Most book lists are about people’s “favorites”. Having read well over 500 books in my adult life, I couldn’t possibly list favorites unless given a genre. But I tried to pick out ten books that had a massive influence on how I think about both myself and the world.

1. Julian Jaynes, The Origin of Consciousness in the Breakdown of the Bicameral Mind

This is the book that changed everything. I read it one fateful week on summer vacation. I remember feeling a sense of excitement like no book had ever given me, like I was reading a religious text. Jaynes puts forth a daring theory of consciousness, the origin of the religion, and the evolution of the human species. Many people consider Origin of Consciousness to either be the work of a genius or a crackpot. I am firmly convinced of the former.

The writing is beautiful, poetic even. The book is backed up by a surprisingly array of evidence from every conceivable field of human study. Jaynes himself was a bachelor for life, a Princeton psychologist who turned down the prestige of the professorate class so that he could pursue his research independently.

The only single-author, peer-reviewed publication I ever got in grad school was a paper in Phenomenology and the Cognitive Sciences that defended Julian Jaynes’ theory of consciousness. I have probably read the book at least ten times by now. I have spoken at a conference for the Julian Jaynes Society. I remain convinced Jaynes’ impact has yet to be truly absorbed by the intellectual class.

2. Richard Rorty, Philosophy and the Mirror of Nature

I read Philosophy and the Mirror of Nature during my undergrad and it influenced my thinking in a fundamental way. It introduced me to the school of philosophy known as American Pragmatism as well as the broader field of continental philosophy and the phenomenological tradition. Rorty brilliantly critiques Decartes’ vision of how the mind works, what Rorty calls the “Glassy Essence”. In its place, Rorty offers a view inspired by William James, John Dewey, and Martin Heidegger. These figures eventually became prominent in my own thinking. Rorty had a beautiful albeit cryptic prose style and this book led to my eventually doing my Master’s thesis on Heidegger’s book Being and Time.

3. Nassim Taleb, The Black Swan

This book woke me up from a great slumber. Taleb showed me how statistics actually works in the real world. The central thesis is that huge, unpredicted (and unpredictable) events can uproot everything, events he calls “Black Swans”. A great example is 9/11. Or the 2008 financial crisis. But we know that Black Swans will happen eventually even if we cannot know for sure when the next one is coming. So the best practical advice for living is to build up our defenses so that we become Black Swan-proof.

Taleb is brash, angry, and absolutely narcissistic. But he’s also clearly a genius, well-read, and this book was a breath of fresh air. It changed how I think about markets, economics, Wall Street, investing, nutrition, academia, intellectualism, how I live my life, and so much more.

4. Julia Serano, Whipping Girl

Whipping Girl is a classic in the burgeoning field of what’s known as “Trans Feminism”. In it, she dissects the roots of transphobia and what she calls “cis-sexism”, exposing the double-standards that trans women face everyday. She particularly focuses on the traps surrounding the nature of femininity and how trans women get shit for either being too feminine or too masculine, never able to satisfy our critics. The book is now a classic and near and dear to the hearts of trans folks everywhere. The book was highly influential on my own trans philosophical thinking. My forthcoming book aims to be Whipping Girl 2.0.

5. David Foster Wallace, Consider the Lobster

Consider the Lobster is one of DFW’s collections of nonfiction essays. He is probably my favorite American writer. A true genius, both in terms of his writing and his sheer knowledge of the world. I also read Infinite Jest, his magnum opus work of fiction and enjoyed it immensely. But his nonfiction has always stuck in my mind more and has influenced my own writing style. DFW is wry, clever, with biting insight into modern culture and an astute observer of human nature. This book introduced me to the world of “literary” writing and made me aware of the cliquey circles that famous writers run in. Sadly, DFW killed himself in his forties, succumbing to his lifelong struggle with depression.

6. Martin Heidegger, Being and Time

I don’t even know what to say about this book. It’s famous for being nearly impossible to understand. But somehow I spent two years studying it to write my Master’s thesis at Louisiana State University. Eventually it started to make sense to me. But my interpretation differed from most respected Heidegger scholars.

Heidegger was writing in the tradition of Husserlian phenomenology and has been incredibly influential in the world of continental philosophy, a field I admittedly no longer keep up with. But Heidegger was a towering giant in his day. Cryptic and mystical, Heidegger was obsessed with language and the history of philosophy. Being and Time is frustrating as hell to read but it does contain some deep insights into the nature of human experience.

7. Andy Clark, Being There

Andy Clark is both a philosopher and a cognitive scientist, someone who blends both so superbly the book is simply teeming with interesting ideas about how minds work, artificial intelligence, robots, and so much more. The book takes the work of Heidegger and pragmatism and translates it into the framework of modern cognitive science. Being There is simply fun to read. The book was highly influential to my own understanding of how cognition works.

8. Erich Fromm, The Art of Loving

Fromm was a famous psychoanalyst in the mid 20th century famous for his book Escape from Freedom. The Art of Loving is a tiny little book about human relationships but was highly influential to how I thought about all the serious relationships I’ve been in. Fromm’s thesis is simple: there are two types of love: puppy love and commitment love. Puppy love is a feeling, it happens to us. And it is fickle, usually fading over time. Commitment love is something we must work on consciously. It is an art-form and we have an obligation to become Masters of it. It taught me that love is not just a passive state of emotionality but something we can consciously work on to become better partners.

9. Alan Watts, The Way of Zen

Alan Watts is probably my favorite philosopher of all time. But most “professional philosophers” probably wouldn’t even consider him a “real” philosopher. He laughed too much. Didn’t take himself seriously. He was more interested in living life well than constructing clever arguments. He considered his lecture style to be entertainment.

But crucially, Watts was involved in importing the ideas of Zen Buddhism to America in the mid 20th century. Consequently, Watts was my introduction to Zen and the art of meditation, which has proved critical to my mental health and self-care over the years, especially after I’ve been hospitalized in psych wards. More than any modern philosopher, Watts truly lives up to the roots of philosophy: loving wisdom.

10.Stephen Hawking, A Brief History of Time

This is the book that cemented my atheism as a teenager. One of the last holdouts in my mind was the Cosmological Argument, or “Prime Mover” argument i.e. the universe must have had a cause that got it all started. Whatever that cause was, the Prime Mover, that must be God. The Universe needs a Creator. But Hawking developed a mathematical model of the universe that neither had a beginning or an end: it loops upon itself. And it was perfectly logically possible, which in the realm of theology was enough in my mind to finally give up my mental dependence on the Cosmological Argument to secure my (dis)belief in God. I became an atheist, which changed everything. To this end Hawking will always have a special place in my heart.