Permission to Fail - How Redefining Failure Can Pave Your Path to Success

Do you really give yourself permission to fail?

And I don’t mean shrugging off a minor slip-up or giving yourself a pass on something that didn’t matter much. I’m talking about genuinely embracing failure with the same enthusiasm you reserve for celebrating your wins. It’s something we don’t do enough of—especially if we’re caught up in the perfectionism trap. You know, that tightrope where you focus so much on avoiding mistakes that you miss the growth that could come from them?

I was in a writing group recently when our facilitator shared a story that stuck with me. She said, "Everything is disposable. Your next version will be better than your last. If you get too attached, you won’t grow." Let that sink in: if you’re too afraid to fail, you won’t grow.

This got me thinking about all the times I failed—and more importantly, all the times I was scared to fail. What opportunities would I have missed out on if I had let that fear win?

The Triathlon That Almost Wasn’t

Take my mid-20s, for example. I watched my then-boyfriend (now husband) complete a sprint triathlon. At the time, I was...well, let's say “athletically challenged.” I could barely swim (doggy paddle for the win), I wasn’t much of a runner, and my biking skills? Let’s just call them “enthusiastically mediocre.” And yet, as he crossed the finish line, something sparked inside me. I decided I was going to do that same sprint triathlon the following year.

This one had a ?-mile swim, 20-mile bike ride, and a 5-mile trail run. And let me tell you, I had my work cut out for me. First step? Learn how to swim with my face in the water (a minor detail, right?). Picture me in the pool—nose plugs on, clinging to a kickboard, as my friend taught me to freestyle like she was teaching a child. I started running (slowly), and I hopped on the bike (even slower). Failure felt more than possible—it felt probable.

I made it, though. I finished the swim nearly last, got passed on the bike by many folks two to three times my age, and was thrilled to run (read: jog) the whole 5 miles. But guess what? I went on to compete in many more triathlons. Had I feared failure, I would’ve missed out on learning that I’m capable of so much more than I think.

What’s Your Opportunity for Failure?

So, let me ask you this: What’s your opportunity for failure? It sounds counterintuitive, right? Like suggesting you search for your lost keys in a corn maze at night. But here’s the thing—seeking out opportunities where failure is a real possibility means you’re playing at the edges of your comfort zone, and that’s where the growth happens.

Think about it: when was the last time you took a shot at something you weren’t sure you’d nail? Maybe you applied for a job that was a stretch or volunteered to give a presentation when public speaking gives you clammy hands. Whether you nailed it or not, I bet you came out of it with a new skill, a lesson learned, or at the very least, a solid "remember-that-time" story. You may have even been able to say to yourself – “Glad I tried, but that’s not for me!”.

Opportunities for failure are actually growth in disguise. If you only chase the sure thing, you’re essentially living on autopilot, stuck in a loop of predictability. So, what’s next? What’s your opportunity for failure? The thing that makes your heart race just thinking about it. That’s the direction to lean into.

But it’s not just the big obvious “opportunities to fail” that shape us. Some of the most transformative ones are subtle, hidden in what seems like failures.

Career Curveballs

I’ve had a long and winding career path. Each time I switched companies, or positions in companies, I wondered “why can’t I just be satisfied where I am?”.?

Looking back now, I see those moments differently. Each of those pivots was an opportunity to fail, to explore, gain experience, and to get a little bit closer to what I really wanted. Those “failures” taught me something new about myself, and each time, I carried those experiences forward. I wasn’t failing – I was evolving. And each change brought me closer to the life I’m living today.

And here I am, running my own business, finally where I’m meant to be. It’s taken years of trial, error, and countless "fails" to get here. But it’s those failures that led me to figure out what really fits. Had I played it safe and stuck with what I thought I should do, I would’ve missed out on the joy, freedom, and fulfillment that comes from finding my true path.

Of course, there are also those missed opportunities. The ones where I let fear of failure hold me back. Or the times I didn’t recognize failure as the stepping stone it could be and spent too long beating myself up for mistakes instead of celebrating them. If I had realized that earlier—if I had taken a moment to celebrate failure—I could have moved forward faster.

The Mindset Shift

So, how do you shift your mindset to embrace failure? First, not only give yourself permission to fail, but go a step further and celebrate it. Yes, I mean really celebrate it—like it’s 1999 and you’re at the world’s biggest party, dancing with your "failures" like they’re your best friends! Remind yourself that each "fail" is just a chance to try again and improve. It doesn’t mean you’re not making progress—it means you’re evolving. Every failure brings you closer to success, as long as you’re willing to keep going.

So, I challenge you: give yourself permission to fail and throw a little party when you do. Ask yourself, "What is my opportunity for failure?" and see where it leads you. You might just find that what you’ve been afraid to lose wasn’t as valuable as the growth that’s waiting for you on the other side. It’s time to celebrate those fails - they’re the stepping stones to the life you’re meant to live.