Boot Camp Day 8: What to Do, What to Do?

I love to-do lists. It’s great to gather the details of your life into concise bullet points, to organize the universe of tasks by priority or category or color-coding. It’s great to check things off a list.

I have a lot of problems with to-do lists.

I don’t like being told what to do—even by me. I never know how to deal with recurring tasks. Do I really need to remind myself to make my bed? Once upon a time, I did. If I take it off the list, will a day come when I forget to do it? On the other hand, it’s an easy job to check off early in the day to get some to-do list momentum going.

But then, there are tasks that happen with predictable frequency that still come as a surprise to me. I have to deposit payroll taxes? Again? There’s a quarterly report due?

And then there are those tasks that are pressing and urgent and critically important, and if I don’t write them down on a list, I forget them the very second I stop paying careful attention. That ticket for the red light I didn’t run fit into that category. I put it on a list weeks ago, but then I stopped looking at the list on a regular basis because it was a tragically flawed list. Too many routine tasks, too many dreary to-dos, mixed with just a few pie-in-the-sky dreams that were so ambitious, I should never have put them on a list in the first place. “Create documentation for paperless business processes.” Yeah, right, like that’s ever going to happen.

I have to confess: A month ago, I was a listmaniac. I was putting every blessed thing on my to-do list, which I managed via a simple, free online Wiki interface. I’d start each day’s list by copying the previous day’s list, removing any items that had been completed, and turning off any recurring items that had been highlighted to indicate that they’d been done. Then, as the day progressed, I’d obsessively add new tasks to the list as fast as I could think of them, creating categories (“Starfall work,” “Writing objectives,” “Personal development,” “Promoting world peace,” and so on), sorting, contemplating, prioritizing, long-term planning, occasionally actually getting something done and highlighting it to signal its completion, and dreaming of someday never having to do this any more, because frankly, to-do lists are NOT what I want to be spending my time on.

I’ll tell you more about my system if you want to know…and if you’re the kind of person who knows what to do with a to-do list.

I used to have a system that worked, a long time ago, when I was still working at the University of Houston Printing Department. I had one main list of things to do, and also a list of things that had been done. I kept them in the Stickies utility on the desktop of my Macintosh. As I generated tasks needing to be done, I’d stick them on the to-do list, making some kind of judgment call about where they belonged in priority in relation to everything that was already on the list. I’d generally keep myself focused on the top of the list. When I completed a task, I’d cut it from that list and paste it at the top of the other one, which was only broken up by subheads to indicate the date I’d accomplished things. The second list was just something to look at to convince myself I was getting something done.

That system worked okay at that job, where a lot of my work was reacting to other people’s needs—my boss, our office manager, our clients, my staff. There weren’t a lot of big projects, mostly lots of small tasks, so it was fairly easy to sort priorities, and the system didn’t need a lot of complexity. I tried to carry it over into self-employment, but managing a business was a whole new ballgame. The projects got bigger, the scope of responsibilities got wider and deeper, and I had to set my own priorities. The Stickies system fell by the wayside.

Through all the years of managing the graphic-design business, I’ve experimented with lots of time-management systems. I’ve taken some workshops, read a few books, and tested various schemes. I should mention that I’m missing the gene that enables most human beings to operate a calendar. I’m serious. I’ve owned calendars, I understand the underlying principles of how they represent time, but I’m completely clueless when it comes to using one to run my own life. Mostly, I come back to some form of list or another. Sometimes a system works for a while. Sometimes it breaks down.

As I said, I was a listmaniac a month or so ago. I thought, for a moment, that I was on the verge of designing a new system that was going to be great—interactive, portable, fun to use, satisfying. But I ran into the stumbling block of too darned much stuff that I don’t especially want to do. I also found that I was loading up my list with easy stuff—things that were easy, but not urgent, or things that I could readily delegate to someone else, or things that maybe didn’t even need to be done at all. I became frustrated, and I quit my list cold turkey for a week or so.

When I went back, I was surprised to find that I’d accomplished a few of the things on the list. I copied the list to a new file, removed the completed items, fixed the highlighting again, and dedicated myself to a new effort. Then I let another week go by. When I returned to the list again, I could hardly stand to look at it. I started to realize that there was something fundamentally wrong with the design—and I don’t just mean the graphical elements of the design, but the conceptual design.

The next day, I didn’t even try to work from the list. I handled the first few important tasks that popped into my head. Late in the evening, I wondered what I’d do the next day. Go back to the list? Give up on it entirely? I started thinking about designing a completely different way to decide how to spend my days.

(To be continued….)

© 2008 Edward F. Gumnick