“Should I work around X, or should I actively try to defeat X?”

I find that if I don't see the path to victory, I can often hem and haw like that. A solution is "baby steps".

Just start down one path, and see what you find. You don't have to have to see the full path before taking a step. If you went down a bad path, you can backtrack and go down the other.

I'm guessing that I'm not the only one here biased towards thinking over doing. Think, Choose, Do. More action, less contemplation.

This important divide is the question of optimizing around, or powering through.

The dangerous word there is "optimize". Because everything can always be better. So I try to think of a goal, and then do worse. What's the quickest, most half assed job I could do? How much of the problem would that solve? Get some solution as quick as you can, and then improve if you feel the need to. Often you won't.