against yourself, even though the rest of your life tells a different story?

This Week’s Gentle Practice

Pause for 30 seconds every day this week and acknowledge something you’ve handled that wasn’t easy.

Second Act Sunday #55

Inspiring, inspiration, inspired. Whatever derivation of the word you want to use, I don’t care! I hated all of them. The word meant nothing to me. A platitude, a patronising load of hogwash.

I’m pretty sure that most disabled people have had it thrown at them at some point; I certainly have. Not on a daily, weekly or even monthly basis, far from it. But often enough for the word to lose all meaning, if it ever had any in the first place.

Inspiration is not a word to be used to describe a former Software Engineer turned coach from the West of Ireland who just happens to get around on four wheels rather than two legs. Coming from the Latin “to breathe into”, to me the word belonged to people like David Attenborough, Martin Luther King or Stephen Hawking. Those are the people who breathed life and fire into the bellies of the people they touched. Not me, nope, I wasn’t buying it!

Somewhere along the way, though, my relationship with the word began to shift. I realised that by closing myself to being inspired, I was losing so much.

I released my grip.

Don’t get me wrong, I still didn’t want to be reduced to somebody else’s idea of “inspiring” simply because I happened to move through the world differently. But I no longer needed to reject the whole thing. That release meant inspiration didn’t have to come from Attenborough, Hawking, etc. It could come from a conversation, a song, a book, a stranger, a sunrise.

And once I accepted that I was free to be inspired by whatever moved me, I had to accept something else too: other people were free to be inspired by whatever moved them.

Even me.

I didn’t have to understand it. I didn’t have to agree with it. I just had to stop trying to control it.

What inspires someone else is none of my business. My brother said as much to me a couple of years ago.

Once I accepted that inspiration doesn’t have to have an instantly recognisable name or a heroic feat, I saw it all around me. In my clients, my family, my friends, everywhere.

It sure as hell was everywhere this week. Kate O’Connor, English, Rhasidat Adeleke and Andrew Coscoran in the European Athletics Championships in Birmingham; Ellen Walshe, Mona McSharry, Daniel Wiffen and the rest of the Irish swimmers in Paris. Our tiny little country mixing it with the very best in Europe, and we’re not done yet!

I’ve always been inspired by people at the top of their game in sport. Federer, Nadal, Hamilton. People getting the absolute best out of themselves. That breathes life into me.

But it doesn’t have to be elite sport.

This week I also listened to talking with on Substack. A completely different setting. This was a conversation about addiction, recovery, creativity, getting lost and finding a way back. Utterly, utterly inspiring.

And I get it from my clients all the time. They’re not winning medals or standing on podiums. They’re making changes in their lives, facing things they’ve avoided, taking chances, figuring themselves out. They breathe life into me.

So do my family. My friends. Books, songs, conversations, moments I could easily have dismissed once upon a time.

That’s what loosening my grip gave me.

I stopped deciding in advance where inspiration was allowed to come from.

It can come from excellence. It can come from struggle. It can come from someone famous or someone sitting across from you having a coffee.

Sometimes it’s huge. Sometimes it’s barely noticeable.

But when something breathes a little life into you, why on earth would you want to shut it out?

This Week’s Journal Prompt

What keeps coming back into your mind lately? A person, a conversation, something you read, something you saw, a moment you can’t quite shake. Why do you think it keeps returning?

This Week’s Gentle Practice

For the next few days, notice what keeps popping back into your head. Don’t analyse it straight away and don’t decide whether it’s important. Just write it down. At the end of the week, look back and see what keeps repeating. There may be something there worth a deeper look.

Second Act Sunday #54

I’m in the market for some branding, sales and marketing support. I’ve been looking around for someone to work with for what seems like a hundred years, but things have advanced in the last couple of weeks. I’ve been following a few people who might be able to help me for quite a while, and I’ve had some great conversations.

This past week, yet another email from one of those people dropped in my inbox with a link to book a call, which I did. Immediately after booking that call, I got a prep video to watch. At the end of that video, I was a little less convinced this was the right person. Then I just forgot about it, as I tend to do. A couple of days later, I got a text from one of this person’s team confirming I would attend and that I’d watched the prep video.

Straight away, my gut reaction kicked in, and I texted back that I wasn’t sure this was for me, but I was prepared to listen.

As soon as I got on the call, I knew my gut reaction was right. The guy was very nice, very friendly, very interested, but he clearly had a job to do, which was to get as far into my wallet as possible. The call was scheduled for 30 minutes, but we ended up speaking for 60 minutes.

And it was an exceptionally valuable conversation.

Early on he asked he asked me how much money I wanted to make every month. I dutifully answered.

Then asked me what was important to me. I answered straight away. Honesty, integrity and a few other nice fluffy things. The answers came out quickly, but as I was saying them, they didn’t feel right. Not wrong exactly, just hollow.

Finally, he asked me what difference I wanted to make in the world, and that answer came out just as quickly as the previous questions. But this time it felt true, and that surprised me.

Over the next few days I started thinking about why two answers that had both come so easily could feel so different. I thought again about what was actually important to me, and this time completely different answers came up. I also kept thinking about the question of what difference I wanted to make in the world, because that answer had felt so clear the moment I said it and still does.

I also realised that the three questions he asked me felt completely backwards.

How much money do I want to make? What’s important to me? What difference do I want to make in the world?

I think I’d ask them in the opposite order if it were me.

What difference do I want to make? What’s important to me in how I go about making it? And then, how much money do I want to make?

I absolutely want to make money. I will never deny that. I like what money can provide. Choice, freedom, security and the ability to do more of the things I care about. But I’d rather have some idea of the life I want to create before deciding what number I want to attach to it.

All of these insights feel really important and clarifying, which brings me to my core point.

I didn’t particularly connect with the guy. I didn’t like the feeling of being sold to, and I’m still pretty sure I was right about what he was trying to do. It would have been very easy to decide that because I didn’t buy into him, there was nothing of value in what he had to say.

But he asked me questions that really got me thinking.

I know I do this. I make quick judgements about people, and once I have, it can be easy to stop listening properly. I suspect we all do it to some degree. This conversation reminded me that someone doesn’t have to be my kind of person to teach me something.

The people we disagree with can teach us things. People we don’t particularly like can teach us things. Even people whose motives we question can occasionally ask exactly the right question.

I’m glad I replied to that text saying I wasn’t sure this was for me, but I was prepared to listen.

I was right that it wasn’t for me.

I’d have missed a lot if I hadn’t listened anyway.

This Week’s Journal Prompt

Think of someone you don’t particularly connect with.
What do they see, know or do well that you might be overlooking?

This Week’s Gentle Practice

Listen without needing to agree.
Have one conversation this week where your only job is to understand what the other person is saying, without deciding whether they’re right while they’re saying it..

Second Act Sundays #53

“The world’s hardest working band”. So was the tagline of The Commitments, the 1991 adaptation of the Roddy Doyle novel. There’s little doubt that “hard working” has to be said for most journalists in Ireland this week. A week of emotional extremes with several miles of column inches written on just two stories.

It began with the naked, unfiltered joy of Co. Mayo winning the All-Ireland Football Championship for the first time in 75 years and ended with deep, deep grief at the death of singer Glen Hansard in a motorbike accident on Wednesday morning.

The aforementioned film was when I, and probably most people, first heard of Glen Hansard. He went on to have success with his band The Frames, of which I’m almost entirely ignorant, and to win an Oscar with Marketa Irglova for the song “Falling Slowly”.

As soon as I heard of his death, I watched this clip (please watch it) of him singing with a young busker, Padraig Cahill, on Grafton St. in Dublin. It’s one I watch often when I need a lift. It seems Glen just came upon Padraig while on his way somewhere, and however it transpired, they duetted “Falling Slowly”.

Busking was Glen Hansard’s spiritual home. So much so that he continued to do it long after he had anything to sell or any money to make. On Christmas Eve 2010, he busked for the homeless in Dublin. Then he did it again and every year since. It’s grown far beyond that point. It’s now a well-established Christmas tradition aired live on national radio.

I didn’t know Glen Hansard, never met him, never been to one of his gigs, but the man’s generosity of spirit is utterly undeniable. In the days since his death, that generosity has filled a fair chunk of those column inches. I sense he had a fierce ability to hold hope for people who needed a hand holding it for themselves, the homeless, the busker, whoever. I’m still not sure why, but his death has affected me far more as the week wore on. The best people don’t have to say anything, you can just feel it, and I think he was one of those people.

There are a few lines in “Falling Slowly” that go like this.

“But you have suffered enough. And warred with yourself. It’s time that you won.”

That was most definitely the attitude of the Mayo team in the final on Sunday. They hadn’t won a final since 1951, allegedly because of a curse put on the 1951 team that they wouldn’t win again until every member of that team was dead. This was their 12th final since 1951 but their first since the last member of the 1951 team died in 2023.

This county had suffered enough, and those players knew it. They battled against Kerry, who were the reigning champions, going for their 40th win. At one point, they were 7 points down. This is where most of the country went, “here we go again”, I certainly did. This team are different gravy. Their belief, their hope that could put an end to the 75 years of suffering, kicked in, and they went to work. They clawed themselves back into the game and eventually won by 3 points.

That’s only the beginning of the story, though. What followed were scenes of joy, in the stadium and at the following day’s homecoming, that most people won’t ever forget. I’ve seen more grown men cry this week than I ever have, and I think ever will. Just listen to this commentary from Mayo local radio.

After the win and as the TV interviews started, it really struck me how deeply uncomfortable the players were to talk about their own performance. It was all about the team, the collective, the belief and hope that they could be the ones who could write a new story.

I used to buy into the mantra that hope is not a strategy. Now I believe it is THE strategy when combined with action, be that 100 training sessions before the final (a fact) or fundraising.

Glen Hansard held hope for individuals, the homeless dreaming of a fresh start and the busker dreaming of success. Mayo held it collectively. Every one of them knew what they were capable of and held that hope for everyone who couldn’t hold it. When the last point went over the bar with 30 seconds to go, they handed that belief over to every Mayo person and all hell broke loose.

P.S. No journal prompt or practice this week. It will return next week.

Each Sunday, subscribers receive a short, gently challenging email designed to support their journey into what’s next. Whether you’re mid-pivot, post-burnout, or just feeling a subtle pull toward something more, this series offers grounded guidance without the fluff.

Thanks for reading! Subscribe for free to receive new posts and support my work.

Every edition includes:

• A short, personal letter — something I’m thinking about, noticing, or grappling with

• A reflective journal prompt — not a to-do list item, but an invitation inward

• A gentle weekly practice — small enough to fit into your life, powerful enough to shift something

You won’t find hacks, hustle, or 10-step plans here. Just honest reflections and grounded nudges toward a second act that feels truly yours.

Because midlife isn’t the beginning of the end, it’s the end of pretending.

And what comes next might be your most meaningful chapter yet.

Second Act Sundays #52

English was my favourite and best subject at school by a country mile. Essays, poetry, reading pretty much anything. That was my happy place.

Then in 1991 I left it all behind.

The thought that words might make me a living never even crossed my mind. So I did a degree in Computer Science.

For pretty much the next 30 years, I continued to read; it was still my happy place, but writing didn’t really feature.

There was a mortgage to be paid, a car loan to be paid, deadlines to meet. Writing really never got a look in. There certainly was the odd foray into courses like the short creative writing course in 2002, the aborted journalism correspondence course a few years before that. Looking back, these did play an important role. They kept the pilot light on in that part of me that wanted to write.

Then, about 15 years ago, I found the world of online writing. The good old-fashioned blog. Looking back over the small graveyard of abandoned blogs I started, it should have given me a clue about where my future lay. They were all in or around the ideas of either human potential or musings on relationships of all kinds.

The next evolution of that was Medium.com. That started with great promise for me in 2018 but eventually fizzled out like all the rest. I suppose I could have decided that this long trail of half-finished stuff meant that I didn’t have the discipline, the stamina, the skill, etc, etc. The strange thing is, though, that I never really doubted for a second that writing would come back into my life and stay there.

And so here we are. A year on from starting The Second Act Sunday.

Why is it sticking this time?

I have some hunches, but I don’t see much value in mining those today. Substack is definitely a core reason. It’s simple, easy and accessible. My other hunch is that I suppose I’ve always, very secretly, thought of myself as a writer of some kind or another. It might never have occurred to me that words could make me a living, but in a lot of ways that’s the way it’s turned out. I talk to people for a living, and for the last 52 Sundays some people have been reading the words I write here in this newsletter.

I went through a lot of the last 51 posts this week, and there are some real high points, like when I wrote about Jaffa Cakes, which seemed to really strike a chord. There were some real low points too, like when we lost two of our dogs, Bella and Cyril. Frankly, there is some awful drivel in there as well. The good, the bad and the ugly, you might say.

The last year has taught me much. As I pondered it this week, I was curious about why skipping a week was never an option. Ever.

The answer is quite simple, I think, and reassuringly boring. Its provenance could be anyone, but I’m going to give this one to James Clear. Writing is part of my identity. I just had to have a little discipline and a little structure, and the habit stuck.

Today reminds me a little of the day I was one year alcohol free. That was an entirely different journey to creating an identity-based habit. Alcohol was very much part of my identity, so infinitely more discipline was needed to bed the habit in. Once I did, it allowed me to see a future where being alcohol free was part of my identity.

Those two journeys ended up more or less in the same place. I don’t really think about alcohol anymore, and I don’t really think about not writing on a Sunday anymore.

I don’t drink, and dare I say it, I’m a writer.

I won’t deny I’m feeling a little bit proud this morning.

This Week’s Journal Prompt

What have you returned to again and again throughout your life, even after abandoning it?

This Week’s Gentle Practice

Write one identity statement you usually soften with “sort of,” “maybe” or “a bit.” Remove the escape hatch.
“I am a writer.”
“I am an artist.”
“I am building a business.”

Each Sunday, subscribers receive a short, gently challenging email designed to support their journey into what’s next. Whether you’re mid-pivot, post-burnout, or just feeling a subtle pull toward something more, this series offers grounded guidance without the fluff.

Every edition includes:

• A short, personal letter — something I’m thinking about, noticing, or grappling with

• A reflective journal prompt — not a to-do list item, but an invitation inward

• A gentle weekly practice — small enough to fit into your life, powerful enough to shift something

You won’t find hacks, hustle, or 10-step plans here. Just honest reflections and grounded nudges toward a second act that feels truly yours.

Because midlife isn’t the beginning of the end, it’s the end of pretending.

And what comes next might be your most meaningful chapter yet.

Second Act Sundays #51

I woke up the other day and couldn’t hear properly out of my right ear.

I assumed it was earwax, picked up some drops from the pharmacy and thought that would be the end of it. It wasn’t. By the following morning, things had become noticeably worse, so I booked an appointment with the doctor.

In a few minutes, he’d cleared the blockage.

The difference was immediate and stark

I walked into the surgery hearing the world one way and walked out hearing it another.

Here’s the thing, though.

In the space of just a couple of days, I’d already become used to not hearing properly.

I’d kinda stopped noticing it. My brain had simply adjusted. What had felt strange on the first morning had become normal by the second.

I’d adapted.

We often think of adaptation as something that happens over months or years, but this week proved to me that it starts much sooner than we realise. Give us a new set of circumstances, and we begin recalibrating almost immediately. We compensate. We adjust our expectations. We carry on.

It’s one of the most remarkable things about being human and is a large part of why we are the dominant species on the planet.

Without that ability, we’d struggle to cope with change, loss or uncertainty. We recover because we’re capable of adapting. We move house, start new jobs, become parents, retire, learn new skills and eventually settle into lives that once felt unfamiliar.

The same thing happens with the enjoyable parts of life.

For the last six weeks, many of us have fallen into a new routine because of the World Cup. We’d do a bit of work, check the fixtures, watch one match, maybe another later in the evening. Before long, it simply became part of the rhythm of the day. It did for me, anyway.

Now the tournament is ending, and social media is full of the inevitable jokes.

“What am I supposed to do tonight? There’s no football on.”

They’re only memes, of course, but they make the same point.

It doesn’t take us very long to accept a new normal.

The trouble is that our ability to adapt doesn’t distinguish between the things that serve us and the things that don’t.

We can become accustomed to a healthier routine, to writing every Sunday, to walking every morning or making more time for the people we love.

We can also become accustomed to being constantly busy, constantly tired or constantly putting off the things we keep telling ourselves we’ll get round to one day.

It rarely happens all at once.

We simply carry on until one day we realise we’ve stopped noticing that things could be different.

The blocked ear disappeared after a few minutes in the doctor’s surgery.

The thought it left me with has hung around.

I’ve been wondering what else I’ve adapted to without realising it.

Some of those things will be worth celebrating.

Others might be worth challenging.

The trick, I think, is remembering that just because something feels normal doesn’t mean it has to stay that way.

This Week’s Journal Prompt

What have you accepted as "just the way things are" without ever consciously choosing it?

This Week’s Gentle Practice

Take a few minutes to appreciate one way you've adapted that has made your life richer or more resilient.

Applications are now open for the sixth cohort of The Second Act Blueprint.

It’s a seven-week programme: a small group, honest conversations, and someone in the room holding belief with you until you can carry it yourself. You’ll find all the details here, including a link to book a call with me if you’d like to talk it through first. There are six places, and applications close once they’re filled.

Each Sunday, subscribers receive a short, gently challenging email designed to support their journey into what’s next. Whether you’re mid-pivot, post-burnout, or just feeling a subtle pull toward something more, this series offers grounded guidance without the fluff.

Thanks for reading! Subscribe for free to receive new posts and support my work.

Thanks for reading The Life Design Collective Substack! Subscribe for free to receive new posts and support my work.

Thanks for reading The Life Design Collective Substack! Subscribe for free to receive new posts and support my work.

Every edition includes:

• A short, personal letter — something I’m thinking about, noticing, or grappling with

• A reflective journal prompt — not a to-do list item, but an invitation inward

• A gentle weekly practice — small enough to fit into your life, powerful enough to shift something

You won’t find hacks, hustle, or 10-step plans here. Just honest reflections and grounded nudges toward a second act that feels truly yours.

Because midlife isn’t the beginning of the end, it’s the end of pretending.

And what comes next might be your most meaningful chapter yet.

Second Act Sundays #50

I disappeared down an AI rabbit hole this week.

It started with one question. The answer was good, so I asked another. Then another. Before long, I was exploring scenarios I hadn’t even thought of when I started. Every answer opened up another possibility. Every possibility seemed to deserve another question. Hours passed without me noticing.

At first, it felt like good thinking. I was being thorough. I was reducing risk. I was making sure I hadn’t missed anything.

Except I had.

I’d missed the simplest explanation because I didn’t slow down and allow myself to see it.

The more important the decision felt, the more convinced I became that the answer had to be complicated. I assumed there must be another angle I hadn’t considered, another risk I hadn’t spotted, another question I ought to ask before I could move forward. AI was more than happy to help. Every answer generated another avenue to explore, and I followed it.

By the end of it, the whole experience had become toxic.

Not because AI is toxic. I think it’s one of the most extraordinary tools I’ve ever used. I spent 30 years in IT, and I appreciate its value.

It became toxic because I stopped using it to think more clearly and was using it to create certainty. Two very different things.

When I eventually stepped away from the computer and walked away, the answer was embarrassingly simple.

It had been there all along.

Nothing had changed except my thinking.

I’ve been reflecting on why that happened, and it was little to do with AI. AI simply exposed a habit that’s easy to fall into. When something’s important, it’s tempting to assume the answer must be complicated. If the stakes are high, surely the solution must be equally sophisticated.

But life doesn’t always work like that.

Complexity quite often feels intelligent. It feels responsible. It creates the impression that every angle has been considered and every risk has been explored. The more I thought about it, the more I realised I wasn't making the decision any better. I was just making it more complicated.

The irony is that the simplest explanation is often dismissed first, because it feels too obvious. We can spend hours searching for a better answer when the right answer has already presented itself.

That’s the trap I fell into

Research matters. Curiosity matters. AI is an extraordinary tool. But there comes a point where more information no longer improves the quality of a decision or a situation. The law of diminishing returns kicks in big time.

Knowing when to stop is every bit as important as knowing where to start.

This week reminded me that wisdom isn't found in exploring every possible path. It's found in noticing what we've overlooked. Sometimes the answer has been sitting in front of us all along. We just stopped believing it could be that simple.

This Week’s Journal Prompt

What obvious possibility might you have dismissed simply because it seemed too simple?

This Week’s Gentle Practice

The next time you find yourself searching for one more opinion, stop and ask, "Do I need more information, or do I need to notice what's already here?"

Applications are now open for the sixth cohort of The Second Act Blueprint.

It’s a seven-week programme: a small group, honest conversations, and someone in the room holding belief with you until you can carry it yourself. You’ll find all the details here, including a link to book a call with me if you’d like to talk it through first. There are six places, and applications close once they’re filled.

Each Sunday, subscribers receive a short, gently challenging email designed to support their journey into what’s next. Whether you’re mid-pivot, post-burnout, or just feeling a subtle pull toward something more, this series offers grounded guidance without the fluff.

Thanks for reading The Life Design Collective Substack! Subscribe for free to receive new posts and support my work.

Thanks for reading The Life Design Collective Substack! Subscribe for free to receive new posts and support my work.

Every edition includes:

• A short, personal letter — something I’m thinking about, noticing, or grappling with

• A reflective journal prompt — not a to-do list item, but an invitation inward

• A gentle weekly practice — small enough to fit into your life, powerful enough to shift something

You won’t find hacks, hustle, or 10-step plans here. Just honest reflections and grounded nudges toward a second act that feels truly yours.

Because midlife isn’t the beginning of the end, it’s the end of pretending.

And what comes next might be your most meaningful chapter yet.

Second Act Sundays #49

On Sunday evening, I knew what this week’s newsletter would be about and as it turned out, the week provided another brilliant example to back it up.

Last Sunday, Louth, the smallest county in Ireland, reached the All-Ireland football semi-final. For a county with very little history of competing for All-Ireland titles, it was quite an achievement.

Then, on Friday night, Argentina beat Cape Verde in the last 32 of the World Cup.

Argentina won, 3-2, and it took extra time to do it. The reigning world champions, with Lionel Messi and world-class quality all over the pitch, needed every last ounce of it.

Cape Verde is a group of islands off the coast of West Africa, home to just over half a million people. This was their first World Cup. They went through the group unbeaten, drawing with Spain, Uruguay and Saudi Arabia. Then went toe to toe with the world champions for 125 minutes, coming from behind twice. Their goalkeeper, Vozinha, is forty years old and said all he wanted from this World Cup was for his mother to see him play.

The match started at 11 pm, and I only intended to watch for a few minutes. I assumed the result would be evident and inevitable from early.

I went to bed at 2 am.

I’ve seen this story before. We all have.

For me, it was my home club, Kilbride, winning the Roscommon Senior Football Championship in 2000 for the first time in living memory. It was Leicester City winning the Premier League in 2016. A few weeks after that, it was Connacht winning the Pro12.

Last Sunday, it was Louth.

On Friday night, it was Cape Verde.

Yes, underdogs sometimes win. There’s nothing new or groundbreaking in that, but when they win, unexpectedly, multiple times in the same year or the same competition, it becomes much more implausible to explain it away as “just one of those things”.

So why does this happen when there is no material change in the quality of the players?

Well, at some point, someone starts seeing a different future before anyone else can. A manager. A coach. A leader. They refuse to let the story that has always been told become the story that will always be told.

“Why not us?”

Then they go to work. For as long as it takes.

This is about holding belief.

Over my years as a coach, I’ve come to see that saying you believe in someone and holding belief in them are two very different things.

Anybody can tell someone they’ve got this. Anybody can tell someone to believe in themselves. Those words ask very little of us.

Holding belief asks much more.

It means staying with people when they’re struggling, without shrinking your view of what they’re capable of.

It means holding that belief when they can only catch glimpses of it themselves.

It means holding it when they finally begin to see it clearly, because that’s often the moment old doubts start reappearing.

I don’t know what was said in the Louth dressing room or inside the Cape Verde camp. I wasn’t in the room when Kilbride won in 2000, beyond being part of the club, and I certainly wasn’t at Leicester or Connacht. So I can’t claim to know what happened in any of them.

What I can tell you is that I’ve seen holding belief change people.

I’ve seen it in coaching. There’s no perfect question that does it, and I’ve never once convinced anyone into it. What does it is staying with people through the sessions when they can only see a fraction of what I can see.

There comes a point in almost every one of my coaching relationships when something changes. The client starts saying things they would never have said in the first session. They make decisions they’d been postponing. They stop asking whether they’re capable and start asking how they want to do it.

By then, my belief has done its job. They’ve taken that belief from me, and they are holding it themselves.

Louth. Cape Verde. Kilbride. Leicester. Connacht.

Behind all of those teams, there was (is) somebody who refused to accept the story that had always been told. They held belief.

And they kept holding belief until everyone else could carry it too.

This Week’s Journal Prompt

Think of a time you surprised yourself. Who, if anyone, saw it coming before you did?

This Week’s Gentle Practice

Bring to mind someone in the middle of a difficult chapter. Instead of trying to solve it for them, ask yourself what you still see in them that they may not be able to see today. Then find a moment this week to tell them.

Applications are now open for the sixth cohort of The Second Act Blueprint.

It’s a seven-week programme: a small group, honest conversations, and someone in the room holding belief with you until you can carry it yourself. You’ll find all the details here, including a link to book a call with me if you’d like to talk it through first. There are six places, and applications close once they’re filled.

Each Sunday, subscribers receive a short, gently challenging email designed to support their journey into what’s next. Whether you’re mid-pivot, post-burnout, or just feeling a subtle pull toward something more, this series offers grounded guidance without the fluff.

Thanks for reading The Life Design Collective Substack! Subscribe for free to receive new posts and support my work.

Every edition includes:

• A short, personal letter — something I’m thinking about, noticing, or grappling with

• A reflective journal prompt — not a to-do list item, but an invitation inward

• A gentle weekly practice — small enough to fit into your life, powerful enough to shift something

You won’t find hacks, hustle, or 10-step plans here. Just honest reflections and grounded nudges toward a second act that feels truly yours.

Because midlife isn’t the beginning of the end, it’s the end of pretending.

And what comes next might be your most meaningful chapter yet.

Second Act Sundays #48

Ted Lasso has been one of the most popular shows on TV in recent years. It's funny, of course, but there are more layers to it than that. An optimism, maybe even a vulnerability, that people identify with. And characters that are almost always much deeper than they appear on the surface.

It came up in a conversation I had with a friend yesterday.

This wasn’t a casual conversation. It was one we planned. I needed her support to help me get clearer on why people would want to work with me.

As we talked, I described how clients often arrive with a specific issue, alcohol, midlife, career, whatever. Most of the time, that issue resolves. And that’s when they tell me things are “fine.”

That’s exactly when I get more curious. That’s when I’ll ask, what would more than fine look like?

That question sometimes gets a look. A kind of “but isn’t fine enough?” look.

And that’s when my friend said, “You’re kind of like Roy Kent.”

She reminded me of that scene in Ted Lasso where Rebecca has just finished a date, which was ok, not amazing, not a disaster, but ok. That prompts Roy to say, “Don’t you dare settle for fine”.

Now, anyone who knows anything about football knows that the inspiration for Roy Kent is Roy Keane. One of the greatest players Ireland ever produced, and one of the greatest leaders the game has ever seen.

Saipan.

Every Irish person knows what that word means. Roy would not accept the quality of the training facilities ahead of the 2002 World Cup. They were fine. That was enough for most. Not Roy.

Whether you agreed with him or not, that moment forced a question Ireland hadn’t quite asked itself before: Is participating enough?

I think about that a lot in the context of what I do. Because “fine” in someone’s life is the equivalent of a training pitch that’s just about good enough. Functional. Acceptable. Nobody’s complaining.

What struck me yesterday was that my friend had helped me articulate something I’d been struggling to put into words.

I don’t coach because I think people are broken. I don’t coach because I think everyone should be chasing more money or a bigger job.

I coach because I have a fierce belief that people are capable of more than they currently believe about themselves.

I don’t need to know what that “more” looks like. That’s not my job. My job is to sit alongside someone and never stop believing there’s another possibility worth exploring, even if they’ve stopped believing it themselves.

One of the moments I love most is when a client tells me things are fine.

Sometimes, fine is exactly where someone needs to be. It can represent years of hard work, healing, and courage.

But sometimes fine is where we’ve stopped being curious.

There are moments in all of our lives when our own belief runs out. We can’t see what the people around us can see.

The place to start is just getting curious about the word itself. If fine is what you’d call things right now, what is it about them that’s fine? What’s good? What’s working? And is there anything, even a small thing, that might be better?

I’m not here to tell you fine isn’t enough. But if you find yourself wondering what’s on the other side of it, know that the curiosity itself is the thing. Getting curious is enough to get started.

This week’s journal prompt

Pick one area of your life and finish this sentence: things are fine because...

Keep writing. Don’t stop at the first answer.

This week’s gentle practice

This week, when someone asks how things are going, resist the first answer that comes to mind.

See what comes up instead.

Each Sunday, subscribers receive a short, gently challenging email designed to support their journey into what’s next. Whether you’re mid-pivot, post-burnout, or just feeling a subtle pull toward something more, this series offers grounded guidance without the fluff.

Every edition includes:

• A short, personal letter — something I’m thinking about, noticing, or grappling with

• A reflective journal prompt — not a to-do list item, but an invitation inward

• A gentle weekly practice — small enough to fit into your life, powerful enough to shift something

You won’t find hacks, hustle, or 10-step plans here. Just honest reflections and grounded nudges toward a second act that feels truly yours.

Because midlife isn’t the beginning of the end, it’s the end of pretending.

And what comes next might be your most meaningful chapter yet.

Second Act Sundays #47

As I look back on the week just gone, three moments stand out.

The first was Lewis Hamilton’s victory for Ferrari in Barcelona.

The second was a conversation with a dear friend that touched on a traumatic, life-threatening experience she survived some years ago.

The third was a clip of Lionel Messi during Argentina's first match at the World Cup.

All three resonated with me in a similar way.

They are completely different stories involving completely different people in completely different circumstances. Yet each time I thought about one of them, I found myself feeling something familiar.

I spent a few days wondering what that was.

Eventually, I realised that the word I kept circling around was defiance.

Lewis Hamilton’s victory felt significant because of everything that had come before it. When he joined Ferrari, the expectations were enormous. It was one of those sporting stories that seemed destined for greatness. An iconic driver driving for an iconic team. Instead, he endured a difficult period marked by disappointing results, criticism, scrutiny and growing questions about whether his best days were behind him. At times, he appeared to question that himself.

He had already achieved more than most drivers ever will. He had won world championships, broken records and secured his place in the history of the sport. There were plenty of reasons why he could have stepped away. Instead, he stayed. He kept showing up, kept learning and kept working. When he stood on the podium in Barcelona, people celebrated the victory, but they were also celebrating everything he had come through to get there.

A conversation with my friend brought a similar thought to mind. We were talking about a traumatic, life-threatening experience she survived some years ago. It wasn’t new information. I had known about it for a long time. Hearing it mentioned again simply reminded me of the determination required to keep moving forward after something that could easily have changed the course of a life.

What happened to her was significant. It shaped part of her story, but it did not get to define the whole story. She refused to allow a single event, however profound, to have the final word. There was a defiance in that which I deeply admire. A determination to continue living her life rather than organising the rest of it around what had happened.

Then there was Messi.

The clip showed Argentina in possession while play unfolded around him. For what seemed like an age, he appeared almost motionless while players around him moved, passed and searched for opportunities. Messi watched. He was reading the game, absorbing information and trusting what he was seeing. There was no sense of urgency in his movements and no need to force himself into the action.

What fascinated me was the confidence that was required. He trusted his understanding of the game enough to resist reacting to everything happening around him. He stayed with what he could see unfolding in front of him and waited for the right moment to emerge. When it did, he was ready. A couple of touches later, the ball was in the net.

As I reflected on these three stories, the similarities became clearer. Each contained an act of defiance.

Hamilton refused to accept that a difficult period defined him.

My friend refused to allow a traumatic event to define her.

Messi refused to abandon his own judgment and get swept up in everything happening around him.

The circumstances were very different, but the energy felt remarkably similar.

I suspect that is why these stories resonated with me so strongly.

Many of us are tempted at times to accept the version of the story that is immediately in front of us. The easier path is often to stop questioning those conclusions and settle into them.

The people who inspire me most keep participating in life. They continue to care, to believe, to create and to remain open to possibilities they cannot yet see. Their hope is neither passive nor naive. It is a decision. It is a refusal to hand the final word to fear, pain, disappointment or despair.

Perhaps hope is one of the most powerful forms of defiance available to us.

It says that the story is still being written.

It says that this moment, however difficult, does not own everything that comes next.

And in a world that can give us so many reasons to despair, continuing to hope may be one of the most defiant things we can do.

This week’s journal prompt

Where have you shown more resilience than you give yourself credit for?

This week’s gentle practice

Write down five challenges you have already come through.

Each Sunday, subscribers receive a short, gently challenging email designed to support their journey into what’s next. Whether you’re mid-pivot, post-burnout, or just feeling a subtle pull toward something more, this series offers grounded guidance without the fluff.

Every edition includes:

• A short, personal letter — something I’m thinking about, noticing, or grappling with

• A reflective journal prompt — not a to-do list item, but an invitation inward

• A gentle weekly practice — small enough to fit into your life, powerful enough to shift something

You won’t find hacks, hustle, or 10-step plans here. Just honest reflections and grounded nudges toward a second act that feels truly yours.

Because midlife isn’t the beginning of the end, it’s the end of pretending.

And what comes next might be your most meaningful chapter yet.

Second Act Sundays #46

I turned 54 this week.

This birthday sent me back exactly ten years, to the person I was at 44. I tried to remember what I imagined my life might look like a decade later.

The honest answer is that I probably did not think about it very much.

I was getting on with life. Working. Living. Doing what needed to be done. Change was happening, of course, although I was not paying much attention to it. I had no clear picture of the person I would become or the decisions I would make.

Then, at 45, I stopped drinking alcohol.

At 46, I trained as a coach.

At 50, I left the corporate world after a career of almost 30 years.

At 52, I began writing here on Substack.

And this week, at 54, I spent two days in a room with a group of people learning a new coaching skill. Team coaching.

I am writing this in the bedroom I grew up in, at my parents’ house. This room holds so many earlier versions of me. The surroundings are familiar, but the person sitting here has changed in ways I could never have imagined,

He could not have imagined the hundreds of people I would coach. He could not have imagined the career I would eventually leave or the work I would move towards. He could not have imagined these Sunday newsletters being written.

Yet here I am.

We are all changing, whether we pay attention to the process or not. Ten years will pass. Our circumstances will shift. Our bodies will change. Our priorities will move. New versions of us will continue to arrive.

Intentional change allows us to have some influence over who arrives.

That does not require a detailed ten year plan. I certainly did not have one. I still don’t. Much of my change began with a single decision. I wanted to see what life would feel like without alcohol for a while. That decision created space. The space led to questions. The questions led to coaching. Coaching led to a new career. The new career eventually led me here.

One change opened the door to another.

Looking back, the process appears much neater than it felt while I was living it. Real change never unfolds in a straight line, ever. There are doubts, false starts, difficult days, weeks, months and moments when we wonder whether anything is moving at all.

Intentional change requires time and effort. It asks us to repeat actions long after the initial excitement has disappeared. It asks us to stay with uncertainty. Embrace it even. It asks us to keep going before the evidence has fully arrived.

That is where compassion becomes essential.

When we are trying to change, the conversation inside our own heads can become hard. We question why we are taking so long. We compare ourselves to people who seem further ahead. We decide that a difficult week proves we are failing. We demand certainty from ourselves while doing something that is uncertain by its very nature.

Compassion changes that conversation.

It allows us to say, “Of course this is difficult. I’m learning.”

It allows us to notice effort as well as outcome.

It allows change to become a relationship we build with ourselves.

The person I was at 44 did not need to know everything that was coming. He needed to make the next decision available to him. The person I was at 45 needed to do the same. Every version of me carried something forward, including the versions who were confused, frightened and uncertain.

I wonder what the 64 year old version of me will think when he looks back at today?

I have no idea what his life will look like. I do know that it will be different. That’s the inevitability of change.

The decisions I make now will shape the person who arrives. So will the conversations I have with myself. So will the things I practise, the risks I take and don’t take, the people I spend time with and the ideas I allow myself to pursue.

Your future self is on the way too.

You do not need to know exactly who they will be. You can begin influencing their direction today.

A question for this week

When you imagine yourself ten years from now, what do you hope that version of you will thank you for beginning today?

A practice for the week

What kind of person do you want to be ten years from now?

Where are your current choices taking you?

Name one decision you need to make differently.

Take one step in the direction of that change every week for the next 4 weeks.

Each Sunday, subscribers receive a short, gently challenging email designed to support their journey into what’s next. Whether you’re mid-pivot, post-burnout, or just feeling a subtle pull toward something more, this series offers grounded guidance without the fluff.

Every edition includes:

• A short, personal letter — something I’m thinking about, noticing, or grappling with

• A reflective journal prompt — not a to-do list item, but an invitation inward

• A gentle weekly practice — small enough to fit into your life, powerful enough to shift something

You won’t find hacks, hustle, or 10-step plans here. Just honest reflections and grounded nudges toward a second act that feels truly yours.

Because midlife isn’t the beginning of the end, it’s the end of pretending.

And what comes next might be your most meaningful chapter yet.

Second Act Sundays #45

I have never been one for burning the boats. I understand the appeal. Make the decision, remove the escape route, force yourself forward. It sounds powerful. There is a romance to it. There is also, for me anyway, a whiff of unrealistic nonsense.

My own life has changed in a different way. Over the last eight or nine years, it has become almost accidentally unrecognisable through small decisions, repeated choices, experiments, and conversations. I changed my relationship with alcohol. I trained as a coach. I moved away from IT. I built a different working life. It happened one step at a time, no dramatic decision required.

Next year, I would love to do a third section of the Camino de Santiago with my brothers. We have done two sections already, in 2022 and 2024. They were funny, exhausting, meaningful, and full of moments we could never have planned for. I want more of that road, those conversations, that shared purpose, and that unexplainable thing that happens when you move together.

The honest truth is that I am not in the same physical place I was two years ago. So last week I went walking with a very good friend. Over three or four days, we walked between 25 and 30 kilometres. Enough to test myself. Enough to notice how my body responded. Enough to learn something.

What I found was encouraging. I can probably do it, with preparation. I also need to be honest about the last Camino. I think we got it wrong to a degree. It was probably too long. We got it done, and I am proud that we did, but getting something done does not automatically mean every decision was wise.

I also need to remember that when I talk about doing the Camino, I am talking about something we did together. My brothers did a huge amount of the pushing, lifting, carrying, problem-solving, and hard yards. That said, anyone who thinks doing it in a wheelchair means sitting it out is welcome to try doing a Camino in a wheelchair and report back after day two.

So yes, there is research to be done. How long should the next section be? What terrain are we looking at? What support will I need? These are responsible questions. They are an act of respect for all of us and for the journey itself.

There is another trap, though. Too much research can easily become procrastination. It sounds mature and sensible, but underneath it all, it may just be fear delaying contact with reality. You can map every obstacle until the whole thing starts to feel impossible.

So that is where I am. I know more than I knew last week. I know I have preparation to do. I know we need to choose the next stretch with more care, more respect for the distance, and more awareness of what it asks of all of us.

I also know that if I wait until every obstacle has been researched, mapped, measured, discussed, and emotionally processed, I may still be sitting here this time next year with a very impressive plan and no story worth telling. At some point, the road has to become more than an idea. At some point, you prepare as best you can, gather your people, and begin.

This week’s journal prompt

What am I trying to know from the safety of the armchair that can only be learned on the road?

This week’s gentle practice

Make two short lists. First: “What I genuinely need to know before I begin.” Second: “What the road can teach me later.” Then take one small step from the first list and leave the second list alone for now.

Each Sunday, subscribers receive a short, gently challenging email designed to support their journey into what’s next. Whether you’re mid-pivot, post-burnout, or just feeling a subtle pull toward something more, this series offers grounded guidance without the fluff.

Every edition includes:

• A short, personal letter — something I’m thinking about, noticing, or grappling with

• A reflective journal prompt — not a to-do list item, but an invitation inward

• A gentle weekly practice — small enough to fit into your life, powerful enough to shift something

You won’t find hacks, hustle, or 10-step plans here. Just honest reflections and grounded nudges toward a second act that feels truly yours.

Because midlife isn’t the beginning of the end, it’s the end of pretending.

And what comes next might be your most meaningful chapter yet.

Second Act Sundays #44

One of the things I hear most often from people who have changed their relationship with alcohol is, “Why didn’t I do this years ago?”

I have said it myself. It usually comes after the fog has lifted a bit, after sleep has improved, after the mornings feel less like punishment and more like actual life, after the person has begun to feel some pride in themselves again. There is often a kind of disbelief in it. How could something that seemed so difficult, so tangled up in identity and routine and reward and social life, turn out to create so much freedom once they finally stepped away from it?

But I do not think that question should be used as a stick to beat ourselves with. “Why didn’t I do this years ago?” can easily become another form of self criticism, another way to look back and decide we were weak. I do not believe that is the truth. I think people change when enough of them is ready to change. Not when part of them knows, intellectually, that life might be better without the constant negotiation. Readiness is deeper than information. It is the moment when the benefit of choosing one path over another is not worth the cost.

There is an old saying, often described as a Chinese proverb, that the teacher appears when the student is ready. I love that, because the teacher is not always a wise person gently handing us a life lesson. Sometimes the teacher is exhaustion. Sometimes the teacher is another morning of regret. Sometimes it is noticing that the thing we once used to take the edge off just isn’t working.

And there is no surprise, really, that this often happens around midlife. By our 40s and 50s, and sometimes earlier, life has a way of bringing us to a stop. We may have carried on for years, doing what was expected, keeping things moving, performing competence, being useful, being sociable, being the version of ourselves that other people recognised. Then the old deal starts to feel expensive. We’re less willing to absorb the cost. The part of us that still wants a real life starts making more noise.

That moment is uncomfortable, but it can also be brilliant. There is something deeply positive about reaching the point where you say, “No. Enough of this shit.” That is NOT failure. That is life breaking through. It is the part of you that still believes there is more available than managing, recovering, regretting, repeating. It is the part of you that is no longer willing to abandon new possibilities for the sake of the old comfort.

So if you find yourself wondering why you did not do it years ago, perhaps the kinder and more useful answer is this: because you are ready now. And ready now is enough to begin.

This week’s journal prompt

Where in your life have you been waiting to feel fully ready, and what might “ready enough” look like this week?

This week’s gentle practice

Once a day, pause and ask:

What is one small thing I’m ready to stop carrying?

Then do one tiny thing that honours the answer.

Each Sunday, subscribers receive a short, gently challenging email designed to support their journey into what’s next. Whether you’re mid-pivot, post-burnout, or just feeling a subtle pull toward something more, this series offers grounded guidance without the fluff.

The Life Design Collective Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

The Life Design Collective Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

The Life Design Collective Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Every edition includes:

• A short, personal letter — something I’m thinking about, noticing, or grappling with

• A reflective journal prompt — not a to-do list item, but an invitation inward

• A gentle weekly practice — small enough to fit into your life, powerful enough to shift something

You won’t find hacks, hustle, or 10-step plans here. Just honest reflections and grounded nudges toward a second act that feels truly yours.

Because midlife isn’t the beginning of the end, it’s the end of pretending.

And what comes next might be your most meaningful chapter yet.

Second Act Sundays #43

This week, I spent time with people I am working with to create a coach training opportunity for people who have come through addiction. I will be leading the coach training side of it, and it connects deeply with something I have believed for a long time: lived experience is one of our greatest assets. Addiction is the doorway into this particular work, but the wider theme is adversity, struggle, recovery, rebuilding, and the wisdom that can grow from having to find your way through something difficult.

Real life teaches in ways theory cannot. Being knocked, questioning yourself, rebuilding, adapting, recovering, or beginning again after a hard chapter changes how you meet people. People who have come through great adversity often develop a particular relationship with change because they know how long it can take, how frustrating it can feel, and how much courage it takes.

I think this is why some of the shiny coaching culture leaves me cold. You know the type of thing: the certainty, the big promises, the carefully staged success story, the “spray and pray” approach where you DM a thousand people, push hard enough, and hope a handful eventually say yes. Fair play to whoever can operate that way, but it has never felt like me. To me, it’s about the quality of the conversation rather than the volume of the noise.

A person who has changed after years of feeling unable to change carries something incredibly powerful. Whether the struggle was grief, illness, shame, failure, exclusion, fear, burnout, heartbreak, trauma, or just feeling stuck, there is evidence in that person’s life that change is possible. That evidence gives them a belief they can hold for someone else who has lost sight of their own possibility.

Carl Rogers gave us the idea of unconditional positive regard, and its place in good coaching feels self-evident to me. Being met without judgment is powerful, especially when someone has spent years judging themselves. Lived experience can add a more authentic belief in the person’s ability to change. That belief comes from having been through struggle, finding a way forward, and knowing there was nothing magical about you. You changed as an ordinary human being, through effort, honesty, support, and repeated choices. That gives you a powerful belief to hold for someone else: if change became possible for me, it can become possible for you too.

This goes far beyond coaching. It can show up in friendship, family, community, leadership, or any honest human relationship. When you have been through your own struggle and found some kind of way forward, you may become better able to sit beside another person without rushing to fix them. You can see more in them than they can see in themselves right now. You can keep believing in their ability to find their way, without taking over, dragging them, or making their life about your answers.

That is the part of this that speaks to me most. A person goes through something hard, does the work of finding their way back to themselves, and maybe later realises that the experience they once wanted to hide has given them something real to offer.

They can sit beside someone who is struggling and believe in them without trying to rescue them. They can hold steady when the other person is full of doubt.

That is the gift inside lived experience: proof that change can happen in an ordinary human life, offered gently to someone who cannot yet believe it for themselves.

This week’s journal prompt

What have you lived through that gives you more faith in people than you might otherwise have had?

This week’s gentle practice

Listen to someone without preparing your answer while they speak.

I started drinking alcohol at 19. A late bloomer, I think you’ll agree.

I got my first job in IT at the age of 21.

Those 2 things, alcohol and my tech job, continued uninterrupted for 24 years, until I was 45.

That was when I quit booze, trained as a coach, and eventually began the journey of leaving corporate life to work as a professional coach.

None of it was instant.

None of it was planned really, and it certainly wasn’t neat.

But it changed everything.

I sometimes look back and realise how long I had been circling the edge of change before I actually took action. There were signs. There were questions. There were moments when I knew something in my life felt flat, even if I didn’t know what it was.

I did not wake up one morning with a perfect plan.

I started by get curious about what change might look like and asking myself some deep questions

That is really where The Second Act Blueprint came from.

Last spring, I created it as a small group course for people who want to take a proper look at their lives. People who are not falling apart, but who know something is asking for their attention.

Maybe something has shifted.

Maybe something has ended.

Maybe something is beginning.

Maybe life looks fine from the outside, but inside, there is a sense of, “I don’t want to just keep going like this.”

The next group will be the fifth cohort.

So far, it has been a very meaningful thing to run and witness.

The group is intentionally small, with a maximum of six people, because I want people to feel seen, heard, and properly supported.

Over the course, we look at where you are now, what has shaped you, what you may have outgrown, what still has energy for you, and what kind of next chapter you might want to begin creating.

But more than anything, it is a space to pause, reflect, and begin again with more honesty.

This may be for you if you have already made changes.

It may be for you if you are thinking about making changes.

It may be for you if you have that hard to ignore feeling that something in your life is asking for attention.

All the details are here

If it speaks to you, I’d love to chat.

xx

Gary

Each Sunday, subscribers receive a short, gently challenging email designed to support their journey into what’s next. Whether you’re mid-pivot, post-burnout, or just feeling a subtle pull toward something more, this series offers grounded guidance without the fluff.

The Life Design Collective Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

The Life Design Collective Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Every edition includes:

• A short, personal letter — something I’m thinking about, noticing, or grappling with

• A reflective journal prompt — not a to-do list item, but an invitation inward

• A gentle weekly practice — small enough to fit into your life, powerful enough to shift something

You won’t find hacks, hustle, or 10-step plans here. Just honest reflections and grounded nudges toward a second act that feels truly yours.

Because midlife isn’t the beginning of the end, it’s the end of pretending.

And what comes next might be your most meaningful chapter yet.

Second Act Sundays #42

This week has been a week of big and dramatic events, both around me and for me.

It started last Saturday evening when my cousin and I went to support our local rugby team, Connacht, in their final home game of the season. We had to win it, and thankfully, we did that with relative ease. It was also a chance to say goodbye to a couple of retiring players who had given their entire careers to the team. Everyone cheering and willing the team on, followed by everyone united in gratitude for the service of the retiring players. It struck me at the time that the experience was everything a sports club should be. Going hard into battle with the opposition but pausing at the end to recognise what was really important, the people.

On Sunday, the GAA Football Connacht Final took place. This isn’t a post about GAA, so I won’t go into it in detail (Google it, it’s worth it). Suffice to say, it is a uniquely Irish organisation for uniquely Irish games. The core of the GAA is that sense of place. You support where you're from, which differs from some other games like soccer.

I’m from Roscommon, and we were in the final (against Galway, where I live). Better still, it was at home and even better than that, we won!

It was a brilliant game. End-to-end from beginning to end. The scenes at the end were almost as good as the game. Pure, unfiltered joy. Thousands of people streaming onto the pitch. Hugging, crying, cheering. All of it.

When all of that died down, the party started in the streets. More joy, more smiles, this time aided by a pint or two.

I watched it at home with my Dad. A thing I know, I’m really fortunate to be able to do. Again, that sense of gratitude sat with me, and honestly, it’s still with me that I was able to experience that joy on the TV and at home.

On Tuesday, I hosted a webinar on “Thriving In Midlife”. A few people gathered online, listening to me talk about the path of change I’ve been on for the last 8 years. 8 years ago, I was a Software Developer. Everything was fine, but no more than fine. Now I’m a coach supporting people to change their relationship with alcohol and, by extension, the person they want to become. It doesn’t feel like a job, and I am so grateful to have found it.

The final two things that happened this week were that two podcasts I was a guest came out. On those, I got to share my journey from giving up alcohol in 2018 to today, where I support others to do exactly that.

On one of the podcasts, I kicked back against the power of gratitude. I more or less said it was cliched nonsense. I write this knowing that this past week has proved me absolutely wrong. I didn’t write down 3 things every day I was grateful for; I experienced it. I felt it, and let me tell you, if that’s the feeling you get from being grateful, I’m sold.

This week’s journal prompt

Where did gratitude become something you felt recently, rather than something you thought about?

This week’s gentle practice

Look through your photos from the past few weeks and choose one image that captures a feeling you want to remember.

Each Sunday, subscribers receive a short, gently challenging email designed to support your journey into what’s next. Whether you’re mid-pivot, post-burnout, or just feeling a subtle pull toward something more, this series is here to offer grounded guidance without the fluff.

The Life Design Collective Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Every edition includes:

• A short, personal letter — something I’m thinking about, noticing, or grappling with

• A reflective journal prompt — not a to-do list item, but an invitation inward

• A gentle weekly practice — small enough to fit into your life, powerful enough to shift something

You won’t find hacks, hustle, or 10-step plans here. Just honest reflections and grounded nudges toward a second act that feels truly yours.

Because midlife isn’t the beginning of the end, it’s the end of pretending.

And what comes next might just be your most meaningful chapter yet.

Second Act Sundays #41

Today’s newsletter is a little bit different. Usually, my ramblings are observations on whatever has stayed with me from the week just gone. This week, that’s still true, but in addition, I will be inviting you to explore the process of change in a webinar I will be running next week.

This is completely standalone, but I won’t pretend it is not by way of an introduction to the next cohort of my program, The Second Act Blueprint, which starts on May 26th. I won’t insult your intelligence by pretending I’m not trying to sell you something, I am, but more of that anon. I’m labouring the point because yesterday, I got an email from someone I’ve never met saying she was thinking about me and she was worried. But I need not be worried because for $297, she’d fix the problem. I will stop doing what I’m doing the day I become one of those people. Anyway, I digress.

When I quit booze in 2018 and started coaching around the same time, it was all shiny and new, and very exciting. Novelty was the order of the day. After a few months, though, it just became my life. I slowly took on the identity of a non-drinker and even more slowly took on the identity of a coach, well, a part-time one. A few years after that, alcohol had faded to complete irrelevance, and I had left my old career behind for full-time coaching.

It was only then that I looked in the rearview mirror and connected the dots, to paraphrase Steve Jobs. Fundamental changes had happened in my career, my health, physical and mental, my energy, and some of the people around me. That hit me like a ton of bricks, and I had to dig into it. The reason it fascinated me so much was that there was no “burning the boats” in the process; I hadn’t packed up and moved to Bali. I hadn’t moved at all, in fact. It took me 5 years to transition into full-time coaching; I hadn’t dumped all my friends. In fact, I gained dozens. I might not be too far off the mark to say that it was an enjoyable experience. That struck me as going against the popular narrative that to make fundamental, sustainable change, you have to take dramatic steps. That’s not how I did it. So how did I do it?

That’s what I spent the spring of 2025 thinking about.

Well, when I quit booze. I joined a platform that supported people to change their relationship with alcohol. This was very different from anything out there at the time. The core of this platform was a community. Everyone was on the same journey to change, supporting each other through successes and struggles in a non-judgmental way. This community underpinned my process of change, and I now believe a supportive community/collective to be one of the core elements of change

That community gave me room to explore the other core elements of my journey of change. Room to get honest about what I actually wanted my life to mean. Room to notice what was draining me and what was filling me up. Room to start trusting myself again, just enough to take the next small step. Room to figure out who I actually wanted around me, and to let some connections deepen while others fell away. Room to reclaim some of my time and start deciding, consciously, what deserved it. And eventually, room to believe that something genuinely different was possible.

None of that happened quickly. But looking back, those were the things that changed. And they changed because I finally had the space to let them.

Creating that space to explore these questions of what we want, where our energy is going, etc., is what led me to create my small group program “The Second Act Blueprint”. A 7-week space to explore what you want next, what needs to shift, and how to begin moving toward it.

It’s also exactly what we’ll give some space to next Tuesday evening. A free hour on Zoom - “How to Thrive in Midlife”. An honest look at what actually shifted, and how it might apply to wherever you are right now.

If you’d like to join me Register here, no boat burning needed.

This week’s journal prompt

Where in your life do you need more room to let change happen?

This week’s gentle practice

Choose one small thing this week that creates space for what you want next.
Ten minutes with a notebook. A conversation. A no. A walk. Keep it tiny.

Each Sunday, subscribers receive a short, gently challenging email designed to support your journey into what’s next. Whether you’re mid-pivot, post-burnout, or just feeling a subtle pull toward something more, this series is here to offer grounded guidance without the fluff.

The Life Design Collective Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

The Life Design Collective Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

The Life Design Collective Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

The Life Design Collective Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Every edition includes:

• A short, personal letter — something I’m thinking about, noticing, or grappling with

• A reflective journal prompt — not a to-do list item, but an invitation inward

• A gentle weekly practice — small enough to fit into your life, powerful enough to shift something

You won’t find hacks, hustle, or 10-step plans here. Just honest reflections and grounded nudges toward a second act that feels truly yours.

Because midlife isn’t the beginning of the end, it’s the end of pretending.



And what comes next might just be your most meaningful chapter yet.

Second Act Sundays #40

So it’s been quite the week for me here on Substack. I have 15% more people subscribed than I did this time last week.

It all started when I posted a note simply saying that I had posted 82 (this is 83) and still thought I was behind. That seemed to strike a chord, and the note went as “viral” as I’ve ever gone. We’re not talking Kim K numbers here; just over 100 people responded to the note in one way or another.

Why?

Well, four reasons, as far as I can tell, which I will detail below.

1. First and foremost, people were pleased for me. This is loosely connected to my theme a couple of weeks ago that people, generally, act with good intentions. People also generally like to see other people succeed when it’s done with genuine effort. I would like to believe I did that in publishing 82 articles here on Substack before today. We can all be cynical and dismissive on occasion; that’s human, but when it comes down to we like seeing each other win in the right way.

2. People recognise the results of persistence and consistency. We all start something from different places, but generally speaking, we start from scratch with any new endeavour. I started from scratch here 16 months ago. I think people recognised that this week, but from 2 different standpoints this week. The first are the people who are right at the start of the journey. Maybe they saw the possibilities in my note, and I would like to think they saw ordinary as well. It was nothing more than me showing up 82 times. Typing some sentences and pressing publish. The second standpoint is the people who’ve built something. Several times this week, I’ve had confirmation from people way, way ahead of me that this is how they did it. Simple and persistance and consistency.

3. Of course, that was just one note. What happened for the rest of the week was much more interesting to me and maybe more valuable. I put a lot of effort into posting more notes, commenting on people’s writing and supporting a few others in the same way people had supported me. I’ve done that before, but this time it had nothing to do with wanting to grow my audience on Substack. I just enjoyed supporting people and being interested in them. The thing I’ll take away from this piece is that when being consistent feels hard, there’s something to get curious about there. For me, it was that I wasn’t bringing a genuine interest in other people to the activity. Getting genuinely interested made things effortless.

4. The final piece goes back to the bit in my post about feeling behind. So many people recognised this. I think it’s entirely normal and entirely human. But behind what or who? The person who started 2 years ago? The person who posts 5 times per day and started 6 months back? The “behind” feeling comes from comparison. Roosevelt said, “Comparison is the thief of joy”. I used to buy into that wholeheartedly, but now I believe it to be only half true. If we use comparison to create a story about how shit we are at x, y or z, then Roosevelt was right. If we use it to learn and figure out the next best right move, then I think it has enormous value.

A 15% jump in subscribers is nice. But what I’m actually taking from this week is simpler: show up, mean it, and get curious about the people you meet along the way. The rest seems to sort itself out.

83 posts in. Still behind. Still here. That’s enough.

This week’s journal prompt

Where in your life right now does "behind" show up, and behind who, exactly? Can you name them?

This week’s gentle practice

This week, pick one person in your world, online or off, whose work or effort you genuinely admire. Tell them. Not to network, not to be seen doing it. Just because you mean it.