Your Systems are Situational

Your systems are situational. Hear me out.

My personal systems were always two systems: one for work, one for home. And they worked incredibly well.

At work, I existed on Slack reminders and Gmail's snooze feature. The system was essentially this: things would pop up when they needed my attention, and not before. It worked for years. At home, I used Apple Reminders. It was not clean, but it had geofencing and time-based alerts, so I could say "remind me when I get home" and get a nice little pop-up at the front door.

The cracks showed one day when I was on an airplane, flying from Warsaw back to Amsterdam.

Around that time I had started developing ideas for a few side projects (including my advisory business, Otterstein.org #shameless plug). And the side projects didn't cleanly fit into either system. They weren't work, so I couldn't use Slack to remind myself. I didn't have Gmail set up for the side business yet because it was still in idea-mode and I was on an airplane without wifi. And my personal system didn't fit either, because the projects needed more management than a simple reminder was capable of.

So somewhere over Germany I had to admit it: both systems had to come down. Not patched. Torn down, and something completely new built in their place. Something durable that accommodated not just my personal life, not just my professional life, but a potentially infinite number of future passion projects (And if you know me, you'll know that when I like to solve problems, I like to solve a single problem that solves a 1000 later problems).

Rebuilding, I held myself to three rules. The capture mechanism had to be as frictionless as possible and identical for all three territories. The reminder mechanism had to be located in a single interface. And all the three had to stay clearly delineated from each other. I built the workflows with the least negative friction I could manage. I'm a strong believer in the power of positive constraints and positive friction, but this had to fit simply into how I already move through a day.

And what this became for me was a realization: the systems I had made were not durable. They were situational. They worked for the situation they existed in. But as soon as I evolved, and this is not a company speaking (this is a very personal one), I needed a system that worked for the new version of me.

We don't know what the future versions of us will need. But we can build systems with durable components. If you assume you will have more interests in the future — and you will — then you can assume you'll need to capture those things, to be reminded of those things, to manage the tasks that come with those things. The interests are unknowable. The needs are not.

The systems we build need to account not for an unknowable future, but for a very likely one.

Companies do the exact same thing, at scale. The approval flow that works at ten people, the priorities that live in one head — these are situational systems wearing the costume of durable ones, and they hold right up until the company evolves into a new version of itself. That's the pattern I wrote about in my previous little article Everything breaks at 3 and 10, but it took being stuck on a plane ride from Warsaw alone with my thoughts for me to notice I'd been doing it personally.