Plan, but don't plan the outcome.I think it's important to remember that our culture tends to imprint a default sort of black and white thinking on us even when this attitude is not really part of our personal outlook or philosophy. Many people over the years who have come to talk to me have objected to the idea of letting go of an outcome believing that such an approach will turn them passive and that they then won't bother to make responsible plans. We need to remember that reality is not that kind of an either-or proposition. Larry's little reflection here is very helpful in that regard, I think.
It is all right to make plans, but it is not okay to insist on a particular outcome. Sometimes I may do things expecting particular results, but in focusing on the goal instead of the things I should do to reach that goal I may create a set up for disappointment. I can take action, but I cannot rigidly determine the results. When my mind is not set upon the end state, I can be sanguine about failures by saying I did my best (returning the focus to my behavior). With emphasis on what I'm doing instead of emphasis on where I'm going, I will be able to handle the times when things didn't work out.
"Abandon all hope of fruition" is a slogan in the Tibetan system of training the mind and heart. My own primary meditation teacher used to emphasize that slogan with me repeatedly! (Ha! I needed it.) And the teaching rescues me these day repeatedly, too. I'm very grateful for it.