The easy answer would be to win the lottery. If I’m guaranteed not to fail, that means I’d win, right? But that feels like cheating. The premise of this question already breaks reality, so I might as well think beyond money.
If failure wasn’t possible, I’d probably start with something I could do perfectly. Maybe run a company? After all, success there ultimately leads to what the lottery gives you: money. But the funny thing is, once you have money, money stops being the point. So maybe that’s not the best use of my one perfect attempt.
Perfecting a skill feels more satisfying. Because when you perfect something you love, value follows you anyway. Maybe I’d choose writing. Writing is useful everywhere—whether you’re leading a team (need documentation), writing a blog/book, or trying to express something that matters. To write perfectly would mean I could tell any story, explain any idea, or reach anyone in exactly the right way.
Of course, I could also take it to the extreme. Maybe I’d save the world. Why stop small when failure isn’t possible? If I could actually do that—end suffering, fix climate change, cure disease—that would be the obvious choice.
But maybe the deeper point isn’t about what I’d do if I couldn’t fail, but about what disappears when failure does. Fear, embarrassment, wasted time—all the friction that makes us hesitate. Humans cope with failure by glorifying it: “You must fail to succeed.” If failure were gone, maybe we’d finally see what we really want, stripped of all the excuses.
If I couldn’t fail, I’d still choose writing. Because even in a world without failure, the thing I’d want most is to connect—to say something that matters.
johnro 