Pomodoro Productivity

A week and a half ago I read series of blog posts by Mac Deutsch in his Month2Master  series about how he mastered the New York Times Saturday crossword in just 23 days. I solve (or try to solve) the NYT crossword every day, and while I’ve seen some really marked improvement in my solving abilities since I started (about four months ago), I certainly haven’t mastered Saturday puzzles yet. I can get through a Wednesday on my own, but generally need some help for anything after that. (Quick backstory for those of you unfamiliar with NYT crosswords: The difficulty increases every day with Monday-Wednesday having themes, Thursday having a bit of a gimmick, then Friday and Saturday are themeless and hard. Saturday NYT Crosswords are generally regarded as the most difficult crosswords available.)

So, I was pretty interested to see someone learn how to do really difficult crosswords so quickly. As a brief summary, he built a couple ‘trainer’ tools and essentially studied large quantities of clue-answer data and next-letter data. It was an impressive case study in learning a skill very quickly, and, while I enjoyed reading about it, it’s certainly not something I would want to do. I enjoy the mental exercise of doing the crossword every day, and while I’m sure I could improve my solving skills rapidly if I tried, I think I’d miss the struggle of it all.

My biggest takeaway from M2M wasn’t how to learn to solve Saturday crosswords. It was something called Parkinson’s Law which states that “work expands so as to fill the time available for its completion”. What an idea, I thought. And it’s obvious, right? Taken to an extreme, if you give yourself forever to do something, you’ll probably never do it because you still have time and it doesn’t matter if it’s done today or tomorrow.

I’m no stranger to deadlines or getting a lot done for all the various things I do. But, over the past weeks, I’d been identifying some issues with the way I accomplish things. Here they are, for the world to see:

  1. Most of what I do relates to immediate needs: Gotta get my roster printed for the game this weekend, gotta get this piece edited so it can go up today/tomorrow, gotta get the meet up in a few days posted on reddit, gotta make sure my house is clean enough for the people coming over tomorrow, etc. etc.
  2. I have a billion things floating through my head constantly. I’m pretty good about keeping my tasks organized in my head and not forgetting to do things. Somehow I’ve managed to do that for a long time over a lot of different projects/responsibilities. It’s a neat thing to be able to do, but it has some obvious downsides. When I’m constantly thinking “Oh gosh, I can’t forget to do X thing later”, it’s distracting from the task I’m currently trying to accomplish.
  3. Worse, I got into a mindset of “I should do things whenever I think of them, that way I’ll never forget.” This also worked in that I wasn’t forgetting things, but I was constantly interrupting a task to go do another task. Things got done, but it was confusing and definitely suboptimal.
  4. On top of that, I’m a generally distraction-prone multi-tasker. Back in my eSports days I got into the habit of being hyper-responsive to anyone at any time. I’m sure the people who needed things from me appreciated that, and in fairness, a lot of my job was making sure people had necessary information so it probably wasn’t the worst habit to have at the time. However, it doesn’t suit itself towards real focus, and probably hasn’t served me well since then.

For a long time, these issues were just downsides to a functioning system, but I’ve been increasingly unsatisfied with my suboptimal task/life organization. At this point in my life, I think it’s important to try a lot of things and leave myself open in that way. I’ll have time to specialize and start saying no once I have a broader experience of the world. My best friend used to constantly be telling me not to take on any new things. She had to, because I have a nasty(?) habit of wanting to do everything and never saying no to new opportunities and she could tell it was getting to be too much for me. She wasn’t wrong, and I even put it in the song: “I try to be too much at once.”

But, I couldn’t keep saying ‘no’ to things for long. A little over a month ago, I said ‘yes’ to becoming the Managing Editor of Stumptown Footy, and that’s when my task-management started to fall apart. 

I wasn’t accomplishing as much as I wanted to. I was constantly dissatisfied with my productivity. A couple little things slipped through the cracks (which absolutely does not happen to me).  Reading M2M was the push I needed to actively do something to get these things sorted out. I decided my first step was a good to-do list app. I’d used project management tools in the past, but this time I wanted something more designed for personal use. I did some research and ended up installing a combination of Todoist (a ‘Getting Things Done’ app) and Toggl (a time tracking app).

I separated all of my different things into ‘projects’ (which function as separate lists in Todoist) and started adding things. Since then, every time I think of something I have to do, I add it to Todoist. Not having the weight of trying to remember my to-do list is incredible. It’s game-changing. I signed up for Todoist ten days ago, and it says I’ve accomplished 130ish tasks so far. If you add in the ~30 open tasks I have right now, then we’re at about 16 tasks per day. Sure, some of these things are minor and easily done, but remembering to do the thing takes the same amount of brain power regardless of the size of the task.

Not having to actively remember everything I have to do is so remarkably good I cannot say enough about it. I feel dumb for not doing this sooner.

Toggl didn’t have quite as profound of an immediate benefit, although I’ve definitely felt it helping.  I went into it thinking that it would be good to quantify the amount of time I actually spent working. While cool, that only had secondary affects on my productivity as a sort of integrity-based ‘I don’t want to be doing non-productive things while the timer is running’ incentive. Then yesterday, I discovered Pomodoro.

Pomodoro (just the Italian word for tomato) is a very simple time-management technique that works like this: Set a timer for 25 minutes. Work on a task for that 25 minutes, staying single-task focused, ignoring all distractions. When the timer rings, take a short break. After four pomodoros, take a longer break. That’s it. Just focus for 25 minutes at a time, then reward yourself for that focus.

Toggl has a Pomodoro feature, so I turned it on and gave it a shot. I loved it instantly. It is hard to ignore all distractions for even 25 minutes. It’s just hard to do. But, in a way, it’s extremely liberating, because when you think about it, there’s not much in the world (and certainly almost nothing in my average day) that can’t wait 25 minutes for a response. And that’s the maximum amount of time my Pomodoro timer will keep me from replying to a text. When you really think about it, the average pomodoro-caused wait time is 12.5 minutes, which is actually still a pretty good response time.

Not only does Pomodoro force you to single-task for 25 minutes, it trains your brain to think in a more focused way for longer periods of time. Even after just a couple days of Pomodoroing, I can feel it getting easier.

So let’s recap and collect my findings so far with my initial list of problems.

Todoist immediately solved issues 2 and 3. Having somewhere to keep my task list simultaneously let me not have to try and remember everything and thus not feel like I had to do everything as soon as I thought of it. Toggl (largely through Pomodoro) solved issue 4 by forcing me to stay single-task focused.

This still leaves issue 1 to be solved, but I think this will come as I get better at using my chosen tools. I still whiff deadlines on Todoist sometimes, which I think is partly because I’m still learning to be more productive in my work time (do more with less), and because I’m still learning how to assign the appropriate load (and maybe combination?) of tasks to each day.  That said, solving issue 1 (having more time for and getting more done on bigger, longer-term projects) is key and essentially the main goal of this whole thing. Issues 2-4 were obstacles in that path.

Now let’s talk about what I think can work better.

Firstly, Pomodoro is great, but I’m not sure how to apply it to smaller tasks that only take a couple minutes to complete, and are also dissimilar to them. The whole point of single-task focus is that you’re not changing around what you’re doing all the time because it’s disruptive. But when I have five or six totally different things to do, the disruption comes no matter how well I focus on those tasks individually. I suppose the most obvious improvement would be to group those tasks better, but that’s not always possible.

Second, as mentioned, I’m still occasionally blowing deadlines on lower-priority items. I already said that I think this will improve as my tool-fluency increases, but I don’t want to dismiss the possibility that there’s a discipline element here as well. It’s something to keep an eye on.

Third, I think part of the point of Time Tracking is to figure out how you’re losing time, not just how you’re spending it. I was reading a time-management article on Copy Hackers, and Joanna Wiebe mentioned a tool that keeps track of whatever apps and windows you’re focused on and displays it to you in graph form (she also mentions Pomodoro). While this probably won’t work for my Work stuff (because sometimes I have to talk to people and I also work on two different computers), I think it’s probably worthwhile looking into installing on my personal computer and running while I’m working on non-work things.

Overall, though, I feel better about things. I feel like I’m having more productive days, and while, like any process of change, there are still moments of panic and anxiety, I definitely feel a general improvement not just in what I’m getting done, but my overall satisfaction with it.

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