Hey Reader,
At 21, I was working with Chris Eubank Sr. ringside at world title fights, my name wasn’t on the poster — and it shouldn’t have been. In my view managers, promoters and agents should work in the background - the glory is for those who get in the ring, not work outside it. But equally at that time, I thought legacy meant proximity to greatness: the titles, the limelight, the roar of the crowd.
At 30, after selling a business, I thought legacy meant the exit cheque.
At 42, after publishing books that outlast trends, I thought legacy meant words that would still be read when I was long gone.
Now, in my 50s, I know this: legacy and lifestyle are not the same thing — and most entrepreneurs get stuck because they never decide which one they’re building.
And here’s the kicker: lifestyle can be just as powerful a choice as legacy, if you make it consciously. The problem is when you try to do both. That’s like training for a marathon while bulking for a bodybuilding show. You’ll exhaust yourself, and you won’t win either race.
A lifestyle business is designed to serve you now — cashflow, flexibility, freedom.
A legacy business is designed to outlast you — systems, succession, equity.
Neither is better. But they are different games, and the rules don’t mix.
The entrepreneurs I see thriving are the ones who pick. Some are running lifestyle businesses that give them incredible freedom: working 4 days a week, spending time with their kids, travelling without stress. Others are building legacy businesses with succession, equity, and scale baked in — the kind you can sell, step away from, or pass down. Both are winning.
The ones who suffer are the ones stuck in the middle. They want lifestyle-level freedom and legacy-level equity — but they’re building without clarity. It’s a slow, exhausting death of a business that never pays them properly in the short term and never creates value in the long term.
McKinsey research shows that companies with a long-term horizon achieved 47% higher revenue growth and 36% better profitability than peers. Meanwhile, Payoneer found lifestyle entrepreneurs consistently report higher satisfaction, even when earning less than corporate peers. Both models work — but only if you know which one you’re in.
There’s no “right” answer. But there is a wrong one: not choosing.
When I was running Dyson’s PR and marketing around his kitchen table, James Dyson wasn’t thinking about lifestyle. He was thinking legacy. Every decision was about building a company that could outlast him.
Years later, when I co-ran a $150m fund investing in tech, we didn’t back “lifestyle” founders. We looked for scalable, sellable businesses. Equity was the name of the game.
But today, in my own business, I’ve consciously chosen elements of lifestyle too. I take 17 weeks off a year. That’s not by accident. It’s because I know my business model is designed for both profit and freedom. What I haven’t built (in this business) is a business I can sell.
The point? I’ve played on both sides. And I’ve seen entrepreneurs win on both sides. The only failures are the ones trying to straddle both.
3 ACTION TIPS / TOOLS
- Pick Your Horizon
Write down your 3-year target. Does it read like lifestyle (time, cash, flexibility) or legacy (equity, exit, succession)? Be brutally honest. Peter Drucker said: “There is nothing so useless as doing efficiently that which should not be done at all.” If you’re optimising the wrong game, you’re running hard in the wrong direction.
- Audit Your Systems
Lifestyle businesses can survive with you at the centre. Legacy businesses cannot. Do the “bus test”: if you disappeared tomorrow, what survives? Research shows 76% of founders believe key tasks require them personally — yet the majority could be trained or systemised. Legacy requires that shift.
- Redefine Success on Your Terms
Lifestyle rewards are measured weekly (freedom, flexibility, joy in your work). Legacy rewards are measured in decades (brand value, equity, impact). Decide your reward model and stop measuring yourself against the wrong one. If you’re building for lifestyle but judging yourself against legacy metrics, you’ll always feel like you’re losing.
Lifestyle isn’t a cop-out. Legacy isn’t the only path. Both can be powerful, both can be profitable. But only if you choose.
You don’t have to build an empire. You don’t have to work four hours a week on a beach. But you do have to decide: are you optimising for cashflow or a company?
Because building in the middle doesn’t give you the best of both worlds. It gives you the worst.
We’ve got this …
