Notes on a digital declutter

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I gave myself a few days to think about Digital Minimalism, wondering if a declutter might be a good idea. I found myself feeling so moved and have spent some time teeing it up.

Newport’s take on how to do that starts from what I guess you could call a naive footing, dumping everything and then considering it without a lot of preconception. I think that is fine, but I’d been giving a lot of this some thought already, have done a few declutters in the past, and had heard Newport talk before reading his book, so I colored outside the lines and skipped a few steps with some parts, but kept a few things from his approach, too.

I have a few things in mind:

I want to radically pare back the number of tools hanging from my belt. I keep a lot of things hanging around for this edge case or that, this possible scenario or that. I decided to reduce as much as possible by getting rid of things that repeated each other. For instance, I like Ulysses well enough but it repeats other things and it has a subscription fee. So, yes, it can post to and has a few other tricks, but none that I need. I’ve also bounced back and forth between RSS readers for whatever reason, but Feedly’s native app works great for my workflow.

I’ve also built up a lot of papercuts with the things I do use regularly, such as:

  • How do I block a site in Feedly so that I can keep a little serendipity with a few eclectic sources without constantly bumping into the same site with a paywall I’ll never click through?
  • How do I get something into an Obsidian inbox using a shortcut to keep me from pecking around inside Obsidian and ultimately forgetting the fleeting note I wanted to create?
  • Why does pick the images it does to send when I crosspost to Twitter?
  • Can I get more folders in SaneBox without paying more? How much would I have to pay to get more?
  • I’ve got good automated note import into Obsidian, but am I linking ideas and and concepts adequately? (A: No.) How can I fix that?

And I want to do the sort of core thing, which is unplug my brain from all the social media inputs and stuff that doesn’t feel nutritious.

The more I thought about it all, the more I realized there was a project there. Turns out that trying to be more intentional means doing stuff like writing it all down and prioritizing.

Fixing Todos ๐Ÿ”—

So, realizing I needed to capture tasks, I started by cleaning up my todo situation. I’ve been living in a few places over the past few years. I recently tried to retrench on Apple’s Reminders because it has gotten pretty good, but it turns out not good enough. It’s great that you can nest reminders under each other, it is terrible that when you painstakingly set up a morning routine with subtasks and then turn on recurrence, the only thing that actually reoccurs is the parent item.

I also gave Obsidian a shot, on the premise that it is pretty much org-mode except with Markdown, an actually good mobile app, and no dependency on Emacs. It is great, but it also has some challenges in terms of making quick entries, and the task management stuff that would take it to the next level has a lot of the same issues most plaintext todo systems have in terms of awkward and visually cluttery metadata. org-mode does a great job of hiding or restyling that stuff, but you’re still living in Emacs, and the power comes at the cost of a complex and sometimes brittle pile of configuration code and stability-threatening Emacs extensions.

What else? Omnifocus, Todoist, Remember the Milk, Trello, and Workflowy all suggested themselves. I won’t go into why not for each, but it came down to “want Apple-native, a good mobile experience, decent capture, subtasking, recurrence, decent in-task notes, and integration with my calendar.”

So, I went with Things. I’ve had a license for years, I’ve always preferred it to Omnifocus for its relative visual calm.

I could have kept my old Things tasks around and cleared them all out, but I decided to just wipe and start over, and borrowed a page from Getting Things Done by doing an initial braindump into my new trusted system (for tasks, not ideas … that’s Obsidian, but I’ll get into that some day). A lot of the things I knew I’d want to get to in my digital declutter came out during that dump. I made myself sit still, get everything out in its simplest form without trying to schedule, label, or organize.

Once I did the braindump I did start looking for organizing principles. Things has the whole “Areas” concept, so “Personal” and “Work” presented themselves as obvious candidates for top-level. I also added a “Meta” area, which I’ll get to.

So I hucked everything into either “Personal” or “Work” then started sorting into projects, subtasks, and tags.

The “Declutter” project had a lot of items, so I took advantage of Things’ ability to create headings, and broke the project into:

  • Tools
  • Services
  • Media Outlets
  • Practices
  • Social Media

Into each I put all the things I use or have around, all the papercuts I’ve thought about, and all the questions I wanted to answer:

  • What do you need a break from?
  • What do you need to do to be intentional about this thing? Is that practical or useful?
  • When you adopted this thing, what aspirational idea did you have about it?

Daily/Weekly/Monthly Routine ๐Ÿ”—

Recurrence in my todo tool is important to me because I want to codify a daily routine I’ve had on and off over the years, starting back when I was stationed at Ft. Bragg and started and ended the day with a pen, a legal pad, and a list of tasks:

  • Morning: Write down deliverables. Start doing things.
  • Evening: Make sure you crossed everything off you managed to get done. Tear off the sheet, copy over the undone stuff to tomorrow’s list and leave the pad front and center on your desk when you shut down for the day.

Since then, I’ve tended to move todos into a digital tool, but that list is just part of the daily page.

For starters, there are some prompts for morning and evening:

  • What are the three most important things today?
  • What are you most concerned about right now?
  • What are you most happy about right now?
  • What happened today?
  • What went well today?
  • What could have been improved today?

I also have tasks for each morning:

  • Reviewing todos and blocking time in my calendar to get to them.
  • Reviewing places where a deliberate break will be a good idea.
  • Reviewing the day for manageability and pushing things out that aren’t time sensitive if I need some space.
  • Review my email inbox

My weekly and monthly kickoffs are pretty similar in shape and intent: Try to predict where I’ll need time or space and get ahead of the week or month.

To support this routine, I tweaked Sanebox to send me work email digests at the beginning and end of the day so I can quickly sweep through and bulk archive or flag things.

Writing it down ๐Ÿ”—

Getting my todos straightened out and having a daily routine to stick to gave me a safe space to think in, so I turned to Obsidian and set up a few pages to write down everything I was thinking about.

I’ve got a tentative Zettelkasten-like folder and document structure using a few plugins:

  • Daily pages as a recipient of fleeting notes. Fleeting notes are meant to be ephemeral, so I could have gone with a lot of things, but I also added …
  • … the Lumberjack plugin, which allows me to make Shortcut actions to do quick capture under a “Fleeting Notes” heading on my current daily page. The action lives as an icon on the dock of my iPad and iPhone, and I can get at it from the task bar on my Mac.
  • Zettelkasten numbering for permanent notes
  • Readwise to import highlights from Pocket, Kindle, and web clippings into a “Literary Notes” folder

Thanks to Things and Obsidian having URL schemes, it’s possible to link back and forth between the two apps, so my Things declutter project can link back to the index page for the writing I’m doing about that project in Obsidian and vice versa.

Progress So Far ๐Ÿ”—

That’s a lot of table-setting, but I had some downtime today so I was able to dig in on some of the actual tasks in the project: Unsubscribing to media, deleting apps, asking questions on support forums or via help forms to address papercuts, disconnecting auto-posting tools, paring down follow lists, fixing papercuts as I was given answers or figured things out for myself, comparing features on tools in the inventory.

Something I never used with Things before but now really appreciate is the Logbook area, where completed tasks go. I’ve adopted the practice, when a task is about answering a question or learning something, to include the answer in the notes. I really like being able to end the day by going back to the Logbook and seeing everything I checked off.

Now for the hard but nice part ๐Ÿ”—

All of this was to get me into a place where I can unplug from social media for a month.

Things I’ll stop doing:

  • Looking in on social media.
  • Posting anything to social media, including automated stuff.
  • Adding any new digital tools, even just to play with them.
  • My nightly pre-bedtime YouTube binge.

Things I’ll keep doing:

  • Reading and keeping notes

  • Writing and posting small entries about what I read

  • Taking pictures and posting them to my blog

  • Writing about my declutter:

    • What do you need a break from?
    • What do you need to do to be intentional about this thing? Is that practical or useful?
    • What aspirational ideas do you have about this thing?
  • Keep in touch with people over email, texts, Signal, etc. Hopefully even more.

  • Reach out to people with whom social media is my only real contact and make sure there’s a way to stay in touch. I don’t see a bright future for Facebook in all this.

Things I’m adding:

  • A daily journal practice.
  • A real effort to maintain a Zettelkasten for my reading and writing. This feels intimidating for some reason. The system is easy, but I’ve only recently restarted my reading habits and I’m curious about what will emerge. I’ll be sure to document whether I’ve become an idiot.