Re: "the problem I've always had with these types of systems is that there's always that one item on your to-do list which ends up more complicated than you expected", I 100% agree. To avoid being subjective like you mentioned, I often prefer to time-box my tasks if I think there's any risk of the scope being unclear. So instead of:

- Migrate photos from iCloud to Google Photos

I'll start with:

- Spend 1 hour trying to migrate photos and write down where I left off

This avoids the issue of being unsatisfied at the end of the day because something didn't get done or something took longer than expected.

If something absolutely has to get done and cannot be time-boxed, I like to veer conservative and either start way earlier than necessary or devote a whole day or more to doing just that one thing (example: taxes - start early, work fire drill - drop everything until it's done).

Thanks for checking it out. I think that's a real problem with all to-do lists. I often have to break down my to-dos into smaller chunks just so I can have the satisfaction of checking them off. I used to write "write to-do list" on my to-do list.

Perhaps it would be worth adding a To Don't list? I mean, it's not the To Do List that makes or breaks us, but doing things we shouldn't be doing (that pours sand in the gas tank of productivity).

That said, and perhaps this is outside your scope, what kills me is social media. I know #duh :) let me finish :) For example, I'll be stuck on something semi-pressing so I'll post it on SM. That leads to checking back for answers. Or having something to share to SM and not wanting to forget about it later so it becomes a now thing.

To some extent that's what this does, it has a to-don't list of sorts; the list of sites you'd like to block. I'd suggest just deleting all social media accounts, you won't miss them. Email is still king.

Yes. But __maybe__ if the To Don't stared you down as well that would be helpful. Maybe even keep score somehow? Evidently, afaik, a score is a good nudge when it comes to influencing human decision making / behavior.

Ultimately, these things fail us (or us them?). I'm what-if'ing a couple of tweaks that might help just a little bit.