I think of another book that I read – what was it called? – Night Train to Lisbon. I wouldn’t say it’s in that same category, but sometimes there was just a line in a book that changed my life in some way, and it came at a critical juncture. The line was, “Given that there is so much in all of us, what happens to the rest?”

Well, many. I think Steinbeck, for example, was one of my favorites, Somerset Maugham, Hemingway. Quite a few.

That really crystallized for me what some really passionate founders who could write some code could do to change things, and this gave me the confidence to say, “You know what? They can do this. We can definitely do this.” ... So without a doubt, Reddit would not exist if it weren’t for Masters of Doom.

I picked What Is Ancient Philosophy? by Pierre Hadot. That book, and philosophy as a way of life. And this is where Hadot brings out that philosophy is not primarily about the propositional. It’s not primarily about declarative discourse. Philosophy is a way of life in which you’re training skills, states of mind, perspectives, traits of characters, and those are all the components of virtue.

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.

And the most fulfilled, centered, grounded, happy people I know are people who made the choice to be part of an effort to actually make the world a better place. ... I would say, to me, the path of least regrets is to at least make a short-term commitment to say, “Let me work to make a real difference in the world.” The worst that could happen is you decide to move into something else later, but you’ll always take with you what you’ve given and what you’ve gained through that experience.

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.