Checklists are no fun
When we bought our 1940s vintage house, none of the interior doors on the main floor completely closed. I figured out a process: mark the edges where the door scraped the frame, remove the door, remove all hardware and slather with paint remover, carefully plane the door's edges, and reinstall the door with all hardware. I made a checklist for this process: bedroom door, hall closet door, study door, and so on.
The study door was the hardest. An old screw snapped in half while I was unscrewing it, lodging itself in the wood near the hinge. Worse, the screw had snapped off at the wood surface, so there was no metal to grab with pliers and twist to remove.
The more I examined this task, the more sub-tasks I found. I had to buy a screw extractor. I had to make a wooden jig to use the screw extractor safely since it would rip up the wood otherwise. I had to buy a dowel and wood glue to fill the hole left by the screw extractor. I had to do all of this in steps, and record this, because the task wouldn't actually be done until the door was perfect.
I had set out to fix an interior door and ended up with a fractal of a checklist and a sense of futility bordering on existentialism. After all, you can subdivide a task into an arbitrary number of sub-tasks.
I've relied on checklists to keep myself motivated and try to feel accomplished (whatever that means) for decades now. But I realized that they don't give me a sense of satisfaction, even if I finish a task and can check it off.
Checklists don't match how our brains function in projects with variable scope, like home maintenance. We run into cascading dependencies, tasks that reveal other tasks.
Instead, I decided to abandon the entire home improvement checklist and focus on a sense of accomplishment. I like the idea of being a generalist, always learning new skills. I now know how to use a screw extractor, and that motivates me more than a checkbox.
I still use checklists for tasks that with a concrete completion state, like scanning and emailing a form or renewing my passport. But otherwise I'm not making a checklist. It's a hard habit to break, but the alternative is feeling like success is a fight you're always losing.