Backstory

It’s 2013. I’m at a music festival in the foothills of northern Japan, dancing like an idiot to the Happy Mondays, thirty years of nostalgia washing over me.
And out of nowhere, a thought arrives with a clarity I wasn’t expecting.

I was 43. Managing Partner at a global advertising agency in Hong Kong. By every external measure, doing well. My planned move to Shanghai had just fallen through and the company was figuring out what was next for me – Paris, Tokyo, New York were all on the table.
All great opportunities. And yet potentially all wrong.
Because underneath the scramble, a voice I’d been successfully ignoring for years had started to get louder.
If I take the next promotion, I’ll never leave. One day I’ll be lying on my deathbed wishing I’d taken the time to find out what I actually really wanted from my life.

I’d spent my entire career looking at the opportunities being offered – and it had never once occurred to me to consider the one I could give myself. In this case to simply resign. To end what was and trust whatever would come next.
It still took me two months to actually do it.

Money, status, power, comfort – they’re not easy things to walk away from. Mine was status. I’m almost embarrassed to admit how much of my identity lived in my bloody Cathay Pacific Gold card. And it wasn’t just internal. My boss seemed annoyed that I was resigning. My colleagues thought I’d lost the plot. My father seemed disappointed – it never fails to amaze me how much weight I was still giving to his opinion…

That tension, between what the world seems to expect from you and what something quieter inside you is questioning, I’ve come to think of it as the beginning of every real transition.
But here’s the thing about transitions. Sometimes the seed is planted years before you’re ready to act.

Three years before that music festival in Japan, I was on a plane from Hong Kong to Bangkok. My grandfather had just died. I was on my way to a business meeting I had absolutely no interest in attending.
And I wrote a note to myself:
“One day I will build a retreat on an island. Connected to an orphanage.”
I was daydreaming, I think, imagining a place where curious people could gather, hang out, learn, think, talk, eat well, and ask the questions that normal life doesn’t leave room for. A place I actually wanted to visit.
I had no idea why I’d written “orphanage.” Maybe it reflected some of the guilt I was feeling at the time of seeing sometimes destitute kids whilst living my expat luxury life. I’d folded the note, put it in my wallet, and forgot about it.
So I resigned. And I travelled for 3 months. And I agreed to lead a start up in Sydney.

What the saying leaves out is the part where, almost immediately after jumping, we grab the nearest branch.
Mine was a tech start-up in Sydney teaching kids to read. I hate tech. I don’t have kids. But it sounded impressive. I was already an investor in the company. It kept the status story alive. My dad stopped being disappointed. And I had something to say when people asked what I was doing.

But my heart was screaming no the entire time.
Two months into the start-up, the truth became impossible to argue with. This wasn’t it. This wasn’t why I’d left the corporate world. I let go of the branch.
And the void I’d been trying to avoid arrived.
I was now living in a friend’s spare room in Sydney with no real idea what came next. The voice in my head was going nuts. What have you done? You left a great career for this? Maybe you were talentless all along. Maybe you’ve been winging it your whole life and now everyone’s going to find out. Excruciating!!

I didn’t have a name for what I was going through at the time. I’ve since learned it’s called the Messy Middle – that disorienting space between the life you’ve left and the one you haven’t yet found. Knowing the name doesn’t make it less messy. But it helps to know it’s a recognised part of the journey rather than evidence that you’ve made a catastrophic mistake.
Eventually I stopped trying to figure out what to do next and started asking a simpler question: what am I actually interested in?
The honest answer was the human condition. It had always been.

An NLP course in Hong Kong. A mindfulness programme with a man I’d briefly met in Chiang Mai on my travels and had largely dismissed previously. I was also struggling with my own truth so I decided to create a workshop on authenticity with a friend of mine in Hong Kong. We managed to find 9 participants who paid us a few dollars for the privilege (certainly not a money making scheme but I learnt so much in the process) I also joined my parents on a holiday in Sri Lanka (something I would not have done had I stayed in the corporate world). This turned out to be the last holiday I would have with my Dad as he died less than 3 years later.

One experiment led to another experiment. My participation in the online mindfulness program led to an invitation to train as a facilitator in Chiangmai, Thailand. And there, unexpectedly, I met an old man with a ponytail and a wicked smile who turned out to be the founder of the Asia Leadership Institute, the only retreat-based executive coaching organisation in Asia. He is one of the world’s top coaches, working with senior leaders from all over the world. He offered to mentor me in coaching and facilitation in exchange for help with the marketing of one of their new team programs.

It turned out he’d also built an orphanage for Burmese children on the Thai border. A place called Schools of Hope. I showed him the note.
He smiled. “You’re on the right path,” he said.
That’s the thing about the messy middle that nobody tells you. You don’t find the path. The path finds you, but only if you’re willing to stay in the uncertainty long enough for it to appear.

I spent two years apprenticing, travelling the world with the institute, coaching leaders, facilitating retreats, slowly learning a craft I hadn’t known I was looking for. We expanded the business into a truly global operation and I became a partner in the enterprise. The wonderful thing about being a coach and facilitator is that you have to do the work on yourself in order to be effective with others. In so doing I started to discover more of what I really wanted from my life.

2500 years ago there was, how might you say, a lot of wisdom happening….Confucius was influencing China, at the same time the Buddha was influencing India and SE Asia and then there were the ancient Greeks. I’d spent time in China, and Southeast Asia, it seemed to make sense to shift my attention toward Greece. The examined life. The question that Socrates and Aristotle and Plato never stopped asking: What does it mean to live well? Or maybe I just wanted to see how it had changed since my last visit at 18 on my first boys holiday (a right of passage for all British people).

I had an old Greek friend in London who I’d been friends with for more than 20 years. His name was Manos. Whenever I passed through London, we’d end up in the same pub, getting drunk over pints of Guinness and putting the world to rights. Twenty years earlier he’d given me a book on counselling and psychotherapy. Inside he’d written: “Go change the world in your own way.”
I was selling advertising at the time.
I found the book on my shelf one afternoon and called him. Let’s finally do this. Let’s follow this ridiculous note I’ve been carrying in my wallet and go build something in Greece.

He linked me up with a crazy anarchist in Athens to go check things out.
I explored Athens and then a small island called Aegina just forty minutes by fast boat from the city. Not the obvious postcard Greece. Something quieter, older. More weathered.
The day after I arrived, I went for a walk behind the main town.
And I saw it.

A vast derelict building. Stone. Four hundred metres long. Bars on every window.
I asked a local what it was. A derelict prison. A place of torture and pain during Greece’s dictatorship in the early 70s and now left abandoned as if people were unsure what to do with it.
I then noticed that above the door was engraved the word ‘Orphanegeo’. It turns that before it became a prison it was the first orphanage ever built in Greece. Constructed in 1828.
I stood there for a moment. Then I put my hand in my pocket and pulled out the note.
“Build a retreat on an island. Connected to an orphanage.”
Synchronicity or coincidence…

Regardless, I knew, standing on that street, that I was exactly where I was supposed to be.

In September 2022, Manos and I ran our first Laughing Heart retreat. Seven days. Six people from different parts of the world – The Odyssey of Intent – filled with philosophy, mindfulness, island exploration, boat trips, ancient olive groves and adventure.
Something happened that week that we hadn’t quite predicted. People dropped the performance. So did we. And in the space that opened up, they found something they’d been looking for, sometimes without knowing they’d been looking at all.

That’s what Laughing Heart is.
Not a retreat business. Not a coaching business. Not a wellness business. A space on an island, around a fire, over good food, with honest conversation and where seekers who have spent years living someone else’s idea of a good life come to explore their own.
We gather in Greece. On that island. Not far from that orphanage. To ask the questions that matter. Together.

With good food, maybe a glass of wine.

And a great deal of laughter.

Aaron