What Happens When You Achieve Everything?
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What happens when you achieve everything you've spent your adult life chasing? All the things that seemed unimaginable when you were starting out are suddenly yours. The house. The car. Financial security. Time. Freedom. What happens then? I'm currently in Scotland, spending time with my family, and I've been having long conversations with my dad, who's 85. He was a successful property developer who retired in his fifties. He'd earned the right never to work another day in his life. He bought a cottage in the countryside and settled into what most entrepreneurs would call the dream. Long walks with his dogs. Regular gym visits. Reading. Music. Time with the grandchildren. But then he received a phone call. Then a couple of emails. Someone asked him to look over a property deal. He told people he was retired. "I'll just help out this once." And slowly, almost inevitably, he was working again. On his own terms. Less frenetic. More selective. But working nonetheless. Thirty years later, over coffee this morning, he was talking me through the latest property deals he's involved in, a couple of AI start-ups he's backed, and a new online system he's built to make money. I didn't ask him why. I already knew. "It's not the pursuit of happiness. It's the happiness of the pursuit. It's neither the journey nor the destination. It's who you become on the journey." — Jimmy Carr Psychologists call this the arrival fallacy: the belief that reaching a major goal will finally deliver lasting happiness. Research suggests something more nuanced. Swedish researchers tracked lottery winners for up to twenty-two years. Their life satisfaction increased and stayed higher. Their day-to-day happiness barely changed. Money answered the question, 'Do we have enough?' It couldn't answer the harder one: 'What should I do on Monday morning?' I see this constantly in my work with business owners. The founders I sit across from are relentless—resourceful, driven, and often consumed by the pursuit of growth, success, and eventually an exit. And yet research from the Exit Planning Institute suggests that around three-quarters of business owners regret selling their company within a year. Not because the deal was bad. Because of what came next. They spent years engineering the perfect exit: Tax. Yet almost nobody spent even a single afternoon engineering the life they were exiting into. Businesses aren't just things founders build. They're machines that manufacture meaning. Every Monday morning your business subtly answers dozens of questions for you. Where should I be? Sell the company and, overnight, all of those answers disappear. It makes sense when you think about it. For most founders, a business isn't simply a source of income. It's an identity, a routine, and a source of progress. There's a mountaineering statistic that captures this perfectly. Above 8,000 metres on Everest, most climbers who die do so on the descent, not the ascent. The climb has a single obsession: reach the summit. The descent asks a completely different question: Who are you now that the thing you've organised your life around is over? My dad's answer was simply to find another mountain. Smaller. Less consequential. But a mountain all the same. I'm not convinced that's the only answer. But it's certainly better than having no answer at all. Author Mitch Anthony put it perfectly: “True wealth is having enough money to sleep well at night and enough purpose to leap out of bed every morning.” The wealth management profession has traditionally obsessed over the first half of that sentence and largely ignored the second. I think that's a mistake. Success solves money problems. It doesn't solve meaning problems. So if you're head-down, building towards some future version of 'made it,' ask yourself something now instead of waiting until the day you arrive. When you picture yourself ten years after selling your business: Who needs you? Because one day you'll stop climbing this mountain. The only question is whether you've already chosen the next one. Until next time, Alan. PS — If this resonated, hit reply. These are some of the most meaningful conversations I have with founders—not about money, but about what comes after money. PPS — My recent podcast guest, Andrew Hulbert, discovered this firsthand after selling his business for £70 million. He thought buying a yellow McLaren would make him happy. It didn't. He sold the car, bought a farm, and found a far more meaningful next chapter. It's a wonderful conversation—I hope you enjoy it. YouTube | Apple/Spotify |