Essays on Technology and Culture

Another Task Management Journey

A few weeks ago, I bemoaned the state of my personal data. While I’ve only made inroads on that front since then, thinking about my data problem, and how to solve it, gave me cause to look at my task management system, and the piles of crap and cruft that have built up within. Part of the problem I have with task management, along with notes and bookmarks, is my desire for a universal solution. I want something I can load in all my personal projects, my work projects, my day job projects, my writing… and I’d settled a while back on OmniFocus, the 800-pound Gorilla of Task Management.

OmniFocus is a fine piece of software, and well worth the price. However, it wasn’t working the way I needed. The problems I had with OmniFocus as a task management system were as follows:

  1. My day job forces me to use Windows, so the only way to view my OmniFocus data at work is to either lug my iPad in, or use my iPhone. Neither of these are elegant, easy, or look great in front of the boss.
  2. So much of my day job work is cranking out widgets. A task comes in (by email), and often needs to be done that day. if I’m not already working on something, I tackle it immediately. There are some projects that are longer in duration and scope, but not many. Either way, the pain in the butt of entering those tasks into OmniFocus, even with MailDrop, is too much.
  3. OmniFocus is absolutely crap for creative tasks that don’t have well-defined “Next Actions.” Something like “Write blog post” is too vague, “Write 500 words” is too specific. It’s a pain in the butt, and no good for tracking my progress on many creative tasks.

Then, Nick Wynja turned me on to Trello. I’d used Trello (very) briefly while working for The Startup, and it didn’t click with me. Something about the UI, the multi-dimensional scrolling piles of lists, and the general visual chaos of the office Trello boards left me scrambling for another solution (OmniFocus, natch). With Nick’s praise, I decided to give it another try, and after a day or two of experimentation, I found Trello to be perfect for my day job, and pretty good for tracking my writing.

I use Trello like a simple Kanban board. At the day job, I keep one list of cards for Future tasks, and stuff I’m waiting on. I keep another for stuff I need to do today, and another list of whatever is done. When something comes in to my inbox that needs doing, I either create a new card, or just forward the email to Trello. At the end of each day, I archive the cards on the Done list, and add whatever upcoming stuff needs doing to the “Today” list so it’s ready when I get to my desk. For my writing, it’s even simpler: A list of idea cards, a list of works in progress, and a list of what’s done.

What Trello sucked at, at least for me, was letting me manage any other sort of task. This left OmniFocus for just tracking day-to-day todos, and that seemed… excessive. I played around, first with Reminders. When that proved too simplistic, I went back to Things, enticed by the Mac version’s gorgeous Yosemite update, and the iPhone version’s new UI as well. A week and a half of using Things reminded me exactly why I switched away: Things doesn’t work the way I work. I like the ability to view things by project, or by context, and Things just doesn’t have that. The path was clear.

Saturday, I launched OmniFocus, selected everything, and deleted it all. I grabbed my notebook and pen, pulled up the “Trigger List”, and scribbled away all the stuff I need and want to do. I came up with new contexts, and I set them up. I loaded all my tasks, projects, and (non-day job) professional obligations into OmniFocus, built them out, and now I’m starting with a clean slate. Whatever was important carried over, but that’s because it was still on my mind. The majority of stuff I thought I needed to do vanished into the digital ether, and if any of it should become important again, I’ll know about it.

There’s a lesson I’m opting to take away from this experience. It’s never a bad idea to audit yourself. Thinking about the tools I use, and how I use them, gave me insight into where I was falling down, and helped me put together something better suited for what I do and how I think. I’ve been trying to cram square pegs into round holes when it comes to just keeping track of what I need to do. It’s true, one should never focus on the tools over the work, but it was worth the disruption to figure out what works best for me. We’ll see if this sticks, of course.