9/100: How do you overcome the fear of failure?
Progress and perfection can’t share the same seat.
Yet, you hesitate. Pacing the base of a mountain trying to measure it, when the truth you seek is in the climbing. The failing. The revision. The monotonous, mind-numbing one foot in front of the other. For what you seek will find you in motion, on the path, at the altar of persistence, of practice. When no one is watching, or wishing, or clapping.
And when your doubt and disappointment finally break, you’ll reach the peak to find progress asking, again, what’s the last thing you did perfectly?
I was on a boat in the middle of nowhere last month, dressed to fly fish, fearful I might make a fool of myself or break something. The rod was sleek, the line was thin, the bait was dazzling and delicate. Our guide paddled upstream, explaining the basics.
When I yell SET, he said, you can’t hesitate. You have to pull without thinking. Most people hesitate, and if you wait, you not only lose the fish but you tangle your line, making it even harder to act again.
I whipped half circles for an hour, and still, every time he yelled SET I’d feel my breath hitch and my wrists freeze. By the time I pulled, the fish was gone, my line twisting into a wiry knot.
You’ll catch one, he assured, just trust yourself and pull.
I was on that boat in the middle of nowhere because I’d tried and failed and persisted at something for 15 years. I’d taken shitty photos and videos and audio, I’d bartered for gear and corrupted SIM cards, I’d practiced on friends, and family, and anyone who’d let me. And I trusted that if I kept experimenting, iterating, and revising, one day I’d make work I admired.
Failure isn’t some moral or personal shortcoming. Failure is practice. Failure is data. Failure is a prerequisite, a gateway. It’s an inseparable part of the process. It means you’re doing, for there is no failure without an attempt. And with our brief and painful and wondrous time on this earth, I’d rather risk short-term embarrassment than life-long regret.
I whipped another half circle near a shady patch of stone and bush, dragged my line, and waited. Five seconds later, a tug. SET. A tiny fish dancing at the end of my line.
A reminder of how, with patience and persistence, you can set your feet and pull from this life, despite fear and without hesitation, what is rightfully yours.
9/100: How do you overcome the fear of failure?
Thank you for watching, reading, and listening. I’m looking forward to reading your answers to this one, friends. Big or small. When was the last time you overcame the fear of failure?
*Ah! I had to upload this again, ya’ll! Sorry for the double email in your inbox. Living the question on this one lol.





I feel like I've been in a sort of creative-motivation paralysis for some months... I want to do so much, and still have no desire to follow through. Is it failure? Is it burnout? Is it this depression? Is it feeling like it won't matter? All of the above. Relearning patience with myself and reminding myself that one day, the moment will come.
I’m terrible at failing. I typically abandon and start over or don’t return. But there are a couple places where I try and try again. Writing is one of them.
I show up to the blank page every week and write imperfectly. Over the years I’ve gotten better. But just this weekend I wrote in my journal, “I want to be masterful at writing personal essays.”
To answer your question, I keep showing up. I keep trying. It’s the only way that works for me.