“Trying is the first step to failure.” — Homer J. Simpson
It’s a dumb joke. But like most things Homer says, there’s a weird little sting of truth buried in it. Especially if you’ve ever tried something new and immediately felt like you were 10 steps behind everyone else. That’s what sparked this whole line of thought for me – I was having a conversation about failure the other day, and it cracked open a bunch of memories and realizations I didn’t know I’d been carrying around.
I remember being 14 and telling my dad how much it bugged me that any time I got into something – baseball, music, whatever – there was always someone better. Someone who’d been doing it longer, who’d already figured it out, who looked effortless while I was still trying to get the glove on the right hand. That used to really bother me. Still does sometimes. You start something and instantly realize you’re not going to be the best. So what’s the point?
And I’ll never forget what my dad said. He didn’t get philosophical or go into coach mode. He just said, “You don’t have to be the best. But you can always be good at what you do.” That hit. And it’s stuck with me ever since. Because “good” isn’t mediocre. Good is owning your space. It’s about being trusted, being dialed in, knowing your lane, and showing up fully. That mindset gave me room to breathe. Took some of the pressure off. And I think that space is what allowed me to keep pushing – to get better without being paralyzed by perfection.
Freedom Through Failure
Over the years, I’ve come to believe that when you have no fear of failure, it’s an absolutely incredible place to operate from. You start taking swings you wouldn’t have dared to take before. You’re more creative. You’re looser. You’re not protecting some fragile image; you’re just in it. I’ve always said I have no pride, and I mean that in the best way possible. I don’t let pride get in the way of learning. I’ll fall flat on my face, try again, and keep going. Maybe it’s a mix of humility and just enough ignorance to not overthink things. Maybe it’s stubborn curiosity. Whatever it is, it works.
But I’ve also learned none of this really unlocks until you put your ego in the back seat. And I don’t mean kill it off entirely – we need ego to walk into burning buildings and make decisions under pressure. Firefighting without confidence is a nightmare for everyone. But breakthroughs – in life, in leadership, in relationships – don’t come from ego. They come from ego death. From being willing to step aside and let the Observer in.
Your Observer sees things clearly. It’s not invested in protecting your pride. It’s not trying to justify or defend. It just notices. The ego, on the other hand, will twist every outcome to preserve your comfort. It’s a master manipulator. It’ll tell you that if things don’t go a certain way, then the motives don’t count. That if you didn’t win, you failed. That you should’ve been farther ahead by now. The Observer says, “Interesting – what can I learn from this?” The ego says, “You’re not enough.”
And for me, the ego test has always been simple:
**Are you “on”? Or are you a moron?**That’s what I tell myself. It’s blunt, but it works.
If I’m too proud to ask questions, too defensive to hear feedback, or too obsessed with the result to see the pattern, then I’m not really “on.” I’m reacting, not leading. I’m missing the lesson.
Where the Growth Lives
And the biggest lesson? If you’re not failing anymore, maybe it’s time to move rooms. Maybe you’re no longer growing. Maybe you’ve started optimizing for praise instead of progress. That shows up fast – in your job, your leadership, your marriage. We all love the comfort of being admired. But sometimes we need to trade admiration for challenge. That’s where the edge is. That’s where we sharpen.
You want to stay sharp? Get in rooms that make you sweat. Places that make you rethink what you know. Find people who force you to elevate. And yeah, it’ll be uncomfortable. We joke and call it a Jesus time out – that moment when you’re humbled so fast, you can only sit there and stare at the wall. But those moments? That’s when real shifts happen.
This stuff applies at the hall. But it applies even more at home. I think most firefighters are better at managing ego in the firehouse than they are in their own kitchen. At work, we’ve got rank, roles, and expectations. At home, we’re stripped bare. And that’s where the Observer matters most. That’s where pride causes the biggest wreckage. You can have anything you want, but not everything you want. Sometimes, playing your absolute best still won’t be enough. And that doesn’t mean you’re failing. It just means you’re still becoming.
The Reminder
And in case any of this hits close to home – if you’ve been stuck, doubting, second-guessing – I just want to say you’re not alone. Most of us stretch ourselves further than we admit. That’s what makes me proud to walk among firefighters – people wired to push, to grow, to keep showing up. But even the best of us get stuck sometimes. This isn’t a warning. It’s a reminder: you’re probably in the right room already. You’re just not done moving.
Because the truth is, failing often doesn’t make you weak.
It makes you a threat to the old version of you.
Kory Pearn is a career firefighter and captain; and the founder, publisher, and editor-in-chief of CRACKYL Magazine.
