Coordinating the Chaos

Once upon a time, life was more manageable. I worked a corporate job and used the approved corporate tools to keep my work organized — Microsoft Outlook and Microsoft OneNote — from around 2005 until 2018 — and around 2013 supplemented it with Todoist for the small number of purely personal goals and tasks on my plate. I had used Scrivener for writing since 2013; all of my stories and novels were part of that suite.

When I left Priority Health, I lost all of my Outlook data, including calendars. I persisted with OneNote (my non-corporate notebooks, that is) and a personal version of Outlook until around 2020.

My world got more complex in 2021. Between the end of the pandemic lockdowns and the growth of my consulting business, plus various literary endeavors and my final transition away from W-2 employment, the only "corporate tools" I had were the ones I selected for myself. Using some sort of electronic system for calendars, tasks, and notes was mandatory; the particular toolkit, though, was harder to tease out, relative to how I think.

So I migrated in a few different ways:

• Visual Studio Code + Todoist: First iteration post-corporate was to throw everything into Visual Studio Code and go hard-core into locally hosted plain-text files. I used Todoist for tasks and VSC for both my personal notes and writing. It worked well enough, but VSC's power as a text editor didn't fit neatly with my needs for a coherent, opinionated environment for personal organization.
• Logseq: I wanted "one ring to rule them all," and also to support daily journaling, so I used Logseq. It's an outliner with some ability to manage tasks and calendars and also daily notes, so I retired Todoist. But because it's an outliner, it's not good at long-form text like novels (and searching becomes unwieldy), and the Logseq Sync platform was buggy and on occasion I lost my data or my edits to task lists. Data corruption is a big red flag. After I lost some important updates, I got fed up and pivoted again.
• Obsidian: I then pivoted to Obisidan. It's not an outliner like Logseq but otherwise (thanks to its massive plug-in library) is very similar. But I never felt "right" about Obsidian tasks; at the time, the plugins weren't all that sophisticated about missed recurrences and more nuanced recurrence patterns, because it still operated in a Markdown format.
• Obsidian + Todoist: I eventually gave up on Obsidian's task-management features and went back to Todoist.
• Bear + Todoist: Obsidian was "too powerful" — the feature set prompted me to keep wanting to tweak the system instead of just using the system. So I figured that since my use case was more narrow, and because I had managed to lose a daily journal after leaving Logseq, I'd flip to Bear because it was prettier and better integrated with my Apple device ecosystem.
• Noteplan + Ulysses: But Bear was too light on organization; it's use of nested tags, which seemed clever at first, didn't match how I think of information. And I really wanted to get back to the "one ring" logic of an app that handled journaling, notes, and tasks in a single UI. Noteplan did that, but I peeled off my writing into Ulysses. Ulysses is a better focused tool for long-form writing; it plays nicely with Vellum and separating them out meant that my searches didn't commingle notes with chapters.
• Noteplan + Ulysses + light PARA/Johnny.Decimal: Diving into Noteplan's hierarchical structure and thinking more carefully about how to organize information at a structural level led me to loosely overlay a PARA system and a Johnny.Decimal system over the top. PARA stands for "Projects, Areas, Resources, Archives" as a top-level way of organizing information and tasks. Johnny.Decimal is a method for categorizing information into a decimal numbering system — like what you'd find in a library.
• Craft Docs + OmniFocus 4 + Ulysses + heavy PARA/Johnny.Decimal: I really, really, really wanted to love and stick with Noteplan, because on paper it's ideal for me. But the developer of Noteplan enforces an exceptionally opinionated approach to managing tasks; he believes that tasks shouldn't be moved or edited frequently because people should think carefully before planning. Well, OK then. I found that getting just a few days out of sync threw my entire task structure (usually around 500 items) into disarray, and Noteplan's resistance to batch rescheduling tools meant I'd have to spend literally a full day manually rescheduling myself. That was not sustainable. So I dropped the "one ring" thinking and picked a best-of-breed ecosystem logic. I settled on Craft Docs for notes and daily journaling and OmniFocus 4 for tasks. OF4 is more robust than Todoist but not as heavily resourced as a full-fledged project-management tool. I've stuck with Ulysses, but doubled down on my PARA/J.D system — enhancing it to make it work for me, while integrating it even to the level of my filesystem.

What I've Learned About Myself

Biggest take-away is that I need an infrastructure but it took a lot of tool-hopping to finally figure out the "why" of how different approaches to info-management make sense to me.

What works for me:

• Easy capture of quick thoughts/to-dos on Apple Watch, iPhone, or iPad.
• Easy surfacing of tasks and also easy changes to tasks lists in light of a shifting calendar.
• Hierarchy trees > tag clouds.
• Backlinked notes are incredible.
• Calendars and tasks have to be two-way streets. Time blocking, which I started with Noteplan, helps minimize the movement of tasks by clustering like-related activities into protected parts of the day/week.
• Scheduled project reviews.
• PARA and Johnny.Decimal across all notes, tasks, and files. I've aligned them such that the list looks like this:
  • 10 - Professional [related to work/business]
  • 20 - Initiatives [long-term outwardly-focused activities that are open-ended and not organized around a specific goal, like trade associations or church volunteering]
  • 30 - Projects [non-work activities with a clear end in mind]
  • 40 - Areas [long-term inwardly-focused activities that are open-ended and not organized around a specific goal, like hobbies and household management]
  • 50 - Strategy [bucket list, major life goals]
  • 60 - Reference [evergreen information that's useful but not associated with an initiative or project]
  • 70 - Social [related to people and institutions]
  • 80 - Animals [related to TheMenagerie™, by species]
  • 90 - Archive [never delete!]

What doesn't work for me:

• Open-canvas applications like Obsidian that lure me into tweaking the framework instead of doing the work.
• Excess friction in rescheduling tasks on the fly.
• Weak search tools within an app.
• Notification overload.
• Anxiety about lost or corrupted data.
• Single POV task lists — I want to see both its place in the hierarchy list, but also cut across hierarchies using simple tags.
• Markdown-first tools are lovely but they have no way of surfacing items where my intent was X but I fat-fingered it as Y.

Everyone's different. It's taken me a few years to refine my setup, and I don't doubt that I'll continue to tweak it over time. The goal is for the infrastructure to "just work" without excess tweaking or data-sanity checks.

I'm getting there.