It’s remarkably easy to leave the office and build yourself a new set of chains.

You work from home.

You choose your own hours.

You tell yourself you’re lucky because you love what you do.

And then you spend 60 hours a week at a laptop.

Is that freedom?

If you’ve ever launched without a perfect plan and found yourself unsure if you’re still heading in the right direction, this story about a trail, a missing map, and a distant castle is for you.

Yesterday I went mountain biking at Kielder—with no map, no signal, and four hours before I had to get back to my dog.

The drive up to Kielder was spectacular. I was winding up and down hills, over blind summits, with these huge rolling landscapes opening up in front of me.

Every few minutes I was thinking:

Wow.

This couldn’t be any more beautiful.

Then I pulled up at the reservoir and genuinely felt like I’d stepped into another country. New Zealand, maybe. Giant lakes, rolling hills, enormous skies, a castle in the distance.

Spellbinding.

I went to hire a bike from next to Kielder Castle; the guy measured me up and handed me a brand-new Trek mountain bike.

“Do you have a map?” I asked.

He handed me one.

It didn’t show the cycle routes.

Excellent.

I’d scanned the route options online before I left for this great adventure, and ChatGPT confirmed that I could do a blue trail in the time I had. What I hadn’t established was whether there was one blue trail or several, how long they were, or where exactly they went.

And I had absolutely no phone signal.

So I stood at the start of a trail and thought:

Well... it’s blue.

Let’s just go.

And then it got hard.

Really hard.

Tiny winding bends. Steep descents. Huge hills.

Every so often I’d come across a sign basically asking:

ARE YOU SURE YOU’RE CAPABLE OF THIS?

Jesus.

Apparently I had selected the “beginners to intermediate” route, but I would describe it as “intermediate with occasional moments of questioning your entire life”.

At one point I was coming down a ridiculously steep hill, feathering the brakes as lightly as I could, while the back wheel was skidding around underneath me.

I was thinking:

Too hard.

Too hard.

What am I doing?

And then...

I screamed with delight.

Because I was flying down a hill through puddles, mud spraying up my back, all over my legs and even onto my face.

I screamed.

I shrieked.

I laughed.

I was completely filthy.

And I was having the absolute time of my life.

At one point, two hours into the ride, I reached what felt like the top of a mountain and suddenly saw the castle in the distance.

“CASTLE!”

I shouted, and went to pull over to take a photo.

Almost straight into another cyclist.

He was the only other cyclist I’d seen in two whole hours.

Eventually, I reached a point where two people were standing looking at a map.

I practically skidded to a halt.

“Do you know which way the castle is?”

They laughed.

“Yeah. You’re on the lake trail. Just keep going that way.”

“Oh, thank God.”

“Yeah... the signage isn’t that good.”

You’re not kidding.

We got chatting.

They’d moved up from Windsor to Newcastle and were exploring on their bikes too. I was debating whether I had time to go to the viaduct because I needed to get back for the dog.

“Go on,” they said. “You might as well.”

So I did.

And I’m so glad I did.

The views were breathtaking.

More rolling landscapes. More enormous skies. More moments of thinking:

I can’t believe this is real.

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Eventually I made it back, returned the bike on time, said goodbye to my new friends and drove home absolutely exhausted, covered in mud and feeling ridiculously happy.

And afterwards I realised something.

I had trusted myself.

Not because I knew what I was doing.

I didn’t.

I didn’t have the perfect map.

I didn’t know exactly where the trail would take me.

I didn’t know how difficult the next corner would be.

I didn’t know when I’d reach the end.

I simply knew that I’d picked a route I thought I could handle.

And then I trusted myself to deal with whatever came next.

That feels like a pretty good metaphor for where I am in life and business at the moment.

Because I’m realising that it’s bigger than trusting the process, your plan, or even the trail; it’s trusting yourself.

You will make big life-altering decisions every day as a founder, and then, what’s worse, you will question them every damn day.

Have I done the right thing?

Is this crazy?

Am I out of my mind?

Should I be doing more?

Should I be working harder?

When instead, I think we need to be asking a much more uncomfortable question:

What is the point of building a life with freedom if you don’t actually let yourself enjoy it?

Because that’s the thing about yesterday.

If I’d known exactly what was coming, I might have worried about it.

I might have decided the trail was too hard.

I might have spent another hour researching which route to take.

Instead, I picked blue.

And I went.

And along the way I met people who pointed me in the right direction.

I discovered views I hadn’t expected.

I got covered in mud.

I nearly fell off.

I screamed with delight.

And eventually, somehow, I ended up exactly where I needed to be.

Maybe that’s the lesson.

You just need to follow the trail.

And remember to look up occasionally.

Because there is a lot of beauty along the way.

And honestly?

If we’re not going to stop and enjoy it...

what are we building all this freedom for?

Caroline x

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P.S. If this landed, share it with one founder who needs to hear it today.

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P.P.S. Reply and tell me: where are you 'trusting the trail' right now—one turn you're choosing to take without a perfect map?

It’s the middle of August. A beautiful, gorgeous English summer day. 23 degrees, blue skies, the slightest breeze.

And I’m standing beside a lake in a bikini, about to climb into a sauna that is apparently already at 90 degrees.

I’m wondering what the hell I’ve got myself into.

The latest cold water therapy craze has arrived: hot sauna, cold plunge, repeat.

The setting is beautiful. A little black cabin sits beside the lake, with pretty steps leading down into the water. Trees hang over the edge, ducks are happily swimming around and quacking.

Although I do find myself wondering how much duck poo I’m about to get into.

I have flashbacks to open-water swimming when I was younger. The water is an almost electric green, and we’re reassured that it’s specially treated, so apparently this is going to be a very wholesome experience.

I take a deep breath and step into the sauna.

Within seconds, I realise I’ve forgotten to take off my necklace.

It’s burning into my neck.

Then my earrings.

They’re burning too.

I wrap them around my water bottle, leave them outside and bravely walk back in.

I take the corner spot at the back.

Big mistake.

Within seconds, the heat is wafting around the room and hitting my head. My scalp feels like it’s on fire.

“Wow. I don’t know if I can take this.”

One of the women kindly offers to swap places with me.

She’s wearing something I’d never seen before: a sauna hat. It looks rather like a tea cosy perched on her head.

“Does that help?”

“Oh yes. You lose 30% of the heat through your head.”

I’m thinking: I don’t want to keep more heat in. I want less.

But I swap places anyway.

There are six of us in the sauna, and as we start chatting, I discover that two of them are from Lithuania.

They are serious sauna people.

They come every Friday and Sunday. This is their special place. And they like this particular sauna because it’s the hot one.

“How hot?”

“It’s about 90 now.”

“Right.”

“But we like ours at 120.”

“120?”

They say it casually, as though we’re discussing the temperature of a cup of tea.

The young guy sitting next to me smiles.

“I think it’s time to add more water.”

He picks up the ladle and pours water over the hot coals.

Steam rises.

The temperature intensifies.

My eyes feel like they’re bleeding.

“That’s me.”

I bolt.

Straight out of the sauna and into the lake.

Three other people follow me and immediately plunge into the freezing water.

I take a more tentative approach.

One step.

Another.

Holding onto the rail.

“Oh my God, it’s freezing.”

Eventually I just have to take the plunge.

And yes.

It is very cold.

My toes start going numb.

So I haul myself out.

“Right. Back in.”

Round two.

This time we start talking more.

The Lithuanian couple beside me tells us how much they love their saunas.

The young guy explains that he’s a cyclist and he’s training for a race. He has a weigh-in the next day and needs to lose three kilos.

“Three kilos?”

Apparently, yes.

He’ll use rehydration salts afterwards.

His mum is there too, watching him with enormous pride. He’s going to race in Australia, and she and her husband are funding the bikes, the trip, everything.

He’s 19.

He’s completely focused.

He’s going for it.

And I find myself thinking: I can’t decide what’s more impressive – losing three kilos after one sauna or the fact this guy’s going pro.

Then he picks up the ladle again.

More water.

More heat.

More steam.

I’m out again.

A few minutes later, the Lithuanian guy decides the sauna isn’t hot enough.

He disappears outside.

We hear loud clanking and rustling coming from underneath our sauna cabin.

Then he comes back in.

“The guy should have been here half an hour ago. I’ve put more wood on.”

Chris and I look at each other.

Who exactly have we got ourselves into a sauna with?

Then another guy arrives, late because he’d been stuck in traffic.

He takes the corner spot I’d originally occupied.

Within seconds he’s looking deeply uncomfortable.

And once again, the ladle comes out.

More water.

More heat.

And this time the woman looks at me.

“You mustn’t run. You’ve got to bury your head down and stick it out.”

So I do.

I lower my head.

I stay.

And, eventually, it becomes more manageable.

I last a couple more minutes.

Then I’m back in the lake.

And this time I’m alone.

Everyone else is still in there.

They’re sticking it out.

And I’m standing in freezing water thinking:

Why?

What exactly are we trying to prove?

Why do we feel the need to make ourselves uncomfortable simply because we can?

Is there something inherently valuable about proving that you can tolerate more?

And I realise that this isn’t really about saunas.

It’s a question I keep coming back to in my own life.

Because ambitious people are very good at pushing.

We push through.

We work harder.

We say yes.

We stretch ourselves.

We take on the thing that scares us.

We prove we can do it.

And sometimes that’s exactly what we need to do.

Sometimes the discomfort is the doorway.

Sometimes you need to stay in the room a little longer.

Make the pitch.

Send the email.

Put yourself forward.

Get in the freezing lake.

But sometimes I wonder – are we confusing stretching ourselves with proving ourselves?

The sauna lady was delighted when I went back in.

“Well done. You managed not to run that time.”

And I did feel a tiny bit proud.

I had proved I could tolerate it.

But did I need to?

I’m still not sure.

One of the guys then said something interesting.

“When you get back in the water after you’ve let yourself get that hot, it’s not uncomfortable like before.”

So I thought:

Okay.

I’ll test the theory.

And on the final plunge, I went right out into the middle of the lake.

I let myself float.

And for a few seconds, it was actually wonderful.

The cold didn’t feel quite so brutal.

I’d earned the contrast. The reward. The feeling of I did it.

And then, about ten seconds later, I was absolutely freezing again.

“Okay. Time out. I’m done.”

And I laughed.

Because perhaps that’s the other thing.

So this week I’ve been thinking about that.

Not about doing less.

Not about staying safely inside my comfort zone.

But about getting better at asking myself:

Why am I doing this?

Am I curious?

Am I excited?

Am I growing?

Am I trying something new because I want to?

Or am I quietly trying to prove something?

This week, I’ve actually done a lot of things that were outside my standard MO.

I’ve put myself forward for opportunities without knowing exactly where they’ll lead.

I’ve explored new ideas without trying to secure a final result.

I’ve tried new experiences and not pushed myself until I hate them.

I’ve spent time with new people and enjoyed slowing down.

I’ve walked, climbed, explored and said yes to new things – and I’ve had a really lovely week.

Not because I’ve forced myself to achieve something or worried about slacking.

But because I’ve been interested in my own life.

And perhaps that’s the bit I’m taking with me.

There is a difference between challenging yourself because you want to discover what’s possible and challenging yourself because you need to prove you’re enough.

I’m increasingly interested in the first.

And much less interested in the second.

So, as I head off to Northumberland for two weeks of walking, hiking and exploring, I’m going to try something slightly different – and I’d like to invite you to try this too.

The Curiosity vs. Proof Test

Before you step into the fire, ask:

1. Why am I doing this? (Curious / Excited / Growing vs. Need to prove I’m enough)

2. What would “enough” look like here? (Specific outcome vs. vague endurance)

3. If I removed the need to impress, would I still do it? (Intrinsic vs. performative)

This week, pick one thing you’re about to push into. Run it through the test.
If it’s mostly proof, either redesign it (smaller, safer, more experimental) or choose a different challenge that feels more like discovery.

Because my realisation is that maybe making your mark isn’t always about stepping into the fire.

Sometimes it’s knowing when to step out.

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I’d just completed a meditation session with the practitioners at The Sanctuary on Koh Phangan.

I was lying on the sand, listening to the waves crash—drinking fresh coconut milk for the first time.

I felt totally and utterly chilled out.

Spacious.

Free.

An idea came to me like a thunderbolt. The kind of idea that makes you sit up and think: this could be something.

Earlier that day, one of the coaches had talked about her process:

Dream → Desire → Do.

First you dream it.

Then you build the desire until you genuinely want to do it.

Then—and only then—you act.

And I realised something uncomfortable.

I think I’ve always done it in reverse.

I’ve always been very good at making things happen.

Big dreams. Big career aspirations. Big financial goals. Big ideas about what my life could look like.

And when I wanted something, I went for it.

Hell for leather.

I figured things out. I adapted. I made it work.

But here’s the question I’ve started asking:

Just because I can make something happen, does that mean it will make me happy? Or will the cost be too great?

Because there’s a difference between I can and I want.

And I’m starting to think I’ve spent quite a lot of my life proving the first without spending enough time exploring the second.

What do I actually want my life to feel like?

The question that sent me somewhere unexpected

This week, I was asked a deceptively simple question:

“When you wake up two years from now, what’s happening?”

Not what have you achieved?

Not how much money are you making?

Not what does your business look like?

How do you wake up?

How do you feel?

That question sent me somewhere unexpected.

I thought about the happiest moments I’ve had over the last year.

Skydiving.

Mountain biking across huge suspension bridges.

Going to a festival on my own and meeting wonderful people.

Volunteering in Turkey, saving baby turtles.

And there was a pattern.

They weren’t necessarily the moments where I’d achieved something.

They were moments when I felt deeply connected.

Adventure. Learning. Novelty. Courage. Community.

Doing things that scared me. Being somewhere completely different. Feeling part of something.

And suddenly the question became much clearer:

How do I design a life that gives me more of that—and how does my business support it?

So this time, I don’t want to blindly launch myself into the next big thing simply because I can.

I’m noticing what happens when I don’t force it.

Letting the dream take shape.

Allowing the desire to build.

Exploring without immediately turning everything into a project.

Following the threads

Here’s what I’m doing now.

Not sitting around waiting for the perfect answer.

Exploring. Following threads.

I’ve started looking much more closely at what’s happening around me in North Yorkshire.

7am coffee raves with Rant & Ramble.

Beautiful historic venues and world-class hospitality at Grantley Hall.

Dance festivals with orchestras at places like Castle Howard through Ministry of Sound Classical.

Wellness, wild swimming and experiences that push you to your edge — including a spot in York I’m going to explore this week.

I’m noticing what catches my attention.

Where I feel curious.

Who I want to meet.

Where my existing skills might be useful.

And what I might discover that I haven’t even thought about yet.

I don’t know where any of these threads lead.

And that’s OK.

For once, I don’t need them to become something immediately.

I can just follow them.

I’m lit up by people who do interesting things.

And I’m noticing where I might discover something completely unexpected.

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What about you?

It’s easy to get caught up in the doing.

The next target. The next promotion. The next launch. The next house. The next number.

The next thing we’re supposed to want.

And there are good reasons for all of it.

Supporting your family. Creating security. Giving your children opportunities. Having the little luxuries. Building something you’re proud of.

But underneath all of that, I wonder:

What are you actually building your life for?

Who would you be around?

What would you be learning?

Where would you be?

And most importantly:

How would you feel?

I’m starting there.

Dream.

Build the desire.

Then do.

In that order.

If you’re a founder, coach, or creator who’s suddenly resistant to the very work you know matters, this is for you.

Here’s what’s likely happening—and how to move forward without forcing yourself.

This weekend in Belfast, one of my very good friends got me thinking about motivation when we started talking about the week ahead. I knew exactly what I needed to do, but, to put it simply, I didn’t want to do it.

The problem started when one of my scarily clever friends in tech gave me one particular thing that would help me revolutionise my business.

To build an AI agent.

I’ve mapped out the process. (with a lot of help from AI)

I know how to build it.

I know it would save me time.

And yet…

Every cell in my body is saying: please don’t make me sit at that computer and do that.

And I realised this is where many of us get stuck.

When old tools stop working

For a long time, I was exceptionally good at getting myself to do the work.

Set the goal, and (in the words of my darling ex-boyfriend) become a machine.

But I’m beginning to realise something:

What motivates us in one phase of our lives isn’t necessarily what motivates us in the next.

And more alarmingly: perhaps what got us to where we are isn’t what will get us where we’re going.

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Sometimes we keep reaching for the same tools because they worked before.

More discipline.

A bigger goal.

A tighter schedule.

More accountability.

Push harder.

Get up earlier.

Just get on with it.

And sometimes those things are exactly what we need.

But sometimes they aren’t.

Sometimes we’re trying to solve a new problem with an old version of ourselves.

And that’s where I think coaching becomes really interesting.

Because even though I’m a coach, I can’t always coach myself.

Sure, I can sit down and work through my thoughts.

Write the questions.

Challenge my own assumptions.

Make a plan.

But when you’re inside your own head, there are things you simply can’t see.

You can rationalise your resistance.

You can mistake fear for lack of motivation.

You can convince yourself you need a better strategy when actually what you really need is to think differently.

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The Question Behind the Resistance

You can keep trying to force yourself forward when the real question is…

Why don’t you want to go there anymore?

Or perhaps:

What would make you want to?

That is what good coaching gives you.

Not someone telling you what to do.

Not endless role play or being given homework for the sake of it.

It’s having someone outside your own head who can ask the question you haven’t thought to ask.

Someone who can help you find a different way of looking at the problem — and then help you turn that insight into momentum.

So, if you’ve read this far and felt that same dread — about the AI agent, or whatever your version of it is — maybe, just maybe, you’re trying to move forward using a version of yourself you’ve already outgrown.

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I’m still figuring out what that means for me.

But I’m pretty sure sitting in front of my laptop and telling myself to just bloody well get on with it isn’t the answer.

So, for now, I’m going to keep asking better questions. To get curious about what would make me excited to do the work. Because if the last seven years as a coach have taught me anything, the answer is never working harder; it’s getting clearer.

And definitely, to let someone else ask the questions ;)

I’ll be curious to know if any of this lands for anyone else, or if it’s just me. Drop me a comment below or hit reply and let me know what you’re resisting this week.

Caroline x

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Errr… HELL YES.

This is the woman whose book once made me sob on the floor as I realised how thoroughly I had abandoned my own desires to do what was expected. Her writing cracked me open to the cost of not living in integrity with myself.

So when I saw that Camino invitation, it wasn’t just a “nice opportunity” moment.

It was a full-body knowing: this is the kind of room I want to be in now.

The application was long and deliciously tricky.

You had to pitch yourself.
“Why you? There are only 30 spaces.”

Of course they did. This wasn’t just a brilliant piece of marketing for a paid experience; it was a doorway.

Filling in that application made something very clear:

This is how great marketing feels on the other side: like a genuine invitation, not a tactic.

And this is how magical building your business can feel when you start knocking on doors, even when there are no guarantees they will open.

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The mindset shift to make business development fun

I may or may not get one of those 30 spaces, but I am genuinely excited to put myself forward for opportunities that give me that feeling.

You know the one – the tingle of “what if…?” and “just imagine what could happen…”

So I sat down and asked a bigger question:

What if all business development could feel like that?

Not like slogging through follow-ups.
Not like forcing myself into another marketing strategy I secretly hate.

Because here’s the messy middle for any expert in their craft:

You know exactly what it takes.
And sometimes that’s the problem.

You stop wanting to do the thing you’re best at, simply because you know exactly what it costs.

My specialist skill, my craft if you will, is business development.
It’s built my whole career and business.
But it doesn’t always make me feel alive.

Every follow-up, every rejection, every “circling back” email – it’s not for the faint of heart.

And because I know what it takes to build from the ground up, I found myself thinking:

“If building this business means I have to do ALL that again… I don’t want to.”

That’s what the mind does: it reminds you of all the hard things, and you forget you have the ability to make each action infinitely more enjoyable.

So I started to play with different ideas:

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Years ago, I did an experiment

I went to five entrepreneurial events in two weeks. I didn’t send a single cold email.

Instead, I focused on being fully present in the rooms, on the train rides between them, and even in the friend’s house I was staying in.

I left that fortnight with five new clients: two from the events, one from a train conversation, and one from a referral over dinner at my friend’s. After that, my business grew on referrals for five years.

In the last two, I’ve intentionally worked with a handful of clients to create space for the kind of work – and life – I want next.

So when I talk about Caminos over funnels, this isn’t theory. It’s a reminder to myself that business development can be fun and an invitation for you to try something different too.

This is your permission slip

If you’re building a business — or simply wanting more opportunities that set your heart and life on fire — ignore the hacks for a moment.

Forget the “perfect funnel”.
Forget the “proven outreach template”.
Forget the rules about how you’re supposed to do it.

You don’t need another set of rules. You need to give yourself permission. Permission to start following the work and the rooms that feel like a full-body HELL YES.

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Over to you…

What makes your whole body say “HELL YES”?

Who are the people that inspire you and make you feel more like yourself?
What are the places where you feel most alive, most energised, most you?
What are the experiences you keep thinking about and then talking yourself out of?

And what if your next big opportunity could start there?

Because sometimes the most powerful business development question isn’t:

“Who should I pitch to?”

It’s:

“Where do I want to show up?”

If you’ve read this far, I’d love to hear from you:

Drop it in the comments.

Let’s collect a thread of full-body HELL YES ideas and see what doors they open.

Caroline x

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For the last few months, I haven’t written here—not because I had nothing to say, but possibly because I had too much.

I’ve been travelling, thinking, and re-evaluating what I actually want. Somewhere in the middle of that, I made an offer on a little home in North Yorkshire that I’m going to make my own.

That feels like quite a big deal.

Not just because of the house, but because of what it represents:

What does it actually mean to build a life you want to live?

For a long time, my answer was performance.

Doing more.
Achieving more.
Building the business.
Hitting the next goal.
Becoming better, faster, sharper.

And I still care about ambition. I still love big ideas. I still love working with people doing extraordinary things.

But I’m starting to think the goal isn’t just about doing your best.

It’s about building a life that actually fits you.

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Work that gives you energy, not just results.
People who expand your world, not just your network.
Ideas you want to follow, not ones you feel you “should” pursue.

I want to build a business that makes more room for that

Hikes on Thursdays.
Spin classes.
Time with family.
A home. A community.

Work that challenges me—without the constant pressure to prove, push, or perform.

Like sitting with a founder until we find the exact words for an idea they've been circling for months. That work still lights me up. It just doesn't need to come at the cost of everything else.

I’ll share what I’m learning—about building a business, making money, and communicating ideas that actually land.

And what I’m seeing in the founders I work with: people building, pitching, risking, and quietly asking better questions about the life they want alongside the business they’re growing.

I don’t have neat answers.

I’m increasingly suspicious of people who claim they do.

I’m much more interested in the messy middle and what comes next.

So this is me, asking that question in public again.

Welcome back.

I’m glad you’re here.

Not in the way you might think.

I don’t get addicted to smoking.
Or alcohol.
Or drugs.

I get addicted to the rush.

To the feeling.

To the moment when your body goes electric and the world narrows to a single pulse.

And I will chase it to the ends of the earth.

When I was 16, I fell in love for the first time.

With dancing.

With house music.

With the hedonistic, hypnotic rhythm of Ibiza.

I went there with friends that first summer.
And then I went back.
And back.
And back.

By 21, I wasn’t just visiting — I was working there as a dancer.

There is nothing quite like the moment the beat drops and your entire body surrenders to it. When you’re surrounded by friends, sweat-soaked, wild-eyed, completely alive. No past. No future. Just bass and breath and euphoria.

That feeling?
I chased it for years.

Fast forward.

Now I’m standing at 9,000 feet over Wanaka.

Heart pounding.
Door open.
Cold air slicing through the plane.

I’ve wanted this since I was 13, since watching Point Break and deciding that one day I would throw myself out of a plane just to feel that kind of freedom.

And then I did.

I have never been so excited to let go of control.

The drop is violent and silent at the same time.
Adrenaline detonates through your bloodstream.
Your skin tingles for hours afterwards.

And now?

I want to do it again.
And again.
And again.

I’m already Googling the safest places to skydive. Thailand is next. I’m checking travel routes. Watching the weather like a hawk.

If I love something, I don’t dabble.

I go all in.

I’ve done it with tennis — flying across countries for singles holidays, signing up for Friday night social sessions in London, moving my life around morning Italian lessons and afternoon sessions with a pro. Tournaments in the Caribbean. Chasing the edge of improvement.

When something grips me, I follow it wherever it leads.

And here’s the question that’s been circling me lately:

Why have I never felt that same electric pull toward my work?

It got me thinking, maybe burnout isn’t exhaustion.

Maybe it’s boredom.

Maybe it’s what happens when capable people stop stretching.

When we operate below our edge.

When we mistake safety for success.

Don’t get me wrong — I love what I do.

But what if work could feel like standing at the open door of a plane?

What if the start of your best endeavor yet felt like stepping into freefall?

What if building your next chapter wasn’t about safety — but about expansion?

I’m fascinated by what happens when you take yourself to the edge of your ability… and then step past it.

That’s the moment identity shifts.

That’s the moment confidence isn’t theoretical—it’s the real you.

So here’s the wild idea that’s forming:

What if I hosted mindset retreats where we face fear head-on?

Not metaphorically.

Literally.

What if we built a few days around courage, clarity, and expansion—culminating in a skydive?

A room full of high-performers who are ready to test their own ceiling.
Who want to feel alive again.
Who are ready to step into the best version of themselves.

Imagine the conversations the night before the jump.
The silence in the plane.
The laughter after landing.
The recalibration that follows when your nervous system realises:

“I am capable of so much more.”

This might be madness.

Or it might be magic.

Would you ever want to come with me and jump out of a plane?

If that sparks something in you, hit reply and tell me.

If enough of us are curious…

I just might build it.

Caroline x

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Twenty-five degrees.
Sun warming my skin.
A drink within reach.

I remember my head nodding forward and thinking, surely not now.

When I woke up, I panicked.

What did I miss?
How much of the match was gone?

And then—as I blinked awake and looked around—something quietly landed.

It wasn’t that I’d missed the match.

It was that there was nothing to miss in the way I’d imagined.

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The Australian Open had been on my bucket list for years.

And in many ways, it was brilliant.

You wander in at 11:30.
Ten minutes through the gates.
Deck chairs waiting.
Palm trees lining the courts.
Bands playing. Big screens everywhere.

It felt more like a festival than a sporting event.

There was no pressure.
No stress.
No urgency.

You could drift—from court to court, bar to bar, shade to sun.

At first, I loved it.

But as the day went on, something felt… flat.

People weren’t really watching the tennis.
They were there to be seen.

When the biggest match of the day came on—Alcaraz—I thought, this is it. This will change the energy.

So I settled in.

And that’s when, almost comically, I fell asleep.

When I woke, I didn’t feel embarrassed.

I felt clear.

There was no collective tension.
No held breath.
No, we are here for this.

People wandered in and out mid-rally.
Drinks in hand. Conversations flowing.

It wasn’t about devotion.

It was about having a nice day out.

And to be fair—that’s not wrong.

It’s lovely.

But it isn’t electric.

And that’s when Wimbledon came rushing back to me.

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Last summer, I went to Wimbledon alone.

Up at 5am.
Queuing in the dark with strangers who felt instantly familiar.

There was buzzing—not because it was comfortable, but because it mattered.

When the gates opened, we rushed in laughing, breathless.

Freebies galore.
Picnic blankets.
Non-alcoholic gin.
Deck chairs and games.

Then more queuing—the good kind.

The kind where people tell you who they’re hoping to see.
Where they’ve come from.
How long they’ve waited for this moment.

I ended up on the back row of a show court.

The players warmed up, casually hitting shots that made the crowd gasp.

The woman next to me grabbed my arm.

“Did you see that?!”

“I know!” I laughed. “Do you know who he is?!”

“We are so lucky to be here.”

We didn’t even exchange names. But we were grinning like idiots.

I remember it all vividly.

The effort didn’t drain the experience.

It ignited it.

And that’s when something deeper clicked. This realisation wasn’t really about tennis at all.

For the last few years, I’ve been working remotely. Online.

Watching people have breakthroughs that change the course of their lives.

It’s deeply rewarding. But it’s slow. Gentle. Sometimes it takes months—even years—to see the transformation.

I told myself I wanted that. A gentler pace. Sustainable work.

But last year in Malta, something shifted. I ran a two-day intensive training, and I watched someone transform in front of my eyes.

Someone who blended into the room at the start of the day…became someone who took the trophy by the end—the person everyone was talking about.

Fast. Dramatic. Extraordinary.

I now know transformation doesn’t have one speed.

Some change arrives quietly—layered, subtle, almost invisible until it’s irreversible.
And some arrive in a flash—a moment of courage, clarity, or conviction that changes the direction entirely.

Both matter.

And for me, it’s critical I have space for both rhythms in my life.
The slow becoming—and the moments that remind me I’m alive inside it. A life that doesn’t push me forward…but gently pulls.

So I’m curious.

What pulls you forward?

And where, if you’re honest, are you just having a “nice day out”—when what you really want is to feel electric again?

Caroline x

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Ancient. Vast. Humbling. It was also intense.

Twelve days of early mornings, five a.m. flights, and relentless movement from one end of the country to the other. The kind of journey that fills you with awe and drains every last drop of energy. I expected the highlights to come from temples or tombs. Or perhaps from my slightly unhinged experience on a sleeper train.

But the moment that stayed with me most didn’t arrive in the desert at all.

It came on the final day, inside the Egyptian modern art gallery, viewing work that made me ache with desire and awe and quiet recognition.

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Now, as I sit on another long journey—an eleven-hour train ride from Sydney to Melbourne—something curious is unfolding.

Messages are appearing from people I haven’t thought about in years.

Old connections resurfacing. Names rising gently back to the surface. Reminding me of a very different life I once led.

At the same time, I keep hearing the words of a client I’m working with—Alex—echoing in my mind.

When she speaks about why she created Rise & Radiate, from the importance of space. To the guidance to understand and reflect. Of stepping far enough away from daily life that you can finally hear what’s calling you.

She said people often come to her not because something is broken but because something inside them is waking up. A part that’s been quiet for a long time.

That landed deeply.

What’s usually missing isn’t courage or ambition. It’s space when life gets loud.

Space for the magic.

Space for serendipity.

Space for the deeper voice beneath the noise.

I’ve come to believe that the moment we stop forcing answers, the world around us finally softens.

And in that quiet, something gently begins to speak.

A version of you that was never abandoned—just temporarily packed away.

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Over twenty years ago, I used to sculpt.

I studied light, form, proportion, and how emotion lives in shadow and light.

Creativity wasn’t something I struggled with—too many ideas was.

There is no timeline on having the right idea, but there is forever a deep desire to speed up the process.

I’m chasing that feeling of finding my next big idea, because once you do, you feel your pulse catch fire, and you genuinely can’t think of anything else.

Like, when I decided I loved selling creative ideas.

Life gathered pace.

Responsibility. Momentum. Achievement.

Slowing down is not a strength of mine.

So when I arrived in Sydney, and my sister Lisa unexpectedly produced tickets to see Ron Mueck—a sculptor whose work I once studied deeply—something inside me shifted.

In the gallery, the air was so still I could hear the hum of the lights. Lisa leaned in, absorbed in his dark, mysterious world.

His figures are hyperreal, unsettling, and tender.

They show you what we want to believe—the composed surface, the careful exterior—and then, when you look closer, the uncomfortable truth beneath.

The vulnerability we hide. The reality we don’t want to admit.

I remembered that old studio smell—plaster and sweat—and something long-dormant flickered awake.

That same recognition I felt in Egypt.

I never wanted to be the one making art—not because the process isn’t beautiful, but because what thrills me is finding the idea itself. Even though for me, that is by far the hardest part.

And suddenly I wondered:

What is the artwork I am feeling called to create? — even if that artwork isn’t polystyrene, stone, clay, or paint, but vision, awareness, provocation, and possibility.

For the past few months, I thought my calling might be to find a co-founder. To launch a startup. To build something tangible.

Maybe that’s still true.

Or maybe my work is earlier in the process.

To sense what’s emerging. To name what needs attention.

To shine light where change is waiting.

I don’t yet know what form it’ll take—perhaps something environmental, perhaps something else entirely—but I can feel its edges.

As the train rolled on earlier today, the announcer’s voice cut through the carriage:

“Today is the International Day of Acceptance.”

I don’t know if that was intentional or a coincidence. But it stopped me.

Acceptance—not of where we’ve already arrived, but of where we are right now.

In between. Unfinished. Becoming.

Accepting that not everything needs to be clear yet.

That clarity often follows space, not effort.

Right now, I’m somewhere between cities. Between chapters. Between identities. With no Wi-Fi. No distractions. And more time to think than feels comfortable.

And perhaps that’s exactly the point.

I’m learning that what returns in the quiet is never random. It’s what’s been waiting patiently for us to notice.

So I’ll leave you with the question that’s been quietly travelling with me these past few weeks:

What part of you has been quiet for a long time?

And what might happen if you didn’t rush to define it—but simply gave it room to breathe?

Maybe that’s where change begins.

Drop a ❤️ if this resonated, and let me know in the comments—what’s the part of you that’s been waiting?

Caroline x

P.S. If this idea of creating space to listen again speaks to you, Alex’s next Rise & Radiate session might be exactly the environment you need.

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Not a polite nausea. This was violent, imminent, amplified by every jolt of the rattling Egyptian sleeper train.

Top bunk. Roommate passed out below. No escape.

I grabbed my phone and messaged Cliff: Can I crash in your lower bunk?

Sure, he texts back. Hesitant, but yes.

Except: Egypt. Muslim country. Unmarried woman in a stranger’s cabin? Strictly forbidden.

12 hours earlier…

Cairo’s shiny new station gleamed like a mirage—vast pillars, polished floors reflecting sunset gold. Our guide grinned: “Leave expectations at the door. Only way to love Egypt.”

The train that pulled onto the platform moments later made his point crystal clear.

Ancient. Dusty. Clanging like a relic.

I’d accepted the top bunk without thinking. Why would it matter? Top bunk, bottom bunk—one of those inconsequential decisions you make in passing.

I couldn’t see the downside yet.

We settled into our cabin. The guard came round with a special key to lower the bunks. Metal clanked. The ladder unfolded. My roommate climbed into the lower bed and was asleep within minutes.

Me? I have a talkative evening ahead of me.

Cliff—a British traveller from my group, an elderly gentleman, and a Cayman Islands startup investor—had texted inviting me to join him for a bottle of red wine. He was curious about my work with founders. I was more curious about why someone chooses to live where he does.

Conversation flowed. Another traveler, Rebecca, joined us. She told us about nearly being arrested for drug trafficking in Goa because of her ex-boyfriend’s baggage—literal and otherwise.

Then Cliff smiled and said, “I can top that. I was once accused of murder.”

Rebecca and I froze, glasses halfway to our mouths.

He’d been sixteen, in France, when twelve people were killed and a murderer was on the loose. Wanting to help, he’d offered information to the police—and found himself their prime suspect.

The story unfolded. Eyes widened. Laughter followed. Cliff had a killer punchline, of course, but we were also laughing because there’s something disarming about strangers telling the truth when there’s nothing to prove.

Eventually, we drifted back to our cabins.

I climbed the ladder to the top bunk, lay down, and immediately knew I’d made a mistake.

The room felt smaller than before. Darker. The motion of the train intensified—my body swaying in ways my mind couldn’t override. The wine didn’t help. That quiet certainty arrived, the one you don’t argue with.

If I stayed here, I’d be violently sick.

This wasn’t discomfort I could think my way out of.

I texted Cliff. “You still awake? Got a favour to ask”.

He agreed, though somewhat reluctantly. But I still needed the guard—only he could lower the bunk.

I pulled on trainers over my pyjamas and walked the length of the train, crossing between carriages where you can see the tracks rushing beneath you. By the time I reached the final carriage, my “I have a plan” confidence had completely evaporated.

Inside, five men sat smoking, eating, and talking loudly.

I explained I was unwell. Asked if there was another lower bunk available.

No. The train was full.

I explained about my friend. The guard checked his list. Looked up.

“Is he a man?”

“Yes.”

“Are you married?”

In Egypt, a Muslim country, sleeping in another man’s cabin if you’re unmarried isn’t acceptable.

Somewhere between pleading and humility, I stopped trying to sound reasonable and simply told the truth. If I stayed where I was, I would be sick. My roommate was already unconscious. I needed help.

The guard paused. Studied me. Then nodded.

He walked me back to the cabin, unlocked the mechanism, lowered the bunk, and left without ceremony.

That night, I slept—thanks to a man who’d once been accused of murder, a guard who bent the rules, and a willingness to stop insisting that things should make sense.

The next morning, I woke as the sun rose over the desert, the train carrying us south to Aswan. I felt oddly calm.

Egypt has a saying: Inshallah. God willing. It’s not optimism or pessimism. It’s acceptance that some situations are not good, not bad—just what is.

This week has reminded me how much energy we waste negotiating with reality—especially when we’re out of familiar territory.

New positions. Novel cultures. Fresh chapters.

We arrive with expectations and experience, only to find that neither gives us control.

Sometimes the most capable thing you can do is leave your expectations at the door—and respond to what’s actually in front of you.

Last week, I wrote about why Egypt isn’t a place I could easily navigate alone. You can read that here.

This week, I’m learning that navigating the unexpected, like travel, becomes lighter when you stop bracing for outcomes and start trusting the journey to meet you where you are.

What’s a time you had to let go of expectations and trust a stranger?

Drop a ❤️ if you liked this story, and let me know in the comments if you’ve ever felt out of control in unfamiliar territory—I’d love to hear your story too.

Caroline x

P.S. Names have been changed for privacy, but the gratitude is real. To the guard and my fellow travelers—thank you.

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I’m sitting in a beautiful restaurant in a wonderful hotel overlooking the Nile. The sun is warm on my skin. A waiter refills my glass. This is exactly the scene I imagined when I booked the trip.

And here’s the thing: I’m enjoying it, just not in the way I expected.

Not in the “solo travel, this is so empowering!” Instagram way. But in a quieter, slower way that’s teaching me something I didn’t know I needed to learn.

It started well.
On the York train to Manchester Airport at seven in the morning, with minus five degrees outside, I met an Egyptian man heading to Jerusalem.

When I told him I was going to Cairo, his face lit up. He insisted on connecting me with his best friend there. “You’ll have so much fun,” he said. It felt like a sign.

I have friends who’ve lived in Egypt. They love it. Their stories gave me the confidence to take the leap: my organised tour didn’t start until the 7th, so why not go early?
Get some sun. Explore Cairo solo for a few days. I’ve travelled alone before. Why not?

The flight was chaos—a three-hour delay, barely any air conditioning, and the kind of journey that frays your nerves before you’ve even arrived. I’m talking about a man with a suitcase he wasn’t sure was his and an attendant refusing entry to another man as the flight was full and his luggage was not even on this plane! Sorry, what? Oh, and don’t get me started on the HEAT. The whole flight—red-faced, wondering if it would ever end.

By the time I landed, my baggage was missing, and so was the luggage of five others. Thank god someone had put those apple tags in theirs and knew they were somewhere in the airport. Mental note: Buy Apple tags.

When my luggage finally came to me, I fought through the crowds of taxi drivers and made it to my hotel at 2 a.m.; I’d been awake for twenty hours.

The room was beautiful.

The bed was like concrete.

I didn’t sleep.

The first full day was a fog of exhaustion.

A friend with an injury kindly took me to lunch at a stunning spot in New Giza, pyramids rising in the distance. It was exactly what I needed. Then I went back to the hotel and slept for six hours.

The next day, I tried to do what solo travelers do. I took the metro. I followed recommendations to the old town. Within twenty minutes, I realised this wasn’t going to work the way I’d imagined.

Men stared. One stopped me to question where I was going.

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The streets were chaotic—traffic, noise, and the overwhelming sensory reality of a place I didn’t understand yet.

When I reached the souk, I saw what everyone else had done: coaches, guides, and groups moving together. No one was navigating this alone the way I was trying to.

That’s when it hit me: just because I can do something alone doesn’t mean I should.

At least not right now. Not like this.

Here’s what I’ve learned in the days since:

Sometimes you don’t know until you try.

I could have researched Cairo for months. Read every blog post, watched every video, and asked every friend who’d been here. And I still wouldn’t have known what it actually felt like to be here alone until I arrived.

Would I have made a different choice if I’d known? Probably.

I might have skipped the solo days and just arrived when my tour started. But I also might have talked myself out of the whole trip — paralysed by trying to know everything before taking the leap.

There’s a balance, isn’t there? Between doing your homework and overthinking yourself into inaction.

It’s okay to slow down.

I’ve spent the last few days finding a different rhythm.

Not trying to tick off sights or prove I can navigate like a local. Just… existing here.

Walking along the river (after buying a ticket 25 Egyptian pounds, which is around 40p—you can’t just wander freely, something I have taken for granted in Europe).

Sitting in parks. (also ticketed by a few pence—cash really is essential here) Watching the sun on the water.

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Every time I get in a car, my nervous system lights up. The driving here is absolutely wild.

The Uber I took home tonight had me gripping the door handle the entire way. But I’m learning that not every moment has to feel comfortable to be okay.

This is just a moment.

In two days, my tour starts. There will be structure, guides, and a group. It will feel completely different. And I’ll probably love it.

But these solo days aren’t a mistake. They’re just… teaching me something different than I expected. Not “you can do anything!” but “it’s okay to figure out your limits in real time.”

So what’s the takeaway here?

Do some research. Not so much that you never leave the house, but enough that you’re not completely blindsided. Ask people who’ve actually been there. Not just “is it amazing?” but “what was hard? What surprised you? What do you wish you’d known?”

Trust your gut. If something feels off — whether that’s a situation, a neighbourhood, or just your energy level — listen to that. You’re not being weak. You’re being wise.

Adjust as you go. My plan didn’t work the way I imagined. So I slowed down. I found quieter ways to be here. I stopped trying to perform “successful solo travel” and started just… being present with what actually is.

Your experience might be different. Some of my friends adore Egypt. They feel completely at home here. Maybe it’s me. Maybe it’s the timing. Maybe it’s just that what works for one person doesn’t work for another, and that’s okay.

The sunshine is still warm. The Nile is still beautiful. I’m still here.

Just moving a little slower than I planned. And learning that sometimes that’s exactly what you need.

What about you? Have you ever jumped into something that turned out differently than expected? How did you adjust? I’d love to hear your stories — the messy, imperfect ones where you figured it out as you went.​​​​​​​​​​​​​​​​

In my experience it’s often the fastest way to learn and the most memorable. Drop me a ❤️ or comment below if this resonated and sparked a memory for you.

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You know that feeling when your year looks incredible from the outside—but inside, you’re still quietly asking, “Is this actually my life… and do I want it?”

That was my 2025.

Planes, stages, new cities, familiar faces.
It looked like a highlight reel.
It felt like a plot twist.

Amid all the movement, 3 lessons landed hard—ones you can use whether you’re travelling the world or just wondering what’s next from your kitchen table.

Lesson 1: Test-Drive Your “Dream Life”

Whatever you imagine as a dream life—go and test it.
Not in your head, not on a vision board, but in real life.

Book the flight.
Work from the city you can’t stop thinking about.
Try the version of your business you keep talking yourself out of.

When you layer those experiments with everything you already know about yourself—your energy, your values, your patterns—the answer doesn’t arrive as a neat pros and cons list.
It hits like a thunderbolt: Yes, more of this or No, this isn’t it.

You don’t find clarity by thinking harder.
You find it by living the question.

Lesson 2: Walk It Out, Write It Down

This year moved fast.
Faster than my inbox, faster than my plans, faster than my nervous system at times.

What kept me sane?
Creative walks and getting the words out of my head.

A walk—no podcast, no call, just you and your thoughts—gives your brain space to catch up with your life.
And when you write about it—a journal entry, a blog post, a scrappy note in your phone—you turn experience into insight.

You give yourself a record of who you’re becoming.
You give other people something they can recognise themselves in.
And maybe one day, if you keep going, the world gets to read the book you didn’t know you were already writing.

Movement clears the fog.
Writing turns what you learn into a gift.

Lesson 3: Use Your Gifts, Go Slowly

Figuring out how to use your gifts to make a difference in the world is time well spent.
It doesn’t have to be fast. In fact, the best things in life rarely are.

We live in a culture obsessed with speed: next launch, next pivot, next milestone.
But the dolce vita—the sweet life—isn’t about doing more. It’s about doing what actually lights you up, slowly enough to feel it.

That might mean:

• Serving fewer clients, more deeply.

• Saying no to “shoulds” that look impressive but feel dead.

• Making time to explore what becomes possible when you stop performing and start following your real desires.

You are allowed to build a life and business that feel good on the inside, not just impressive on the outside.
You are allowed to enjoy the process.

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A Question for You

So as you look back on your own year and ahead to the next one, ask yourself:

• What’s one part of your “dream life” you’re willing to test-drive in real life?

• What tiny ritual—walks, writing, or something else—could help you process it?

• And where could you slow down, just enough, to let your real gifts lead?

Hit reply or drop a comment and tell me:

What’s the experiment you’re going to run next year—for more of the life you actually want?

Here’s to a bigger, bolder, and braver 2026!

Until then, have a very Merry Christmas and a Happy New Year.
Caroline x

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If busyness were an Olympic sport, you’d be on the podium this week.

You’re doing a hundred things well—and still feeling behind.

End‑of‑year deadlines. Leadership decisions. Family logistics. The quiet pressure to also be reflective, grateful, strategic, and somehow full of festive cheer.

Instead, your brain is hosting strategy meetings at 3am, rehearsing conversations that haven’t happened yet, while the to‑do list breeds overnight.

Here’s the thing no one tells leaders:

The problem isn’t the endless juggle. It’s thinking you’re failing because of it.

You’re not.

You’re moving fast—with a lot at stake—and December amplifies everything.

December Wants You Reactive. The Bigger Game Is Staying Visionary.

Right now you have two options:

• White-knuckle your way through December like every other year

• Or make a couple of small shifts that protect your energy and your ambition

A confession (so you don’t feel like it’s just you)

I finally did it. I booked the big adventure—the trip I’ve been dreaming about for years: Egypt, Australia, New Zealand, and Thailand.

This is supposed to be the trip of a lifetime. The freedom I’ve been working towards. The reward for building a business that supports the life I actually want to live.

So why does the to-do list feel like it’s wrapping around me so tight I can barely breathe?

Travel vaccines.
Client progression planning.
Tax admin.
Insurance quotes that would make anyone wince.
Spreadsheets open at midnight.
Medical appointments booked like standing meetings.

And the question that won’t leave me alone:
Why do we always need another holiday to recover from preparing for a holiday?

Maybe you’re working to your own deadline. Maybe Christmas Day is it. Maybe earlier. Maybe later, like me.

Different context. Same nervous system reaction.

The irony isn’t lost on me: I’m a coach known for helping leaders achieve focus—and here I am, consumed by busyness, juggling a million details, ticking off the days, instead of enjoying the journey.

Sound familiar?

The paradox no one warns you about

You know what to do. You’ve taught other people what to do. You have the tools.

And yet—when life accelerates—those tools stay neatly unused in the drawer.

Until 3am hits. Until the mental list starts looping. Until your body says, Enough.

That’s not a discipline problem. It’s a pace problem.

And this is where most high-performers get it wrong:

We try to stop the busyness.

Good news—you don’t need to.

In fact, the answer is completely counterintuitive.

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Ask Bigger Questions—Not Harder Ones

Before January ambushes you, pause now and ask:

• Who do I want to be next year?

• Which clients do I want more of?

• Where do I do my best thinking?

• What environment actually supports my performance?

Hold the long view while you deal with the immediate demands.

Your brain is always scanning for direction.

Give it something worth scanning for.

How to Keep the Vision Active (When December Gets Loud)

This week, despite the chaos of pre-travel prep, I pitched two opportunities for March and April that support my goal to travel more while working. Nothing dramatic. Just quiet, intentional moves that strengthen next year.

And suddenly?

The endless to-do list reorganized itself into now / later / irrelevant.

Want that too? Grab your pen and paper and give yourself the gift of 3 minutes.

1. Weekly strategic check-in (3 minutes, no fluff)

Before every weekend, ask yourself:

• What did I do this week that genuinely moved my goals forward?
• What got in the way?
• What needs to change next week?

You don’t need answers to every problem.

You just need the goal you actually want in your line of sight.

In my experience—and with the leaders I coach—when you move the big pieces, the small stuff gets quieter.

2. Before every key decision—breathe like it’s part of your job (because it is)

Before sleep.
Before opening your laptop.
Before replying to the email you really want to fire off.

Take 4 slow, intentional breaths. Inhale for 4 counts, exhale for 4 counts.

Slow breathing isn’t a wellness add‑on. It’s a cognitive reset.

It’s the fastest way to tell your nervous system: We’re not being chased. We’re choosing.

If you’re triple‑checking Slack before bed or mentally rewriting emails at 2am, your nervous system is stuck in execution mode when it could be in strategic mode.

One minute of intentional breathing changes the gear.

Final thought (the one I want you to hear)

You don’t need to be calmer.
You don’t need more discipline.
You don’t need to “get through” December.

You need one big, compelling idea in your mind—and two simple practices that keep you aligned with it—while everything else moves.

That’s what winning against December looks like.

Caroline x

P.S. What’s the big idea you want to hold steady into 2026—the one that makes the noise worth it?

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That question hit me last week in Florence, when I learnt about Anna Maria Luisa de’ Medici — the last of the Medici line. She couldn’t rule. She had no heirs, so her line ended with her. But before she died, she made one extraordinary move.

She gifted the entire Medici art collection—centuries of beauty, power, and identity—to the people of Florence. Not to the crown. To the city.

With one condition in her will: the art could never leave Florence. It would always belong to its people.

That decision changed history.

A woman denied power found a way to leave a legacy that outlasted rulers. She couldn’t rule—but she could reshape what remained.

For days I couldn’t shake her story.

Maybe because this year, I’ve been provoked to give my work and life a bigger why, a bigger stage, to really show myself what I am capable of.

It all started this time last year, when I stood at the top of the Shard and was named one of the top four business strategists in the UK—a surreal, pinch‑me moment.

My client Tara stood beside me—she’d done the deep work of transforming from someone buried under pressure to someone thriving with purpose.

When the winner of the public vote was announced, it wasn’t me.

Tara saw my shoulders sag for a split second, and as I started to clap, she turned me around and said,

“Caroline, you’ve already won—you’ve changed my life.”

Those words went straight into my heart. But I didn’t get it yet. Not fully.

I spent the next year chasing proof.

I built programs, took stages, and formed partnerships. I said yes to opportunities I thought would prove I’d ‘made it’—convinced that legacy meant scale.

More people on my list. More stages with my name on them. More proof I was worth the trophy I didn’t win.

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Until last week.

After spending the day in Florence with another long-term client, Alex, she wrote to her community about what our work together had unlocked. She said:

I read it alone on my laptop. No applause. No stage. Just her words on a screen.

And I felt more seen than I did at the top of the Shard.

That’s when the Medici story clicked.

Impact isn’t about how high you climb—it’s about how deeply you reach.

Anna Maria Luisa de’ Medici couldn’t take the throne, but she carved a legacy into the fabric of humanity through the people and culture she chose to empower.

That’s what I want to build.

Work that outlasts a crowning moment.
Transformations that echo long after.
A body of work that gives people back to themselves.

Because happiness at work isn’t frivolous. It’s foundational.

And meaning isn’t built in moments of recognition—it’s built in the quiet transformations.

What if your legacy isn’t the thing you build—but the people who become braver because you existed?”

One year later, I finally feel it. Legacy isn’t the trophies or titles. It’s the people who say, ‘You changed my life,’ and mean it long after the applause fades.

And I wonder if you feel it too?

That nagging sense that the metrics you’re chasing—revenue, exits, awards—aren’t actually measuring the thing that matters.

That maybe the people you’ve quietly changed along the way—your team, your clients, the people you’ve mentored—are the real legacy.

But no one’s clapping for that. No one’s giving you a trophy for it.

So you keep chasing the next milestone, the next proof point, and the next ‘I made it’ moment.

What if you’ve already won—you just don’t know how to see it?

So I’ll ask you: What are you chasing that you think equals winning—and what if you’re wrong?

If that question is stirring something in you—if you’re ready to redefine what winning means and build a legacy that feels true—reply to this email and let’s explore what’s next.

Here’s to the next chapter—and to playing much, much bigger. ✨

Caroline x

P.S. If this week’s story resonated, forward it to someone who’s been questioning their own definition of winning. Or drop a ❤️ in the comments—your support helps more people find this story.

You know you want 2026 to be bigger, better, and bolder.

Me too.

But here’s the question that’s been keeping you up: Do you keep doing what you’ve always done, or do you start taking your own advice and behaving like the person you most want to be?

Three weeks ago, I made the biggest decision of my life.

I decided I was going to travel the world.

Not a “quick reset in Greece” kind of trip. A “close the chapter and choose myself again” kind of decision. My once-in-a-lifetime reward for what I’ve built. My reset before the next wave begins.

I thought clarity would rush in as soon as I gave myself permission.

It didn’t.

That’s when I learnt something every founder eventually discovers:

The big decision is easy. It’s the micro-decisions that expose who you really are.

Visa rules.
Budgets.
Tax years.
How long can I pause operations?
How soon do I ramp them back up?
Is two months too short?
Is six months too long?
A year?

When you finally choose the leap, that’s when the real work begins.

You need to close things down, sever ties, and say goodbye to the old version of you. Last week it was clothes. This week it was friends and a quiet questioning – am I really going to do this?

So when a friend texted: “Come to Rome this weekend — let’s have some fun,” I booked a Black Friday flight in under 90 seconds.

That spontaneous “yes” became the beginning of a chain reaction that taught me more about strategy than any whiteboard session ever has.

The €11 Bus That Called My Bluff

Someone asked me recently how I make decisions.

I didn’t realize it until I said it out loud:

I make decisions based on value, not comfort. If it feels expansive, I go.

So when I considered stepping back into travel mode, I suddenly thought, ‘What else could I get out of this trip?’

Seeing one of my long-term clients in Florence - hell yes!

Exploring a city I’d only ever skimmed past and then a long-held longing rose up: Siena.

It had been on my list for years — the “one day” city. The “not now” city. The “after the next project” city.

This time? €11 on a bus (faster than the train). Bargain!

So I got up early, caught the 10am bus, and arrived in the sun-soaked square I’ve seen in films and photos a thousand times — especially that James Bond one where he sprints impossibly across steep angles and cobblestones like his ankles aren’t made of bone.

I sat opposite the piazza, Christmas market huts under construction, drills screaming in the background, sipping a beer in the winter sun… and realized:

I couldn’t walk on the square.

The one place I’d dreamt of seeing — the place that has baffled my mum and me for years (”How do horses gallop on that?!”) — and the barriers said: Not today.

Close, yet so far. Not perfect. But real.

And maybe that’s the point.

Think about your last product launch. The one that looked flawless in the deck but required three pivots in the first month. Or the hire who checked every box on paper but wasn’t the culture fit you needed. Or the strategic partnership that made perfect sense until you actually tried to execute it.

The gap between vision and reality isn’t a failure. It’s data.

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The Florence Hobbit House & the Death of the Fantasy

Of course, this entire adventure is stitched together with decisions made “in the moment”. So when I booked my Airbnb in Florence, I chose the one thing I always choose: the absolute centre.

And what I found was a tiny historical apartment with its own rooftop terrace — the kind of terrace that makes you fall in love with life all over again. A view that feels like stepping inside a Renaissance painting.

It was beyond stunning.

But also: it was a Hobbit house.

No central heating. Freezing stone floors. Doorways that required me to fold myself in half just to get into the bathroom.

The distance between my foot and the basin when I closed the toilet door? Exactly the pitch of a Ryanair seat — meaning, none at all.

Standing upright? Optional.
Gymnastics? Required.
Dignity? Left outside with the luggage.

The thing is… this is what I secretly love.

This is the part of travel everyone forgets. The part entrepreneurship mirrors:

It’s never as clean, elegant, or polished as the fantasy.

It’s always messy.
Always surprising.
Always a little ridiculous.

But that’s where the truth is.

Because while freezing in that hobbit bathroom, I realised something:

I don’t want cold European winter escapes anymore.

Not the bone-deep humidity. Not the laughably tiny rooms. Not the romanticised version of Italy that lives only in my memory.

What I want is real holidays, clarity, space, and light — organised by a pro (thanks Jenny), not left to my impulsive whims that are only okay when you’re young and just don’t care.

Letting go of the fantasy made room for what I actually desire.

A team around me. People planning better than I can and working to build something that gives me a life full of freedom and adventure.

And that is the entire point of action: It shows you what you want by eliminating what you don’t.

Because clarity doesn’t come from sitting still. It comes from moving.

Three Things I’m Doing Differently (Because I Froze in a Hobbit House).

1. I’m letting experts handle what they do best.

My next trip — the big one, the once-in-a-lifetime reset before I build my own fast-growing startup in 2026 — is being planned by professionals. Not by me at 2am scrolling through Airbnb with a glass of wine and a vibe. I’m done with DIY when it comes to rest. If I want this trip to actually prepare me for what’s next, I need to trust people who are better at this than I am.

Monday action: Identify one area of your business or life where you’re still playing amateur because you think you “should” be able to do it yourself. Hire it out.

2. I’m choosing quality time over romantic fantasies.

Seeing my client in Florence, catching up with my friends in Rome — those moments filled me with deep satisfaction. Not because Italy is magical, but because people are what matter. I don’t need to live in Italy to keep that connection. I simply need to return for focused, intentional time with the people who’ve helped me on my journey and who I’ve helped in return.

Monday action: Look at your calendar for Q1. Where are you spreading yourself thin trying to be everywhere? What would change if you chose three deep connections over ten shallow ones?

3. I’m building like a co-founder, not a solo operator.

I know in my (currently chilled) bones that I want to find my co-founders and build my own fast-growing startup. Not solely have a lifestyle business. That means I stop doing things on my own and accept help in all areas of my life where I need it. I lean hard into trusting others and trusting myself to figure it out. I want to be a co-founder working with experts in their field so I can thrive in mine.

Monday action: Write down the version of yourself you most want to be in 2026. Now ask: what is that person doing today that you’re not? Start there.

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The piazza in Siena was closed. The Hobbit house was freezing. The trip wasn’t what I’d imagined.

And that’s exactly why it worked.

Your next imperfect decision won’t look like the deck you pitched yourself. It won’t feel as smooth as you hoped. But it will show you what you actually need, not what you thought you wanted.

And in 2026, when you’re building something bigger, better, and bolder, you’ll look back at this moment — the one where you stopped perfecting and started moving — as the turning point.

So what’s your €11 bus? What’s the decision that feels small but expansive?

Book it. Take it. Let it teach you.

The fantasy is dead. The real work is just beginning.

Caroline x

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This week whilst going over my itinerary with my personal travel agent, past client and friend, Jenny Hendron, I realised something painful:

I can’t take my old life — or my old wardrobe — with me.

Not metaphorically.

Literally.

I opened my cupboards, and everything in them felt wrong.

Beautiful, yes.
Well-made, yes.
Pieces I’ve loved… absolutely.

But not right for this next chapter.

Not for a woman who needs to carry her life lightly.
Especially not for someone whose joints, bones, and back refuse to lug half a life around the planet.

Suddenly the question wasn’t just:

Backpack or trolley dolly? (It’s trolley dolly. Obviously.)

It was:

Who am I now?

And what actually gets to come with me?

I leave in 5-weeks. That’s how long I have to decide which version of Caroline gets to board that plane.

A friend helped me out last week over coffee:

“Pack your stick deodorant, sun cream and your tampons; these are the things you can’t easily pick up when you’re out in the back of beyond.

The rest? Let it go.

You’ll buy what you need when you need it or simply make do.”

So I went home and looked at that dress — the heavy, expensive one I wore on TV, the one I’ve kept for years “just in case”.

And I pulled everything out along with it to reorganise. Again.

But this time… something cracked open.

I held dresses that fit like a dream. Colours that make me look alive. Pieces I’ve kept far longer than I’ll ever admit.

And still the voice inside whispered:

“…this isn’t who I am anymore.”

That’s the quiet heartbreak of decluttering no one warns you about.

And with every item I held, a deeper truth bubbled up:

“If I keep holding onto it… isn’t it costing me more than if I let it go?”

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Because here’s what I realised in the middle of wardrobe chaos:

It’s not just the clothes.

Everything feels slightly outgrown right now:

Habits.

Routines.

Ways of working.

Old identities.

Ideas about who I “should” be.

It’s not dramatic.
It’s just growth.
The quiet kind nobody notices until suddenly everything feels… wrong.

Like a life you’ve technically still “fit” into but don’t want to wear anymore.

And here’s the real kicker:

I don’t yet know what the new version looks like.

I don’t have “the plan”.
I don’t have the full route, the full wardrobe, or the full vision.

But I do have “a simple plan”.

So now I’m asking myself — and you:

What needs to be let go…not because it’s “bad”…but because it’s no longer right for where you’re going?

And these lessons apply to more than wardrobes: the habits you’ve outgrown, the cities that no longer fit, the jobs you’re clinging to out of fear, the relationships you’ve been meaning to release, and the dreams you haven’t admitted you’re done with.

I listed three dresses yesterday.
And for the first time in weeks, I felt lighter.

Not because my wardrobe was emptier—but because I’d stopped carrying versions of myself I’d already outgrown. So now instead of staring at what no longer fits, I’m looking online for the best travel clothes for 2026.

Caroline x

P.S. Join me in the end-of-year clear-out. Comment with one thing you’re ready to release — a dress, a habit, or a plan that’s expired. Let’s clear space together.

P.P.S. The TV dress? Listed with the others. Space made. Now taking recommendations for the perfect travel dress — send links!

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24 hours.

37 tabs open.

6 episodes of ‘Race Across the World’ devoured.

3 travel agencies’ advice contradicting one another,

Oh, and an existential crisis about whether I am a “backpack person” or a “trolley dolly person”.

This was the result of my big announcement last week.

Not the “big career win” kind of announcement.
No.
The other kind.

The buy your life back, and go see the world kind of announcement.

When You Forget Your Own Advice

For the last 7 years, I’ve been living in Rome in Italy, building my coaching business, Vincita, from the ground up. I’ve helped hundreds of clients step into their personal and professional greatness to win the moments that matter to them.

So when I looked at my calendar and realised I’d been ‘building’ for seven years straight... I knew. It was time to stop building and start living.

The moment I decided to do it? Something hilarious happened: I immediately forgot everything I tell my clients about overwhelm.

Instead, I dove headfirst into research. Which, if you know me, is never a good sign. As it creates overthinking.

Masses of it.

My hare-brained ideas spiral into a tangled mess of doubt. Because here’s the fear I haven’t said out loud yet:

What if I come back and the only thing that’s changed is my bank balance? What if this is just an expensive distraction from doing the real work?

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The Village Shows Up

And then something beautiful happened. My overwhelm was met with an army:

• The Planners (James, my nephew, sent me his legendary “round the world” spreadsheet from when he travelled a few years ago. It is… a masterpiece.

  Layers. Tabs. Formulas. Flight times, costs, excursion budgets, optimal timings, risk assessments — honestly I think he could run NASA).
  

• The Adventurers (Cathy, my OG friend who met two Irish girls in a bar in Aus and continued around the world with them, with zero plan, and came back blissful).

  No plan. No tabs. Not a spreadsheet in sight. More alive than ever — her advice?

  “Don’t plan everything. Let the magic happen.”

• The Guides (Lucy Dobson and Jenny Hendron, travel experts who swooped in like fairy godmothers) –

  → Lucy, who started an independent travel business after years on cruise ships. Her sage advice: ‘Start understanding budgets for each location and be prepared.’

  → Jenny, a past client whose zone of genius is adventure holidays. She’s been sparring with me all week, got me hooked on Race Across the World and is stretching my thinking with questions like, ‘Have you considered community-based travel?’

All this wonderful advice – the menu of ideas, the destinations, and the harsh realities of not being able to do absolutely everything – was sobering.

It’s reminded me of the fork in the road I hit when starting my business 7 years ago; I knew that the overwhelm would hold me back until I committed to it.

Back then, I invested in a business coach to guide me on the path. Her best advice echoes every time I start to feel small and spiral into a meltdown, the ultimate voice of doom screaming, ‘What if this doesn’t work out?’

She would gently ask, ‘What if it does?’

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How to Stop Comparing and Start Doing

Here’s what nobody tells you about big life changes:

There’s always someone who did it ‘better’.

Someone more organised.
More spontaneous.
More brave.

Someone with the perfect system or the perfect surrender.

And if you’re not careful, you’ll spend so long comparing approaches that you’ll never actually GO.

So here’s what I’m choosing instead...”

I’m choosing my way:

Prepare a little.
Feel a lot.
And let the rest reveal itself as I go.

Because for me, travel is never really about the sights—it’s about the people: the reunions, the strangers, the surprises, and the serendipity.

Like this week in Bedford, reconnecting with old friends who filled my heart in a way I can barely describe. Well, I want that — everywhere.

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The (Loose) Plan

First stop: Egypt.

Not because it’s logical or optimal or on the travel blog’s Top 10 list. Because when I close my eyes and ask what calls to me... I see pyramids. I see five days of permission to be doing this MY way – starting with a flight length I can actually handle.

Plus my new passport has arrived. The next decade is upon me. So come hell or high water, that flight to Egypt gets booked this week.

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If there’s one lesson in all this, it’s this:

You don’t need the master plan. You need the momentum.

You’re choosing the path that fits YOU — Not the right time. Not everything figured out. Just the courage to say, 'I’m doing this my way’.

Because here’s what the spreadsheet-makers and the free spirits both know: the trip that changes you isn’t the one you plan perfectly. It’s the one you actually take.

Caroline x

P.S. If you could take one month to go anywhere—no excuses, no logistics, just pure desire—where would you go? Tell me in the comments. (And then ask yourself: what’s actually stopping you?).
P.P.S. If this story resonates, would you forward it to one person who needs permission to take their own leap?

Choosing Living Over Preparing

The average person will spend 37% of their income for 30 years to own a home.
I’m choosing to spend mine on something that terrifies me instead.

Not because I’m reckless.
Because I finally realised the scariest thing isn’t running out of money — it’s waking up at 65 and realising I spent my whole life preparing to live instead of actually living.

I’ve been dreaming of going to the Australian Open for as long as I’ve loved tennis—which is to say, a very long time.
But the thought of being on a plane for 24 hours, knowing how drained and disoriented I’d feel on the other side, has always made me say: hell no.

It’s easier to stay in Europe. Comfortable. Predictable. Easy.
But lately, I’ve been asking myself — is comfortable really what I want anymore?

Choosing Freedom Over Security

I’ve been on a long hunt for a place to call home — something beautiful, stable, mine.
A place where I could finally put down roots, build the business I’ve been dreaming of, and stop feeling like I’m in transition.

But every time I get close, something in my body says no.

I saw two houses this week that, on paper, could have been perfect. Affordable. Practical. “The smart choice.”
But standing inside them, every part of me screamed this isn’t it.

I told myself I was looking at an investment property — the first lie.
When the estate agent said one would bring in £850 a month and another £650, all I could think was, ‘It’ll be another ten years before this makes me any money.’
By then, I’ll be 52.

When I told my mum, she said, “At your age, darling, is this what you really want?”
And she’s right — but not in the way she meant.

She was warning me against making a smart investment instead of buying my forever home to live in.

I heard: ‘Don’t spend your prime years locked into something that keeps you from really living.’

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Choosing Today Over Someday

So instead of buying property that feels like a trap, I’m getting crystal clear on what I actually want.

Remember that old saying, “I want never gets”?

Well, in my experience, not knowing what you want is the real blocker. Every time I tell the universe what I want with my whole heart – it arrives.

So here goes:

I want to meet new people who spark something in me.
I want sunsets, open skies, and long conversations with strangers.
I want to feel alive — not locked into what’s sensible or expected.

What would your list be?

You might think this is just wishful thinking or even dreaming. Well, another brilliant saying that I read somewhere is that:

The Wake-Up Call

Someone close to me was rushed into emergency surgery last month and nearly didn’t make it. Twice.
They’re recovering now, but there is a long road ahead; that week and the uncertainty have jolted me awake.

Life isn’t guaranteed. We don’t know how much time we get.
So I’ve decided to stop saving what I truly want for later.

Instead of investing my savings in something that might own me more than I own it, I’ve decided to invest in me—in memories, in experiences, in adventure.

Some will say this is privilege. They’re not wrong. But privilege unused is privilege wasted. The question isn’t whether you have advantages—it’s what you’re doing with them.

Follow the Feeling

I have a business that gives me freedom — the kind I’m finally ready to use.
So I’m taking it.

In the New Year, I’ll be travelling the world for three months.
I’m going to Australia.
And yes, I’m dreading the jet lag.
But I’m dreading a low-energy life even more.

I know what some of you are thinking:
’Must be nice. I have kids. A mortgage. A boss who’d never let me disappear for three months’.

Fair.

But here’s what I’ve learnt:
The cage isn’t always external. Sometimes it’s the story we tell ourselves about what’s possible.
Sometimes it’s waiting for permission we already have.

And if you’re honest with yourself — who do you need permission from?

The Real Risk

Will this delay other dreams? Maybe.
Could I come back broke and regretful? Perhaps.

But I’m more scared of being 60, financially secure, and emotionally hollow.

The simple truth is: you can always make more money.
You can’t make more time.

And here’s what I know from coaching hundreds of high achievers through their own pivots:
The ones who create real, lasting change all share one thing —
They don’t wait for permission.

They make bold moves not because they’re certain, but because they’ve built the mental muscle to trust themselves to figure it out.

Choose Today

So this is me, redefining what “home” really means — how belonging might not be tied to one place but to a feeling inside us when we’re fully alive.

No mortgage.
No “shoulds.”
No more waiting.

Just me, following the pull of what I truly want.

If you’re in your 30s, 40s or 50s — building something, leading something, or dreaming of something — do yourself a favour and choose you.

You don’t need another certification.
You don’t need another strategy.
You don’t need to wait until it’s practical.

The only thing standing between you and the life you want is a permission slip you’re waiting for someone else to sign.

So here’s my question: will you finally sign it yourself?

Caroline x

P.S. Already got your permission slip? Comment below and tell me what you’re going to do with it.
P.P.S. If you’re building something that matters and need help to stop preparing and start living it — let’s talk. This is what I do.
P.P.P.S. If this resonated, hit the ❤️ and share with someone who needs to hear it.

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I’d just landed in Malta and sent her a photo of my private chauffeur waiting for me at the airport, holding a plaque with my name on it.

“Fuck off! You’re so posh! I don’t think I’ve ever had that happen to me and I’m a fucking actor!” she replied.

“OMG! What the fuck do you do? Who are you? How do you have a private chauffeur?”

I laughed.

“Oh, darling, it gets better. I’m working for the government. I’ve just checked into my 5-star hotel; it’s proper swanky. There’s an infinity pool on the roof, and my bed is Olympic-sized; I can spread eagle across it, and I still can’t get to the other side, but the bathroom is a bit shit, so I’ve requested a change. I’m a total diva right now.”

“Are you a spy!?! What do you mean, you work for the government?! Since when? WHAT? Who even are you right now?”

I told her I was working with advisors to the government of Malta.

“Ok I’m confused I thought you had your own company? Can you break it down for me, you know for someone who doesn’t live in real job world.”

It was a surreal, pinch-me kind of moment. I’d been whisked off in style, living the sort of scene I’d quietly visualised months earlier — and suddenly, I was in it.

How I Created This (And Why That’s the Problem)

Back in April, I’d written it down: I want to live and work in Malta.

I wanted the startup energy, the Mediterranean sun, the feeling of building something new in a place that felt electric.

Six months later, I got the invitation: train founders for Malta’s Startup Festival. The government advisors wanted my help positioning the island to investors. In exchange? Nine days, five-star hotel, private driver, all expenses paid.

I was living the exact dream I’d visualised.

For two days, I trained ambitious leaders and founders. For the rest, I swam in that infinity pool and thought: This is it. I made it happen.

The Truth About Dreams (That No One Tells You)

Somewhere between the rooftop swims and the startup sessions, something shifted.

Malta was everything I imagined.

Vibrant.
Innovative.
Sun-drenched.

I was eating possibly the best Calzone pizza I’d had (this is a major statement after living in Italy for 7 years) and watching the sunset disappear over the horizon that evening, belly full, my heart felt heavy.

This wasn’t home.

That clarity hit like a gut punch.

Because when you lose a dream — even one you worked hard to generate — you lose momentum too.

I found myself spiralling: if not Malta, then where? What and where do I go now?!

But maybe that’s the wrong question.

We can get so caught up in achieving the picture postcard life, but maybe it’s not where we live but how.

On the last day I shared a brunch with one of the judges of the Pitch Black competition, an amazing woman, a VC from Vienna. I asked her what she liked about living there. Her list was long and it was much more about her work and the place and day-to-day life, than the weather and the people.

And that’s when it clicked. I didn’t lose the dream. I just learnt what I was actually searching for.

And honestly? Losing the Malta dream didn’t kill my momentum.

It created space for something better.

The Message That Changed Everything

I voice-messaged my sister that night — almost a mini podcast about the festival, the room upgrade, the sea view, the fashion show (did I mention the fashion show!?), and all the amazing people I’d worked with over the past 9 days. All of it giving me clarity: Malta was a place I would return to again and again, but it wasn’t going to be the place I called home.

Her reply came through the next morning:

“Got it. That makes total sense to me now. Gosh, you are very clever, darling. You’re living the dream, aren’t you? It sounds like you are pivoting in the most spectacular way. I think that’s bloody marvellous!”

I listened to it three times.

Pivoting in the most spectacular way.

Not failing. Not lost. Not spiralling.

Pivoting.

She got it before I fully did. This wasn’t momentum lost — it was momentum redirected.

Testing, Not Committing

Here’s what I’ve realised: Dreams aren’t destinations. They’re experiments.

Trying to answer the BIG questions is overwhelming. Figuring out life, work, relationships, and what will be a good fit forever? Essssh, pass please.

But experiments? Experiments are fast and fun.

And even if it doesn’t work out as you expect, that’s just opening another door for the next experiment. And that could be the moment everything actually begins.

Next week I’ll be in Bedford with two dogs and zero expectations. The week after? Who knows.

But I’m not spiralling anymore. I’m exploring.

And that feels like the most powerful thing I’ve done all year.

If you’ve ever lost sight of your dream or felt the sting of realising it wasn’t “it” — what if instead of seeing this as the end, what if this is just the beginning?

Ask yourself:

What could you try out this month?

Not commit to. Not bet the house on. Just test.

Because sometimes, losing a dream isn’t the end of your momentum.

It’s permission to build something even better.

Caroline x

There’s an old fable: the wolf that wins is the one you feed. After watching 12 founders pitch last week, I finally understood what that means.

Whether you’re pitching investors, asking for a raise, or finally posting that creative project — the move is the same: risk embarrassment and tell your story.

The lesson in the room

Last week I was coaching the semi-finalists of the Pitch Black competition — a dynamic event where there were 100 applicants. 12 semi-finalists. 8 finalists. 2 winners. €120K for the pre-seed category and €300K for the seed category.

In the semi-final training, every founder in the room had a different level of preparation, confidence, and skill. Some had clearly been through accelerators and coaching programs; others were still finding their footing.

But what struck me wasn’t who was most polished.

It was who was most brave.

Why bravery beats perfection

The judges couldn’t agree who would win. Some wanted to back the safest bet. Others wanted to back the founder who’d transformed before their eyes—who’d crafted their pitch into a powerful story in just 24 hours.

Let me tell you about two founders who dared to feed the wolf of bravery.

Vlad completely rewrote his pitch 24 hours before the final. He could have played it safe — but instead, he risked everything to make people feel something about cybersecurity training (no small task!).

Halfway through, he forgot his line. You could hear a quiet F-bomb slip through the microphone. The audience gasped — and then leaned in. Because what they were witnessing wasn’t perfection. It was real courage.

He gathered himself, carried on, and absolutely owned that stage. It was raw. Emotional. Powerful.

That’s one shape of bravery: the guts to fall apart in public and still stand.

Then - Thomas showed a different kind of bravery.

During the semi-final, his pitch was all semiconductors and cooling systems — technically brilliant, emotionally empty.

But when he rewrote his pitch from start to finish, he transformed every line from facts to feelings, from cooling systems to why this matters for the world. He let go of everything he knew was “safe” and trusted the story.

When he stepped up for the final, it was like watching a completely different person. Every judge saw it. Every person in the room felt it.

He didn’t just pitch an idea — he pitched possibility.

The results:

Vlad didn’t win the prize — but the judges told me after how they had fought for him.

Thomas won €120K — for showing what transformation looks like when you stop hiding behind what feels safe.

Both proved something powerful:

Transformation isn’t about getting it right—it’s about being willing to get it wrong on the way to something better.

These founders expanded their possibilities. They stopped asking, “What if I fail?” and started asking, “What if I win?”

And that shift — that single thought — is what feeds the right wolf.

Discover what you’re truly capable of.

Every time you choose courage over comfort, every time you risk embarrassment and dare to be better, you strengthen the part of you that can move mountains.

Feeding the right wolf isn’t about control. It’s about energy, faith and being willing to look a little foolish. These are the ingredients to discover what you’re truly capable of.

Putting this into practice is something I am challenging myself with now. This week, I’m pitching to people who could change the course of my business forever. If it goes badly, I’ll probably mutter my own F-bomb. But I’m doing it anyway.

What will you challenge yourself to do?

If you take one thing away from this story, I hope you will be more like Thomas and Vlad.

Take the risk.
Say the thing.
Rewrite the story.

You might stumble. You might even mutter a quiet F-bomb halfway through.
But you’ll rise — bolder and freer — and more opportunity will come your way than ever before.

Go feed the wolf of bravery.

Caroline x

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P.S.

The Pitch Black Finalists:
Pre-Seed: Lemons in the Room (Alessandro), Ice Caps (Thomas), Open Cyber AI (Vlad), So Me (Connie & Molly).

Seed: BrainTrip (Jurij), Edumentors (Tornike), StudiesIn (Gent), Everybody Counts (Keith).

All with great pitches, fantastic stage presence and passion and purpose, they each made you feel.

The judges were in:

🏆 Pre-Seed Winner: IceCaps Thomas Galea

Thomas came into training speaking technical. He left telling a story that lit up the room — a TED Talk in the making. His transformation was remarkable, and his delivery, combined with a brilliant idea, blew the judges away.

💛 Runner-up & Audience Award: Lemons in the Room Alessandro Napoli

A crowd favourite with heart and purpose. This Firenze-based team is one to watch — making a meaningful impact in the health space and winning the audience over completely.

🧠 Seed Winner: BrainTrip Jurij Dreo

Revolutionising the way we diagnose dementia and brain disease — fast, accessible, and life-changing innovation for the aging population. Their work will touch millions.

🚀 Seed Runner-up: Edumentors Tornike Asatiani

A founder who took a risk to move from rehearsed to real — telling a story that ignited imagination and emotion. A brilliant performance and a bold move that paid off.

🐉 Welsh Dragons – SoMe Connie Sishton Molly Sishton

Two powerhouse sisters, launching their app in just two weeks and proving what it means to scale with fire. They came, they pitched, they owned the stage.

I couldn’t be prouder of how each of them embraced the challenge to stand up, speak their truth, and tell the story that matters most.

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