My friends say that my calendaring practice is atypical (and mock me incessantly for it). They're not wrong, but I'll contend that most people underutilize this ubiquitous tool. A calendar is not just a reminder device for keeping track of external events. Used right, a calendar can be a full-fledged tool for thought. For me, it's a dynamic journal with a wide range of useful, meaningful, and surprising perks.

Here are some of the more idiosyncratic reasons I value my calendar so much:
  1. Scaffolding for a memory palace: Calendar events inevitably neglect most relevant details about the past, but nonetheless they can serve as a trigger to place you in your memory palace. They create anchors in your mind that can help you recall other details.
  2. Chronometer of the past: It's instrumentally useful when you're trying to figure out the chronology or casualty of some that's happened to you in the past. For example, my boyfriend and I couldn't remember the day we started dating, so we scrolled back in my calendar's history to determine when to celebrate our anniversary.
  3. Self reflection: It's a useful tool for honestly reflecting on how you use your time. I've changed some behaviors from looking back on past weeks and seeing that I'm spending more time than I thought on things that I don't actually care about.
  4. Planner: Calendars are helpful for visualizing your time, which gives you superpowers over how you spend that time. While this isn't too far off from how people already use calendars, I think it's vastly underrated.
  5. Pleasant nostalgia: It's pleasantly nostalgic to look back on the person you used to be. 😊 While doing my taxes recently, I was scrolling through my calendar to remind myself of my various income sources (i.e. for the "Chronometer" reason), and it made the experience of doing my taxes actively pleasant because it was a nice reminder of all of the interesting things I did in 2018. What a good year that was!

Most people I know use calendars solely as a way to coordinate events in the far future and/or with other parties. They generally have the following, fairly limited purposes in mind:
  • To ensure that they have the same information as the other participant(s),
  • To have a reminder of blocked off time so they don't accidentally double-book, and
  • To store information about the location and timing that they only care about as the event approaches.

There are a few additional steps I take that extend my calendar's usefulness into other contexts, too:
  • I often add events retroactively, i.e. events that have already occurred (which is useless to a calendar user who only uses it to prepare for future events).
  • I add events for personal "events" as well as external ones. For example, I have events for chores, work tasks, sleep, showers, and weekend projects.
  • For personal events, I include a lot of detail in the event title (and sometimes extend into the notes) and don't worry much about editing it to be optimally readable. The purpose is to jog my memory with as much interesting mental state and intention from that moment I created the event as possible, not to communicate as effectively as possible with the outside world. I do try to clean up the phrasing for external events (where there's 1+ invitee) more, since they don't want to deal with my messy brain.
  • I color code my calendars into rough categories. Not sure how useful it is but it certainly makes my calendar prettier to look at. 🤓

One question I always get is "how do you have the discipline to enter everything, especially retroactively?!". One answer is that I don't. I often forget! And that's fine.* The purpose of my calendar diary is not to be a perfect record of how I spend my time. It's a map of the territory, and the purpose is to trigger useful and interesting memories, reminders, and ambitions that don't fit as well in other mediums (including my own mind).

A more useful answer: I think of this input step in terms of triggers—i.e. what moments call for me to add something to my calendar, and what's the reminder? A few examples:
  • When someone invites me to an event, I add the event + location + notes to my calendar. (This one is pretty typical I think.)
  • When I'm planning my tasks for the day, I block off the rough amounts of time I expect various goals to take. This is useful for prioritizing time visually. It's easier to reason about an abstract thing (whether it's a calendar or an essay or a math problem) once you've written it down. These time blocks almost always change through the day as different things come up, or when tasks take longer/shorter than expected; the important thing isn't that they're correct when you first "draft" the events, just that it gives you something to work off of.
  • I have repeating events for things like my daily workout. I often move around the exact timing on a per-day basis, but just having it blocked off as some time in my calendar is helpful so that I remember to make time for it. Below, you can see how I have the recurring "25-minute workout" scheduled every single day in the future for 8:30pm. I don't actually do the exercises at that exact time usually, but it helps me remember that I've budgeted 25 minutes of my day to doing that.
  • I do intermittent fasting on most days, and I mark that eating window on my calendar.

These triggers are somewhat personal, so I wouldn't recommend any specific one to others. These can just be used as inspiration.

The habit has evolved organically over many years, so I don't have a grand strategy that's easy to articulate. This is a brain dump and not at all comprehensive, just the first things that popped to mind. I just hope this sparked some ideas in your head for creative uses of calendars. I'd love to hear about other unconventional ways you use calendars, too!

* I will sheepishly note that at one point I did aim to track everything precisely in my calendar, and whenever I'd accidentally forget something I'd fret that I was "polluting the data". I even went so far as to impose standard titles across like events. For instance, I would slap myself if I wrote one event as "Shower" and another as "Shower time"—how was I supposed to reconcile all this messiness?! I imagined that at some point I'd programmatically analyze the calendar data and get useful RescueTime like insights out of it. I now realize that's a fool's errand, and that a calendar is at best a useful map of my time. I shouldn't even try to mold it into the territory itself, because it's impossible to transfer the depth of richness that is how a human spends their time into a grid, no matter how many different color-coded categories you have.
Thanks to Laura Deming whose email query prompted this writeup!