Some things that work for me:

- Cultivating a slight bias for making a decision; I remind myself that sometimes any decision is way better than no decision. Especially when a) time is a factor, b) managing people who want leadership.

- Prune the decision tree. When no option seems good, I switch modes and look for decisions that seem bad. Like SATs: rule out the bad answers and then guess.

- Calibrate expectations of information. Like Poker: Care about (and attach judgement mostly to) making the right call given the cards on the table, as opposed to winning any one pot.

When I find myself with a tough decision, I remind myself that it's tough for a reason: either the available options are similarly good, or similarly bad, or both. Therefore, the choice between them is not likely actually all that important. In poker you can bet the odds and be sure that there is a correct decision either way. In life you're probably lucky if that's true; it seems like the black swans are prevalent enough to sink almost any strategy.

There is a very rich man (forgot the name) who is making big decisions like this:

  * make a list of pros and cons
  * give each item an importance score from 0 to 10
  * if the sum of pros is at least twice that of the cons: do it

I believe you can do this for small decisions as well, without creating a list. Because most of the time you have a sense about the pros being twice as valuable as the cons.

Edit: Sorry, this comment is a little unrelated because the parent talked about making a choice. My comment is more about 'should I progress'.

> if the sum of pros is at least twice that of the cons

This is very obvious situation. But what if sum is not twice larger? Or if you are not confident in your importance score? This is where game becomes harder.