Your Productivity System Needs to Evolve with You

If you follow this blog at all, you know how much I love thinking about productivity (to-do list tracking, calendar time management, time tracking, etc.). So, hopefully, it should come as no surprise that I believe a person’s system that helps them be productive needs to evolve. As time passes, things change, and so must the productivity system! There are so many changes that could trigger a need to reflect and evolve: a change in service responsibilities, a change in a course, the arrival of a child, a change in how your kids need you, etc.

[This article is also posted on my personal blog.]

So, this blog post is about how I deliberately and conscientiously evolve my productivity system. I’ll focus on what I generally do and provide some concrete case studies in hopes that they will help you think about your own situation.

General Process

My process has two main parts: a mindset and a monthly reflection. There are a few pieces to the mindset. First is just accepting that the productivity system has to change. One thing I find frustrating about a lot of content around productivity is that it doesn’t remind us that there is no “perfect destination” for your system. It has to change. The me of 5 years ago is not the me of now. How can I expect the system I built even 2 years ago to still work now? Accepting this got rid of a lot of resentment because I stopped getting upset that other things were messing up my system. If those things were a systemic part of my life, they were just a sign my system had to change. A concrete example is that just this year, my younger child started preschool, which means their schedule synced up with the other child since they go to the same school and they are both home at 2:45 every day. Having two kids home at that time (instead of one because the younger one was at daycare until 5 before) makes it harder to work from home now.

A second piece to the mindset is that since it is evolving, I should continuously be open to potential changes and be willing to try them. I do this by listening to podcasts and paying attention when the speakers discuss productivity. I use it as a one-sided thought partner to find ways to improve my system. This is part of my philosophy of Kaizen.

For the monthly reflection, I think through a series of questions as part of my monthly check-in, where I update a bunch of different things (like my CV) and think more long-term about my career. These questions center on things like “Is there something taking way longer than expected? If yes, what? Why?” and I remind myself of the sunk cost fallacy and ask myself whether it is still worth doing or what I really need to do to call it done, as opposed to my idealized, perfect done.

Recent Experiment: Longer Time Blocks

During a monthly reflection at the beginning of the summer, I remembered a finding from software engineering research that uninterrupted time is vital for software engineering productivity. I have not read the research, but the general idea is to work for long enough to finish a task rather than be interrupted in the middle. In contrast, I thought 30-minute work blocks were fine, borrowed from the Pomodoro technique. I’d even read some productivity gurus claiming that 15 minutes is enough and interrupting in the middle can be good because you are more likely to hit the ground running at the next session. However, many tasks in my job require more than 30 minutes.

So, I decided to try an experiment that summer because I had multiple big projects to get through. I created as many contiguous work sessions on the same project as possible. This is in contrast to my past strategy of working on each project a little every day. I used this past strategy to mitigate what might happen if a day got derailed, kind of like not putting all of my eggs in one basket. Getting derailed used to happen more during the pandemic when my kids were younger, but on reflection, it didn’t happen all that often anymore.

At the end of the summer, I thought the experiment was a big success. I felt much more productive in a 3-hour work session on the same project than if I had done three 1-hour sessions spread across time and days.

I am continuing this new contiguous task-time strategy during the academic year. However, it’s not fool proof. Meetings require working with other’s schedules, which sometimes break up a day, so work sessions become like confetti time. I am doing my best for tasks to be contiguous though and I stuff the confetti time with tasks I know I can get done in such a short span. In the past I would have just tried to break up larger tasks into those time spans. In addition, I’ve piled quite a few meetings in a single day this semester for the sake of getting that contiguous time. And I’m realizing that I don’t necessarily function well if I have a lot of meetings back to back that require me to bring my A game.

Recent Experiment: Change in How I Use a Timer

Something I borrowed from Pomodoro is using a timer to get me started. Having a timer telling me, “you only have X minutes to do the thing you are doing,” helps my brain focus. The timer, in combination with my time track system, also helped me understand how long something actually took me. These things helped me consciously choose what I should be doing and gave me permission to ignore everything until the timer was done.

However, in the same reflection that got me to change the length of my time blocks, I finally admitted to myself that my current use of the timer needed improvement. I’d fallen into a bad habit of hitting the 5-minute snooze button over and over again. Sometimes, I’d hit it so often I lost all sense of time, and all I cared about was finishing the thing I was doing.

What I wanted to happen was intentionally pausing when the timer went off. And in that pause, I’d ask myself how much more time I needed on this task, given that the timer was set to how long I thought I would need. And then, after this pause, I could change my plans of when I’d do the current or another task(s) to match the new time expectations for the current task.

So, I changed my process in a few ways. First, I changed the snooze button to only 1 minute. And I hate it in a good way. The friction of either hitting the snooze a bunch of times or hitting it once and the timer going off again soon after jars me out of my flow state of “just keep going to get it done.” So, most of the time, I now do pause to figure out what I should be doing next.

Second, I set the timer to give me an audio warning 3 minutes before it actually goes off. Do I always register this warning? Not at all, but it helps my brain start to ramp out of focus mode, which increases the odds of an intentional pause. My original intention was the 3 minute warning would be when I do the intentional pause, but that doesn’t happen all that often. Usually, I hear it and my “just get it done” mode kicks in, and I try to quickly get the task done. Only when the task is one work session of many for a much larger task am I more likely to just pause and think about how to finish nicely so it’s less ramp up when time I pick this up again.

Third, I set the timer to end right when the next work session is supposed to start. If I have to be somewhere, I set the timer to go off 2 minutes + travel time. My rationale here is to try and get myself to take the 3-minute warning seriously. Previously, I always set the timer for 5 minutes before the end of the work session, which means I almost always hit the 5-minute snooze button after every work session at least once, which started the terrible habit of hitting it a lot.

Now that I’ve had these changes for a few months, I can say the results are on the right track, but not perfect yet. I rarely get into a mode of just hitting the snooze until I’ve lost all track of time, which was the biggest thing I wanted to change. The times I intentionally pause are increasing. So, overall, I think things are getting better.

Conclusion

My hope with this blog post is not to give you “the one trick that will solve all your productivity problems!” because I honestly don’t think that exists. But rather to provide permission to face the reality of your current situation and acknowledge that productivity is a journey not a destination. And then I hope this framework helps you think through your own situation and start making incremental progress.

Did I succeed? Please let me know if it is helpful! And feel free to ask me at the end of the fall semester if things are better than they are now!