84 books like The Brothers Karamazov

Published in Poland in 1961, this has been interpreted and misinterpreted a hundred different ways, and I won’t try to repeat that here. However, there is a loneliness haunting the book that I feel that it must be inspired by the social constraints behind the Iron Curtain.

The premise is that humanity has finally found a sentient being in the form of an ocean planet, but all attempts to communicate have failed (to say the least). The planet’s actions are incomprehensible and horrifying. Ultimately, humanity has found another lost soul in the universe, but we will never be friends. We won’t even be enemies. We will be two strangers shivering on a train platform, unable to share who we are or what we think, lonelier now that there are two of us waiting in the cold.

I absolutely love Flannery O’Connor’s short stories; they are like shining gems of literary perfection. She sees through all the meaningless masks and artifices that people put up to mislead and distract, and she describes the motivations at the heart of the conflict. 

No two of her characters are the same, and she brings a clarity of thought and vision like few other authors can. Often, the characters within her short stories make jaw-dropping pronouncements about either themselves or issues of faith or morality. For example, in A Good Man is Hard to Find, the sudden turn of events can be shocking, but there is always a great value to every word she painstakingly wrote in her short life.

Nausea does not rely on the extreme or outlandish scenarios of science fiction to explore philosophical themes. Rather, this novel is about a person’s growing malaise over his conscious relationship to objects, people, and ultimately himself. It reaches into some very fundamental aspects of our relationship to the world, and asks you to look at the mere structure of existence after all particularities (names, shapes, colors, history, etc.) are wiped away, and then asks you how you feel about it. Through an existentialist lens, it also explores certain political questions. And for those more technically interested in philosophy, the novel does a better job of showing existentialism’s relationship to phenomenology than many academic papers. 

This book by Franz Kafka may well be the OG book in the pursuit of weirdness in long-form fiction. Telling the harsh and anxious story of Joseph K’s unexplained arrest, Kafka brilliantly creates a universal allegory for the way we often feel like we must defend ourselves against a world that feels impossible to understand.

This novel by Alabama author Harper Lee is one of my favorite novels. Southern racial prejudice is exposed in the coming-of-age story of the young protagonist awakening to its ugliness and hypocrisy.

The mood is Southern Gothic as the childhood fears of Boo Radley turn out to be unfounded. I love how Lee gives us the perspective of the adult narrator while placing us fully in the world of the children. I love the evoking of childhood fears of the supernatural while learning that the world of living people is much more dangerous.

I consider it a novel that is worth reading every few years.

This was the book that impelled me to write my own account of superstition. I could have also recommended his masterpiece, The Selfish Gene, which I read as a teenager and got me into science in the first place but this unforgiving attack on religion spurred me to write a more balanced view that considered religion as a naturally emerging consequence of cognitive development. In fairness, The God Delusion does briefly mention evidence in support of a natural inclination, but this is outweighed by an agenda (that I do not share) to eradicate religion as pernicious indoctrination. Whatever your opinion of Dawkins, he is undeniably one of the most gifted science writers with a clarity of argument combined with a poetic beauty of prose.

I loved this book for its fantastical portrayal of a Pacific voyage that mirrors the internal conflicts many of us face. Like Pi, who embraced multiple faiths during his ordeal, I searched for answers to reconcile my faith and sexuality across various denominations, religions, and philosophies.

Pi’s story as he journeys across the Pacific, a tiger in tow, allowed me to reflect on the moments when I felt alone, wrestling with my faith in the face of an overwhelming challenge, given my fundamentalist upbringing. 

If you want to know what Kafka’s The Trial would have been like without a sense of humor, try reading Aeschylus. Though this ancient Greek tragedian does not aim for laughs (and does not get any!) his depiction of the furies of conscience has an elemental power and purity like a Beethoven motif or a Picasso masterpiece. The Eumenides may well be the first-ever courtroom drama, with Orestes on trial for killing his mother Clytemnestra. Aeschylus goes straight at the most difficult of human emotions—guilt—and like Sophocles, he explores it specifically in a family context. Who, after all, makes us more guilty than our parents? 

It might seem odd, but there is no real better book than this one to illustrate the challenges of private equity. I use it as an example in my training sessions regularly.

The Merchant of Venice is not only one of the best plays on finance and ethics, but also the perfect illustration of the challenges of start-up investing before it became a profession. This play illustrates how venture financing differs in practice from bank financing. It also conveys the uncertainties associated with entrepreneurship, and how some capital providers are not able to take such a risk.

Shakespeare masters the art of contrasting the perspectives of an entrepreneur and a banker in a short and powerful format. It is a masterpiece and a must-read for anyone who wants to understand the philosophy of start-up investing. 

Philosopher Eric Reitan offers a spirited rebuttal to Dawkins by arguing that belief in God isn’t necessarily irrational or harmful. In particular, Reitan defends the progressive faiths that are based on universal love rather than sectarian division and superstition. I especially enjoyed Reitan’s discussion of atheist philosopher Bertrand Russell, who compared religious faith to a belief in the existence of a “celestial teapot” that travels around the sun in an orbit so distant that it could never be observed by telescope. You can’t disprove its existence, but doesn’t it seem ludicrous? Can you explain how it got there?