100 Books Like The Power of Regret

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.

I loved this book because it builds from the sadness of a life taken far too young to the beauty of deep reflections on the meaning of life, love, and loss. Paul Kalanithi was a brilliant neurosurgeon just completing his years of training when he was diagnosed with Stage IV lung cancer.

Kalanithi, a new father, wrote much of this book while he was dying. As a writer myself, this book caused me to wonder if I could be so open about my reality, in a book or any other form, while dying. I do not know the answer, but I treasure the experience of having read a book that raised such a powerful stirring in myself. Like the other books I recommend, Kalanithi’s memoir is a gift from the book Gods.

This is the most recently published recommendation, and centers around the one thing we all share: mortality.

Pausch was a beloved professor who was diagnosed with pancreatic cancer. He gave a last lecture to his class about the most important things he'd learned in life, drawn into tight focus because of his impending death—a truly powerful narrative about finding what matters.

Ranjay Gulati delves—dare I say—deeply into the significance of purpose-driven organizations in today's business landscape.

The book emphasizes how cultivating a strong, authentic purpose can lead to exceptional performance and long-term success.

What I loved is that Gulati highlights that purpose is not just a tagline but rather a dynamic, guiding force that drives innovation, collaboration, and resilience. He shows how it can help decision-making.

Gulati shares several compelling case studies and practical tools that helped me affirm my position on the concept of organizational purpose. If you’re passionate about transformative leadership, Deep Purpose will inspire you to create meaningful impact in your organization.

I was curious to find how Bronnie Wave became an accidental end of life carer. I found it interesting to read this was often shaped by the outlook of those she was caring for rather than any pre-fixed ideas on her part.

I congratulate Bronnie on a career she has taken to brilliantly which also brings to the reader her unique insight.

This is a book about (social) identity and how our understanding of self is derived from the social groups we are part of.

Two brilliant psychologists, Jay Van Bavel and Dominic Packer, use their own research and insights from social psychology and neuroscience to explain how identity really works and how it influences our thinking and doing every single day.

The book really makes you think about how our social nature impacts on all kinds of decision-making, and it will give you new ideas and insights about power and influence. 

Oh boy, this monumental book certainly expanded my empathetic mind! The greatest lesson? The fact that true empathy requires a compassionate response. That was an eye-opener! This book has really stuck with me. I remember being entrenched and enthralled with every page while on a writing retreat. I can’t thank the author enough for helping me fine-tune my own books about the empathic experience!

Similar in tone to her well-known The Language of Emotions, this book doesn’t dive too deeply into metaphysical perspectives. Instead, this book is primarily grounded in psychology, history, and science. That is the very reason why we highly sensitive souls benefit from books like these; we are admittedly gullible and easy to manipulate if our empathy is uncontrolled! Understanding our abilities through a grounded psychological lens such as this is crucial for our emotional understanding.

Are you stewing about regrets, disappointments, and perceived “mistakes” you’ve made? It’s hard to treat yourself well if you are berating yourself for things you did or didn’t do in the past. This book guides you through proven tools to process what happened. It will help you let go of resentments so you can move on with your life. Once you let go, you can treat yourself better.

Marshall Goldsmith provides a powerful guide for anyone seeking a higher purpose in their personal and professional life.

Goldsmith draws on his experience as a world-renowned executive coach to provide practical advice and exercises aimed at helping readers live a life aligned with their overarching purpose, regardless of the eventual outcome.

Taking inspiration from Buddhism, Goldsmith reveals that the key to living an earned life, unbound by regret, requires committing to a habit of earning and connecting that habit to something greater than the isolated achievements of careerism.

With illuminating stories from Goldsmith's legendary career,  this book provides a roadmap for ambitious people seeking to close the gap between what they plan to achieve and what they actually get done, and to avoid the trap of existential regret that reroutes destinies and persecutes memories.

Friendly tip: I do not recommend reading this novel while isolated from your family due to travel and illness, because this book hits hard in all the right ways.

It invites both the protagonist and the reader to explore the deepest wells of regret and the branching infinities that our life choices produce. In doing so, the novel beautifully confronts the seductive lure of “what could have been” while reminding us of the quiet beauty in what is.

As someone whose mind is often lost in the past or gazing into the future, this ultimate lesson of the book provided a much-needed sense of clarity.