100 Books Like Contingency, Irony, and Solidarity

A timeless meditation on purpose, suffering, and the human spirit. While not about entrepreneurship, this book is essential for anyone seeking to understand the deeper meaning behind their work. Frankl’s insight—that we can find meaning even in suffering—is profoundly relevant for founders navigating hardship and uncertainty. 

What struck me most about it was how Frankl captured the Holocaust not just as a historical event, but as a raw, existential landscape. I’ve seen many films and documentaries about that era, but Frankl’s account stands apart. His lens is philosophical, not just historical. His insight that meaning, not pleasure or power, is the primary driver of human life resonated deeply.

I've focused on the idea myself that many entrepreneurs pursue ventures not for wealth or control, but as a way to fill a deeper existential hole. Frankl’s writing felt honest, profound, and necessary. This is a serious and enduring book I’ll return… show more.

What is the meaning of life? We could take the question further by disposing of our blinkers and asking, what is the meaning of the other lives that may not look like ours? These lives consist of the millions of animals who die in the factory farms built to conceal their suffering and turn them into fungible objects, not lives. Safran’s book is an eye-opening exposition of how we have enslaved animals for food that we don’t even need in the 21st century—damaging ourselves and the environment in the process. One meaning of life: the value of letting other lives have meaning too.

The idea to adapt Conrad’s Heart of Darkness came from my teaching of modern world history every semester. Later in that course, I would have students read Achebe’s novel as a foil or answer to Heart of Darkness. The Congolese in Heart are barely people: they have no names, and they are only really described by parts of their bodies.

This book presents the West African world–the communities, the customs, the emotions, the families–that colonialism destroys. While it is easy to be swept away by the story’s momentum in the last two dozen pages, take some time early in the novel to enjoy the world that Achebe lovingly paints. I think it is among the most human expressions of fiction you can read.  

My book club found this book depressing and shook their heads at my choice. I found it a fascinating account of a life that is meaningful for its owner. The protagonist is a woman dying in an abandoned mental hospital after years of abuse and neglect. And yet, she has a psychological condition that makes her infinitely compassionate towards others: she can only perceive goodwill and love. When she tells the story of her “happy life,” she even feels bad for her rapist. You will love or hate this book. But it will make you think.

The modern age lumbers on like a wounded mammoth, but are its wounds fatal?

This is the question Hans Blumenberg asks in this magisterial, cathedralic book. The project and promise of modernity, Blumenberg points out, consists of the attempted rejection of all arbitrary forms of authority. That is, all powers that cannot justify themselves through human argument and agreement, whether this be derived from the arbitrariness of one’s birthplace or background, unquestioning adherence to tradition, or to nature’s blind and bloody precedent.

Abraded to its minimalist core, it is this kernel of the modern project—the birth of which Blumenberg traces to the late Middle Ages—that we can thank for later advances ranging from civil rights to women’s liberation. But, in the wake of the atrocities that split the previous century in half, the legitimacy of modernity came into question. Technoscience, the handmaiden of modernity, seemed a plausible culprit for gas… show more.

Apart from the existential fiction that I love (Dostoevsky, Kafka, Camus, etc.), this is one of my favorite books of all time. The editor, Walter Truett Anderson, gathered together the best collection ever of essays on the topics of postmodernism, deconstruction (and reconstruction), the wobbly nature of truth in the twentieth century (and now, the twenty-first century), and how we might go about reconstructing the truth now that we have so beautifully and mercilessly deconstructed it.

Authors included are Umberto Eco, Michel Foucault, Jean Baudrillard, Richard Rorty, Bell Hooks, and a ton of other great thinkers on the subject of our postmodern malaise and the difficulties of belief … in anything. If you don’t know this book, you will really, really want to get to know it.

This is one of the books I love most. It is a delightful small book in which Nobel Laureate Frances Crick, who together with James Watson discovered the double-helix structure of DNA, addresses the questions: “What is Life?” and “How did it originate?”

This takes him to the origin and evolution of the Universe and to how life may have originated from the world of atoms and molecules, either here on Earth or, in his view more likely: long before the Solar System and Earth formed, in other places in our Galaxy. His idea is that from its place of origin, long ago near another star, it spread to other planetary systems, in the form of spores of bacteria.

His speculations in this book are scientifically well founded and ingenious. Crick is a wonderfully clear writer and this book, with its brilliant explanations and ideas, is a beauty, which I… show more.

We strive for meaning in our lives. Ford neatly inquires into the different ways we as humanity have developed to achieve this.

He probes into these different "thinking systems," not only asking what is important to them and how they work, but also looking into what they ignore.

This is not only very insightful, I feel it has made me a much more flexible thinker. 

Back when I was an atheist undergraduate college student, this book, among others, saved my life.

I’d walked away from everything religious and hence lacked all moral grounding. Although I was ambitious, I had no clue what I wanted to do with my life. Only what I didn’t want to do with my life.

My animosity against all things religious was huge, but the stoic philosophy of discipline and self-control kept me from throwing my life away.

Oprah is my hero. I can think of no more impressive entrepreneur, from what she started with to what she built and the impact she has had on the world. For many people, understanding one’s purpose and direction is the first step towards becoming a successful entrepreneur and a happy and fulfilled human being. This book will help you begin to do the hard work to get there.