I’m reading Gretchen Rubin’s Better Than Before (possibly again? I’m sure I’ve at least skimmed it or started it before), and thinking (as usual) about how to structure my time.

I don’t have a lot of obligations, and I’m not a workaholic, so what I’m looking for isn’t a “productivity system” as much as a way to make time for the things I want to spend time on. For instance, some of the things that I know are important to me are writing, reading, practicing the piano, and watching movies. I should make some time to finally exercise, too, and I like playing Zelda, so I’d like to carve out some time for that. I never watch TV, but there are shows I’m interested in, so fitting that into my days could be nice, too. Then there are other various side projects, etc.

The trouble is that when I find myself with (frequent) “downtime,” I don’t know which of these activities to choose. Because none of them is urgent — they are more or less hobbies that I want to dedicate time to — none can ever beat out the others as the clear priority. Saying “yes” to reading is saying “no” to watching a movie; saying “yes” to watching a movie is saying “no” to practicing piano; etc.

What timeboxing would (in theory) allow me to do is fully devote myself to these pursuits, because time for the others would be built into the calendar. Timeboxing is sometimes about putting one-time tasks or projects — things that can be “done” — between meetings on a calendar, but in my case, I’m looking to design a dateless week grid with recurring slots for each of these pursuits.

This way, if, say, Tuesday at 8pm is for watching a movie, I don’t have to wonder if I should be reading instead, because there are time slots dedicated to that earlier in the day and on other days of the week. I know there is time set aside for each of the activities that I think of as important to me, so I don’t have to feel like I’m giving something up every time I choose to do something.

Of course, what this means is that for the system to work, I have to watch that movie at the allotted 8pm time slot. It’s only by strictly following the schedule that I can be confident I’ll truly be making time for the things I want to do.

I recoil a bit from this restriction on my time. Of course I feel like I’d rather just wing it when it comes to my free time, and do whatever currently interests me. But that’s what I’ve been doing, and it doesn’t work. It leaves me feeling unfulfilled and frustrated. Usually I’ll end up reading, because that’s easy to choose, I’m always in the mood for it, and it certainly can’t be a bad way to spend time. But it means my piano skills are rusting, and I haven’t seen a single episode of whatever new show I was excited about.

After struggling to find a good tool for doing this — it needs to be flexible enough that each time box can be easily duplicated, resized, and dragged around a calendar grid — I decided to just try it with GoodNotes on an iPad. There are some limitations to this, but for the most part it’s ok.

This was my first time really seeing what a potential timeboxed life schedule could look like, and it was encouraging. I was able to design a week that had time for most of the things I value, including the “trivial” stuff like gaming. Of course, things will come up to interrupt this — plans with friends, unexpected chores and errands, etc. — but in theory, if I “trust the system” and stick to it, it could give me some peace of mind that, no matter what I’m doing at the moment, I have set aside time for all the other things I would like to be doing, as well.

We’ll see if it sticks! (It won’t.)

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