100 Books Like Reboot

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.

This classic is my go-to for the challenges of living the creative life and how to push through them.

In short, punchy chapters, it identifies the main source of blocks writers and artists have and how to push through them.

I love its approach to the workmanlike attitude one needs to have to create consistently and move toward a goal, and how to be clear-eyed about the inner “resistence” we all have that seems to want to stop us.

David Brooks explores how we often climb one “mountain” of achievement—only to discover that true fulfillment lies on a second mountain, defined by purpose, service, and deeper values. This reflects the journey I've taken myself, and that I see so many entrepreneurs and startup founders take, where success becomes less about climbing higher and more about climbing in the right direction, guided by internal transformation and spiritual growth.

We all have that mountain inside of us that we need to climb, and it can be hard to admit that it's the mountain within that matters. I read this during a time of reflection, standing in the “valley” between two phases of life, uncertain of what came next. Brooks gave language to a transition I was already living—moving from outer success to inner fulfillment. His metaphor helped me see that real purpose isn’t about chasing accolades; it’s about showing up with… show more.

Patagonia’s founder doesn’t just talk about building a company—he talks about building one with conscience. I admire how he defines success as humble and fiercely independent. This book is a manifesto for aligning profit with purpose and mission with mindfulness. It challenges entrepreneurs to think not just about revenue, but about the legacy they want to leave behind.

I loved this book because it gave me a behind-the-scenes look at a company I admired from afar but didn’t really know. I’d heard about Patagonia’s commitment to sustainability, but reading about how they actually implement their values—through design, materials, and a “repair, not replace” philosophy—was eye-opening. I also connected deeply with Chouinard’s memoir-style reflections. I appreciated his raw honesty, his resistance to conventional business wisdom, and how he stayed true to his principles. Those are all approaches that deeply resonate with me.

One of the first places I heard about Buddhism was through Allen Ginsberg, Jack Kerouac, and Gary Snyder. The joy of reading Kerouac has worn off a bit, but Snyder and Ginsberg have become lifetime companions and real sources of inspiration for me, not least in their engagement with Buddhism. This collection of poems, essays, letters, and other writings brings them together with a much wider range of writers – Diane di Prima and Philip Whalen, Anne Waldman and Kenneth Rexroth, William Burroughs and Lawrence Ferlinghetti – showing how the best minds of two generations heard, felt and responded to Buddhism in their many different ways. It’s a real treasure-house of words.

This book tells the story of Pamela’s spiritual journey into Zen and other meditative practices. It’s a memoir laden with spiritual stories, a fight against patriarchal norms, and her take on contemporary issues. She offers a feminist critique of aspects of Buddhism while sharing her hard-won wisdom. Her writing is beautiful and thought-provoking.

This is one of the first, and still one of the best, comparisons of Buddhist thought and Western psychology. In contemporary times, the lines between psychology and spirituality have become indistinct, and many seekers are finding benefit within both disciplines (a subject I discuss in my article "When Mindfulness is Not Enough"). Dr. Epstein illustrates how tools learned from Buddhism and psychotherapy can be used together to create a “healthy emotional life.”

If you are looking for a ‘quick fix' or 'how to’ read, this book may at first glance not be the most obvious choice. Awake at the Bedside is not your traditional guidebook. It is a moving and insightful collection of essays written by clinicians, chaplains, caregivers, pioneers in end-of-life care, contemplative teachers, and poets. Each essay sheds light on the different facets of what it means to show up at the bedside and the opportunity to wake up to each moment. I contributed a chapter on spiritual care, but that’s not why I recommend this volume. I recommend it because it is written by caregivers for caregivers—honest, reflective, compassionate, inspirational, and practical. A human and compassionate vision for end-of-life care. 

I read Being Peace about 30 years ago. It’s the first of many books by this Zen Buddhist monk that I’ve read since then.

In one short volume, it captures the essence of what he teaches in his writings, retreats, and videos. Each short segment has layers of meaning and emotion that, over time, settle into the soul.

Despite years of therapy and meditation, my periods of inner peace were few and far between. This book planted a seed that led to more books, a new meditation practice, and eventually to my going to a large retreat, joining a community of Buddhist practitioners, and becoming a therapist myself.

I’ve passed on many of Thich Nhat Hanh’s wise insights and observations to my own clients.

Geoffrey Mann does a great job of laying out the history of Buddhism and Zen and its links to the martial arts. Thoroughly researched and widely referenced, it’s definitely the place to start, and the hardback edition makes a handsome addition to any martial arts library.