100 Books Like The Places That Scare You

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.

This is another unconventional recommendation because it’s not only about grief. Maté is a medical doctor whose work focuses on the damage that unprocessed emotional trauma—including grief—does to the body and how to process emotions in a way that is less likely to lead to physical disease.

I think this book is a necessary complement to books about complicated grief because it provides an understanding of what happens when we do not allow ourselves to fully experience grief in a safe and supported manner, and provides insights into how to do so.  

I’ll be honest: I have only scratched the surface of this book and the questions it asks and answers. How to deal with suffering and remain open to joy and beauty? I understand the book’s content at only the most superficial level. I suspect it’s going to take years for me to go deeper with it. As a writer, I am blown away by Trungpa’s style, which is clear, simple, and relatable. As a psychologist, I am humbled to see how clumsy and awkward our modern approaches are. 

This book met me in one of the darkest seasons of my life after my second divorce.

Pema Chödrön’s voice feels like a steady heartbeat—calm, wise, and utterly human. She doesn’t promise to remove pain; she invites us to stay present with it. Every page taught me that courage isn’t the absence of fear but the willingness to face it with open eyes and a soft heart.

I return to this book whenever I need to remember that groundlessness is not failure; it can be the greatest freedom.

This book offers profound insights on navigating life's uncertainties, with wisdom and compassion.

Chodron guides readers to embrace impermanence and find freedom within uncertainty. She encourages cultivating mindfulness and compassion as tools for transforming fear and resistance into opportunities for growth and awakening.

Through humor, personal anecdotes, and teachings, Chodron guides us to live authentically, discover resilience, and find greater meaning and success in all parts of our lives.

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.

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.

Reading this book helped me change my life for the better. Putting Thich Nhat Hanh’s teachings into practice in my daily life helped me live a more mindful, more peaceful life at a time of great transition in my personal life.

One of the things I love the most about this book is how simple it is to incorporate its practices into daily life. There are sections on how to be mindful about washing dishes or answering the phone! There are also sections that went much deeper, which dealt with how to be mindful of my emotions, which I have found so valuable in dealing with anxiety, difficult situations, and fear.

One of my favorite experiences related to this book was guiding a group of middle school-age kids through a discussion inspired by the “Tangerine Meditation.” Instead of a tangerine, we considered a piece of paper and talked about the… show more.

I like and dislike this book! Ricard is a scientist and a Buddhist monk, and is reported to be the happiest man on earth. I know, respect, and like Ricard, and this book harkens back to the Stoics by suggesting that moderation is the key to happiness. My research says yes and no to this.  Ricard is correct that spending too much time worrying about the past or future will drag down one's happiness. My research, and that of many others, have shown the positive effect of meditation on happiness and here Ricard is masterful in explaining how and why meditation is important. Calmness and self-insight are very important to avoiding depression and setting the conditions for happiness, but, as Ricard notes, we must be in communities of other people to truly thrive. A little wildness is awesome, go for it!