Legacy Play Labs  ·  Founding Cohort 2026

The exit was supposed
to feel like arrival.

A coaching program for the space between — the death of one chapter and the birth of the next.

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Something has ended.
Or wants to end.

You built the business. Had the exit. Or reached the level of success that was supposed to change everything.

And then — sitting somewhere quiet — you waited for the elation. The sense of having finally arrived. The freedom you had been working toward.

Instead: a strange silence. A hollowness where the celebration was supposed to be.

If that sounds familiar, you are not broken. You are not failing. You are standing at a threshold.

The old chapter is over. The new one hasn't begun. And no one gave you a map for this part.

Legacy Play Labs was built for exactly this space — not to rush past what's ending, but to honour it, and to help you discover what wants to be born.

"The chrysalis always looks like nothing is happening.
But something is."
— Carl Jung

This is for you if...

You've had an exit

You sold the business, banked the result, and discovered that the arrival you had been working toward didn't feel the way you expected. Now you're asking what's actually next — and finding that no amount of strategic thinking is answering it.

You've stepped out of the C-suite

A long and successful career. Real impact. And now, for the first time, no title defining who you are. The question of what you're actually here for is alive in a new way — and more urgent than you expected.

You're wearing golden handcuffs

The business is successful. You should feel grateful. But privately you know it no longer feels like a genuine expression of what you most want to contribute. Something is calling. You just haven't found the space to listen.

All three share the same underlying experience: they achieved what they thought they wanted and found it didn't deliver what they were actually seeking. This program is for the honest reckoning that follows.

"Most men go to their graves
with their song still inside them."
— Henry David Thoreau

A note from Chris

I sold my first business at 31. I had spent my twenties building it — and had quietly assumed that the sale would deliver something like happiness. Or at least clarity.

It didn't. I found myself in Bali, sitting on the beach with a cocktail in hand, watching the sunset, expecting to feel it — the elation I had been working toward for years. What I found instead was silence. A strange emptiness I hadn't prepared for.

I had lost three things at once. My sense of purpose — the reason to get out of bed in the morning. My identity — I had inadvertently become what I did, and without the business, I wasn't sure who I was. And my paradigm for finding happiness — the belief that once I built the thing and sold it, everything would be okay.

"The only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven't found it yet, keep looking. Don't settle."

— Steve Jobs

That quote found me early in the search. It was both inspiring and maddening — because it pointed at something real without telling me how to get there.

What followed was more than a decade of searching. Trying on identities. Starting things and stopping them. All the while deferring my own happiness to the other side of a horizon I couldn't reach.

What I eventually discovered is that the answer isn't found by thinking harder. It's found by learning to listen more deeply — to your values, to what genuinely brings you alive, to the quiet voice that already knows what your greatest contribution could be.

Legacy Play Labs is everything I learned on that journey, built for founders who are standing where I once stood.

"What if what you would die for turned out to be the same thing that made you come alive?"

The Program

Legacy Play Labs works across two interconnected dimensions. The place where they meet is where your next great chapter lives.

Pillar One

Legacy

What do you want to have stood for? What would make this chapter of your life feel genuinely well spent? What would you be willing to die for?

"A man who has not discovered something he would die for is not yet fit to live." — MLK

  • Clarity about what you would actually dedicate your life to
  • A north star that makes every future decision easier
  • A felt sense — not an intellectual answer — of what your life could mean at its fullest
  • The ability to say, with conviction: this is what I stand for
I
Pillar Two

Play

What genuinely lights you up? Where does time disappear? What did you love before success taught you to be strategic about everything?

Memento mori. Memento vivere. Remember to die. Remember to live.

  • Rediscovering what made you come alive before ambition took over
  • Identifying the work that energises rather than depletes
  • Permission — genuine, felt permission — to follow what calls to you
  • The first concrete steps toward a life that feels like play
II

Legacy Play is the project and the person you'll be most proud of on your deathbed, which enables every day to unfold as a playful expression of your deepest self.

Six Sessions

Six conversations. Each one goes somewhere the last one made possible.

Session 1 Orientation & Alliance

You leave with a clear sense of where you are in your story — and why the disorientation you've been feeling is not a problem but a threshold. We also design exactly how we'll do this work together, so the container is genuinely yours.

Session 2 The Clearing & Identity

You leave having consciously honoured and released the goals that no longer fit — not with guilt or grief, but with clarity about what they were really seeking. And you begin to see, perhaps for the first time, who you are when the achievement is stripped away.

Session 3 Legacy

You leave with a visceral, felt sense of what you would dedicate your life to. Not a vision statement. Not a five-year plan. Something deeper — the north star that will anchor everything that follows.

Session 4 Play — Part One

You leave reconnected with what genuinely made you come alive — before success taught you to be strategic about everything. And you leave with your first experiment in motion: one small act of following what feels alive rather than sensible.

Session 5 Play — Part Two

You leave with new data from the first experiment, a second one designed, and three genuinely different possible futures mapped out. The pressure to find the one right answer begins to dissolve. What wants to emerge starts to become visible.

Session 6 Integration & the Legacy Play

You leave with a clear and felt picture of your legacy play — the work and way of being that is genuinely, authentically yours. Not a plan. A direction. One that honours both what you would die for and what makes you come alive.

Three founding spots.
No charge.

I'm taking three founders through the full six-session program at no cost — in exchange for their honest feedback and a testimonial if the work delivers. This is a genuine collaboration, not a free taster.

The Founding Client Offer

Six sessions. Free. In exchange for feedback.

  • Six sessions across the full program
  • Both Legacy and Play pillars fully explored
  • Structured exercises, frameworks and experiments
  • A daily practice running across the six weeks
  • Honest feedback invited throughout
  • Testimonial requested if the work genuinely delivers

Only three spots available. After this founding cohort, the program moves to a paid rate. If this is resonating, now is the right time to reach out.

Apply for a Founding Spot

What is your
legacy play?

The work you'd be most proud of on your deathbed. The thing that, every day you pursue it, feels like play. If that question is alive in you — this is the right conversation to have.

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