Plans

• 03 January 2022
• reflecting

For the last several years, I’ve had a daily planning routine. While I’d begun that routine in the Moleskine that was always nearby, I moved it onto my computer about a year ago, taking advantage of Obsidian‘s daily notes capabilities. I set up a template for those notes that allowed me to capture a few morning thoughts, a sense of the day’s schedule, a few key priorities, and then any later notes from meetings or events during the rest of the day.

It’s been great having this reliable space for thoughts and notes, but it hasn’t been so great for planning at the level of the day. For one thing, my actual calendar is elsewhere — in Outlook, where it needs to remain so that my colleagues can find times to meet with me as needed. For another, my actual task lists and projects are elsewhere, too — in Things, which works extremely well for me. Beyond that, though, the daily notes version of my schedule and goals more or less records a plan already made, rather than allowing me the necessary distance and vision to build that plan.

I did some poking around looking for a planner app that might allow me to bring together my calendar, my task list, and my notes in more flexible ways. Ideally, I’d want to be able to assign tasks to available time on the calendar, to take notes on events, and to keep tabs on progress toward whatever goals I might have. Unfortunately, I haven’t found an app whose developers’ brains work the ways that mine does. (Yet. I could still imaging finding the right thing.)

Finally, a tweet from Nyasha Junior made me reconsider my approach.

I read through the piles of excellent responses she received, and explored a lot of great-looking paper planners. And in the process it hit me that what I was looking for was something with the flexibility of paper and the convenience of the digital — which made me start thinking about my reMarkable.

I originally bought the reMarkable in order to have a focused, paper-like environment for PDF reading. Since then, the release of the Zotero beta for iOS has taken over most of that space; the workflows for extracting highlights and notes into Obsidian are just too good to ignore. But the reMarkable remains unbeatable for both pen-on-paper feel and for single-tasking focus: whatever document you’re in is where you are, with no apps or notifications to distract you.

So I started searching for, and found, a reMarkable-based planner. In some ways — technological ways — it’s super simple: it’s a giant PDF. But that simplicity disguises enormous flexibility. Careful linking allows you to move from pages representing calendar months to pages for weekly and daily planning, as well as additional pages for goal setting, project planning, habit tracking, and more.

It doesn’t connect to anything, except my brain and my hand. So each day’s plan requires me to copy my calendar events and my tasks — but at least so far, the act of doing so seems to open up possibilities for the rest of the day, allowing me to think about how the pieces fit together. It’s a bit reflective, and it allows me to doodle in ways that planning apps don’t.

I’m literally one day in with this new system, so it remains to be seen how it works over the long haul, and how I might maintain the connectedness of my Obsidian notes while having this separate space for planning. But so far I’m encouraged, and thinking about how a small return to longhand exploration might shape the days ahead.

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