I also tried to do this for work, not because I was required to but because I was curious, and I also found it exhausting. Maybe logging only the main things would feel better.
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I’ve been using Obsidian lately. I’m curious to know more about what you did to pull up a prompt. That could be a slick change.
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I’ve done the text prompt a couple different ways.
One was with HammerSpoon. The config is in Lua. I could bind a function to a keyboard shortcut, have it bring up a text field, and append the input to my file based on getting the current date.
I also did something similar with AppleScript (which actually uses some JavaScript now) and used the native features of macOS to setup a keyboard shortcut. If I remember correctly this required some nonsense with Automator (maybe Shortcuts would be the way to go now). All of this was done because I was having some weird behaviors and wanted to get rid of HammerSpoon to reduce possible causes. HammerSpoon didn’t seem to be the problem.
Previously when I was on Windows I’d use AutoHotKey for this kind of thing.