Spend your time on something meaningful. Not on parties, and not on taking it easy. That’s not good enough. […] When you’re young, you think: Let’s party, do drugs, drink, waste it all, right? But as you get older, you look at what you’ve accomplished. And when you get old, you’ve run out of time. You have to ask yourself: Why am I here? Can I contribute anything to humanity, to society, my work?

It’s very hard to give people advice, because you don’t know their personality. Personality is a big part of that. Everybody is faced with passing opportunities. Many people watch the opportunity come and watch it go. I say, if an opportunity comes and you have got the self-confidence, grab it. Ride it for a bit. If it’s not the right opportunity, do something else, but be positive about opportunities.

I think fear and fear of the unknown and perceived failure is what holds people back. For me, I am more scared of complacency than having something not work out. I'd rather take a leap of faith and fall than stand on the edge forever.

Courage is more exhilarating than fear and in the long run it is easier. We do not have to become heroes overnight. Just a step at time, meeting each thing that comes up, seeing it is not as dreadful as it appeared, discovering we have the strength to stare it down.

I applied to one firm in every sector. This was the most half-hearted job search. “I’ll apply for that management consulting firm and this investment bank…” and I applied for five jobs altogether, because my heart wasn’t in it. And thankfully… I’m so glad I didn’t get any of those big jobs! Because that made this decision easier.

There were definitely teachers who made a huge impact. I think about a woman whose name was Mrs. Fish who was my seventh grade English Language Arts teacher. What I remember about her was just how hard she pushed. I thought I was a perfectly strong student at this point, but she just pushed everyone to their limits. That was very instrumental for me. In fact, all the teachers I remember had that same thing: they just had such high expectations and wouldn’t stop pushing. I think she just conveyed the idea that good wasn’t good enough, and I think the skill development and critical thinking skills that that year developed were also instrumental. But I also think, I don’t know, there’s something about that year that probably instilled within me that ethic that you just have to keep pushing to get better and better, and that if you work hard enough it will pay off.

The Fountainhead , I think, pretty much saved me in the initial years of Teach For America. I loved that book, but I’m not sure books were the seminal thing that guided my path. ... I think it was sort of about “the creator against the world,” and I was probably feeling at that point that I was up against lots of boulders, to pull off the big idea of Teach For America.