100 Books Like Dangerous Friend

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.

Hillman’s essay on Betrayal sat inside my belly like an irritating grain of sand that turned into a pearl of inner Wisdom. He said trust cannot be fully realized without betrayal because prior to betrayal we are naive. It is only after betrayal when we know the risks—only then, is genuine trust established. However, this is not about trusting your ‘betrayer’ …it is about learning to trust yourself — your inner source of wisdom and creativity that inspires you to create value out of all of life’s experiences, and rewards you with the courage to create your life anew, independent of circumstance.

Though Hillman focused on father betrayal wounds, the message is universal: “Forgiving is not forgetting…it is the remembrance of the wrong within a wider context."

This book was published years after mine, but I wish it had been around when I was going through my life upheaval. The author writes about relationships and has an intelligent and thoughtful take on marriage. You might not agree with her philosophy, but her book is eye-opening, will challenge your assumptions, and shares information that might help people as they rebuild their lives after widowhood, infidelity, and divorce.

Among the proliferation of contemporary self-help books, Myths, Rites and Symbols elucidated what I consider to be a 'missing link’. As Eliade described ancient and indigenous initiatory rites of passage I discovered there are specific stages of transformative growth after the shock of betrayal. Initiation ceremonies often begin with isolation and separation—an existential crisis designed to train a novice (and the reader) to confront symbolic death and embrace the unpredictable vicissitudes of life’s ordeals as spiritual tests. The process awakens self-discovery and inner wisdom, which inspires a spiritual rebirth, renewed creativity, and a purpose-driven return to life.

Eliade planted a seed in my imagination: reframe separation as a ‘sacred separation’—and use the shock of betrayal (and its many ordeals) as part of a grand, personal ceremony of initiation.

A long time ago, I used to own part of a Jazz club. There was a jazz guitar player named Sunny Greenwich and he turned me onto this book. It is a compelling story of an English man who was a reincarnated Tibetan lama. This book changed my life and it gave me a vision of who we really are, why we are, and how we are. And, how we are all connected to our spiritual selves. When our bodies die they go back to their spiritual selves, and we are just out here to gain experience. This book sent me to some good places and helped open my eyes so I could see the next book on my path.

Moving from the Zen lineages over to another branch of this tradition, Tibetan Buddhism, Chögyam Trungpa Rinpoche was famous for making the esoteric accessible. In this book he covers a wide variety of topics ranging from the four foundations of mindfulness over to advanced Buddhist views around taking vows and maintaining sacred outlook throughout one’s day. Bonus: there’s a section devoted to a number of modern day issues where he offers Buddhist teachings on relationships, art, and money.

If you want a clear explanation of Tibetan spirituality, and gain a deeper understanding of sutra, tantra, and Dzogchen, this is your book! Namkhai Norbu Rinpoche’s direct and clear style of teaching is vibrant in this book. And like its title, this book is the crystal that with one’s awareness or rigpa, can bring light into your practice and everyday life.

I vacillated wildly on which of Pema Chödrön’s books to include here, as many of them cover Buddhism in such a way that the teachings are made modern and relevant to whatever readers are going through. This book, for example, covers the ancient lojong, or mind-training, slogans of the Buddhist master Atisha and shows how this very old text has a lot to say about how we can live a life based in mindfulness and compassion. I don’t think you can go wrong by picking up any of her books (or any books written by any of these authors, frankly), but this one fits best for our purposes for a strong introduction to the fundamental teachings of Buddhism.

I particularly like the way this book embraces pluralism. Although the term "pluralism" is sometimes maligned by friends who lean right politically, a few facts are clear, including that our society is becoming more and more multicultural and pluralistic, and that diverse people will generally live more harmoniously together the more they understand and respect each other. This is a profoundly important truth for kids to learn in this book. The less we and our kids "other" (exclude or see as a threatening other) people outside of our own ingroup, and the more we live by the Golden Rule, applied to all other humans, not just to people in our ingroup(s), the better off we will all be in our increasingly diverse religious landscape. Religious literacy is more important now than ever.

This book is a wonderful collection of the lives of six Tibetan female mystics, brought together by the American Lama Tsultrim Allione, the emanation of the renowned 11th-century Tibetan yogini, Machig Labdrön, and one of the few women Lamas in the world today. The book includes an extensive autobiographical preface and introduction in which Lama Tultrum Allione shares her own story and experience of the difficulties and triumphs of women in Tibetan Buddhism, and of women pursuing a spiritual life in the West with candid honesty. The stories of these remarkable women's pasts and brought together in this book offer a wealth of insight and encouragement for both women and men who aspire to a spiritual life in the face of adversity.