The Truth About Failing (and Why You Should Keep Doing It Anyway)
Not long ago, a dear friend confided that they thought sailing came naturally to me. That it was something I just got. Let me assure you, that couldn’t be further from the truth. Sailing has been one of the most challenging—and rewarding—journeys of my life. But it’s a journey paved with failure.
When I first set out to pass the German sailing exam, I failed. Three times, in fact. And not in a “Oh, I just missed it by a question or two” kind of way. I failed miserably. The combination of my own performance anxiety and the complexity of mastering technical sailing terminology in German—my second language—was overwhelming. Yet, I kept showing up. I failed, and I failed again, until one day I didn’t fail anymore.
Looking back, I see that those failures were not obstacles. They were essential steps in the process.
The Difference Between Fear and Danger
Fear is a fascinating thing. It can save your life when there’s an actual threat, like a lion charging at you. But fear can also masquerade as danger when you’re simply stepping into the unknown. If you’re afraid of trying something new—afraid of failing or looking foolish—that fear isn’t a signal to run. It’s a sign that you’re stretching, growing, and daring to do something extraordinary.
And here’s the kicker: failure is not the opposite of success. It’s part of it.
Why Failing Miserably Is a Good Thing
When we see someone excelling—whether it’s in sailing, cooking, public speaking, or any other skill—it’s easy to assume it came easily to them. What we don’t see are the countless hours they spent practicing, struggling, and failing along the way.
Failure feels awful in the moment. It can make you question your abilities, your dreams, and even your worth. But every failure is a step forward. Every misstep teaches you something—about the skill you’re trying to master, about yourself, and about what it means to keep going even when it’s hard.
The Power of Tiny, Invisible Improvements
One of the hardest parts of failing repeatedly is that the progress you’re making can feel invisible. It’s easy to think you’re getting nowhere when, in reality, every small mistake is teaching you something that brings you closer to mastery. Those tiny improvements might not be noticeable to anyone—not even you—but they’re there.
It’s like sailing against the wind. Each tack feels like you’re barely moving forward, but when you look back, you realize how far you’ve come.
Do It Anyway
So, what do you do with the fear of failing? You acknowledge it. You thank it for trying to protect you. And then you do the thing anyway. You try. You fail. You get back up. You fail again. And again. And you keep going, trusting that each failure is a necessary step toward something greater.
I know it’s hard. I know it’s scary. But I also know you’ve got this. Seriously.
The next time you’re standing on the edge of something new, whether it’s sailing, starting a business, or pursuing a long-held dream, remember this: you don’t need to get it right on the first try. Or the second. Or even the third. You just need to keep showing up.
Success isn’t about never failing. It’s about failing a hundred times and still believing in the possibility of success.
