As a NASA astronaut, Mike Massimino spacewalked four times to repair the Hubble Space Telescope. When he retired in 2014 and began giving talks about his experiences, he assumed audiences would want to hear about the thrills of those exploits. Instead, he found himself fielding questions that were broader and deeper: How did he weather disappointments? What did he do to build trust with colleagues? Why didn’t he give up when NASA rejected him three times before accepting him?