“Don’t call me lucky. I’ve failed more times than you’ve tried.”

It’s 9:21 a.m. on a Sunday in Austin, Texas, and I’m sitting with the notes I’ve taken over the last few weeks.

It’s 22 degrees, sleet on the ground, and completely silent. Unlike the Windy City, everything shuts down here when it drops below freezing. I don’t mind it, honestly.

I hear faucets dripping, the heater running thank god, and a few brave souls trying to drive on a couple inches of pure ice.

I look at my phone and, like I often do, I get lost staring at my lock screen. I zone out completely. When this happens in public, I usually get a few concerned looks.

If only they could see what I’m looking at. The title of this week’s issue.

I drift because it doesn’t bring up one emotion. It brings up all of them.

I feel motivated to take more chances. To act without fear.

It feels like hitting the second minute of a cold plunge. Needles piercing every inch of my skin, while at the same time a strange sense of calm settles in.

It grounds me. And given how superstitious I am, it reminds me that the relationship I’ve built with failure is directly tied to whatever success I’ve found.

There’s a thin layer of anxiety too. How much longer do I have to keep stacking failures?

There’s also pride. I’ve fallen a lot. And I keep getting back up.

It pulls me in deeper.

Somewhere along the way, my comfort with failure created a cycle I no longer panic around.

Try. Fail. Adjust. Try again. Repeat.

I wouldn’t say I’ve mastered this, but I’m comfortable moving through it. If only I applied that consistently to every part of my life, but that’s a conversation for another time.

I’m willing to bet most of you reading this understand that cycle.

You’ve read about it. Heard about it.

Living it is a different story.

When you’re in it, everything feels heavier. You don’t feel worthy. You don’t feel good enough. You just lost. And now you’re supposed to adjust and do it all over again?

There isn’t a word that does that experience justice.

The toll is real. It’s heavy. And I don’t care who you are.

But just like stepping out of cold water, something shifts. You start to feel the strength that comes from accepting the loss, changing your behavior, and taking the next step forward.

Now imagine going through all of that, and someone casually comments at a dinner party about how lucky you got.

It’s not about denying luck. Of course some things have to break your way. That part is inevitable.

What stings is how it erases the work. The failure. Everything it took to get there.

That’s the part worth locking in on.

Luck, by definition, is chance. You can earn more opportunities to get lucky, but you can’t control it completely.

If you failed once and never tried again, there isn’t much to pull from that.

If you’ve failed over and over and you keep committing to the cycle, you’re doing it right. That isn’t just the process. That’s the goal. Everything after that is out of your hands.

I remain at my lock screen, thinking back on the times I’ve moved through that cycle. The ones that reshaped me. The ones that forced adjustments I didn’t even realize I was making at the time.

And then another thought surfaces.

What happens when you succeed at the task, but still lose in the bigger picture?

That feels like the next evolution of the cycle. When the process works, the discipline holds, the decisions are sound, and still something breaks against you anyway.

Bad luck has a way of showing up like that. Quietly. Indifferently. Undoing progress without asking permission. Not because of a missed step or a lazy adjustment, but simply because it can.

That’s a harder loss to reconcile.

Because at that point, you didn’t fail the process. You honored it.

You showed up. You adjusted. You stayed in motion. You stacked the small corrections that no one ever sees.

If you’ve remained loyal to who you’ve become through those journeys through the cycle, if you’ve consistently corrected course where you could, then what else are you actually looking for?

Not guarantees. Not outcomes. Not immunity from loss.

What you’re left with is something quieter, but sturdier.

A way of moving forward that doesn’t collapse when things break the wrong way.

A path that still exists, even when the scoreboard says otherwise.

And maybe that’s the point. Not escaping the cycle, but evolving within it.

Continuing to take the next step, not because you’re certain of where it leads, but because it’s who you’ve proven yourself to be.