[Reflection] #40: Why Raising Your Risk Threshold Is the Key to Freedom?

I recently read an article by Noah Hawley in The Atlantic, which recounted his visit to a private gathering organized by Jeff Bezos in 2018. The guests arrived by private jet (paid for by Jeff Bezos), each of their children was looked after by a nanny (paid for by Jeff Bezos), and in their rooms awaited luxury bags filled with luxury products as gifts. He writes:

The closer I get to the world of wealth, the more I understand that being truly rich doesn’t mean amassing enough money to afford superyachts, private jets, or a million acres of land. It means that everything effectively becomes free. Any good can be acquired, but nothing can ever be lost, because for future trillionaires, no level of loss could significantly change their global position or personal power. For them, the word failure has ceased to have meaning..

A billionaire who invests in a startup with a one-in-a-thousand chance of success, who funds a rocket that explodes, who bets on a completely random tech, risks nothing vital. Failure chips away at a fraction of his fortune, never the foundations. He can fail ten times and succeed once, and still come out ahead. Risk, for him, is almost a game.

The average guy who quits his job to start his own company, or who embarks on a career change at 35, with a dependent child and loans to repay every month, he has only one shot, or almost. Each failure eats into resources that can’t be replayed: savings, housing, family stability, sometimes mental health, and time, which can never be bought back. He doesn’t diversify his bets. He bets everything on a single horse.

Same word. Not the same game. For one, a gamble. For the other, a matter of survival.

So what do we do, on our own scale?

In my opinion, risk-taking is proportional to freedom. So we must be able to raise our risk threshold.

We won’t become billionaires overnight, but we can build, little by little, our own safety net, not just in money, but in everything:

→ Savings and passive income, before taking the leap, not after
→ Skills in very diverse areas, to not be useless, neither in an AI-dominated world, nor in an apocalyptic world
→ A network that responds to us even without our title or current status
→ A “quick-sellable” skill as a backup, to never be at zero
→ A reduced lifestyle BEFORE embarking on a risky project, not when you can’t make ends meet
→ Solid physical and mental health
→ Not being just your job, otherwise failure becomes a full-blown identity crisis
→ Testing in parallel before giving everything up (side project, part-time, sabbatical)
→ Organizing to “buy yourself time,” artificially pushing back urgency: a year of savings, for example, or just free time to think/plan better. Free time you can afford thanks to automation via AI, for example

The rich have financial capital as their safety net. We can build ours with of finances, social life, skills, time, and health. It takes longer to build. But it works too.

Abundance changes what we dare to create

And there’s one last, simple point I’ve observed on my very small scale. When I’m in an environment of abundance—a perfect example: I had almost unlimited Codex tokens for two weeks, and I was suddenly no longer limited to “priority” projects or essential features. I created far more interesting, polished, and ambitious things. Things I would never have taken the time to do in “priority” or “pure efficiency” mode.

Abundance doesn’t just increase risk-taking. It unleashes imagination.

That’s exactly why we must fight against the poverty mindset (survival mentality), not to deny the reality of our constraints, they are very real, but to create “pockets of abundance” in which we dare to create and dare to push ourselves a little further each time.

A little more savings.
A little more skills.
A little more risk tolerance.

It’s not just wealth that makes you free. It’s the ability to absorb a failure without everything collapsing. And that, that can be built.