Earlier today I heard myself say these words to the LaGuardia airport lost and found, "I left my shoes in the shuttle terminal on Wednesday - did anyone turn them in?"
Had to run between 2 terminals (not connected, so had to go outdoors) and of course missed the flight anyway. And the really bad part about running is when you do miss the flight everyone else at the airport gives you that "I'm so sorry, you're the woman who was running, aren't you" look when you have to pass them a second time to reticket.
But before I bothered to reticket I changed into shorts and sandals, resulting in the shoes that never got repacked. The missed 5 minutes turned into 6 hours of other travel. And then the shoes discovery.
I think it's always worth it to try, even if there's little chance you can make it. Whether it's a flight, a deadline, an opportunity. Because, what if ....