Making Timeboxing Work for You

One of my absolute most powerful tools for getting things done is timeboxing. This one is well-known and well documented, so I make no claim to novelty on this, but that's not what this space is about (recall Matt Webb's 15 rules for blogging #6: Give up on saying anything new. Most people haven’t read my old stuff. Play the hits.).

Here's an abbreviated list of ways I deploy timeboxing in my day-to-day.

  • Fixed Schedule Productivity. Cal Newport's term. The idea of being rigid in your daily working hours, meaning you start and stop at specific times (almost) no matter what. The idea being that you get more done if you take away any tendency to extend your working hours (because, for instance, you haven't been effective enough during the day). Worked brilliantly for me as a freelancer and I consistently tracked more high-quality work hours in a shorter period.
  • Paper Schedule. I've seen this one in a few places over the years. Every morning as part of my morning startup routine, I prepare a paper schedule where I plan out what I'm working on that day and when. I make this with reference to my calendar and task management software, and try to consistently allocate appropriate amount of times to different things (which makes me better at estimating task durations). Paper because the act of preparing it is important, and it has an air of impermanence and flexibility. This is also where I decide whether this is a deep, lossy, or hybrid day.
  • Pomodoros or other sprints. Pomodoros are mostly a measure of last resort for me now, but I do longer 90- and 60-minute sprints on deep work days, using some of the same principles. The ideal is that they're spent working intently on one thing for a fixed period, with any excess time spent overlearning, but I keep things more flexible than that when I need to. I use the same principle in my morning routine, spending a fixed period of time working on admin, stopping when the timer goes off.

Several threads that run through all of this:

  • Being intentional about my time. Making proactive decisions about what I'm working on and when, being realistic about how much I can fit in, and developing and reinforcing the knowledge over time of how long it actually takes me to do different things.
  • Parkinson's law. 'Work expands to fill the time available for its completion.' Giving yourself a constrained period of time to complete a task makes it much more likely the task actually gets done, usually without any material compromise in the quality of the output. (But also remember Hofstadter's law.) There are limits, obviously. You can't time-hack your way to writing a novel in an hour. But as you develop a clearer sense of how long different tasks actually take you (which requires being intentional about your time, see above), you can also hone a sense of where the lines are that meaningfully impact the quality of the output (Will a novel I take a decade to write be better than one I write in a year? Almost definitely. Will it be ten times better? Hard to quantify, though it feels doubtful. Will it be better than the combined output of writing ten novels in that same decade? Unlikely.).

I've fallen into a rough habit of three posts a week on here, targeting Mondays, Wednesdays, and Fridays, which I'm aiming to maintain. Next week will likely be quiet, though, as I'm away at an event.