Regret

Most people make big decisions by asking what could go wrong. I used to do the same. I'd map the risks, weigh the downsides, and usually talk myself out of moving. The framework I use now asks a different question: which choice would I regret more?

The idea is simple. Regret of inaction almost always weighs more than regret of action. You can recover from a bold move that doesn't work. You can't recover time spent playing it safe when you already knew what you wanted.

Put yourself at the end of your life and look back at the decision in front of you. If you take the cautious path, how much does it hurt to have skipped the other one? If you take the bold path, how much does it hurt to have walked away from safety? Whichever regret feels heavier is your answer. The honest one, not the safe one.

After finishing my master's in Italy, I had to choose between a stable finance career in Paris, the expected move, the one that looked right on paper, and going to Africa to work in private equity, learn fast, and push my limits. Paris was the safer answer. Africa was the one I would have regretted missing. I went. Taking that path made it significantly harder to return to traditional finance roles in Europe later. It cost me certain opportunities and made some doors close permanently. But it reshaped how I think, how I take risk, and who I became professionally. It also started building something I didn't expect: a tolerance for risk. Each decision taken this way exposes you to real outcomes. You learn that loss is survivable. The threshold for bold moves gets lower over time.

This doesn't mean the bold choice is always right. There are decisions where the cautious path is genuinely the better one, and the framework will tell you that too. The point is not to manufacture courage. It is to be honest about what you want, separate from what you're supposed to want.

I don't regret any major decision I've made. Not because they all worked out. Because I chose the paths I would have regretted skipping. That's the only standard that matters at the end.