Email is a cruel master.

McCoy and Chapel exchanging disksWhen I first started working in an office, in the 1980s, we shared files via “sneaker net” – taking them back and forth on floppies. Very high tech. For customers and prospects, we sent and received documents overnight through FedEx, then we sent and received faxes. When we first got email, we could only email other people in our building. Then, of course, we could finally email through the Internet.

Over time, my In Box became my master, often to the detriment of my true priorities. For a long time, my In Box had thousands of messages, except on January 1, when I’d declare “Email Bankruptcy” and I’d archive them all. Usually, I’d answer the most recent email first, figuring anything urgent that had fallen would prompt a follow-up email that would then become a priority. Not an ideal way to treat coworkers and customers…

I experimented with using Categories in Outlook to better organize emails that didn’t have to be responded to immediately. But it turns out that Outlook on iOS doesn’t support Categories, and—since I like to go back and forth between my Mac, iPhone, and iPad—that didn’t work for me. I created folders instead, and I would drag emails to the relevant folders. But then I ignored what was in the folders.

It took me far too long to figure out what task management techniques work for me.

We had been using Wrike for project management, but it was too much work for what I wanted, so I ended up going with a simple spreadsheet of all our projects. Then I’d list the next thing I needed to do for each project and prioritize the projects.

Unfortunately, this had some problems:

  • I’d spend time answering emails in the wrong order rather than working on the first task.
  • I’d find it hard to get started on the first task.
  • I’d skip tasks to work on lower priority tasks.
  • I wouldn’t get to some of the lowest priority tasks for weeks or months.

Experimenting with Gamification

Meanwhile, Wordle and Duolingo were teaching me that I really liked maintaining streaks, and I read about “No Zero Days.” Could I gamify my task management? I found an iPhone and Mac app that tracks your streaks called, appropriately enough, Streaks. Initially I just had this set up to track streaks for priorities #1 to #5 each day, setting my priorities at the end of my work day for the next work day.

But with this approach I wasn’t overcoming my resistance to getting started. My #1 priority was often hard to do. So I reconceptualized my “1st Priority” as “Quick Win.” It’s not the first priority in the traditional sense of being the most important thing you need to work on: “Quick Win” is something you want to do and something easy to do. The goal is to get you working on your to-do list with as little resistance as possible.

Then I realized that big items were often languishing on the list. So “Eat the Frog” on my priority list is usually the thing that I didn’t do the day before that I should have. For instance, I had a real block on the “Eat the Frog” task of the day when I wrote the first draft of this post, and I put it off until 5:30, but I didn’t want to lose my streak. I was just going to spend 15 minutes on it. Then I realized it was easier than I expected. Whew. Turns out the whole thing only took 45 minutes.

Priority #3, “Later Gator,” has been key. It’s for those regularly scheduled lower priority tasks that you put off on purpose. The missing piece for me has been getting around to actually doing this lower priority stuff. I had been Snoozing email tasks but then I just never did them, and I had to Snooze them again and again and again. So a few months ago I tried a weekly cadence: Monday mornings are for project management review, Tuesday mornings are for financial tasks and dunning slow-paying customers, Wednesday mornings are for strategic projects, Thursdays are for general administrivia, and Friday mornings are to catch up on emails I wanted to read that weren’t priorities (newsletters, association emails, FYIs from folks, etc.). When I’m reading my email, I’ll now drag tasks that can wait up to a week to the appropriate folder; for instance, I try to pay my vendors in a week or two, so as I get their invoices I drag them to the Tuesday (Finance) folder; I drag issues of a strategic nature to the Wednesday folder, and so on. I then track my streaks actually doing these tasks using Streaks; they are set up to remind me once a week, on the right weekday (otherwise they show as disabled). This has worked great! (Though you’ll notice from the screenshot I missed last Friday’s Weekly Wrap.)

Time Management

Typically, if I spend at least 15 minutes on a priority I will mark it as complete. I can usually psych myself up to do anything for 15 minutes. “No Zero Days!” And yet I’ll often find that once started I keep going. For instance, I’ve been reviewing the categories for my work expenses for my taxes. Not fun. But one day last week I ended up spending 45 minutes on it, when I’d meant to spend 15, so I made good progress.

For bigger tasks, I’ll typically work up to 90 minutes. The Pomodoro technique never worked for me: it advocates for working for 25 minutes and taking a 5 minute break the first three times, then a longer break. I find that I can work for 90 minutes, and enjoy doing so, then I need a change of pace.

In the morning, that’s typically a coffee break. I’ll spend 15 minutes on one of my fun streaks. Those fun streaks are what have produced most of my books, many of which were written during coffee or lunch breaks (see “Conlanging on 15 Minutes a Day”). You can see in the screenshot my current streaks are about using Esperanto, writing a blog post like this one, Unsplashing my blog (updating the art to use Unsplash assets), working on my Civscape card game, and “barfing forth apocalyptica” (in the Bakers’ phrase) as I do some GM prep for my Apocalypse World campaign.

Know yourself! Some people have more energy in the morning, some at noon, some in the afternoon, i can do higher effort tasks or tasks with more resistance in the morning, which are harder for me to do in the late afternoon. That is why “Eat the Frog” is my #2 task rather than later in the day. In fact, I’d argue that good task management is about knowing yourself and experimenting to discover what works for you and what does. A little gamification was the key breakthrough I needed.

Turning to streaks and a simple to-do list has finally liberated me from the tyranny of having email drive my priorities.