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.

I find the story in Imji Getsul (“English Novice”) incredibly moving. Lobzang Jivaka (Michael Dillon) was an extraordinary human being: the first trans man to have successful genital surgery and a pioneering (anonymous) writer on the subject. Outed by the British tabloid press, this deeply private man fled to India and became a Buddhist novice. In Ladakh he insisted on overcoming his own privilege as a white gentleman, starting at the bottom of the monastic hierarchy in gruelling physical conditions (which ultimately killed him). This book is an honest, funny, and powerful account of personal change and the meeting between cultures.

Tulku wrote a great resource to facilitate learning and practicing meditation and opening up the mind to its innate healing powers and abilities to center and calm the soul. Another book that deserves to be read more than once.

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. 

This is a diary of an English woman who moved to Japan in the 1950s to study Zen at one of the most prestigious temples at the time and become the first female to be sanctioned by the Soto School of Japan to teach in the West. The diary takes us through her years of arduous training in Japan, through the challenges that beset her, and gives a truly moving account of her brilliant mindset throughout her grueling ordeal to become a Zen priest. 

This was the first book I ever read that changed my life. It came along at a time when I felt I was missing something. I didn’t know a lot about Buddhism at the time, and therefore didn’t recognize that what I was feeling was a universal phenomenon and that the Noble Eightfold Path was a secular template for contentment. I have read many other Buddhist books since then, but none of them have spoken to me like this one did. I have a notebook that contains entire passages of Buddhism Plain and Simple, and regularly refer back to those passages today.

Looking for the vehicle to understand Siddhartha Gautama’s journey to enlightenment and teachings but worried you’ll never remember the four noble truths or eight-fold path? Search no more, my friends. Of all the books on Buddhism ever written this simple and compact distillation delivers what Siddhartha (the Buddha) taught which is really nothing more complex than, “You must figure it out for yourself, but here’s how I did it.”