how i fight procrastination

when i’m dragging my feet on something and telling myself “i don’t feel like doing it”, it usually means:

  • the task i’m putting off seems like it’s just one task because it’s been phrased that way (e.g., build a tent in the backyard) when really it consists of many more tasks (rake the yard, research tents, drive to the store, buy a tent, drive home, read the instructions, build the tent, recycle the packaging), but i haven’t explicitly broken it down into the subtasks yet. (tip: explicitly breaking down the “one” task into its components makes it much easier to digest and get started.)

  • the task doesn’t seem important enough to warrant my attention. (tip: if it’s not important, why are you doing it? declutter your toDo list by removing it or deprioritize it by punting it to your "someday" list.)

  • the task requires more mental effort than i have energy for.

  • i anticipate feeling feelings i don’t want to feel while working on the task (boredom, frustration, anxiety, etc.).

strategically position the light at the end of the tunnel

to combat procrastination, one general strategy i use is setting time boundaries. if i know that the unpleasantness has a fixed end, i can usually find the motivation to get started. once i get started and the end's in sight, i can usually find the willpower to make it to the end.

for example, healthy-gail had decided i wanted to run a 5k in x minutes. lazy-gail hated running. to convince lazy-gail to get over it and give in to healthy-gail's desires, i broke my workout down into 5-minute chunks. okay, lazy-gail, run for five minutes. after five minutes, if you want to stop and go home, you can. surely lazy-gail wasn't so lazy that she couldn't endure five minutes of running. knowing that i could stop and go home if lazy-gail was in agony, made the daunting task of "go running today" much less scary. and after those first five minutes were up, lazy-gail was convinced that running wasn't so bad and could endure another five minutes. and then another. and so on.

cool. time boundaries. what are other examples?

5 minute brain dumps

five minute brain dumps work like this:

  1. pick a problem. (for example: i want to start a blog, but i don't know what to write about.)

  2. set a five minute timer.

  3. list out as many solutions as possible until the timer ends. don't spend time judging your solutions as good or bad; just list them all out. it's really important not to judge your ideas/solutions during this exercise. we're going for volume and creativity here.

at the end of five minutes, your problem might not yet be magically solved, but most of the time, i find that my motivation has spiked, and i'm ready to continue tackling the problem. the reason for reserving judgment about your solutions is that you don't want to engage the part of your brain that keeps telling you this is hard. i'm no good at this. i'll never get this done. remember, we're looking to generate motivation, not kill it.


pomodoros work like this:

  1. pick a task (or a set of tasks) to work on.

  2. set a timer for 25 minutes.

  3. work on the task(s) until the timer ends.

  4. take a 5 minute break.

  5. repeat steps 1-4 three more times.

  6. take a 25 minute break.

  7. repeat steps 1-6 however many more times.

pomodoros work really well for tasks that don't require a lot of time to get into a flow state. my favorite use for this technique is in doing chores. i hate doing chores, but i like having a clean and tidy space, so i minimize the time i spend performing the actual chore work by cramming it into 25 minute chunks.

a similar tactic i used to use was inviting a friend to come over in half an hour. suddenly, cleaning my room only took 20 minutes when historically it'd take me an hour to tidy up.

there are a ton of pomodoro apps out there that can do fancy things (like vitamin r), but i prefer the simplicity of brain focus (android / iOS). to each their own.

1 month experiments

i tend to think of my life as a continuous set of experiments. i seem to find it harder than most people to guess whether i'll love something without trying it first, so i give myself a set amount of time to explore, take notes, and then evaluate my feelings at the end of the time period. the duration of these experiments vary greatly depending on the situation, but one month seems to be a good starting point when you have no idea how long you should pick. after all, at the end of the month, you can always extend the experiment if you feel you don't have enough data to draw a conclusion.

framing my thoughts/ideas as experiments motivates me to take action instead of letting ideas or "i should"s hang out in theoretical land. there are times when i get stuck in indecision, repeatedly asking myself obnoxious questions like should i do it? should i not do it? what if i hate it? what if i suck at it?

by reframing things as an experiment, i don't have to answer those silly questions because now the new task i need to accomplish is "conduct the experiment of wearing a dress every day to see whether people listen more to me" instead of "make people listen more to me". there's no pressure of a desired outcome to make you feel like you failed (e.g., if no one listens to you). instead, you focus on being curious, trying the thing (e.g., wearing a dress every day), and seeing what happens.

some examples of experiments i've conducted:

  • eliminating beef/pork from my diet (1-2 years).

  • sleeping with a mask and earplugs (1 month).

  • work-life integration (2-4 weeks).

  • going out every friday night (1 month).

  • tracking how i spend every minute of every day (2 months).

  • living in taipei (6 weeks).

  • joining a community/cult/thing (6 months).

  • journaling first thing in the morning every morning (1 month).

  • attending grad school (1 year).

7 lifetimes

several years ago, i came across this comic. for those of you who are averse to clicking links, i'll transcribe it for you:

here is something true: one day you will be dead.
here is something false: you only live once.
it takes about 7 years to master something.
if you live to be 88, after age 11, you have 11 opportunities to be great at something.
these are your lifetimes.
most people never let themselves die. (speech bubble: i’ve just always *known* i was good at organizing spreadsheets.)
some are afraid of death. (thought bubble: i’m only trained to do one thing, and if i’m not doing it... then what am i?)
some think they are already ghosts. (thought bubble: i was good at basketball, but then i hurt my ankle. now i spend most of my time mentally simulating a reality where that didn’t happen.)
but you have many lives.
spend a life writing poems.
spend another building things.
spend a life looking for facts.
and another looking for truth.
these are your lifetimes.
— Saturday Morning Breakfast Cereal

the comic says 11 lifetimes, but i started my post-schooling life at 23 and am guessing my brain+body will be reasonably functional until i'm 71, so that leaves me with seven lifetimes. my first lifetime is almost at its end. i've spent it mastering operationsy generalisty administrativey planningy executiony work in the tech industry. awhile back, i had this thought of seven years for mastery? really? i seem to be pretty damn good at my job, though, and it's only been four years... i (sorta blindly) trusted in the comic and committed to seeing things through. after working four years at a gigantic company, i took a job at a much, much smaller one, and then an even tinier company than that, then worked part-time at a small non-profit, and now work at a medium-sized research-focused non-profit. and yup, turns out there was a lot more to learn -- starting a company, influencing culture, raising money, being resourceful, commercial real estate, hr-y laws and ordinances, ... on and on.

i'm sure there's more for me to learn and master within this role/field, but i like the idea of having a set 'lifetime' to motivate me to both 1) resist the temptation to dump my career for something shiny and new before i've become an expert, and 2) take risks and not fall into a trap of being comfortable and living unchallenged.