"Uncertainty" would not exactly be the first word that comes to mind when one thinks of Steven Pinker's current position in the world. But that wasn't always the case. There was actually a stretch in Steve's early career in which he found himself in the throws of uncertainty and anxiety. In this conversation, we dig into a lot of Steve's early career experiences, as well as his process as a writer. One of the things that stood out to me in what Steve said was that from early on he had an overarching sense that he wanted to study human nature. But it wasn't always precisely clear to him what that entailed -- or at least there were a number of paths he could've taken to get there. Obviously, he did quite a bit right throughout the process, but it was nonetheless fascinating to see the bets he made that paid off and how he balanced his options while equivocating about what the right move was. In addition to the nature of humans and their societies, we also talked about important subjects like the content of Steve's closet (including his notable collection of cowboy boots) and his advice for sourcing potential mates through literary and philosophical correspondence.

Steve's official title is Johnstone Family Professor in the Department of Psychology at Harvard University. You will recognize him from his books -- including The Language Instinct, How the Mind Works, The Sense of Style, and Enlightenment Now -- as well as whatever mean thing Nassim Taleb has most recently tweeted about him. Be sure to keep an eye out for his forthcoming book on the tools of rationality.

Here are the topics we covered in the conversation:

- The contents of Steve's closet, including his notable collection of cowboy boots

- Steve's literary romance with his wife Rebecca Newberger Goldstein - Some further advice on how to source potential mates from philosophical disputes - His early education in Quebec, getting a two year diploma at Dawson college

- The moment when Steve realized he wanted to study psychology, and how the political situation of French Canada sparked his interest in human nature and society

- Meeting his advisor in grad school, Stephen Kosslyn, a foundational figure in cognitive science

- Why going to Harvard was a poor choice for Steven and the moment when he thought he'd made a huge mistake

- His biggest sources of anxiety during graduate school: including early job prospects and his "crisis of confidence" about whether his work was rigorous enough - Putting the pieces together on mathematical models of learning and children's development of language capabilities to come up with his first influential thrust of research

- Coming up for the idea for Steve's first book, The Language Instinct, during a moment when he wasn't sure what to do next

Then we went deep into Steve's writing process:

- How Steve thinks about structuring a book when he's starting out and how strictly he adheres to his outline

- How Steve tests out the clarity of ideas and gets a sense of what people will find interesting

- The points in his books he was most surprised to get push-back for - How Steve manages his huge amounts of research and literature reviews

- Some of Steve's writing rhythms and habits

- The overlap between teaching and writing

And finally:

- The nature of being a controversial figure

- The two pieces of advice Steve most often gives to his students