The Curse of the To-Do
Chucking the checklist state of mind
I’ve been under the weather lately. And by the weather, I actually mean my to-do list, aka task list. We all have ‘em, at least most of us well-adjusted people grappling with an unfathomably complex world. The only of us who don’t have some way of keeping track of the things we intend to do might be the purely enlightened and the purely degenerate. For us middle managers (as in, middle class of life management), to-do lists are essential.
Shall I review how they work? That would be a waste of ink. Or a waste of energy producing pixels on the screen you’re reading this upon. You know how to-do lists work, they basically teach it to you as you’re learning to use a pencil.
But this post is going to take a deeper crack into the curses to-do lists can foist upon their users, and even though I haven’t avoided their pitfalls – not even by a longshot – we can start by admitting there’s a problem.
Unless you’re living in a monastery and have nothing to do but sweep floors, pray for 14 hours a day, and make cheese… whatever system you use is bound to become infernally complex. Post-it notes tumbling out of your pockets, Apple Reminders categories up the wazoo, and season-old items that are perpetually Due Today, which you again punt down the road.
One very immediate and apparent problem is your method is likely to start suffering from a heinous signal-to-noise ratio. The whole point in a to-do list is to guide you toward the next thing to do. When you’re inundated with thirty things you’ve been kinda-wanting-to-do for three months, it becomes really hard to discern the things you actually need to do, and the whole to-do system goes down in a fiery mess. You start scrawling urgent lifelines on the back of napkins.
You’re seeking information and guidance, but you’re confronted with a list of unfulfilled wishes, dreams, and aspirations. No bueno.
Let’s back up, because there’s something more insidious going on. I said I wouldn’t waste pixels by explaining how a to-do list works, but I sure as hell am going to use some pixels to explore what’s going on in the psyche of the to-do list addict, as they reach for their Bujo® (that is, Bullet Journal®. Had a good laugh when I saw this contraction).
Editor’s Note: despite intense pressure from Greenpeace lobbyists against Mr Mandel’s wanton use of energy for needless explanations, he was unwilling to remove anything from this post and threatened to chain me to a tree in a Greenpeace-certified logging forest, should I continue to harangue him. “Harangue” was his word, not mine. Therefore, forgive me dear reader, for the needless ravaging of the planet and the manner in which these following paragraphs will perpetuate our climate emergency. The Author is a stubborn fellow and clearly has no conscienc—
Jesus! This editor is out of control. Happily I got my hands on this post before he tried to publish it and cut off his puritanical ramblings. I don’t know what I pay him for, he does nothing but harangue me and interfere with continuing my to-do list completion streak. Anyway, on with the show:
Here’s a familiar situation – an idea flits across your mind and if you have the iron discipline and focus of a samurai, you don’t let that idea interfere with your carrot-carving project. You know your life would be a worse mess of chaos than a Jackson Pollock painting if you followed every idea that came across your mind, much like Dr Seuss wrote about in Hunches in Bunches. But never mind Dr Seuss, back to the carrot carving. You set down your carving knife and type a task into your phone, maybe even setting a due date. You resume carrot carving.
What just happened is completely ordinary, and highly encouraged by productivity professionals, yet it’s a little strange. Some notion just presented itself to your awareness, and you’ve essentially mailed it to yourself in the future. When your future self receives the package, the impulse that fuelled the notion in the moment will likely be gone. And so what do you do? Do you entrust your actions to the to-do list, believing in its ∞ wisdom, letting it guide your decisions and activities? Do you spend your time fulfilling the hopes, dreams, and aspirations of a past version of yourself?
There’s a way in which doing this exact thing is very important if we want to get anything done at all. Sometimes the thing that occurred to us while carrot carving is that we need an extra block of tofu for dinner on Wednesday, and we can mail that idea to the version of ourselves who’s at the grocery store and can actually do something about it. We don’t need to improvise a grocery list every time we have the option to buy food.
But there’s something more confusing that can happen. We find ourselves with the aspiration to do a creative project, or to send an email to someone we love. But for whatever reason (like the high-stakes pressure of carrot carving) we can’t fulfill that wish in the moment. Speaking from my anecdotal experience of living inside my own head … I find there can be something slightly fulfilling in adding an item to the to-do list, even though adding it does nothing in the way of getting the job done. Now it’s there, though. So surely, that’s better than nothing…
The result is that we defer our actions and scatter the energy that led to our ideas. We no longer find the old impulse, but we do find ourselves with instructions on a thing that some old version of us wanted to complete.
And this brings us to the weirder, more subtle problem of turning to the list for guidance on how to spend the most precious, non-renewable resource we have: our time.
Life and all of experience is a string of moments. Once the moments have passed (or, are past), we lump them together and start to conceive of this strange container called Time. Within certain constraints we have flexibility on what to do with these moments. I fall into this trap constantly of looking ahead at a few unplanned hours and jotting down items that want to complete, which creates a train track for me to move through these moments. Mile-markers, if you will.
No longer is it a formless series of moments streaking by, it’s a bunch of tasks that I’m moving between. And sure, there are things to complete, jobs do need to get done. But there can be a terrible trap of seeing these tasks as the thing that makes the time fulfilling, but as Tara Brach says, The doing never delivers.
I’ve had days of knocking a tremendous amount off a to-do list, and being surprised at how empty I feel at the end of it. I’ve been acting out a script that nobody but past versions of myself cares about, and believing in it with almost religious fervour. And many of those moments get sacrificed at the altar of productivity.
One of life’s most frightening experiences is to honestly stare into empty time without a plan. This is the heroic element of The Ferris-Cameron Continuum. Both of those characters are staring into the same emptiness, Ferris has trust in it while Cameron is cynical.
The to-do list is a marvellous tool to extend ourselves through time. Instead of being amnesiacs who need to reinvent the wheel every time they need to move something, we’re able to carry our good ideas forward and have them arrive later on, when we’ve finished carving carrots and can actually enact them.
But all that glitters isn’t gold: there’s the dark side of the to-do list that keeps us on a narrow track, forever guided by past versions of ourselves, living out ancient aspirations, and rarely if ever stepping into the ever-present emptiness.
🎙️ Listen to the podcast extension of this post on Follow the What’s That 🎙️