Where next?

One day Alice came to a fork in the road and saw a Cheshire cat in a tree.  "Which road do I take?" she asked.  "Where do you want to go?" was his response.  "I don't know", Alice answered.  "Then", said the cat, "it doesn't matter".

But, of course, it's rarely that simple.  It would be nice to be capable of approaching decisions with this kind of equanimity; on the other hand, I would not like to reach the point where I could happily flip a coin.  Some degree of emotional investment in a decision has got to be a good thing; is this incompatible with a belief that either choice, once made, will turn out for the best?