Here are 100 books that Playing Big fans have personally recommended if you like
Playing Big.
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I’m the author of a deeply introspective book about the difference between chasing success and truly living a successful life, told from deep within the startup trenches. I’ve spent decades navigating those trenches myself, which is why I’m so passionate about this theme. These books echo the questions I’ve lived, and continue to live, about meaning, purpose, and what truly matters. I picked these five books because they have shaped my understanding of success—and the deep, often messy, work it takes to redefine it from within. Together, they have shaped my belief that entrepreneurial success isn’t just about what we build, but who we become in the process.
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…
One of the outstanding classics to emerge from the Holocaust, Man's Search for Meaning is Viktor Frankl's story of his struggle for survival in Auschwitz and other Nazi concentration camps. Today, this remarkable tribute to hope offers us an avenue to finding greater meaning and purpose in our own lives.
It is April 1st, 2038. Day 60 of China's blockade of the rebel island of Taiwan.
The US government has agreed to provide Taiwan with a weapons system so advanced that it can disrupt the balance of power in the region. But what pilot would be crazy enough to run…
I’ve spent years working with women who are expected to be confident, decisive, and polished, but are rarely taught how to build those skills. Through my work in politics, public service, and coaching thousands of women, I’ve seen how small, often invisible habits can keep capable women from being fully heard or respected. What I love most is helping women with the practical, everyday moments, like how to say no without apologizing, set boundaries, and build real influence. I’m passionate about leadership because I’ve watched these shifts change careers and lives, and these books reflect the lessons I come back to again and again.
I love this book because it reminded me that creativity isn’t something reserved for a certain type of person, it’s something I get to claim.
This book is for all us types who don’t see ourselves as creative or working in a creative field; it simply lays out our ability to bring creativity to our work.
This book taught me how we need to take risks with our creativity, especially when deciding what we want and how to get it. I connected with its message about imagining more for your work and life.
Readers of all ages and walks of life have drawn inspiration from Elizabeth Gilbert's books for years. Now, this beloved author shares her wisdom and unique understanding of creativity, shattering the perceptions of mystery and suffering that surround the process - and showing us all just how easy it can be.
By sharing stories from her own life, as well as those from her friends and the people that have inspired her, Elizabeth Gilbert challenges us to embrace our curiosity, tackle what we most love and face down what we most fear.
Whether you long to write a book, create…
I’ve passionately pursued the art of screenwriting for decades now, with all the ups and downs that go with that—from the peaks of Hollywood projects winning big awards (I was a writer-producer on HBO’s Band of Brothers), to scripts nobody wanted to read and when they read them, they didn’t want to do anything with them. And everything in between. It’s been my career my entire adult life—doing it, teaching it, and helping others understand the requirements of good screenwriting.
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.
A succinct, engaging, and practical guide forsucceeding in any creative sphere, The War ofArt is nothing less than Sun-Tzu for the soul.
What keeps so many of us from doing what we long to do?
Why is there a naysayer within? How can we avoid theroadblocks of any creative endeavor—be it starting up a dreambusiness venture, writing a novel, or painting a masterpiece?
Bestselling novelist Steven Pressfield identifies the enemy thatevery one of us must face, outlines a battle plan to conquer thisinternal foe, then pinpoints just how to achieve the greatest success.
A Duke with rigid opinions, a Lady whose beliefs conflict with his, a long disputed parcel of land, a conniving neighbour, a desperate collaboration, a failure of trust, a love found despite it all.
Alexander Cavendish, Duke of Ravensworth, returned from war to find that his father and brother had…
I was driven to become a veterinarian for as long as I could remember. Then, in high school, I developed a love of performance. I felt stuck. Should I choose art or science? I chose science, and despite a great career, I felt like something was missing. When I reconnected with my creativity through stand-up comedy, entrepreneurship and other non-artistic creative outlets, I found out what I had been missing. Why do we drop creativity for science? It was a common story. I dove into the research on creativity, and was blown away by how a bit of creativity can make us happier, more resilient, and make workplaces more effective.
I was pulled into this book as I entered the world of a secret society of Flaneurs or Wanderers. I loved the secret intrigue of how the author found the symbol for this secret society in a used book and how it spurred a curious exploration of why we wander.
I used the ideas in the book to slow down, use my curiosity, and re-engage with my human qualities that are so often buried in the busyness and connection to tech all day long. This book was a welcome, cool drink of water on a hot day, filled with great stories and illustrations.
From the internationally bestselling creator of Wreck This Journal...
wan*der verb \ wan-dar\ to walk/explore/amble in an unplanned or aimless way with a complete openness to the unknown
Several years ago when Keri Smith, bestselling author of Wreck This Journal, discovered cryptic handwritten notations in a worn copy of Walt Whitman's Leaves of Grass, her interest was piqued. Little did she know at the time that those simple markings would become the basis of a years-long, life-changing exploration into a mysterious group known only as The Wander Society, as well as the subject of this book.
The beauty of time travel stories is that under the tech, or the supernatural, they can be anything. And for me, they are everything. Paradoxes, puzzles, that oh-so-delicate space-time continuum: an infinite blank canvas for exploring human emotion, psychology, and choices. Just like everyone else, I have regrets, big and small, things that I wish I could change, sliding doors that may have taken me down the wrong fork in the road. With these books, each deeply personal and therapeutic in their own way, you may be able to see your own life choices anew, just like I did. Enjoy!
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.
The #1 New York Times bestselling WORLDWIDE phenomenon
Winner of the Goodreads Choice Award for Fiction | A Good Morning America Book Club Pick | Independent (London) Ten Best Books of the Year
"A feel-good book guaranteed to lift your spirits."-The Washington Post
The dazzling reader-favorite about the choices that go into a life well lived, from the acclaimed author of How To Stop Time and The Comfort Book.
Somewhere out beyond the edge of the universe there is a library that contains an infinite number of books, each one the story of another reality. One tells the story of…
I’m a clinical psychologist, which gifts me the experience of being part of people's journey of looking at their lives differently and transforming. Early in my career, throughout my academic studies, I was particularly curious about and drawn to existential perspectives. Sadly, with multiple losses of close loved ones, I was pushed into grappling with existential questions at a more personal level. Yet the pain of loss created shifts in perspective that have helped shape who I am, and the work that I do. I have found that connecting with people, travel, and books are avenues that help me continue to ask questions about life and inspire new directions.
My Ishmael is a book that got my mind thinking. It raises many questions about how we live and whether that is the best way to live.
I enjoyed how these questions are explored through a relationship between a child and a gorilla as it holds the reader in a place of curiosity, as opposed to judgment. This approach sits well with my values and makes it an easy read. One of my favorite quotes is “The only way you can be insulated from harm is by not existing, and that's no way to live.”
Daniel Quinn's Ishmael was the winner of the Turner Tomorrow Fellowship, a prize honoring fiction that offers creative and positive solutions to global problems. This extraordinary novel has become an underground bestseller and a testament for a burgeoning spiritual movement. Mr. Quinn's new novel is a companion piece--not a story that follows the first but rather a story contemporaneous with the first. In it, the Ishmael saga takes a startling direction that is in no way prefigured in the original.
The gorilla licked his lips--nervously, it seemed to me. "I think we can safely say that I'm not prepared to…
The Duke's Christmas Redemption
by
Arietta Richmond,
A Duke who has rejected love, a Lady who dreams of a love match, an arranged marriage, a house full of secrets, a most unneighborly neighbor, a plot to destroy reputations, an unexpected love that redeems it all.
Lady Charlotte Wyndham, given in an arranged marriage to a man she…
I’m a clinical psychologist, which gifts me the experience of being part of people's journey of looking at their lives differently and transforming. Early in my career, throughout my academic studies, I was particularly curious about and drawn to existential perspectives. Sadly, with multiple losses of close loved ones, I was pushed into grappling with existential questions at a more personal level. Yet the pain of loss created shifts in perspective that have helped shape who I am, and the work that I do. I have found that connecting with people, travel, and books are avenues that help me continue to ask questions about life and inspire new directions.
Braving the Wilderness sparked a shift in my perspective on self and relationships.
What struck me most was the separation of belonging and fitting in. I realized how much energy I had put into fitting in, all the while betraying what was true to me. Not only did Braving the Wilderness get me thinking, but it also provided practical steps on how to do things differently.
Since reading the book I have changed how I interact with others, steering away from connection through shared enemies, and instead moving towards connection through authenticity and vulnerability.
My favorite quote: “We can spend our entire life betraying ourself and choosing fitting in over standing alone. But once we've stood up for ourself and our beliefs, the bar is higher. A wild heart fights fitting in and grieves betrayal.”
A timely and important new book that challenges everything we think we know about cultivating true belonging in our communities, organizations, and culture, from the #1 bestselling author of Rising Strong, Daring Greatly, and The Gifts of Imperfection.
'True belonging doesn't require us to change who we are. It requires us to be who we are.' Social scientist Brene Brown, PhD, LMSW has sparked a global conversation about the experiences that bring meaning to our lives - experiences of courage, vulnerability, love, belonging, shame and empathy. In Braving the Wilderness, Brown redefines what it means to truly belong in an…
I was driven to become a veterinarian for as long as I could remember. Then, in high school, I developed a love of performance. I felt stuck. Should I choose art or science? I chose science, and despite a great career, I felt like something was missing. When I reconnected with my creativity through stand-up comedy, entrepreneurship and other non-artistic creative outlets, I found out what I had been missing. Why do we drop creativity for science? It was a common story. I dove into the research on creativity, and was blown away by how a bit of creativity can make us happier, more resilient, and make workplaces more effective.
What if reality was an illusion? This book messed with my mind and challenged my perceptions of what I thought was real. It made me think carefully about how I react to and think about my life and helped me understand how we develop biases.
This was one of the first books I read that helped me understand the impact and effects of ambiguity and uncertainty on my decisions, my happiness, and how I approach the world. It was instrumental in developing the Ambiguity habit in my DANCE framework for developing a creative mindset.
World-renowned neuroscientist Beau Lotto reveals the truths of human perception and devises a cognitive toolkit for how to succeed in a world of uncertainty.
Perception is the foundation of human experience, but few of us understand how our own perception works. By revealing the startling truths about the brain and perception, Beau Lotto shows that the next big innovation is not a new technology: it is a new way of seeing.
In his first major book, Beau Lotto draws on over a decade of pioneering research to show how our brains play tricks on us. With an innovative combination of…
When I was a boy, my mother told me every day, “Be a leader.” By that, she meant to remember who you are, stand up for what you believe, do good, and be good. I was only five years old. That daily lesson on the doorstep sunk deep in my heart. For over forty years, I have had a passion for learning, teaching, and practicing small “L” leadership. I have done that as dean of Harvard Business School, president of BYU-Idaho, and Commissioner of Education for the Church of Jesus Christ of Latter-day Saints. I have learned deeply from the books on this list, and I hope you will, too.
This is a small “L” leadership book, and I love its ideas and its examples. When I read it for the first time, it gave me a new perspective on the very personal nature of leadership. The book was jammed (it still is!) with great insights about the connection between what is inside of me and how I could lift and strengthen other people when I lead.
All I have to do when I once again take a look at this book is to read the table of contents–purpose-centered, internally-directed, other-focused, externally open, positive force–and I am reminded that this is a book that helps me stay focused on helping people and organizations thrive. It is a great lift!
A guide to leading with your best self, which in turn drives others to be their best.
NEW EDITION, REVISED AND UPDATED
Just as the Wright Brothers combined science and practice to finally realize the dream of flight, Ryan and Robert Quinn combine research and personal experience to demonstrate how to reach a psychological state that lifts us and those around us to greater heights of achievement, integrity, openness, and empathy. The updated edition of this award-winning book—honored by Utah State University’s Huntsman School of Business, Benedictine University, and the LeadershipNow web site—includes two new chapters, one describing a learning…
This book follows the journey of a writer in search of wisdom as he narrates encounters with 12 distinguished American men over 80, including Paul Volcker, the former head of the Federal Reserve, and Denton Cooley, the world’s most famous heart surgeon.
In these and other intimate conversations, the book…
In 2016, I finished a book that had been three years in the making. I interviewed hundreds of snipers and spent some 9,000 hours wading through neuroscientific research papers. While my own background as a Chemical Engineer helped, it also became a deep dive into a world that opened my eyes. We are on the cusp of understanding what makes us tick as humans, and if we succeed in cracking that, we will become truly unstoppable. Simply put, we are all born, and we will all die, but we now have the power to comprehend the real reason the first event happened before the second one did.
Whenever I feel inadequate, insecure, overwhelmed, and diminished, I come back to this book. Errol was a Navy SEAL Commander. He should be dead by now. His survival is due to a gripping tale of control and recovery through a unique process that can be applied by anyone struggling with life and wondering whether they will ever be able to get anywhere under their own steam.
Errol has a way of writing that makes what he says memorable. The effectiveness of what he says is testified to by his own survival of a traumatic brain injury that should have made him one of the statistics. Reading his account is humbling and eye-opening.
Thrive under any circumstances with insights from an elite combat veteran
In Ice Cold Leader, special forces combat veteran, FBI agent, and business founder Errol Doebler reveals his unknown and silent battle with a traumatic brain injury incurred as a Navy SEAL in the late 1990s, and how he overcame emotional distress, self-doubt, depression, and anxiety to create a successful and happy personal and professional life until the day he discovered his pain was due to an injury he didn't even know he had.
Anchored in gripping tales from his time in the elite services, the author describes the unique…
