In particular I should spend a large portion of my free time (I'm between jobs and not actively looking) trying to make something that will let me be my own boss. Instead, for example, I decided to make a new web app. I'm guessing I tried to make the web app because I thought I could get to MVP in 1-3 days. It ended up being about 20 days, 8-12 hrs a day. But when I finished I wasn't remotely closer to doing something that will let me keep the freedom I have right now. Instead I piddled away those 20 days of productiveness on something that for the most part has no meaning.
Worse, although I made it to MVP it will arguably take another 1-2 weeks to get to "maybe/probably good enough others will want to use this free web app" and, probably because it doesn't seem like too much work (it will be more than I suspect) and because of the sunk cost feeling, if I stop then it was worthless, I'm feeling somewhat compelled to keep working on it, to continue to procrastinate, instead of spending this free time between jobs, or at least some portion of it, doing something that might let me not need a new job..... sigh
That's not why, that's just reiterating what one does.
Recently I came across a thesis by Dr Pychyl that in fact it's emotional - you're looking for a win, a win based on your intellect (or whatever aspect you're exercising). This fits for me.
https://www.wsj.com/articles/SB10001424052702303933104579306... has some leads to follow.
Pychyl has a YouTube channel and a website on procrastination: http://www.procrastination.ca/
Full disclosure, author is my dad.
How do you overcome that?