I struggled with this problem for a long time. I sort of solved it.

The key was to realize that there is a difference between a calendar, a todo list, and an agenda.

A todo list is a list of things that need to be done but usually don’t have a specific time when they need to be done at. They can have priorities or deadlines or fuzzy target dates like “next week.”

A calendar is for storing future concretely scheduled events.

An agenda is a list of things that will happen soon.

Each day I pull things from my calendar, todo list, and prior agenda and create my daily agenda. I also keep notes, doodles, clippings, and references in my agenda.

I use Google calendar as my calendar. It meets my expectations.

For my todo list I use Notion. I break it down into “next, soon, and later”. I add ad-hoc sections like “after the vacation” when needed. Some todo items are scheduled for a specific day or “not sooner than.” I add these to my calendar with an email reminder so they don’t take up any mind space until needed.

Finally, the daily agenda. I use Notion but could probably use a physical notepad. I like being able to archive them as sometimes I need to check when I did something or pull some details from notes. With a digital agenda I can file it into an archive easily.

This is not perfect but it helped me reconcile the rigidity of calendar tools with the need to do keep things freeform in the short term.

I'll add to this to say that I think there are different kinds of todo lists as well. I wrote about [1] a struggle I had with digitizing a whiteboard household chore tracker.

Lately I've been wondering if LLMs can help personalize software. There are so many difference needs users have, yet software is written with a pool of users in mind. I'm very skeptical of LLMs for traditional software projects, but small one-off personal utilities or tweaking existing tools seems more viable.

[1] https://alexsci.com/blog/personal-apps/

I've got a slightly different philosophy.

A calendar is for storing commitments, and a specific date/time is part of that commitment.

I consider a 'to do list' a 'to schedule list', they are potential commitments.

From my perspective, a thing is either a commitment (on the calendar) or not (essentially in a backlog).

I solved it with different colored calendars in g-cal. Monthly => Rough => Detail => Actual.

Monthly is usually dragging a bunch of "all-day" events across multiple weeks. "school ends", "date night?" (across Fri->Sun), "vacation", "vacation pack", etc.

Rough is kindof planning out the upcoming week or two. I'll drag stuff across Saturday afternoon like "go to park?", and "buy paper towels from Sam's?" in the morning.

Detail is "15-min accuracy" of committed things. Doctor's appointments, birthday party invites, haircuts, or anything that is really "controlling" where I need to be or what I need to be doing at that point in time.

The "actual" calendar is for when I want to reconcile what actually happened vs what I'd planned to happen.

If I'm super "on it" with my detail calendar, maybe I didn't do "clean office" because in actuality I was doing "make dinner", "clean kitchen", and "watch movie with kids".

And integrating with work, sometimes I'll block a section (hour) in "actual" called "Work P1". That's supposed to be "the next item in the todo list", but it is sometimes really helpful to cross-check with "actual" and realize I was really "troubleshooting bug", or "helping coworker on xyz" or "continuing design discussion".

The "narrowing" and "accuracy" is helpful to learn how to do, and the big chunky things like "put fertilizer" and "in-laws visiting" help to make sure I don't schedule too much "detail" in times that already have a lot of external complexity.