Project management: Lessons in software and tooling

Spent much of July 2025 deploying and testing

• Leantime
• Focalboard
• Plane
• Briefly, google sheets
• Asana

For keeping track of my tasks across the seven or eight different things I have been actively working on. Turns out

• Asana's the best so far
• Keyboard shortcuts really, really matter. If I can't write into the thing it is useless to me.
• Having templates and structure in place to test out various workflows is really, really helpful – Leantime's "vision canvas" template was a game changer for me in terms of understanding why these things even existed outside of being highly structured task tracking – what all the metadata is even good for.
  • It lets you get on the strategic level.
• That said, I've had enough metadata fetish in my life to know that the lust for it quickly outstrips its utility. I am populating the fields I've been given as fast as I can without overly worrying about if I'm tracking everything just right off the bat.
• Claude integration is great for skipping through the bits of it that are deadening, boring, or overwhelming. Having a mostly-wrong-but-right-vibes draft to edit down is just as good of a way to learn task management as it is a way of learning anything.
• Metadata is organic. Claude likes to annotate tasks with emoji, category-prefixes, and heavy descriptions; the lesson I take away from it is that sometimes the structure helps you think, and sometimes it gets in the way of thinking. Where there is friction it's better to do the locally sensible thing.
• It turns out that local changes is a really good principle in general. If you assume you know what needs to surface in advance of the surfacing, you trip yourself up. If you try to fit all your insights into the categories even when you experience the friction, you get in the way of your own thinking. If you try to eliminate all friction in advance, though, you get in the way of being able to think at all. This is because the leading edge of your work is where all the exceptions will of necessity happen (it's where you start learning your unknown unknowns.)
• Firms surface these exceptions to managers. The whole reason all the beautiful project management structures that exist prioritize the prominent display of whatever is going wrong is that that's where the hyperspecific novel work always is. The way a firm metabolizes uncertainty is via its network of cooperating agents; ideally, if the game theoretic architecture of the coalition of people is resilient to the challenge introduced by a problem, the uncertainty propagates through it, often via bookkeeping tools like these, to an agent who makes a decision that is then fractally semi-destructively implemented by the whole coordinating organism.
• Personally, you can surface these exceptions for yourself, but when I do it it sucks emotionally. [[https://www.lesswrong.com/posts/vzfz4AS6wbooaTeQk/staring-into-the-abyss-as-a-core-life-skill

][Staring into the abyss as a core life skill]] has been very helpful for me in that regard.