Permission to Fail: The Wildest Strategy for Growth

When was the last time you gave yourself full permission to fail?

Not tolerate it.
Not secretly dread it.
Not “allow it” begrudgingly.

I mean truly, wholeheartedly, unapologetically letting yourself fail as part of the work of becoming who you’re trying to be.

Most of us don’t do that. We try to earn our way into excellence by avoiding mistakes… and then we wonder why our progress stalls out.

Failure isn’t the opposite of success.
Failure is the trailhead, the tongue line, the bottom of the climb.

A few years ago, before Wyld Heart, I went through a moment on the river that changed how I relate to failure entirely.

I had signed up for an ACA River Instructor certification course — one of those courses that pushes you to refine the tiny details you’d rather skip over. I had been rowing Class IV for a while by then. I was strong, capable, and comfortable in big water. My identity was wrapped up in being “the one who rows clean.”

On day two, we practiced micro-moves: catching tiny eddies, hitting precise angles, and slowing things down instead of muscling through. It was the kind of practice that humbles even seasoned guides.

One of the drills was a simple ferry across a mellow tongue, or at least, simple in theory. I lined it up, pulled a few strokes, and immediately blew the angle. Entirely missed the mark. Drifted right past the eddy like a beginner on her first day.

I was mortified.

The river didn’t care.
But I did.

And my internal voice went wild:

You should be better than this.
Everyone saw that.
You don’t belong here.
What a stupid mistake.

My stomach dropped. My chest tightened. I felt myself shrink.

But then the Instructor, calm, grounded, observant, just looked at me and said, “Good. Now do it again.”

No drama. No judgment. No meaning-making.

Just: try again.

Something in that moment hit me in a way I didn’t expect. The world didn’t end. The group didn’t lose respect for me. The river didn’t swallow me whole. It was just a failed attempt.

A First Attempt In Learning — even if I didn’t have that acronym back then.

So I rowed back up and tried again. And again. And again.

By the end of the afternoon, I had hit the move cleanly. Not because I was perfect, but because I was willing to fail repeatedly and keep going.

That day taught me more about becoming a precision rower than any “perfect line” ever has. There’s a massive difference between failing at something and being a failure. But most of us collapse those two ideas without noticing.

We fall out of the boat → “I’m not good enough.”
We miss a line → “I’m embarrassing.”
We struggle with a skill → “Everyone else is ahead of me.”
We set a goal and backslide → “I’ll never get it together.”

And once you’ve equated failure with your identity, you stop taking risks entirely. You choose only the things you’re already good at. You choose comfort over curiosity. You choose protecting your ego over expanding your life. But what if failure wasn’t a verdict? What if failure was just feedback? What if falling short meant nothing more than you’re still learning?

Think about the river.

How many of us needed dozens — sometimes hundreds — of repetitions before we got confident in a technical move?

Ferrying cleanly. Entering an eddy without spinning. Reading complex water. Stacking calm, decisive strokes under pressure.

You don’t get there by being flawless. You get there by being willing — willing to flop, willing to adjust, willing to laugh at yourself, willing to get pushed off-line, willing to try again. And still, I watch paddlers (and often myself) beat themselves up for every blown move, every swim, every missed angle. The moment something goes wrong, the whole day feels ruined.

But on the river, failure is simply part of the journey. A rock in the current. A lateral you didn’t quite expect. A bump, not a prophecy.

If you can acknowledge the sting, learn from it, breathe through it, and keep looking where you want to go, you’ll grow faster and more powerfully than you ever will by trying to avoid failure altogether.

If you want to move toward any goal — in your mindset, your fitness, your paddling, your leadership — you must give yourself permission to fail.

Because permission creates freedom. And freedom creates progress.

When you stop being afraid of getting it wrong, you start showing up with courage, curiosity, humor, and resilience. That’s where the breakthroughs happen. And here’s the truth people forget: No one climbs to their next level alone (except maybe Alex Honald). Not even the strongest rowers. Not even the most experienced leaders.

When I look back at every season where I made massive progress, there was always one thing in common: I had someone in my corner helping me see the bigger picture. Someone who didn’t let me tie my worth to my performance. Someone who reminded me why the work mattered.

That’s the kind of coach I aim to be now — the person who holds space for your learning, helps you find the cleanest lines, and supports you when the river throws something unexpected your way.

If you’re ready to work with someone who understands failure as part of the path — not a roadblock — I offer private and group coaching.

Let’s get you moving toward your next level — with permission to fail, grow, and thrive along the way.