The Blue Flower by Penelope Fitzgerald, about the highly relatable journey of becoming the 18th-century German poet Novalis. Every Penelope Fitzgerald book has a sublime quality that comes out of nowhere, and for me this one is the best, with the added poignancy of the best historical fiction: our knowledge that everyone and their problems are dead. 

The Idiot by Elif Batuman, a book that combines being on the vanguard of something (the internet) with the weight of tradition (going to Harvard; this is also the conflict of Legally Blonde). I like this book because it takes its drama from the process of learning, and how painful it is to go through the world before you know what you’re doing – but also how valuable.

The Last Samurai by Helen DeWitt, this is the Great American Home School Novel. It’s a book about how hard it is to be a genius, by a genius. It’s dazzling and funny and it has interesting and provocative things to say about education.

The Confusions of the Young Törless by Robert Musil, my favourite of the classics because of how strange and anguished it is, a painful read that reverses the kinds of moral transformation we expect from this kind of story.