Andy Matuschak, now at Khan Academy and previously working on UIKit:
I had a safe job. People enthused all the time about how lucky I was, what great work I was doing. No doubt: I held a wonderful position! So I felt like an asshole for suggesting anything else.
I’d bring up my real aspirations only occasionally, and whenever I did, I’d feel dissatisfaction grow within me. But then the conversation would end, and I’d anesthetize that dissatisfaction into “someday” with the grind of urgent tasks. Those tasks were much easier to think about than my thwarted ambitions, so my discontent conveniently settled beneath the hum of the day-to-day.