Books for learning to be human

December 23 2025 – 07:35pm

In a recent Love Mondays newsletter, I wrote about the humanities as the science of being human. One reader in particular pointed out this passage:

what is a life well-lived, what trade-offs should a society make, and how do you navigate consciousness and this existence of fortune, desire, suffering, and elation?

And asked if I had book recommendations. I figured I might share them for all.

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I’ll start off by saying I could explore these questions more deeply and intentionally than I have, which was part of the motivation for writing that newsletter – perhaps to inspire myself to dig deeper.

But, these are the books that have been most impactful at teaching me how to be human (along with their Amazon affiliate links), along with my imperfect off-the-cuff recollections.

A tour of it all

A History of Western Philosophy by Bertrand Russell is an outstanding tour of, well Western philosophers – the people who have thought hard about these questions. It’s also the best “read heavy” book. Slowly reading and understanding this added more rigor to my thinking than any book I’ve ever read. Reading a book is trying on someone’s brain and nobody is a more comfortable, yet challenging, fit than Bertrand Russell.

“Navigating consciousness”

Buddhism, Plain and Simple: It’s been like twenty years so I remember very little. But this highlighted how attachment is a source of suffering, and first introduced me to meditation, which I credit for curing me of what I hadn’t realized was probably clinical anxiety.

How to See Yourself As You Really Are, The Dalai Lama: Again, it’s been a long time. I remember it first presenting me with the idea that there is no self.

Waking Up, Sam Harris: Again, a long time. The idea I most remember is that of Dzogchen meditation, specifically how trippy it is to try to “look at yourself” with your eyes closed.

“What trade-offs should a society make?”

The Prince, Machiavelli: Probably a surprising pick. I really appreciate Machiavelli’s ability to tell the truth about filling a certain role at a certain time, which brings up questions about just how much violence is necessary to have peace? – his desperation and ostracization in the moment he wrote this seem to have motivated him to say what nobody else would say. I have written a summary of The Prince.

Madame Bovary, Gustave Flaubert: An allegory about the conflict between rationality and humanity, and so well-written. The whole thing around Hippolyte’s leg and the doctor who screws it up motivated by his own career aspirations is like such an under-appreciated analogy to modern rationality.

Dialogues of Plato and The Open Society and Its Enemies: Listing these together because Karl Popper’s work is so critical of Plato, who presents a pretty totalitarian view of what a society should look like (I remember very little of Plato, and assume his Republic goes into that in more depth). How much structure should be ascribed to a society, and two what extent should new ideas be allowed to freely restructure society?

Sex at Dawn and Sex at Dusk: Listing these together because, hey, this is all about trade-offs. Dusk absolutely dismantles Dawn, to the point I was surprised it wasn’t a bigger deal – I came away thinking Dawn was deliberately misleading – albeit a far more-entertaining read. Dusk especially had some interesting principles about the biology behind mating behavior. Pretty obvious monogamy isn’t the natural state of things, but does that make it a bad idea?

Industrial Society and Its Future (The Unabomber Manifesto): By now hopefully everyone knows Ted Kaczynski wasn’t just a lunatic. He actually had some coherent and compelling ideas about happiness and the faustian bargains we make when we adopt new technologies. I have written a summary of the Unabomber Manifesto.

Utilitarianism, John Stuart Mill: So long since I read this one, and I sense that through age I would scoff at its idealism at some point. But twenty years ago it seemed like a foolproof way to decide what’s good or bad.

“this existence of fortune, desire, suffering, and elation”

Hamlet: This is just so fucking good on so many levels and I don’t know how everyone isn’t talking about Hamlet all day, every day. It gets so deep into questions about sorrow, grief and, well, to be, or not to be and the slings and arrows of outrageous fortune. I also swear reading it will make you a better writer. Fun to see if you can pick out words and phrases that originated in this masterpiece. I fantasize about leading a challenge of reading Hamlet over and over again for a year, with visiting lecturers. I have it on repeat, and if I wake up in the middle of the night, this is what I read to get back to sleep – in a good way. If you have trouble understanding it (which is part of the fun – READ HEAVY!), read the Wikipedia page, and watch a movie first.

It’s Okay That You’re Not Okay: Everyone will experience grief at some point, and this book helped me when an abnormal blood vessel exploded in my mom’s brain and killed her. Grief does not come in “stages,” it’s an integration of a new reality. I interviewed the author, Megan Devine.

With the Old Breed: At Peleliu and Okinawa, Eugene Sledge: I put this in the “suffer porn” category. If you weirdly enjoy reading detailed accounts of just how miserable any type of experience such as war can be, this is for you. It will make you grateful for your own life.

Body Keeps the Score: This is part suffer porn and part useful self help. People have their criticisms, and I don’t know what they are or care. I’ve read this twice and have found it oddly calming.

Loneliness: This is from 2008, so well before loneliness became the hot topic it is today. It’s by a pioneering researcher in the field, John Cacioppo, who sadly passed away too young. Breaks down how loneliness leads to ill health and early death (irony?), and how it works in a vicious cycle of misinterpreted social cues and maladaptive social signals. One of the most-useful takeaways is that loneliness is not about a quantity of connection but quality. I spend more time alone than I have probably in my whole life, in a cabin in the mountains of a foreign land, and feel far less lonely than when I have lived in some of the biggest cities.

Thinking In Bets: Surprising myself here but I have to put some kind of book about “fortune” on the list. It’s a toss-up between this and Nassim Taleb’s Incerto series, but this is a much lighter and still useful introduction to thinking and living in a world that is inherently uncertain. Also, I interviewed author Annie Duke.

The Hacking of the American Mind: Gosh, I have a weird amount of science in my list about the science of being human. This is about how dopamine, which we associate with “happiness,” better described as elation is not a neurotransmitter you can keep steadily pumping through your brain at a high volume, and that serotonin, which brings contentment – a better description of true happiness – is far more sustainable. I interviewed the author, Dr. Robert Lustig.

There are of course far more great books for learning how to be human, and I especially want to read more of the ancients. The Iliad and any ancient text of any religion can be enjoyable.

You might be wondering, Where are all the books on Stoicism? Surely these days nobody can talk about the humanities without talking about the Stoics. Indeed, I generally agree with what I read from the Stoics, but I can’t recall ever feeling impacted by them – perhaps a matter of timing.