5 ways to make task management software work for you

I have a love-hate relationship with task management software. On the one hand, I’m kind of obsessed with it: trying out new task and project management tools is one of my favorite pastimes, and it’s hard for me to resist trying out each shiny new entry in the market. On the other hand, I’m a fairly resistant user: once the honeymoon wears off,  and my task management program is full of a huge list of tasks that I MUST DO TODAY, I find that list so daunting that I tend to avoid looking at it, and go back to keeping my list in my head.

Recently, however, I’ve returned to the task management fold. For the past month I’ve been using Things, a task management app that runs on both my Mac and my iPad (and would run on my iPhone too, if I paid another $9.99). I hate to jinx it, but this time, my task list feels different. Not because Things is the Holy Grail of Task Management I’ve been looking for — I used Things for a while last year, and ended up in the same old avoidance pattern once I accumulated a few dozen items on my to-do list — but because I’m using my task list in a new way. Here’s what seems to be working, and could also work for you:

  1. Minimize your list. In the past few years, I’ve followed the GTD religion of writing down every task that is in my head, so I can free up my brain power to cure cancer or crack the problem of nuclear fusion. But in this iteration, I’ve returned to a piece of wisdom I read many years ago: for right-brain people like me, task lists tend to be generative, inspiring so many ideas that we soon get overwhelmed. So this time out, I’m writing down only the absolutely crucial tasks that I don’t want to lose track of — not the “some day” or “shoulda coulda woulda” tasks that tend to clutter up my list.
  2. Use existing software. As usual, I began my return to task management with my beloved process of investigating new software options. But I caught myself, and decided to just use the same damn software I had already purchased last year. I took everything that was in my old Things list, and archived it, so I didn’t have to deal with that backlog.
  3. Use one device. Syncing is another obsession that typically gets me worn-out with my task management regime.  Even though I use two computers, an iPhone and an iPad, I’ve resisted the temptation to pour hours into figuring out the right Dropbox setup to keep my Things list in sync across all of them. I’m just using it on the single computer I use most of the time, and since I’m only trying to track my major tasks — and not every damn thing — that is working just fine.
  4. Go solo. As a social software addict, I’ve been an intermittent evangelist of tools like Basecamp and Manymoon, which let me share tasks with my team. But one of the reasons I am now afraid to look at my Manymoon list (oh yes, it’s still there) is because of all the tasks other people have recorded for me, and one of the reasons I avoid Basecamp is that I get distracted from my own tasks by looking at other people’s. With Things, I fly solo, and if someone needs to get a task onto my list, they simply tell me about it — and I decide whether and how to put it on my list.
  5. Check rarely. One trigger of to-do list resistance is the feeling that I’m being ruled by my task management software, rather than vice versa. So I look at Things relatively infrequently — once or twice a day, or sometimes not at all. The only reason to look is if I have a major item to add, if I’m trying to decide what to work on next, or if I’ve just completed something and need to check it off.   Looking at my task list when I don’t have any time free to actually work on it is simply a source of stress, and my daily glance is enough to ensure nothing drops off my radar.

I’ve fallen off the to-do list wagon far too many times to feel confident that I’ve finally cracked the task management nut. But I’ve been shocked at how much more productive I’ve been in the month that I’ve used my task list in this moderate, non-fetishistic way. And it’s that productivity payoff — rather than the joy of using geeky software — that could keep me on track and to-doing.