I’ve found that when my calendar is cumbersome to use, I tend to instead make todo items like “remember to calendar that dentist appointment on may sixth”, i.e. a note to self that I’d have to put that in there, and sometimes I’d even procrastinate so much on doing that that I got double booked and messed up.
These past two years when I’ve been using a paper calendar always with me, I haven’t had to do that anymore and at first I didn’t even notice that improvement because it was so natural. Then as I’m considering going back to digital, I’m like “hold on—maybe not. Remember having to tell yourself to calendar things?”. It’s a whole class of tedious and awful todo items that are now just gone because with the paper calendar I just enter them directly and immediately. It’s one big source of stress that no longer exists. I hope that was a problem unique to me, to have “calendaring” as a verb be a chore, a consequence of the way I had set up my system.
So when I first got into GTD in 2006, the first year I had a stack of A7 index cards and a super tiny book with weekly spreads that the entire book was smaller than the stack of index cards so I used rubber bands to keep it together. The GTD stuff was on index cards, “hard landscape” was in the tiny tiny weekly planner. Worked great.
Then, for 2007, 2008, and 2009, I had an A5 size book with one week down the left hand and a gridded/lined page for todo items on the right. 07 and 08 I used Moleskine, 09 I used Muji. I’d keep my context lists separated in sections where I’d be like “uh I’ll probably have more at home sections this week so I’ll make that section a little bigger”. Each week I’d rewrite the context lists, migrate over unfinished things from last week. I’d keep the project list in the back. I didn’t have internet at home during this era. On my work desktop, I had one of the context lists in a gnome app. I had one GTD system that encompassed both home and work, it was just that that one “@work” list lived in the desktop todo item list. If I wanted to add something to that list when I was away from the desktop I’d make a note in my paper book to do that, which was fine because that almost never happened. And projects, including work projects, lived in the back of the paper book. It was just really efficient being able to see at a glance up there what I needed to do, and not being able to see it when I was away from work was also great. Worked great.
An X in the box meant wontfix, a checkmark meant done, and a slash meant migrated away, usually just to the next page but could mean to a specific date or to someone else in which case my “waiting for” list was in the back.
These first four years of GTD were so awesome. The A7 size book with index cards and the A5 size books with rewriting-all-the-context-lists-every-week, both really good systems.
Then in 2010 I made a mistake. I got that same Muji calendar that had worked so well in 2009 but I decided to go with A6 size instead of A5. But no index cards. I was thinking, I’m back in school, work is over, I don’t have that many todo items, it’s just “do school stuff”. And what ended up happening was that I just weren’t using the paper book for anything.
So I gradually frogboiled myself into a digital system.
Also my life became really empty around this time because everyone else was on Facebook which I refused to join.
And by “digital system” I mean a complete mess based on a flat text file where the stuff I wanted to do next was marked by dots, a tangle of cron jobs for appointments, and org for projects but not using full on org mode for todo items (which I’ve tried and hate because it conflates goals and concrete action too much).
This was a system that grew piecemeal like the Rube Goldberg from hell from 2010 through 2021.
It was really quick and efficient… as long as I was at the desktop. I only had a desktop, no laptop, so whenever I had to schedule things when I was at like my physiotherapist’s office I’d have to… guess? I dunno what I was thinking. I was carrying around a paper notebook, one that I kinda still like because I found out a way to combine a sketchbook with nice white blank pages to sketch on with unbleached, super-low-quality lined note pages that I could guilt-free scribble on to journal or write errands list or use as inbox to enter into my desktop system when I got home.
I had a smartphone between 2009 and 2017 but I never migrated my GTD system to it. I’d occasionally set a single appointment as an extra alarm (most dumbphones can do that too) but that was for special occasions; the phone calendar was never the “single point of truth”. For a while I tried a really minimalist yearly spread where I could check if a time was booked and I could easily keep this in my paper notebook but not as easily keep it synced up manually.
Late 2021 to late 2023, I used Apple Reminders and Notes on iPad. That was dumb because I got vendor locked-in, not because of network effect (I didn’t use shared calendars or shared todo lists) but because the app was just so dang good. Except a proprietary app can never really be good because it locks you into a platform and now since I’m thinking of switching to RLCD or e-ink, one of the things I know I’ll really miss is those apps.
But not really because I switched to paper in October 2023! I used a traditional bujo setup with future log for those last three months, thinking that was going to be good for a temporary solution and not having to buy a three-month calendar, because then I got my Hobonichi Techo Weeks paper calendar which I used for 2024 and a new one for 2025. It has the same “week down the left page, free page on the right” that I loved 2007 through 2009, but instead of rewriting the context items I let the list run across a few weeks, and migrate or X out things that have fallen behind. A box in the top right corne r means “this is the oldest page with empty boxes”, and checking it means “no undone things on this page or on any older page. Instead of dividing the page into contexts, I use the life-changing magic of indentation. No steps in means do on InkPalm, one step in means do at home, two steps in means do on iPad, four steps in means errands. Grocery list in the front and “talk to friends” lists in the back.
I remember being a li’l frustrated how the Muji calendar had both a yearly spread, twelve monthly spreads, and 52 weekly spreads. In a digital calendar, that is awesome, but in a paper calendar that’d mean manually copying things from those to each other to get full use of them. So here’s my thinking on that now. The weekly spread is the Single Point of Truth. That’s where things need to go and need to be right. I redundantly and manually copy things to the yearly spread in the front because having the yearly spread is amazing for two reasons: it’s good to have an overview for planning and for longer trips and for knowing when my friends are on longer trips, and it’s good to have a look back over the year on which days were lonely or on which days I hung out with friends & fam. So it’s useful but I still don’t want to get in a position where some things from the yearly got missed and not copied to the weekly and vice versa. Only vice versa, where things that are in the weekly got missed and aren’t in the yearly, that’s less bad because then I still have a single point of truth I can rely on. I also journal and plan there. I have extra note pages in case the journal for a day runs long, I’ll just write a page reference to it. Circled number means “see note page with that number”, squared number means see a calendar spread on that week.
I do use the monthly spreads too, but for mean planing, meal recording, excercises and stuff. And, okay, yeah, some months this is blank because I’m not great at that stuff.
This system has been working great… For January, February, and March of 2025. Not so much 2024. I was experimenting with the idea that “write the 25 things you want to do, now the bottom 20 out of those 25, move that to an ‘absolutely do not do’ list because they distract you from your true goals” and that was a disaster. I’ll write an essay just about that someday once I’ve thought more about it. I still haven’t figured everything out.♥︎ I 2025 has been more traditional GTD and has been better so far.
So for 2026, I’m thinking I might want to go partially digital again! That sounds dumb given how it’s only March 2025 and how I just gushed on how great the paper calendar has been working.
And it really has been great. First of all, it’s a portable system. I don’t have to schlep the entire desktop or iPad, I just have it all in my paper notebook—and I was usually carrying a paper notebook anyway, so I’m not even carrying more stuff. The benefit of having a reliable calendar with me when I’m actually meeting real people whether it’s in a medical context or friends, that’s just awesome. Second, knowing what I want to do today without having to reach for the iPad is also great. It makes it so that I can decide “Okay, I want to do these three things on the iPad and then put it away” and actually having a fighting chance of that sometimes happening that way and me not getting sucked in! Third, no vendor lock-in, and fourth, it’s just cute. It’s an adorable flower book.
But it’s also pretty expensive with the shipping so I might want to go to another brand like a “fauxbonichi” or something local or just back to the bujo future log system which I can do in any notebook.
So here’s my idea:
Only the “hard landscape” of appointments is digital. Todo items, projects, context lists, even planning and journalling, that’s all in a paper notebook (and I can use any old paper notebook which is great because I found a huge stash of adorable old blank notebooks in a storage area the other day when I was looking for a replacement headphone cable). And with structure; maybe I’ll something like a bujo except with the future log digital. When I carried a paper notebook 2010 through 2023, that was a completely free space of scribbles and junk which was great to just get thoughts out of my head. Here, I’ll try get the best of both worlds with some more permanent pages like my reading list and agenda lists and some more scribbly areas, all date stamped. I dunno.
And I’ll only want to do this if… that Light Phone III finally ships and is good, and if I can figure out a way to have a calendar server so I can sync its calendar bidirectionally with a nice gorgeous tablet calendar app. That way I could do my calendaring with a nice and good UI at home but still have access to it when I’m out and about and only have the phone. I’ve been all paper, and I’ve been all digital, and I’ve even briefly tried digital but with a paper calendar, but not the most obvious configuration which is paper but with a digital calendar.
Why? Okay, so there are two advantages. One, while I’ve schlepped around some sort of paper notebook since 2006 in one form or another and I love doing that, it’d be kind of nice to not have to do that. I could go down to the café or board game night and just have the phone in my pocket and not bring my whole purse. The phone would have everything so I’d run no risk of double-booking, and if I entered things in there it’d show up in the home calendar and vice versa. (Alhough where would I keep tissues, keys, weapons, spare headphones, lip balm and a copy of Shirley Jackson’s Dark Tales if I don’t bring my purse?) Second, I could get into the world of sharing calendars with friends & fam! Digitally!
That’s been my thinking for the past month or so but then I remembered the already-almost-completely-forgotten chore of calendaring; when calendar was a verb, and that thought kept gnawing and boiling in me for a few days until this essay that you’re reading now came out. Just to, I dunno, surface my thoughts. And I can update here once I’ve done more thinking because I still haven’t made up my mind. Once that dang phone does arrive I can start experimenting with, I dunno, Radicale or something and see if I can make something work. There’s no rush because I’m committed to my current paper system throughout 2025 (although early fall is when it’d be time to order a new paper calendar for 2026 if I want to stick with my current setup).
There’s also, and this is super tempting, there are paper calendars with microscopic printing and a camera in the pen that makes it so that as you write in ink in the calendar, it can block that same time in your online calendar automatically. It can only do it on an hourly granularity and it’s not bidirectional, i.e. things that are entered in the digital calendar (perhaps from the phone) is not automatically entered in the paper calendar. So going this route, I’d definitively need to move things from inbox to calendar once I’m at home or in a place where I’ve brought that paper calendar. What’s good is, the paper calendar isn’t magic (it just has micro printing), the pen is. So you don’t have to buy new electronics every year as long as you keep that pen. I’d still get half of the two benefits: I could share my calendar with others (but not the other way around) and I could bring a read-only copy of it with me with my phone (but still have to enter things into it at home). Both of those halved benefits still sound amazing compared to what I was dealing with with my dumb desktop text file system from 2010 to 2021 but they also sound like kind of step back from my current Hobonichi Techo Weeks paper calendar (since it is smaller and I can just bring it in its entirety more easily than these microprinted ones). Still tempted just for how cool the idea is and for how it cuts down on screentime compared to a tablet calendar app which is what I’m leaning towards because it just makes more sense. Again, holding off until I can play around with Radicale or similar apps later this summer, once (or if) that Light Phone III arrives.