This article was originally published in The Startup.
I like planning. A lot. Maybe too much.
It’s an addiction that began in high school. Each evening, I was attempting to balance somewhere in the region of 5 hours of studying, writing my old blog, writing for publications and zines, running a small online business, caring for (at one point) 16 pets, and, you know, showering and all that. And bear in mind I rarely got home before 5 pm and usually got up at 6 am.
I started making simple to-do lists for each evening, sketched out in my planner before the bell rang at the end of the final class. Winging it in the evenings wasn’t working. My inability to get everything that needed doing done started to wear on my mind. So the to-do lists became a self-soothing activity. Making them calmed me down.
Because that’s what planning can so easily become: a form of escapism.Crack open a crisp new Moleskine notebook. Open a neat calendar, the days dissected into slots. Pull up a to-do list app with its buttery smooth design.
And you step away from the messy, chaotic world of delayed trains, split coffees, and lost chargers. You step into a serene world where everything is certain, nothing goes wrong, no one panics or procrastinates, and life is logical.
I loved making those to-do lists for precisely that reason. As the final bell rang, I’d smile at the neat color coded list, ordered by importance, complemented with time estimations. Everything was doable. I was unstoppable. This plan would guide me through the evening. I would be the image of restraint and discipline.
It never worked that way. But I kept thinking it could if I found the right planning system. In college and university, I became a planning connoisseur, buying numerous notebooks, trying dozens of apps, listening to hundreds of hours of podcasts, reading books on the topic and becoming fully fluent in bullshit productivity advice.
Having spent hundreds of hours researching behavioural economics for work, I can say with some degree of certainty that we’re all terrible at planning.Maybe some of us are better than others, maybe we make better plans some of the time. But on the whole, we’re far too optimistic.
We assign super-human capabilities to ourselves. We misunderstand time, our own cognitive capacity, and the benevolence of others.
Think about it.
In the last month, how many times did you cross off every single item on your to-do list for the day? How many times did you attend a meeting that didn’t run over? How many journeys really hit the ETA you texted someone before leaving? Of the projects you completed, how closely did you actually follow the plan? Of the detailed plans you made, how many were 100% necessary?
Exactly. That’s why, much of the time, we’re not planning because it’s useful. We’re planning because it feels good.
At the end of the day, planning is escapism. It lets us escape the world where we actually need to do all this stuff. And it’s easy to justify devoting inordinate amounts of time to it because it is in fact a useful thing to do, up to a point.
Sometimes I manage anxiety by sitting down and making a list of all the problems in my life, usually totalling about 70 of which ~10–15 are urgent and would make my life a lot better if they went away, ~20 are medium and have a tangible impact on my well-being, the rest are low-level ‘nice to haves.’ Then I’ll break down all the parts involved and wile away a couple of hours in the process. It feels gratifying to see that, in theory, all my problems have solutions.
The issue is that I can only tackle maybe 2 big problems at once. When I do tackle them, it tends to just happen. I get so fed up I start doing whatever it takes. The planning part is mere self-soothing.
In People aren’t disposable I talked about how the problem with ‘friend matching apps’ (like BumbleBFF) is that the gap between the effort required to swipe right to someone and the effort required to meet up with them, then invest in building a friendship, is too big. The discontinuity stumps us in practice. On the other hand, meeting someone serendipitously, then arranging a casual coffee or invitation to a social occasion is a far more fluid process.
The same goes for planning. Writing down that you want to do XYZ, even breaking it into little steps and putting it in your calendar, is light years away from the effort of doing said thing.
Devoting more and more time to the planning stage is mere procrastination. While I still make a lot of plans, I try to keep to the most basic, simple, starting points — then take it from there.