Thirty years of tweaking the system

I owned 43 actual manila folders. Not as a metaphor — the real thing, one for each day and each of the months ahead, because I’d read about the tickler file and become convinced it was the missing piece. I was an early adopter of GTD, back when explaining it to anyone meant watching their eyes glaze at the word “ubiquitous capture.” A little later Merlin Mann got me on Inbox Zero, which, for whatever it’s worth, is the one that stuck — my inbox was empty when I closed Mail tonight, as it has been most nights for way more than a decade. For years I carried a stack of black A6 Moleskines, somewhere between six and ten of them, one per context, tied together with a leather shoelace. I didn’t keep them in a bag. I carried the stack in my hand, everywhere, so that any thought could be captured on the spot.

I didn’t get my driver’s licence until I was 26, because driving struck me as time I couldn’t be productive in. I’m not joking. I genuinely deferred a normal part of adult life on the grounds that it produced no output.

I’m telling you all this so you understand I am not a productivity skeptic sneering from the outside. I’m the opposite. I went all the way in. I loved it.

And I have to be honest about what it was. All that time I believed I was getting more productive. I was reading the books, refining the contexts, migrating the lists, finding the perfect notebook and then the perfect app to replace the notebook and then going back to the notebook. Paper to digital to paperless and back again, every cycle feeling like progress. But if you’d stopped me on any given day and asked what I’d actually done — not organised, not captured, not filed, but done — the honest answer was often: I spent the morning improving the system I use to do things. The system was the thing I did. The work it was supposed to serve sat in an inbox labelled, tagged, and prioritised, waiting.

That’s the quiet trap, and it’s a comfortable one. Tweaking the system feels exactly like working. It has the same texture — focus, effort, a satisfying sense of order at the end. But it asks nothing of you that the actual work asks. There’s no risk in reorganising your contexts. Nobody’s disappointed if your tagging taxonomy isn’t quite right. The real task, the one you’re avoiding, is still sitting there, and the beautiful system has become the most respectable possible way to avoid it.

Here’s the part I won’t pretend otherwise about: I don’t regret a minute of it. I learned things in those years I use every day. I had genuine fun — the kind of fun a certain sort of person has with a well-made tool and a problem to organise. The irony is that the worst time-sink I could imagine, all those hours not driving, turned into the best classroom I ever had the moment podcasts and audiobooks arrived — a whole golden run of shows, the 5by5 era and everything around it, teaching me more on the move than any system ever filed away. And I still do it. I use Things, I’ve used OmniFocus, I fall off them for months, quit, and then one quiet Sunday I’m back, setting up projects again with the old familiar pleasure. I’ve stopped fighting that. I think these tools are like a good book you reread at different stages of life — the book doesn’t change, but you do, and it gives you something different each time. The notebooks gave the younger me a feeling of control he badly wanted. The apps give the current me something gentler. Same shelf, different reader.

What changed isn’t the tools. It’s me, and what I need them for.

For most of those thirty-odd years the systems were in service of a race — get more done, get ahead, climb the thing everyone climbs. And it worked, more or less; I had a decent run, and I’d be lying if I said the productivity habits didn’t help. But I’m at the stage now where that race is genuinely over. Not lost — finished. I’m not interested in another rung. What I want from a tool today isn’t leverage in a competition. I want it to help me do the handful of things that matter and then leave me alone, so I can spend the afternoon with a gang of rescued cats and dogs who do not care in the slightest how optimised my week is.

That turns out to be the whole design brief.

So I build small tools now, from the far side of all that tweaking. Tools that deliberately give you nothing to optimise — no system to perfect, no dashboard to tend, no settings rabbit hole to disappear into on a Sunday. Because I know exactly where that rabbit hole goes. I lived in it. The apps I make are the ones I wish I’d had when I finally noticed the difference between doing the work and grooming the apparatus around it — tools confident enough to be plain, that run the routine and then get out of the way, that don’t try to become the hobby.

If I could say one thing to the version of me with ten notebooks tied together in his hand, I wouldn’t tell him to stop. He was having too good a time, and he was learning more than he knew. I’d just tell him what took me three decades to work out for myself: the system was never the work. It was only ever the warm-up. And at some point — ideally before thirty years are gone — you’re allowed to put down the apparatus, do the small real thing in front of you, and go and sit with the animals.