For me the worst part is when I have a combination of short urgent tasks and an open ended one. The open ended task always ends up being pushed aside

My support request queue has been routinely emptied this week exactly because of that haha

This is a helpful way to put it thanks. I do the same thing. I have a job that involves juggling creative research and more menial bug reports, and this is exactly what I do.

Man, I am the same way. How have you coped with this? I work in a pretty open-ended environment without a lot of processes, so you can imagine it has been a struggle for me. I have tried to create tickets for myself but I seem to also struggle with defining the "done" state.

Same boat. It's not a magic cure, but my semi-okay-coping mechanism is to make daily to-do lists.

The key though, is not just "making to-do lists".... it's right-sizing the items on them.

Every task should have a finite end state and (this is crucial) shouldn't be longer than 15-20 minutes or so. If they are longer than that, it almost certainly needs to be broken down into constituent tasks.

So even something like "clean my office" probably needs to be broken down a little more -- when I'm on my game I break it down into "vac office", "dust office", "organize desk drawer", etc.

This pairs nicely with the "Pomodoro method" if you've ever tried it.

Not super related, but a friend of mine recently said "If you're the kind of person who is satisfied by a large task list, you shouldn't make todos. If you're the kind of person who hates them, you should."

It seems obvious after it being mentioned, but I noticed a useful corollary: a list of done tasks actually makes me unhappy. So I avoid todo pages where a done list is visible. Hiding done tasks (i.e. archiving done cards on Trello, deleting a row on your todo list instead of strikethrough), etc. has led me to use it better.

This isn't your problem, clearly, but just wanted to share a useful tip.

My only strategy for that problem is to break things down as much as possible into subtasks. That helps because I'm at least more likely to get something done if there's a list of things I can weigh the terribleness of. As the GP comment said that they'd clean their apartment rather than get work done, I'll do the tasks with more clarity to procrastinate doing the tasks with more ambiguity. Eventually, doing the tasks with clarity help clear up the ambiguity in the others.

Maybe the concept of the "wall of awful" will help you understand it more. I struggle with it too though.

https://www.youtube.com/watch?v=Uo08uS904Rg

So much. Open-ended or poorly defined projects can really spiral into attentive dysphoria for me. Productive procrastination – room cleaning and the like – is particularly appealing in that state, just to feel like I'm making progress on something.

The best manager I ever had set it up like so, he'd go:

Here's a large, open-ended problem I want you to solve this quarter. I'll secretly wait while you fix a thousand other unrelated problems that make our business better despite making no visible progress on the open-ended problem. Then I'll reframe your work to show management that the thousand other things you improved are more valuable than the open-ended problem, and get you promoted.

I miss that guy.

Oh, I know this problem. Happens quite often.

A technique I use is to break down the project into smaller pieces. What's the smallest well-defined task/goal I can work toward. Even if it's just setting up the repo, or writing out a README. It's amazing how often this little step can help kick things off.

Definitely. It is one of the reasons I enjoy working in a 2 week sprint setting (all other reasons aside). It forces me to really break tasks down to actionable items

I struggle when there isn’t enough work to do, and when I do scrounge up work, it ends up being non-meaningful work.