Learning to Fail Forward

It’s been a while since I’ve written anything long-form. Other than emails, that is (and sorry to those of you who have to read my mini-dissertations).

But lately, I’ve been thinking about how I can give back. Not just through building or speaking, but by sharing thoughts, stories, and lessons I’ve learned along the way - the raw ones. The unfiltered ones. The ones I wish I could’ve read when I was just getting started, trying to build something from scratch, wondering if any of it even mattered.

Because it does. What we do daily often matters more than we’ll ever realize.

I want Leadership Dispatch to feel familiar, kind of like a shift on the ambulance. If you know me, you know I’ve spent years there. On a shift, dispatch doesn’t have all the answers. They just share what they know and try to help connect the pieces. Sometimes it’s messy. Sometimes things get lost in the handoffs. But even in the chaos, there’s a purpose behind it.

That’s what this blog is: not perfect answers, but real dispatches. Some messy. Some clear. All true.

And yeah, I’m an AI guy. Big time. I advocate for AI almost daily. But this blog isn’t generated. This is me, sharing thoughts in a way that connects human to human. Because in a world that’s increasingly optimized, compressed, and summarized, sometimes what we need is just a small nugget of something real.

Will anyone read this? I’m not sure. But if you’re here, I’m glad. I hope it’s worth your time.

On Failure and Feedback (Or, How Reddit Humbled Me)

Not long ago, I had the opportunity to participate in the Lovable Shipped Season 1 2025 Accelerator. I was pumped. I decided to build something different. Not a SaaS solving a business problem, but a creative puzzle game. Something fun. Something different. A creative stretch.

In week two, I launched it and posted it to Reddit, thinking surely people would get it. Appreciate it. Maybe even love it.

Spoiler: they didn’t. It was confusing. Half of the people couldn’t get past the first level (If you ever need a lesson in humility, Reddit will deliver.)

Turns out, I had encoded the answers to all of the puzzles directly into the source code. Like… literally handed them out. I thought I was being clever. And those who didn’t find the hidden answers? They had no clue how to even play the game. Talk about thinking that your idea is the best in the world, and no one makes it past level 1.

It took me almost two weeks to rework the entire thing. I burned through a lot of credits (full disclosure: I vibecode — meaning I lean heavily on AI tools after planning things out). It was frustrating. But it taught me something I’ve had to learn more than once:

It’s okay to fail forward.

That one mistake reshaped how I approach puzzle design, UX, and product testing. And those lessons are now baked into everything I build, even beyond that game. That same project - the one that I completely reworked after failing - ended up placing 317th out of over 5,800 entries. That’s what failing forward looks like.

We Learn More From Failing Than Winning

Success feels great. It should be celebrated. But if all we ever do is win (pretty sure there’s a song in there), there’s no friction. No feedback loop. No growth.

For me, failure isn’t the problem. It’s what I do in the failure that matters.

Do I get bitter? Defensive? Quiet? Or do I sit with it, pull out the lesson, and get better?

Failure is where I recenter. Failure is where I reconnect with the mission.

In Star Trek (yes, my nerd is showing), there’s a training simulation called the Kobayashi Maru. Long story short: the mission isn’t designed to be won, it’s designed to see how the captain responds to an unwinnable situation.

That’s always stuck with me. Maybe when we train and lead, we need more Kobayashi Maru moments — more practice failing, not just winning.

AI Always Answers — But Should We?

One thing that bothers me about AI, even though I love it, is that it’s always confident. Even when it’s confidently wrong.

And I worry we’re building a culture like that, too.

We celebrate success. We hide failure. We reward people for always having the answer, even when it’s made up. We pretend things are fine when they’re not.

That’s dangerous for humans, and for the systems we build.

If we reward only certainty, we create leaders who fake it, and systems that can’t handle the truth.

Final Dispatch: Let Yourself Miss Sometimes

So this week, here’s what I’m working on:

Letting myself miss. Letting myself fail forward. Not needing to win every time, just committing to keep showing up.

You don’t have to win every race. But you do have to keep running if you want to grow: in your work, your leadership, your relationships, your purpose.

We’ll all stumble. The key is not to stop.

See you soon, – Kyle