100 Books Like The Center Cannot Hold

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.

Every "computer person" should read GEB at least once. Preferably in high school, when you still have the free time to dive deep into all the recreational math exercises. If you're already working 40-hour weeks and wonder who has time for Hofstadter's 750-page "metaphorical fugue on minds and machines," all I can say is: Better late than never!

I loved this book, which I read shortly after recovering from my first major manic episode. I remember sitting on the patio of the LSU student union and thinking, “Yes, this!” again and again.

Written by a medical doctor (a psychiatrist), this memoir offers a unique view of bipolar disorder as Jamison herself has bipolar. I needed to know more about my diagnosis, and I needed to hear it from someone who had experienced it herself. 

Michelle made me laugh, made me cry, and made me feel the full weight of reconnecting with a mother only to lose her.

I related deeply to her sense of self unraveling after losing the person who anchored her world—I lost my own mother in my late twenties. Through her vivid memories of time spent with her mother and grandmother, and her journey of reclaiming herself through the foods of her childhood, Michelle pulled me in and carried me forward. 

Raised in a survivalist family that rejected formal education and medical care, Westover never entered a classroom until age 17.

Her journey from rural Idaho to earning a PhD from Cambridge is a remarkable story of transformation through self-education, resilience, and the pursuit of truth, even when it means questioning your origins.

Like Westover’s father, my father held very strong beliefs separating us from others. But we both instinctively know there was more to life.

This slender, 70-page memoir of a time in which both one woman and the world went mad is a beautifully-rendered portrait of psychosis. Written decades after the episode, Down Below describes the British-Mexican surrealist painter Leonora Carrington’s psychotic break in 1940, the circumstances of which were themselves aptly surreal. As a 19-year-old art student in London, she had fallen in love with the celebrated (and married) artist Max Ernst, and run scandalously away with him to a farmhouse in Provence. After Germany invaded France, the Jewish Ernst was arrested, leaving Carrington so intensely abandoned and shocked by unfolding history that she vomited repeatedly.

She began to unravel as she wandered her way out of France, eventually entering Madrid, which she perceived “as the world’s stomach, and that I had been chosen for the task of restoring this digestive organ to health. I believed that all anguish had accumulated in me… show more.

A remarkable, inter-generational tale about madness amongst accomplished medical men. When the Toronto journalist James FitzGerald reached his father’s age at the time of his death by suicide, he felt the haunting pull of family history. His father and grandfather had both killed themselves, sleeping in the same bedroom in the same house.

Dr. John G. Fitzgerald founded the lab that first produced insulin for diabetics, and was also instrumental in the development of a diphtheria vaccine. His son was also a highly respected doctor. Both were pulled under by the riptide of depression at a time when successful, bread-winning men did not talk of mental anguish.

Resolved not to follow in their footsteps, James FitzGerald instead went into therapy and wrote this intensely gripping book about the shadow side of masculine privilege and the history of medicine and psychiatry in the first half of the 20th century.

Sex is an essential part of who we are. What determines our sexual preferences? Do they stem primarily from nature or nurture? Deirdre McCloskey, an eminent economist, is especially qualified to answer these questions. She began her life as Donald, who was married and in his 50s when he realized that he was really a she and became a woman. Crossing, a memoir of McCloskey’s agonizing, exhilarating transformation, is a fascinating deep dive into sexual identity.

Literature, because it is less rule-bound than science and philosophy, may be more suited to exploring the question of who we really are, can be, and should be. Rebecca Goldstein, who earned degrees in physics and philosophy before turning to fiction, has written several novels that touch on the mind-body problem. My favorite is her first novel, The Mind-Body Problem, the funny, sexy, poignant tale of a young philosopher’s quest to solve the mind-body problem.

This masterful book goes one step further and presents a game-based analogy that goes a long way toward explaining how a quantum computer actually works. Working through the book, one gains an understanding of how qubits can be quantum entangled and how entanglement leads to computing tasks that could not be performed on an ordinary computer. Deceptively simple in appearance, the method leads you deep into the inner workings of quantum logic operations without realizing you are digesting some pretty advanced concepts. The author knows of what he writes, as his theoretical discoveries led to one of the world’s most ambitious quantum computing efforts.