This is part 9 of 30 in the Hammertime Sequence. Click here for the intro.
I’ve been thinking about whether or not regular betting, prediction markets, and being well-calibrated is actually useful, and if so how to practice train calibration on a short feedback loop.
Being able to make accurate time-to-completion estimates, at least, is extremely powerful. This post describes my current strategy for staying calibrated about time estimates.
Day 9: Time Calibration
Of all the cognitive biases in the Sequences, Planning fallacy seems to be one of the most directly harmful and eminently fixable. The goal of today’s exercise is to build a tool for routinely checking your calibration about how long things take.
Although Planning fallacy is the clear antagonist in this situation, I also want to gesture at a second class of failures I’ve been facing which involve systematically overestimating the difficulty of things.
Vortices of Dread
After spending a few days checking my calibration, I was surprised at the sheer number of things I routinely overestimate the difficulty of, mostly because of an ingrained fear of housework and the bureaucratic machine.
Several years ago, I watched my father spend nearly a full week on taxes, reading all the fine print, cross-referencing internet forums, and triple-checking every field. I did my own taxes for the first time last year, expecting it to only be more nightmarish – after all, my father’s experience surely saved him mounds of time already, right? Instead, the whole process took me a single afternoon.
Two weeks ago, I set out to get a travel visa done with a travel agent after months of dread. I blocked off the entire afternoon in the (it seemed to me) likely event that I’d have to drive back and forth to pick up, print, and/or fix documentation. The visit ended up taking a total of ten minutes, not counting the two mile drive.
Last week, I set out on an odyssey to make a photo album for family members, dreading the many evenings I would pore over old files and spend arranging prints. The whole process took two and a half hours from start to finish with the timely aid of Yoda Timers.
What threw my award-winning calibration off so wildly? Two things were at play:
First, most of my System 1 data on how long things take comes from watching my anal-retentive parents. I instinctively feel that cooking a meal takes nearly an hour, that every field on every form needs to be checked twice by every individual involved, that you should always arrive fifteen minutes early, and that the bureaucratic machine is constantly out to Get You. That gave me the opposite of Planning fallacy.
Second, the creeping dread around problems became a self-fulfilling prophecy. Even though I was relieved after finishing my taxes in one afternoon, my memory of the experience is still dominated by the weeks of slowly building anxiety leading up to the event. In contrast, I hardly remember the actual filling out of forms. I suspect System 1 was picking up these awful weeks as signal of doom.
In the next day, keep an eye out for clear-cut work and train your calibration on how long things take. Make a System 1 prediction about how long each activity takes, set a Yoda Timer for that amount of time, and try to hit that time. If you expect something to take longer than an hour, break it up into clearly-demarcated chunks to calibrate individually.
(There is, of course, the confounding factor of the timer, but if you find yourself significantly more efficient with the timer goading you on … maybe that’s something to consider doing regularly.)
If you’re anything like me, you’ll be wildly surprised by how systematically wrong your models are, in at least one direction. If surprised, update!
Share your worst case of Planning fallacy.