Bullish: My To-Do List Revolution

Jennifer Dziura writes Bullish, a career column, for The Grindstone on Fridays and Bullish Life, a life coaching column, for our sister site TheGloss on Tuesdays.

Back when I ran a failing dotcom, I used to both joke and despair about my to-do list. My to-do list consisted of:

  • Many little slips of paper
  • 1-3 legal pads full of scribbles
  • 6-8 Word documents labeled “marketing,” “project management,” “personal,” etc., each of which was at least 6 pages long, single-spaced

Six to eight Word documents multiplied by at least six pages apiece, times the number of lines on a page means that just the Word documents alone had thousands of items on them. And then, instead of doing any of these carefully catalogued tasks (or delegating them — I was very bad at delegating), I would spend countless hours transcribing tasks from the legal pads and slips of paper into the Word documents.

When the Word documents got too overwhelming — which was pretty immediately — I would adopt another list, in Apple’s Stickies program or on a little slip of paper, with the things that seemed really important. Soon, that list would grow to be long enough to require segments labeled “marketing,” “project management,” “personal,” etc. Soon: WORMHOLE!

Years later, I dated a guy who ran a successful boutique design firm and whose to-do list was precisely three items long. I was irrationally infuriated by this idea (because my long to-do lists are virtuous because they show that I am beleaguered!)

I asked, “What if you have three important things on there and then AN EMERGENCY HAPPENS?”

He shrugged. “Something gets bumped.”

That approach is still a little extreme for me, and I do think that people who do a lot of things (see here and here) are naturally going to have more complicated lists.

But after many years of to-do list fuckery, I think I’ve worked some things out. I assume you’re already pretty familiar with the standard advice to prioritize and to break big tasks into smaller parts.

Here are some additional to-do’s.

Stuff Humans Are Good At? Use That.

First, lists themselves aren’t that hot. They don’t map up to the actual time you have available. For that, you need some kind of calendar. (For a pretty basic book on estimating how much time each task will take and scheduling those tasks accordingly, see Julie Morgenstern’s Time Management From the Inside Out.)

But your regular calendar, where you log your appointments, isn’t necessarily the place to record every little task. Does it really matter what time of day you “Call Verizon”? And how do you know how long it will take to … oh, say … write an article? Scheduling in tasks for specific timeslots doesn’t usually work unless the tasks are things you are sure you can accomplish in a particular period of time (for instance, working out).

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