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A stone cairn

The best productivity system that's ever existed

Over the years I’ve tried all sorts of to-do apps, productivity systems, and task management tools. But I keep coming back to one approach that’s unbeatable in its simplicity: a single, prioritized, list of checkboxes.

To make this work, there are a few requirements:

  1. You have to be able to nest to-do items arbitrarily,
  2. Notes (without checkboxes) can intermingle with the tasks, and
  3. It must be easy to re-order items using keyboard shortcuts or by dragging.

So, for example, on a given day my list might look like this:

  • Set up recurring Platform team meeting
    • Later in the week, in the AM, is best
  • Prepare for incident postmortem
  • Implement notifications feature
    • MVP
      • Requirements: [link to ticket or doc]
      • PR: [link to GitHub PR]
    • Make it look good

This is usually followed by a long list of additional tasks I’m tracking — less urgent, but things I still want to get to eventually. I constantly reorder tasks throughout the week as priorities shift.

This method works well because it’s easy to get an overview and the order tells me what to work on next. It also feels very easy to add even the tiniest things as bullet points. In every other system I’ve tried, it feels like too much work to add sub-bullets or notes to a task — and they tend to get lost in the UI.

If you want to get fancy, you can add a “Someday” heading further down to track more vague ideas that you might eventually pull into the main list.

The specific tool you use doesn’t matter, as long as it meets the requirements above. I use Obsidian with the Outliner plugin, but you can probably use Notion or whatever as well.