I find that many high achieving people have the same problem. They get very fixated on knowing everything ahead of time, getting every detail perfect, etc before they ship. They belabor endlessly over every small thing and unfortunately more often than not I find that these people never actually ship anything.
I get why they're this way. Oftentimes these people come from a similar path - tier 1 schools, jobs at name brand companies, etc. They're used to well defined roads with clear rules & parameters. And so the natural inclincation is that when they are thrown into a new game, they first think about the game to try to understand it rather than just start playing.
There’s a story that I love from Art & Fear about a ceramics teacher and a pottery class. The story goes:
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.
I'm not the first to reference this story, but I do think it's an incredibly important one. Per this pottery class, it turns out that actually doing things is often more useful than just thinking about doing.
Once you say it out loud it seems quite obvious. The more you do something, the better at it you’ll be. So if it's so obvious, why do people get stuck theorizing?
The simple answer is it’s hard to do and easier to think. But more specifically, I think it’s because a lot of people don't like to throw away their own work. Implicit in the statement “make 100 pots” is that you have to throw away 99 of them. That can be a tough hurdle for a lot of people to get over. But once you get past the first few, the rest are easy.
So if you want to be great at something, think less and just make 100 pots.