Rules are an endless source of fascination and dread to me. How rules are created and why, how rules accumulate, how a set of rules shapes a system – it’s very, very interesting. Let me give you an example. A couple years ago my wife and I were chatting with our tax advisor and he went off on a little rant about how the tax rulebook in Germany is getting thicker and thicker every year. “When I started out,” he said, “it was half the size! But they don’t know that!” The anonymous They he referred to are the young people working in the tax office today. His point: the young people who are just starting out working in the world of taxes don’t know that the whole world doesn’t come crashing down when you only have half the rules. Even though evidence points to the contrary.
In my personal life, I have a lot of processes, their backbone being two recurring sessions: a "weekly review" every Sunday at 6 pm and a "monthly review" on the last Sunday of each month at 7 pm.
I have two templates (weekly+monthly) in a Google Doc that I'd make a copy of whenever I start a session. Adding something to one of these templates is a very powerful act because it starts a recurring weekly/monthly process that will take time in every following session. I tend to be very picky about adding a new item there, but still, as you describe in this article, the amount of stuff in there naturally increases without a conscious effort to clean it up once in a while.
I'm a big fan of Derek Sivers (https://sive.rs/), and his thoughts about simplicity and letting things go helped me a lot to make simplification a part of my processes.
What I do is pretty simple: I have an item in my monthly reviews that says, "every March and September: go through weekly+monthly templates, remove low-value stuff ruthlessly". It takes 20–30 min to do that, but obviously saves me a ton of time. It also makes me trust my system a lot better because I know I can add random stuff to my templates that sound good at a time (an insightful-sounding James Clear quote to tell myself regularly, a cool-looking productivity hack, etc.) and I know that I can remove it at the next cleanup. (Also, I don't always wait for these official cleanup processes to run; I throw out stuff as soon as they clearly seem unhelpful.)
We did the same at my startup, btw: we used pretty elaborate meeting agenda templates for each type of our recurring strategic and operative meetings, and in one of the wider-scope meetings, we had an agenda item to go through all of our templates and clean them up. I think we also did that at a twice-a-year cadence.
I think this should be a very important part of every company culture.