Productivity Update - Trello and Me

For as long as I can remember, I’ve always been a procrastinator. Don’t get me wrong, I’ve always been able to time manage and plan when I absolutely needed to, but most of the time I could skate by with a last second effort. From time to time I’d make an effort to get organized though. Day planners, electronic organizers, notebooks, a Palm Pilot, more notebooks, various phone apps on Android, Windows, and iOS platforms, I’ve tried a lot of things over the last twenty years.

My Trello board overview and Pomodoro timer.

Nothing ever really took, despite my task load gradually increasing over the years. It’s not that difficult to keep all your organization in your head when you’re a sixteen-year-old kid with only school, a few chores, and a part-time job to deal with. College assignments added additional complexity, but everything was still manageable. But a good software job, five kids, and an aspiring side platform as a blogger/streamer/writer meant I just couldn’t keep all those balls in the air anymore.

Enter John Somnez’s blog on secrets to crazy productivity, and the introduction of Trello to my life.

I’ve been working in an Agile environment for years. Sprints, Kanban boards, and daily standups have been a part of my working life for a decade, but I’d never applied those principles to the rest of my life. With Trello, I started to.

John’s methodology involves assigning Pomodoro estimates to all of your tasks, then taking time at the start of your week to plan out what you intend to accomplish each day. For the first couple of months, I did exactly that. After a while I started to get a pretty good feel for how long common tasks will take, so I stopped assigning time estimates. I still do the daily planning though, which has become a vital component in my week.

Daily planning works like this: at the start of my week, I map out all the things I know I’m going to try to get done. Work tasks, workouts, writing time, Twitch streams, planned chores, and anything else I can think of goes somewhere in the Monday – Saturday list.

This serves three main purposes: first, it’s a reminder throughout the week of what I need to get done. I add new tasks as appropriate when I run into something new that I need to get done. Second, this serves to help me not bite off more than I can chew in a given week. For example, on a typical workday, I know I have time for my work tasks, a workout, and 2-4 additional Pomodoros worth of tasks before I call it a night. Anything beyond that probably isn’t going to get done unless I move an existing task out. Third, I try to list out tasks in the order and priority that I want to accomplish them. This significantly reduces the amount of time wasted on “What do I do next?” questions.

Big personal projects (the reclaimed shipping pallet wine racks I’m building, for example) I break out on their own boards. For these I do a task breakdown and time estimates, then pull individual tasks into my general week planner when I have capacity in my week.

The results have been nothing short of remarkable. You know that feeling of having forgotten something, or knowing that there’s some task left undone? For the first time in years I don’t go to bed feeling that. Closing a task feels good. Clearing an entire day’s board feels great. Pushing tasks off to the next day feels less good, but beats wondering three days later whether you remembered to set a youtube video to launch on time.

The Pomodoro component isn’t entirely flawless, particularly for some of my personal tasks. Exercise routines don’t work well with running a Pomodoro timer, nor do the few tasks where I’m able to legitimately multitask (for example, editing videos while logging elements of my sports card collection). However, for most of these tasks I’ve gotten a good feel for how long they take, which serves the same function of the Pomodoro timer for these things. Dragging a weightlifting task from today over to “Completed this week” means I spent two to three Pomodoros on it, regardless of whether the Trello board knows it or not.

I’ve been running this plan for several months now. My blog is updating regularly, I’m writing more, and more productive at work. Even better, interruptions to my routine have become much easier to recover from. For example, I recently returned from a conference that, between travel and participation, burned a week of my time. It was great, but threw my entire routine out. I was back on track by the end of the week. The previous time I attended a conference like this, I was off schedule for a month.

My next step is going to be teaching my kids to use this system as they start getting into Jr. High and High School. My education was excellent in many ways, but I wish someone had taught me some of these time management techniques a long time ago.