Every risky endeavour comes with a high chance of failure. For big swings, failure is often the most likely outcome. It’s just math.
Risk-takers tend to be optimists. They believe they’ll beat the odds—that belief is what lets them leap in the first place. And because they’re wired that way, they keep trying—until they succeed or until the weight of repeated failure takes its toll. It’s just psychology.
There’s a big difference between failing and being a failure—a distinction even risk-takers sometimes forget. When you take risks, you also risk being labelled a failure—or worse, believing you are one. But that’s very different from failing.
This struck me during a conversation with a close friend who’s had a couple of failed ventures—like me. I’ve never shied away from sharing my failures, but this time felt different. It took me a while to understand why.
Most people aren’t risk-takers and are conditioned to talk about their wins. When they do mention failure, it’s often like a job interview confession: “I’m such a perfectionist that I spend too much time on details…” (Sure.) For people like that, it’s hard to grasp what failing really looks—or feels—like. Because they avoid failure, they assume those who fail must be failures. For risk-takers, that can be tough to face.
I never realised how tough it was for me—until it felt so easy to talk to my friend, who had also failed but still had the fire to try again. Maybe that’s why the advice to “find your tribe” resonates so much: seek out others who are walking the same path.
I’ve always been good at math, and I knew the path I’d chosen would be full of failures. But I hadn’t accounted for the emotional toll of being labelled a failure. Maybe it’s time to learn a little psychology too.