How do you get things done when working on something unfamiliar?

Hi! Very often I seem to struggle to get anything done when I’m working on an unfamiliar subject, specially when I struggle with the documentation. This is not a rant about bad documentation, but an attempt to learn about some stories and strategies from people that can always seem to get things done even in a situation where the documentation isn’t for total beginners and they don’t also have the correct background.

A good example is Prometheus. I struggle with their documentation, but I feel I’m missing some background knowledge as well, but I don’t even know where to get it.

Another one is AWS. I’ve tried to use AWS ECS with an EC2 launcher but I failed to do it by myself. I later found a GitHub example, but I really don’t know what I’m doing.

How do you get your work done in these situations (let’s assume the final answer is not just a couple of Google searches away)? Do you just go down the rabbit whole of whatever seems to be the required background knowledge? Is it trial-an-error? If so, how do you it’s done right and you’re not overlooking anything major when you don’t understand all the variables involved in the problem?

I hope this question isn’t too vague and you’re able to understand the kind of advice I’m chasing.