TL;DR: An iterative approach may be less glamorous, but it’s the only way to truly win.
We like to think of things as having a start and a finish. A project kicks off, work happens, and then it’s done. It’s a tidy story. It’s also, in my experience, almost never true.
I want to tell you about a system I’ve been rebuilding for almost 20 years: my own week.
And it is almost always well-intentioned.
I started, like most people, with a to-do list. Eventually the list got too long and overwhelming, so I began prioritizing it. That helped, until it didn’t, and things got out of hand again. So I started scheduling my tasks. The problem there was my optimism. My timing was way too tight, and missing the mark on one task would blow out the rest of the week.
So I kept iterating. Just this week I’ve introduced a new approach built around time boxing. I’ve cut my week into segments, each one focused on a primary function of my role. I have more confidence in this method than in any that came before it. But here’s the thing: I’m also completely okay with the possibility that it won’t work, and that I’ll have to adapt again. After almost 20 years of adaptation, I’ve made peace with the fact that the journey is never complete.
After building many systems over the years, one truth has become clear: there is no such thing as done. There is always more that could be improved, refined, or reimagined. The real measure of success isn’t crossing a finish line that doesn’t exist. It’s finding a way to keep going.
Simon Sinek talks about this in terms of finite and infinite games. Picture two players. One has a finite mindset, playing to win in a single, decisive moment. The other sees the game as infinite, where the objective isn’t to beat an opponent at all, but to keep playing with strength and sustainability. Over time, the infinite player always wins.
That’s how we have come to approach our projects as well. We don’t believe in single, one-and-done project. We believe winning is a systematic and ongoing process. We apply this to our own business, and we apply it to every project we build for our clients. We don’t just start things. We make them sustainable (let me know if you’re curious how we do that)
And I’d suggest this same truth applies well beyond software. It applies to churches, charities, hospitals, schools, and more. It applies to anyone trying to make a significant difference in the world. The world is messy, and there is no bell that rings to tell you when you have achieved a win. Wouldn’t it make more sense to structure our organisations like we are playing the infinite game and not the finite one?