The List Is Life

Finding a new way to manage my day.

Some people carry uplifting phrases with them for inspiration. “Life is not measured by the number of breaths we take but by the moments that take our breath away.” I used to carry around the opposite kind of reminder: a list of short sentences that instantly depressed me. My to-do list.

Since childhood I carried the burden. My mother or some well-meaning teacher once told me to write a list of the things you need to do, and when you do one, cross it off! That was fine when the items included “color within the lines” and “play catch.” Marking down tasks was gratifying at first. To have begun is to be half done! But as I grew, the list did, too. And it became a monument to the things I hadn’t done.

A to-do list

To fix my problem, I tried to fix the list. I’d write in different colors to prioritize until I could only keep track of all my pens by wearing a bandoleer. I crossed out completed items twice instead of once, as if I couldn’t complete a task because of flawed demarcation between finished and unfinished. I’ve written lists in different places—calendars, special notebooks, and the palm of my hand. I’ve sent myself e-mail reminders until I considered putting myself in my spam blocker. None of it helped get the undone things done any faster.

By now some of you are nodding or shaking your heads. You’ve either had the same experience or know how to get out of it. I want to hear your ideas and solutions. Send your thoughts, best iPhone applications, or whatever you use to help keep track of things or pictures of your to-do list to us at I’ll write another story collecting your best tips and share them to create a more organized world.

Back to the story of how I tried to fix my to-do list. To rescue myself from the slavery of the awful to-do list, I turned to David Allen, the author of Getting Things Done, and Merlin Mann, the author of (among other things). If what you’re about to read makes sense, read these two next. It’s the only way to really understand. If I don’t make any sense, then read these two—they explain it better and more entertainingly.

The first thing I did was blow up my to-do list. It had at least two flaws: It sat in just one place, and each item was unwieldy—a cluster of actions rather than bite-size ones. An example: Digging through the boxes in my garage, cursing the disorganization, I came across an old planner from 1995. “Clean garage,” it said on June 6. That was from an entirely different house. I’ve moved, and the to-do lists have moved with me. The old garage never got cleaned (until we moved), and the new one isn’t clean, either. This can get existential. I’m going to have items on my to-do list that will never get done in my entire existence.

The first trick is to turn the big project into little action items. This is one of the key theories behind Getting Things Done. “You need to break down each noun into tiny little transitive verbs,” says Mann. So now the list reads: Call carpet recycler to dispose of carpet, buy container for baseball cards, and buy hooks to hang tools. I no longer stand at the door of the garage wondering where to begin.

The clustered item is a silent killer. It not only makes cleaning the garage harder because you don’t know where to start. It keeps you from writing things down on your list at all. I want to rock climb. But if I’m thinking in clusters, it just all seems too daunting.

The other thing that kept me from crossing off items is that I had only one list for all sorts of different tasks. So, for example, I’d write “go rock climbing” right after “call Robert Gibbs to schedule daylong interview with President Obama.” Depending on my mood, one of those two things would feel out of place. I’d probably call Gibbs and forget about the rock climbing. I’d do this another thousand times until I rewrote the list and rock climbing wasn’t on it.

So now I have three lists. Whichever one I’m looking at, I know it’s going to have the right kind of items on it. The first is my “Expletive List,” which sits at 10 a.m. on my electronic calendar. If these items are not done by the end of the day, I will emit a barnyard epithet. (I try to be ruthless. If a task can be delayed, it should not be on there.) If I have an expletive event in a day to come, I put it at 10 on that day. There is only a handful of these items every day.

My second list is what Mann calls a “Hipster PDA“—a stack of blank index cards that I carry in my back pocket. When I have a stray thought—whether it’s about a kicker for a story or a reminder that we need a bigger Thanksgiving table—it goes on a card. If I’ve done it right, I lose the nagging feeling that somewhere a flap is open and I’ve lost good ideas. David Allen calls this process “ubiquitous capture.” Theoretically, it frees your brain to keep doing what you were doing before an idea distracted you. To keep writing or reading.

Of course all those index cards are meaningless if you never check them. So at the end of every day, or sometimes multiple times a day, I sort and sift the cards. I add certain items to the “Expletive List” and organize the rest by context, with tabs that read: e-mail, phone call, weekend errand, home errand, at computer. When I have down time, I go to the tab that corresponds to whatever I’m doing and crank through as many of the little actions as possible.

Finally, there’s the “Skydiving List,” which represents the big picture or 36,000-foot view of my life. From there I try do dive down and create small actions that can be performed. It includes questions like “How can I teach my kids about generosity?” or “Do I need to change the filter in the furnace?”

The name also reminds me of the breadth of thinking I’m trying to do: I’m not just thinking about interviews I’d like to schedule for work but long-term adventures like skydiving. (One small flaw is that I don’t actually want to go skydiving. Not in a million years. But I haven’t processed the maintain integrity of all metaphors index card yet.) I check this list—which is in a Microsoft Word file in outline form—once a week, usually on Sundays.

Thinking programmatically about to-do lists may, at first, be a real blow to your  insouciance. The guy who winds up in the kitchen at parties making people laugh is not doing this kind of thing in his quiet time, you may imagine. The guy who does (and worse, tells you about it) may wind up on your list of people you studiously avoid. Self-improvement has gotten a bad rap, in general, because we associate it with excessive strivery and the attendant qualities of self-absorption and general marching dullness. But try to think instead of a more expansive idea of self-improvement—of the sort practiced by James Boswell or Ben Franklin. Franklin was our country’s first great lifehacker; he had trouble seeing both near and far, so he created bifocals. He was also a pretty popular and entertaining fellow.

Does this system work? I don’t hate my to-do list anymore, but the system is leaky. I don’t follow all the steps I just laid out. And big things still slip through. I forgot my son’s lunch today, for example. I have in my pile an index card that simply says “tennis.” Really? Play tennis? Watch tennis? Write about tennis? I have no idea what it means. Also, no matter how well I break down a particular task, I still have to do it. Writing a great outline is not writing a great story.

I have stacks of note cards I haven’t dealt with, but the upside is that they’re in the right place. While I’m reading or spending time with my kids, I’m not nagged as much by the idea that somewhere there’s a blinking red light—that there’s something important I’m not doing. That may not take my breath away but at least it makes me feel like I can breathe.

What’s your trick? We want to know. Send your best tips, systems, or, better yet, pictures of your to-do list to