It’s Never Going to Be Perfect, So Just Get It Done

There are several kinds of procrastination, so it's impossible to generalize.

Some projects require very large time commitment to get right, reworking several times, etc. Some others reach a diminishing return stage very quickly and continued effort is wasted. You definitely shouldn't just take whatever you have in front of you and just rush it until it's barely workable.

The critical skill is to be able to judge without anxiety and with some precision how much additional time is going to improve the outcome, and what is the rough global value (to you) of this improvement. Some projects have long ramps of effort and refinement, some are just not worth the time and can arrive at a good enough stage very quickly.

I think the best advice I could come up with is that if you're having this sort of problem, recognize it, try to deal with the anxiety and get a perspective on the risks vs benefits, and improve. If possible find an environment/hobby /side occupation where you have to make a ton of such decisions to get a lot of practice. College/personal projects tend to be pretty sparse and give a lot of room for failure and delaying I guess.

For me it's been a very slow, progressive realization that I'll never get things I wanted done by just leaving them to an arbitrary later date, or obsessing too much over details. In nothing vs something, something wins.

>I can't say which way causality flows

In my personal experience, it flows both ways. It's a positive feedback loop. When I'm productive, I'm happier, even if being productive means meditating or practicing mindfulness (as long as the dread that comes with "wasting time" is not there, all good), and when I'm happier, I can be more productive. The hard part, for me, was getting the loop started, pushing the rock down the mountain, so to say, getting past the first hurdles of procrastination. What helped me was getting professional help and medicine, but I was a pretty bad case.

An analogy I have used to describe this to family before was an internal combustion engine. Normally, once you get an engine started and keep supplying it with fuel, it'll keep generating everything else it needs to keep running. But it still needs a battery and a starter motor to get it running in the first place. Sometimes just getting it running is good enough, and most engines start with one crank, but other times, something is not quite right and it takes a couple of cranks and maybe some starter fluid to get it started. Even once you get it started, maybe the alternator is faulty, so until you get that fixed, you have to keep supplying electricity some other way to keep it running.

^that + usually when you pair program, you try to explain your thought process and reasons behind the decisions you make to another person, and in doing so, you actually end up delivering. And learning the material through explaining it to others is a very effective and very known technique, so that makes sense.

I'm sure you learned a lot about the problem from maintaining the legacy app.

There is some intuition that develops over the years, but honestly the only reliable way I've found of knowing how to properly solve a problem is solving it multiple times.

For artistic creation I always come back to this anecdote from the book "Art and Fear":

"The ceramics teacher announced on opening day that he was dividing the class into two groups. All those on the left side of the studio, he said, would be graded solely on the quantity of work they produced, all those on the right solely on its quality.

His procedure was simple: on the final day of class he would bring in his bathroom scales and weigh the work of the “quantity” group: fifty pound of pots rated an “A”, forty pounds a “B”, and so on. Those being graded on “quality”, however, needed to produce only one pot – albeit a perfect one – to get an “A”.

Well, came grading time and a curious fact emerged: the works of highest quality were all produced by the group being graded for quantity. It seems that while the “quantity” group was busily churning out piles of work – and learning from their mistakes – the “quality” group had sat theorizing about perfection, and in the end had little more to show for their efforts than grandiose theories and a pile of dead clay."