Once a year, I decide my life is a shambles. It’s in a shambles in just such a way that only one thing can fix it: data entry. And to that end I renew my evergreen quest for the best way to organize my life. All my todos, appointments, stray thoughts, all the minutiæ that make up a modern existence—they all have to go somewhere.

A decade or more ago, I read David Allen’s “Getting Things Done”. It took lots of pages to explain a very simple concept, that keeping the things you have to do in your head is why they never get done. (And also probably why you have anxiety.) You need to disgorge your brain of all the stuff it identifies for you to do, and put it into some kind of system. You also need to break down the things you want to accomplish into smaller pieces. And finally, you need to develop a habit of looking back over all of the stuff and actually doing some of it. Seemed like the perfect prescription for a young designer with terrible time management skills.

Through the mid-aughts GTD (as we were already too busy to say its full name) became one of the internet’s favorite topics. It launched careers and blogs, and likely did some real good along the way. It also dovetailed nicely into a lot of the other organizational concepts du jour, like kanban and/or agile. A few apps originally intended as simple to do lists were remade with a focus on GTD. I’ll note with some irony that David Allen was famously a bit cagey about people using computers with his system. I made a “hipster PDA”, just a collection of index cards held together with a binder clip and popularized by Merlin Mann. The idea was to unload your brain of all that stuff and put it into those cards. Then you’d either do the things, or save them for another day. The hipster PDA gave way to Wunderlist, and Things, and then Todoist.

These kinds of systems hold sway over us because they make logical sense when you read about them on a page. A system that allows you to dump your life in todo form into its loving arms, for someone wracked with anxiety, sounds wonderful. You think you can stick with it, and sometimes you can; other times what really happens is you begin worrying about the system you’ve built more than the things you’re putting into it. You’re unable to just write “buy milk” into your System because it needs a tag. Should that tag be “groceries”? “House”? Normal indecision. But it compounds over time. And what about the bigger things? Don’t I need some place to put notes, too? But they’re outside of The System. How will I associate them with all of my todo items? And this is just my personal life. What about the avalanche of work goals and tasks?

• • •

I was still a full time consultant when Notion somehow danced across my line of sight. I was attracted first by its 1980s Apple aesthetic. (I am an easy mark in that way.) It offered a way to organize all the stuff in your head and in your life under one roof; an external brain, each neuron cross-referenced to every other. Immediately it struck me as the lovechild of Hypercard, Apple’s loved but defunct way of building multimedia slideshows, and OpenDoc, another dead Apple technology that allowed users to assemble documents out of pieces from different programs. We take it for granted now, but the concept of putting a few rows from a spreadsheet next to an image and an embedded video all in the same document was wild in 1996. Notion did that, and so much more. I jumped into it feet first. Here was the unified field theory of my lack of productivity. Getting my shit together was only a few relational databases away. I even persuaded my wife to join me in Notion and we dropped all of our life’s ephemera there, from grocery lists to house renovation plans.

I told myself I would do the bare minimum to set up my productivity system in Notion, but that was a lie. It was only days before I was looking for better ways to do everything; a more clever system for organizing tags, cleaner implementations for my master databases. As I had done a million times before I had made the System the important thing. Years of writing code that would be scrutinized by other (better) programmers made me self conscious and over-critical. I would create and delete databases dozens of times. My System was just one blog post or YouTube video from perfection.

For someone like me the lure is in the process. I like the drive better than the day at the beach, the prep more than the meal. Road signs along the way, carrots cut into neat brunoise. The going is far better than the staying.

If I make myself sit and empty my brain out into the computer, or even a piece of paper, there’s always that moment when I can sense the road looping back onto itself. Before long I’ll need to do all of these things. What then? And what about all the things I’ve captured that I can’t do, but want to? Hike the Sierras. I’m on the other side of the country. Why am I putting this in a todo list? This critical part of my routine can turn inward quickly. I obsess over all the things that I want or need to do, but that I might not have enough context to do.

A concept in GTD that I always loved was the idea of “anytime” tasks. These are things that might take five or ten minutes to complete. You could collect whole gobs of those—sweep the floor, clean the dog bowl—and never run out. Then in idle moments I could always shuffle the deck around and find something to do. But in Notion I started to capture all these items into projects, where their larger context would loom over me. There’s a difference between ‘sweep the floor’ and its larger more ominous parent, 'House'.

There are obvious problems here. Maybe the most glaring is that no one needs to be productive all the time. Looking at it objectively, the idea of applying a Six Sigma style business process to your mundane home life—or even your work life—is, in the parlance of our time, toxic. For me it conjures images of our parents, Dayrunners clutched under their arms, jogging haggard through the gate at the soccer game, mouthing ‘sorry’ as you pack up after the game they missed. It’s one thing to want to be on top of your life; it’s something far more sinister to attempt to cram it all into a meat grinder that generates agendas.

At the same time, I fully acknowledge that so much of the problem is me. I never learned to manage my time, and spent most of my life with anxiety that was undiagnosed but certainly felt. Even now as a medicated and ostensibly well-adjusted adult, I can be sucked into the fetishization of productivity. And inside the bubble of the perfect productivity system is a very lonely place. Putting all the things you want to do in one place—things that you have the best of intentions for, and strive so hard to complete but—and watching them sit and gather dust is sad.