A good combination is to (1) think about the worst case scenario and(2) make reversible decisions. It’d be extremely helpful to (3) consider the potential upsides after #1 and #2.

For example I was planning to move into a new apartment two months ago.

1. Worst case scenario: (1) what if I don’t like it while the contract is locked?
2. Reversible decision: Rent an Airbnb unit in the same apartment for a few days to find out if I like it.
3. Potential upsides: More control over my environment that leads to increase in productivity and happiness.

This process works well for me probably because it’s just like what you have mentioned: Instead of overthinking, find ways to make small decisions often.

And yes, I ended up renting and moving into the new apartment.