The Things That Didn't Work Taught Me the Most

When I talk about the things I've built, it's tempting to tell the tidy version. The podcast that grew. The book that came out. The career that moved forward. But the honest version has a lot more stumbling in it than that, and the more I look back, the more I think the stumbling is where the actual learning lived. Not the parts that worked. The parts that didn't, and what I did next.

I've started over more than once

I spent almost fifteen years in higher education. For a long time that was simply who I was and what I did. And then I left it for marketing and content, which meant walking away from more than a decade of hard-won knowledge and being, in a lot of ways, a beginner again.

That's a strange and humbling thing to choose on purpose. I wasn't the most experienced person in the room anymore. I had to learn new tools, a new industry, a whole new way of thinking about my own value, and I got plenty of it wrong on the way (plenty).

I've come to see that whole arc as a kind of building too. A career isn't so different from any other project. The first version of it is rarely the final version, and starting over isn't proof that the first attempt failed. It's usually just the next draft.

Starting before I was any good

The podcast is the clearest example I've got of trying something I had no business trying yet. When I started The Life Shift, I genuinely did not know how to produce a podcast. The early episodes reflected that (bless them). I was learning the audio, the interviewing, the whole rhythm of it, in public, one imperfect episode at a time. If I'd waited until I felt ready, until I was actually good, I never would have started, and there'd be no show today.

What I know now is that being bad at something at first isn't a sign you're on the wrong path. It's just the toll for the on-ramp.

Almost everything I can do reasonably well today, I was clumsy at in the beginning. The only way through was to keep making the next one.

Failure is information you can't get any other way

Some of the most useful things I've learned came from projects that didn't land the way I hoped. An idea that felt strong in my head and flat in the world. A piece I was proud of that nobody responded to. A direction I was sure about that turned out to be wrong. In the moment, those sting. With a little distance, they read differently, because each one told me something I couldn't have learned any other way. You can't think your way to that kind of information. You have to try the thing and let reality correct you.

That reframing took me a long time. For years I treated a thing not working as a verdict on me. Now I try to treat it as data. It didn't work, okay, so what is it telling me, and what does the next version need to be?

Trying again is the whole skill

Here's the part I keep relearning. The people who build things that last aren't the ones who never fail. They're the ones who are willing to go again. The willingness to make version two after version one disappointed you, to pitch the next idea after the last one got a shrug, to start the next chapter after a whole career stopped fitting, that willingness is the actual skill. Talent gets you the first attempt. Coming back is what gets you everything after it.

And it does get easier, not because the fear ever fully goes away, but because you build up a quiet track record with yourself. You've been here before. You've had things not work, and you've figured out the next move, and you're still standing. After enough reps, a setback stops feeling like an ending and starts feeling like a familiar part of the process.

What building continues to teach me

The longer I spend building things, the less I trust the tidy stories, including my own. Behind almost anything that worked, there's a pile of things that didn't, and a person who decided to keep going anyway. I've changed careers, started over unqualified more than once, and shipped plenty of things that fell flat. I wouldn't trade any of it, because that's where the learning actually happened. If there's one thing I'd want you to take from this whole series, it might be this: the goal was never to avoid failing. The goal is to fail, learn something real from it, and be willing to try the next version.

Lessons from Building is an ongoing series on work, craft, curiosity, and the messy middle where ideas turn into things.