My Path to Personal Knowledge Management (PKM)

My summary of a lifetime of effort…

My Why

I’ve learned two corollaries about my memory:

  • I can’t remember anything without a point of reference
  • I can remember anything when I
    • Can draw it (ie decided on a mental model for it)
    • Connect it to other dots (ie find the pattern)

Core Concepts

Ontologies for Structure

Developing specific categorical frameworks (ontologies) for the purpose of creating organizational patterns (structures).

  • Get Stuff Done (2015-2019) – used GSD for years. For me, it’s productivity to a fault
    • Always felt focused on the next task, which didn’t grow with my mindset
  • Interstitial Journaling (2019-) – great idea I still use for temporal trains of thought
  • Zettlekasten – read about it, never tried it; doesn’t entice me
  • Life OS (2021-2023) – I got into the cult of Life Design with August Bradley for a bit
    • Looks thoughtful, but doesn’t hold up
    • Lots of clicks and clean up tasks that give a false sense of productivity
    • Anyone who’s normalized a dataset will find the design offensive
  • PARA (2023-2024) – good structure for project-focused knowledge
    • Great default of “dump to Archive” to keep it relevant
    • Areas vs Resources takes too much effort to differentiate
    • Ultimately about sorting things, which I’m working to stop
  • Evolving – more at the end (2025) – I’m toying with a new idea
    • Emphasis on pattern emergence over linear projects
    • Integrates commitments but more about experimentation
    • Limited structure as an enabling constraint

Models for Task Management

Not about choosing a system to be effective, it’s about finding one with categories that match how I naturally think.

Core Tools

  • Omnifocus (2005-2007)
  • Evernote (2007-2018) ☠️🪦 <- this hurt
  • Trello (2012-2021)
  • Asana (2013-2017)
  • Todoist (2017-2023)
  • Notion (2019-2023)
  • Reminders (2023-)
  • Obsidian (2023-) – depends on a small but essential list of plugins, and then a ton more to play

Types of Notes

  • Knowledge Management — centralizing then connecting related information on engaging with a topic
    • Recent change (Jan 2025): I’m shifting from a “gather and organize” to “recognize patterns and experiment”
  • Task Management — track what I commit to and complete the most impactful work
    • Project management as a subcomponent to this larger theme
  • Daily Flow – time is my default mental model (and the Obsidian plugins that make it possible)
    • Daily notes as a core intersticle journal (Period Notes)
    • Process for low friction capture (QuickAdd)
    • Custom views for feedback loops (Dataview)
      • Clarity of focus
      • Visibility progress
      • Interesting patterns
  • Creative Flow — I’m a maker, not only a consumer
    • Draw and write freely but backed by a system to find opportunities for reuse
    • Identify opportunities to share publicly without complexity and with assurances of privacy when I need them
    • Space to tinker with code contributions in minor ways to open source (thank you Obsidian community)
  • Portability
    • Systematize preferences for reuse across environments (dotfile management)

NON GOALS

What once interests me but is no longer what I need:

  • Productivity optimization — I now work with my energy rather than rely on willpower
  • Digital hoarding – clipping everything I can to feel like I learned it

Evolution In Progress

  • Habit: every time I get a bit of free time, I consider replatforming for some reason
    • the platform is not (never?) the problem
    • the pattern is the problem

Why? The intersection of task management and knowledge management is a mess.

  • Old pattern:
    • Offload every wishlist idea in the world into my system
    • Complete a small percentage
    • Carry over a debt of todos
    • Get overwhelmed
    • Extend that logic to my knowledge management
      • Carry over a debt of knowledge topics
      • Read a higher percentage of it
      • Never apply it
      • Forget it
      • Get sad that I forgot
  • New pattern:
    • Differentiate the small number of commitments from the infinite amount of exploration
      • Keep a tiny list of larger ideas I’m committed to completing
      • Anything smaller can go elsewhere to not overwhelm this system
        • Small things = iOS Reminders | Big things = Obsidian
    • Knowledge management via concept exploration is most of Obsidian now
      • Forgot why I was doing something? Define the Ideal state before I veer off
      • Overwhelmed by interesting ideas? Focus on the Emergent Pattern rather than raw inputs,
      • Want to really learn? Find a path to apply through Experimenting
      • Don’t get into it as much as I planned? No shame, but don’t carry the debt – clear them: fn Cancel Incomplete TODOs (fn are my custom functions via Templater in Obsidian)

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