The Practice of Iteration

The Practice of Iteration

One of the quiet truths I’ve learned—through years of leading engineering teams, running a sign shop, managing a coffee business, and parenting three kids—is this:

You don’t have to get it right the first time.

You probably won’t.

But if you’re paying attention, you’ll get another chance. And another.

That’s the gift of iteration. Not just in code, but in leadership, in systems, in relationships. The ability to notice, adjust, and try again is one of the most powerful tools we have.

Over time, this idea has become a kind of orientation for me. A posture. A way of approaching the messy, human work of building teams and businesses and families—not with perfection, but with the belief that things can keep getting better.

Engineering Taught Me This First

I learned the shape of iteration first in software. You build the simplest version that works. You ship it. You watch what happens. You adjust. Then you do it again.

A good engineering team doesn’t expect perfection. It expects forward motion. It expects attention. It expects learning.

That mindset is what drew me to engineering in the first place—and what I try to carry into leadership. Not just building better systems, but building how we build.

It’s tempting to wait until you have the right structure or the right process. But what I’ve found over and over is that it’s better to start with something honest, small, and incomplete—and improve from there. That’s how strong practices form: not all at once, but through iteration.

It's Not Just Engineering

At the sign shop, the handoff from sales to production still breaks down sometimes. A detail gets missed. A note doesn’t get passed along. A job runs late, and someone ends up frustrated. When that happens, we don’t scrap the whole system—we adjust it. Then we adjust it again. Each version brings us a little closer to clarity: less friction, better flow, more trust.

The same kind of iteration happens at the coffee bar. We’re always fine-tuning recipes—dialing in espresso, trying new roasts, refining how drinks are prepared and served. The team pays attention. If something’s off, we tweak it. We taste, we test, we try again.

None of this is about chasing perfection. It’s about responding with care to what the work is teaching us. Iteration, in these spaces, becomes a way of saying: this matters. We’re paying attention. We’re not done yet.

Parenting Is Iteration, Too

Nowhere has the practice of iteration felt more personal—or more humbling—than in parenting. There are so many moments I wish I could do over. A rushed reaction. A missed opportunity to listen. A tone I didn’t mean to take.

But parenting, like leadership, is full of second chances. The next morning. The next meal. The next bedtime. Each one is an opportunity to respond differently, to repair, to grow. To show your kids—not just through words, but through your willingness to change—that you’re learning, too.

It’s not about getting it right. It’s about staying present. It's about showing love through growth and adjustment in each iteration.

Build Systems That Assume Iteration

If iteration is a gift, then one of the most important things we can do—at work, at home, in any setting—is to make room for it.

We can build systems, schedules, and rhythms that expect change. We can create cultures where trying again isn’t seen as failure, but as part of the process.

At Webconnex, in the shop, in the coffee bar, and at home, I keep learning this: strong practices aren’t built all at once. They emerge through slow attention, honest feedback, and the willingness to revise.

The work is never done. But it can keep getting better.