Yesterday I was talking with Diego, a friend who’s an architect and has spent the last three years walking a tightrope. Pushing himself to the limit. Designing luxury homes for some of the most well-known people in Europe. He’s brilliant, talented, and ambitious. But he’s also been under massive financial strain for far too long.
The good news: he’s just been approved for a European subsidy program that rewards energy-efficient building. We’re talking about an amount that, according to him, equals what the average person earns over a 20-year career. Instantly. All at once.
And then came the reflection.
“I don’t know if all this suffering was worth it… but if there’s one thing I’m sure of, it’s that the more you’re exposed to volatility, the more asymmetric the returns can be.”
There it is. That one sentence sums it all up.
When Taleb talks about black swans, this is what he means. Positive accidents that change the game. You can’t plan for them, but you can design your life to be exposed to them. Antifragility isn’t about enduring. It’s about benefiting from chaos. It’s being positioned to win when everything else collapses.
Diego experienced that. Yes, there was suffering, but he had built a structure where, if luck ever struck, he’d be ready to capitalize. And it did. Because when you design for asymmetry, you don’t need many wins. Just one. And that one can define your decade.
The next question came naturally: “So what do I do now with all this money?”
That’s when the second part of the conversation began. Diego has two companies. One for renovations, another for professional services. Business has gone well. But now he wants something more. He wants to build wealth. He doesn’t want to return to the edge. He wants cashflow. Income.
He wants freedom.
He told me: “I don’t understand why everyone doesn’t aim for this.”
And he’s right. Because financial freedom isn’t magic. It’s not complicated. It’s a matter of design. And it starts with a very simple premise: live off the flow, never touch your base. If you can do that, you’re free. From there, you can build around what you love.
In his case, he made a clear decision. He’s going to build a couple of homes a year, but on his terms. Unique houses. No rush. With soul. He’s even going to build his own, however long it takes. Because now he doesn’t need to sprint. He’s not trapped. His goal now is not growth out of necessity, but excellence by choice.
That’s the target.
A base that generates income. A core that never gets touched. And some investments with asymmetric risk, that if they take off, change everything. And if they don’t, that’s fine. Because you’re not depending on them.
The problem is, most people are only exposed to stability. Jobs where the best-case scenario is a promotion. Indexed to the mean. Never exposed to positive accidents. Never building anything of their own. Never leaving room for optionality.
Of course, you need a core. It’s not about jumping off a cliff without a parachute. It’s about having a foundation that holds you while you chase those exponential leaps.
An asset that flows. That pays you monthly. That frees you. A system that combines the boring stuff that pays with the asymmetric bets that can scale.
Once that’s covered, you can leave your optional bets on autopilot. Don’t depend on them. Let them mature. Some will die. But one alone can change your whole trajectory.
And if you’ve designed your system right, when that positive black swan shows up, you’ll greet it with a smile. Because you were already ready.
And that’s where I stepped in. Here’s what I told him: