2023 Top 10 Book Recommendations
Welcome entrepreneurs! I’m so glad you’re here.
I’m lucky to get to spend most days in deep conversation with clients, partners, and friends about the things that truly matter in business and life. And because of this commonality, our conversations inevitably turn to books.
I’ve recommended hundreds of books this year, but below you’ll find a list of the 10 that I recommend over and over again.
My goal in providing this list is twofold. First, I hope it helps readers self-select into some of the most powerful books I’ve read over the past few years, and maybe even makes a difference in their lives. And second, I want to start an ongoing conversation with all of you, and perhaps attracts new books into my awareness. So if you end up reading any of these books, I hope you’ll let me know what you think. And if you know a text I need to read, please let me know that, too.
Without further ado…
The 2023 Inside-Out Book List
The Surrender Experiment: My Journey into Life’s Perfection by Michael Singer
Perhaps no book has been more influential to me than Michael Singer’s autobiography, in which he chronicles his journey from a yogi meditating in the woods to a world traveling CEO negotiating a merger between two public companies, which eventually results in his being investigated and ultimately exonerated by the FBI. All of this happens as a result of his conscious, consistent choice to let go of what he wanted his life to be about, and instead surrender to what Life was asking of him in the moment.
Like most startup folks, had you told me years ago that I ought to surrender my own wants/likes/dislikes, and instead do my best to live up to what the moment was asking of me, I would have thought you were crazy, or trying to manipulate me into doing something I didn’t really want to do. And yet, surrender I did. And still do.
The magic of The Surrender Experiment is in the way Singer’s life serves as a spiritual lighthouse, as if it were written specifically for entrepreneurs.
The Three Marriages: Reimagining Work, Self and Relationship by David Whyte
David Whyte is one of my favorite authors. A poet with one foot in the workplace and the other in the human condition, his writing is an experience uniquely suited to high performing clients interested in more than just success.
My favorite book of Whyte’s—and the one I recommend most—is Crossing the Unknown Sea: Work as a Pilgrimage of Identity since it’s so relevant to folks reorienting their work to purpose, which is a big chunk of my work. But The Three Marriages – Whyte’s exploration of the interplay between our marriage to our spouse, our vocation, and ourselves – may be even more broadly applicable.
After reading it for the first time this year, I now find myself recommending it to clients, and to anyone searching for balance, or better yet, harmony, among the different parts of their life.
When Things Fall Apart by Pema Chodron
Part of the work of an executive coach is meeting a person where they are without flinching – even if it’s at the darkest moment of their life, filled with doubt, grief, anger, shame, fear, and more – and then walking with them on their journey out. This work is some of the most meaningful work I get to do, and I feel incredibly honored that some truly special leaders trust me in this way.
When a person is in a spot like that, often they can unknowingly keep themselves stuck by holding on to how things were or should be. Buddhist monk Pema Chodron’s best work (for my money), When Things Fall Apart is written for people in those dark times, and, meeting them where they are provides light, hope, and a bit of structure on the way out.
Leading a company only seems glamorous if you’ve never done it before. Those who have borne the toll of leadership know the inevitability of going through the shit and the importance of being able to navigate out.
The Drama of the Gifted Child: The Search for the True Self by Alice Miller
I’ve written before about this petite nuclear bomb of a book. Suffice it to say that every time I recommend it to someone, I do so with the disclaimer: this book may impact you more than you’re ready for.
Contemporary capitalist society rewards a particular orientation to life – that of the high achiever. But you don’t become a person willing to outwork everyone else for no reason. In DotGC, Miller dives into the core wounds that drive high achievers in a way that is raw, vulnerable, and instructive. So much so that, if you’re one of those she’s talking about, simply reading the book can be an experience that leaves you in tears. Not that I’d know anything about that…
Four Thousand Weeks: Time Management for Mortals by Oliver Burkeman
If a part of you really likes to hustle, or you have a bottomless to-do list, this one's for you.
Under the guise of a deep dive into productivity Ninjitsu, Burkeman instead contextualizes all popular efforts to be more productive as, effectively, anxiety management. His approach to time management starts from the only context in which productivity really matters to human beings (hint: you’re going to die) and unpacks why that leads us to all sorts of unhelpful coping mechanisms. He provides some tactical advice on how to orient to actual productivity—my favorite is the recognition that you will actually experience less than 0.0001% of the available experiences in your life, so rather than trying to up that to 0.00011%, best to focus instead on choosing—but the real magic of this book is that it can change the way you view productivity entirely.
Falling Upward by Richard Rohr
Confucius said, “man has two lives. The second begins when he realizes he has only one.” The transition between those two lives has been one of the most important journeys I’ve made, and I count Rohr as a mentor and guide in that process. A Franciscan monk, Rohr approaches some of the most important topics around navigating the second half of life from a Christian worldview, but in a way that appeals to Christians and non-Christians (✋) alike.
Falling Upward is his most accessible and overarching book about that transition and a great place to start for those who haven’t yet been introduced.
The Courage to Be Disliked: How to Free Yourself, Change Your Life, and Achieve Real Happiness by Ichiro Kishimi and Fumitake Koga
The field of psychology is dominated by the worldviews of Sigmund Freud and Carl Jung, each of whom understood a person’s present behavior to be the result of previous causes. We are so indoctrinated in their work that that previous sentence probably feels self evident. But it’s not.
The Courage to be Disliked is an examination of the work of a third giant of psychology, Alfred Adler, as told through a socratic discussion between a teacher and a student. Adler believed that a person’s present behavior was designed to serve a purpose in the future.
Neither of these worldviews are “right,” but I’ve found that the Adlerian lens is much more common amongst top performers and offers you much more choice as to your future.
The Mistborn Trilogy & The Stormlight Archive by Brandon Sanderson
I’m cheating a bit here in including a grand total of seven books (and counting) under one heading. But having binged all seven this year myself – after years without reading a fantasy novel of any kind – these books have captured me in a way that nothing has for a long time, so I’m going to allow it.
You might wonder what a set of fantasy novels are doing on my list. Well, you might learn something from business books or non-fiction, but good fiction can be transportive. And great fiction can change you, which brings me to…
The Overstory by Richard Powers
The Overstory was the best novel I’ve read in a long time and is probably one of the top five books I’ve read. The story centers around a group of intersecting characters, some of whom are human, some of which are trees, and some of which are, we’ll just say, “related to artificial intelligence.” I don’t want to spoil the story.
When I first read The Overstory, it was impossible for me to go on a walk in my neighborhood without appreciating an entirely different axis of experience – that of the trees and plants. And this experience is so powerful that when I recommend this book to someone, I try to schedule a walk in the woods with them afterward to appreciate the depth together.
Iron John by Robert Bly
For most of human history, the father worked from home, tending the animals, working the field. This meant that the son got to see all aspects of his father – at work, at rest, with his family – and in doing so develop a complete picture of what it was to be a man. And then around the 1950s, fathers started going into the office to work, and suddenly all their sons saw of them was after they arrived home, tired from a long day and wanting to rest. “Dad” was no longer a complete person with energy and verve. He became, for an entire generation, just that tired guy on the couch (as caricatured by Homer Simpson and the like).
Iron John, an exploration of a Grimm’s Fairy Tale of the same name, woke me up to the realities of what it means to be a father and a son. It seems more and more of my friends are becoming new dads this year, and for those fathers blessed with boys, I cannot recommend any book more highly than this.
So those are my 10. The books I recommended this year more than any other.
What about you? I’d love to hear from you.
Want to dive deeper?
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