The99percent.com has a wonderful little article about making daily decisions without overthinking.

Tips:

1. Satisfice. Set criteria for making a decision in advance (as in, “I’ll make the call once I know X, Y, and Z”). Once you have that information, make the choice and move on.

2. Trust your gut. We are designed to process information so quickly that “rapid cognition” – decisions that spring from hard thinking based on sound experience – can feel more instinctive than scientific. Logic is best for simple decisions; intuition is best for everything else.

3. Know when to trust experience. We should trust our expert intuition (based on experience) when making choices about familiar problems. But when we need a break-through solution, we shouldn’t be too quick to jump to conclusions.

4. Activate your network. If you’re wrestling with a difficult decision, consult a friend or colleague who’s been in your situation before. Their insight will likely be significantly more valuable than almost any research.

5. Choose your battles. Ask yourself if this decision is really that meaningful. If it’s not, stop obsessing over it, and just make a call!

And of course, like most entrepreneur skills, the best way to get better at making decisions is practice.

See also: Do the most important thing first in the morning.

Theodore Roosevelt once said,

"In a moment of decision, the best thing you can do is the right thing to do. The worst thing you can do is nothing."

Source: Decision Quotes.

One of the things that prevents us from making good decisions is we aren't all that good at remembering what made us happiest in the first place. But this is a problem we can do something about says Harvard happiness expert Daniel Gilbert: http://www.bakadesuyo.com/whats-the-main-thing-we-can-learn-from-harvar

I wonder if there is anything practice isn't good for...