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You'll Never Get There By Going Straight. Read time: 6 minutes Hey, welcome back. Last week, I talked about going from AI zero to hero in a month and why I wrote my first ever sales email for a friend's course. You can read that (and all past issues, here) Before we dive into the letter. (Personal update about something.) Today I want to talk about why the most important things in my life all came from chasing something else entirely. I Wasn't Trying To Build A Supplement Company I was trying to sleep. That's it. I was a broken, exhausted, anxious former tech founder who hadn't slept properly in six months and had tried everything. Therapy. Sleep apps. Meditation. Alcohol. Sleeping pills I never took because I knew they weren't a long-term fix. A friend suggested I look into brain nutrition over dinner. I thought she was a bit weird. But I was desperate enough to follow up. I booked an NHS dietitian. She recommended DHA omega 3s, B vitamins, and blueberry extract. Within two weeks I was sleeping through the night. At no point during any of this was I thinking about starting a business. I was thinking about surviving. Heights didn't come from a business plan or a market opportunity or a gap I spotted in the supplement industry. It came from me trying to fix my own broken brain and accidentally discovering that the supplement market was terrible at helping people do that. The company I'm most known for was never the destination. It was a byproduct of going somewhere else entirely. The Obliquity Principle There's an idea from the economist John Kay that I keep coming back to. He calls it obliquity. The principle is simple: the most important goals in life are almost never achieved by pursuing them directly. They're achieved indirectly, as a side effect of doing something else. Think about how this plays out. The people with the best relationships didn't usually set out to "optimise their love life." They pursued something they cared about and met someone along the way. The people with the most fulfilling careers didn't usually follow a ten year plan. They followed their curiosity and the career took shape around it. And the most successful companies I've seen, both through my investments and through building my own, were almost never the original idea. They were what emerged when the founder stopped trying to be clever and started trying to solve a real problem they personally understood. Almost Everything Good In My Life Came Sideways When I look back at the things that actually matter to me, almost none of them came from pursuing them directly. Heights came from trying to fix my insomnia. The newsletter came from Joel and I wanting to share what we were learning about brain health. It was never a growth strategy. We genuinely just wanted to translate scientific papers into something useful. The fact that it grew to 250,000 readers and became our primary customer acquisition channel was a complete accident. The Secret Leaders podcast came from the Foundrs community, which came from wanting to bring entrepreneurs together because I was lonely after my startup failed. I wasn't building a media company. I was looking for people who understood what I was going through. Even my angel investing started because founders kept asking me for advice and I thought I might as well put some money behind the ones I believed in. It wasn't a portfolio strategy. It was just saying yes to people I liked. Every single one of those things became something significant. And every single one of them would have been worse if I'd pursued it as the main goal from day one. The sideways approach is what made them authentic, which is what made them work. Why Direct Pursuit Often Kills The Thing I've watched this happen with founders I've invested in. Someone spots a market opportunity, builds a plan around it, and goes after it directly. On paper everything makes sense. The market is real. The numbers add up. The strategy is sound. And then it doesn't work. The founder burns out or loses interest because they were never personally connected to the problem. They were connected to the opportunity. And when the opportunity gets hard, which it always does, there's nothing underneath holding them in place. Compare that to a founder who started because they had a problem they couldn't solve and got obsessed with fixing it. When things get hard for that person, they keep going because the problem is personal. The motivation isn't external. It's woven into who they are and what they've been through. I kept going with Heights through the hardest years because the problem was mine. I'd lived it. I knew what it felt like to be desperate for a solution and find nothing that worked. That personal connection carried me through periods where the business metrics would have justified quitting. If I'd started Heights because I saw a gap in the supplement market, I would have folded in year two. I'm sure of it. What This Means For You If you're sitting there right now trying to figure out what business to start, what career move to make, what direction to take your life, I'd push back on the idea that you need to pick a destination and drive toward it in a straight line. Follow what you're genuinely curious about. Solve problems you personally have. Invest your time in things that interest you without needing to know where they're going. The shape of your career, your company, your life will emerge from those pursuits. And it will be more authentic and more resilient than anything you could have designed on a whiteboard. The best newsletter I ever wrote was one I wrote because I wanted to understand a topic better. The best product I ever built was one I built because I needed it myself. The best investments I've made were in founders who reminded me of myself at my worst, trying to fix something personal and building a company almost by accident. Straight lines look efficient on paper. In practice, the interesting stuff almost always happens on the detours. The Other Side Of This I want to be careful here because I'm not saying don't have goals. I have goals. I have OKRs. I have a word of the year. I plan things rigorously. What I'm saying is that the biggest things in my life were never the goals. The goals keep me disciplined day to day. But the trajectory of my life has been shaped almost entirely by things I stumbled into while working on something else. If you're frustrated right now because you feel like you should have figured out your "thing" by now, maybe you already have and you just can't see it because you're looking in the wrong direction. The thing you're doing on the side, the problem you keep coming back to, the curiosity you can't shake. That might be it. You just haven't recognised it yet because it doesn't look like what you thought success was supposed to look like. You'll never get there by going straight. The good news is that "there" is probably closer than you think. You're just approaching it from an angle you didn't expect. To the scenic route, Dan P.S. If something in your life right now feels like a detour, pay attention to it. My biggest detour became my entire career. |
Serial Entrepreneur and host of one of Europe's top business podcasts, Secret Leaders with over 50M downloads & angel investor in 85+ startups - here to share stories and studies breaking down the science of success - turning it from probability to predictability.
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