Calendar management

My current calendar management system involves one digital source (with three calendars in it) and two analog calendars. The analog parts involve manual copying, which is a bit tedious, but I’ve found it very helpful, especially now that it’s not just me at home. The tl;dr: is that I have three iCal calendars in Apple’s system and I periodically manually copy those to two different analog calendars, one shared with my partner, to get a sense of the shape of the weeks.

Digital

The main day-to-day calendar for me, and the “single point of truth” in my part of this system, is Apple’s Calendar. I’ve got a lot of calendars set up in there (good lord; I just checked and it’s 20!), but most of those are novelties or historical. There are really three that matter:

(See the end for notes on the others.)

“Personal” includes things which only I care about, like meetings which don’t impact my normal availability for other things. The recurring board meeting for the non-profit I’m involved with, for example; it happens duing a time my kid’s in school and my partner’s almost always working, so it’s unlikely to affect them; my partner doesn’t need to see it so I save her the noise and it stays here.

The “Family” calendar includes genuine family activites (birthday parties, kids' after school activities), but also things which are only for one of us but the other needs to know about for timing/availability questions. If I have a medical appointment, for example, it goes on here, since it’ll make me unavailable to the family. The reminder about trash day goes on here. ☺

The “School” calendar includes things like school closure days, but also things like school picture day and parents' events. I usually keep this one hidden (because it also includes a lot of things we don’t need to see regularly) and make it visible when populating the analog calendars. I’m really grateful that our school makes this available in this format.

Analog

The digital calendar is the authoritative one, because it’s easiest to update from various places, copy arbitrary notes/URLs into events, easiest to share with other people, and so on. But it’s not great for showing the “shape” of the week(s) to come, and we’ve got some technical limits on sharing. I maintain two analog calendars to help with this; one just for me, one for the family.

Pocket Journal

I pretty much always have a notebook in my pocket, and I use it in a sort of bullet-journal-lite way. The relevant “module” (ugh) is a “rolling ~4 weeks”. It looks a lot like Ryder’s Monthly Log on the BuJo Monthly Logs page (but a lot messier), except rather than keeping it on a month boundry I start on a Monday and do a line per day until I run out of lines. It doesn’t get most tasks, just things which block time or provide structure to the week. Individual things get a • and very short description; things which span multiple days (like trips for vacations or conferences) get written vertically on the right edge between vertical brackets. The example here is a messier-than-normal example, but it’s the only one in the journal currently in my pocket.

When I get towards the end of one (uh, in theory; really, it’s more like when I realize I’m a week or more off the end of the previous one) I start a new one with the dates and days of the week running down the left, then open my digital calendar and pick out the relevant events. It’s a bit tedious, but only takes about 5-10 minutes every few weeks, and the act of reviwing them this way is worth almost as much as having them written out.

I’ve been doing this for about 10 years. I’m not super consistent about it, but do find it helpful, especially during busier times.

Wall Calendar

The newest component of our calendar system is the lowest tech: a large, laminated calendar we write on with wet-erase markers. We went to OfficeMax (I think?) and looked around and came away with the PM5308-28. It works well for us, but it’s also just what they had (we don’t use the back side at all). The important points are that it’s big, light enough to hang on the wall, and doesn’t come pre-printed with dates. Once a month or so, on a Sunday, I’ll wipe it off and my parter and I will each go through our calendars and put events on there. We have a color per family member, plus one for everyone (and when our niece was living with us, one for “both kids”).

A cropped photo of a wall calendar covering two weeks.

For just myself, this is a mostly-redundant way of seeing the same things that go into my pocket notebook. But my partner has three (!!!) different calendar systems she has to use at work, and very limited ability to share things with me from those. She’s also perpetually frustrated by her work calendars, and asking her to make copies of selected things to another digital one is… well, not in the cards. And even if she could share all her entire calendars with me, it’d be way too much. I need to know which day’s she’s working at which of the two locations she splits her time between, or when she’s working from home, but not what the 6 meetings in a day on the Hill are. And she finds it a helpful way to make things that are otherwise on the Family digital calendar cut through the noise her work calendar creates.

The calendar is hung on a wall in a high-visibility spot at the bottom of the stairs to the bedroom, in a hall between the kitchen and the front door, so it’s really “glanceable”.

This was working very well for us, until about a month ago when the sticky tack we’d used to attach it to the wall fell off and we realized it pulled just a tiny bit of the surface off with it. It’d been up for about 2 years at that point, but we’ve been slow to put it back up without a different plan for hanging it. Like the version in my pocket notebook, the exercise of doing this is worth almost as much as having it actually done, but this being out and visible all the time really increases the utility of the finished product.

Things not part of the system

That’s it for the things that actually matter for the utility of how I manage my calendar today. A quick note on what I did before this system started to form, and a longer one on the miscellany and detritus accumulated around the current system.

Past

Up until a few years into the 21st century, my main calendar system was Plan 9’s calendar(1). I had a handfull of scripts that did things with the output, like feeding it to a “here’s what your day looks like” morning report. Over time, those scripts transitioned to being more about my “daily” tracking files (which I suppose I should also write up at some point), and my “normal” calendar started being the iCal files maintained by Apple’s tools (encouraged by getting an iPod around 2004 and the ease and utility of having all my calendar things synced to that).

I still miss parts of that system, especially the unix-style composability and the simple command-line way of getting my schedule for the next day. I’ve played around with a few ways to recreate that, but haven’t found anything satisfying. I’m going to revisit that soon; it still seems like getting AppleScript to produce a calendar(1)-compatible file should be reasonable.

What are those other 17 digital calendars?!?

I mentioned I have 20ish digital calendars but only really use 3. The rest aren’t really part of the “system”, and are a combination of history, novelty, and… pathology.

My favorite first: I’m subscribed to Atlas Obscura’s calendar of fictional holidays. It’s a fun way to be reminded of when Rex Manning day is or the various holidays celebrated on Discworld. Looking at it now while writing this, it lools like they haven’t updated it since 2016 and have let the certificate drift from the domain name the file is hosted on, so it might make more sense to just download and import than subscribe to.

I have a personal calendar called “micromanage”. I use it only infrequently, when I’m having a hard time balancing the need to focus on something against having a handful of things that need doing. When I’m having that problem, it’s sometimes helpful to micromanage my own time, putting things on here like an hour block to work on porject A, then get lunch, then thirty minutes on project B, then take a walk, then an hour on project C, and so on. It’s rarely used (setting it up is a lot of hassle), but I have a pretty good sense of when that’s what I need.

My partner and I have another shared calendar called “Kids options”. It contains things we hear about which we aren’t deciding to do, but want to remember are out there. Things like our local library’s weekly lego play time. Putting all these on the family calendar would get overwhelming, and we’re not trying to block out the time for them, but it’s nice having a place we can look for ideas when we realize there’s no school on Friday and we should find something for our kid to do.

In the past, I’ve also had one per job (or job-like thing). I keep those around because I’m a bit of a data hoarder. These are usually just for me and functially equivalent to the “Personal” calendar, but this lets me toggle them on and off when I’m explicitly avoiding or focusing on work events. The one notable exception here was when I ran for office in 2022. So many of the things which went onto that calendar happened at odd hours—canvasing on weekends, forums on weeknight evenings—and affected my availability that I shared the whole thing with my partner rather than copying individual events to the Family calendar.

A few are provided by Apple: a US Holidays list; “Birthdays”, pulled from your Contacts; “Scheduled Reminders” (things from the Reminders app with dates attached; weirdly, only on iOS, not macOS); and “Siri Suggestions”. I have the first two turned on and the last two off. I only recently turned the Reminders one off; since most of my reminders with dates are daily recurring things, the signal-to-noise ratio of that one is pretty bad. For the “Birthdays” calendar, I wish (a) there was a way to only include a certain group, and (b) there was a way to include non-birthday dates. Still, having the birthdays automatically included is very nice, so I’ll deal with seeing extra (hope your birthday on Monday was nice, Bekky, even though we haven’t talked in a dozen years!).

A non-profit I work with which uses Google tools and creates a separate account for me includes a calendar which gets meeting invitations on it. The same org has two other calendars from former users which are somehow assigned to me now; there’s nothing on these, but I’ve never figured out how to delete them (I find Google’s tools very confusing here). It also offers a “US Holidays” calendar, essentially a mostly-redundant, slightly lower quality version of what Apple offers, which I can’t figure out how to remove so it just stays off.

I’m subscribed to two “local events” calendars (only one of which is actually local to me). I haven’t done Google’s Summer of Code in a few years, but I’m still subscribed to the calendar for it.

I think that’s all of them.

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