The way I read this is that there are many "games" in life (applying for schools, jobs, dating, etc) where the odds of "winning" each instance are not in your favor, but you only need to win once to win overall. If you treat every absence of a positive outcome as a failure, then you're inevitably going to lose hope and give up.

This is in contrast to gambling where you actually do need to win more often than not to win overall.