Riveting Reads: 2019 Edition

Hi friends!

Because I can’t help myself, here’s my annual “top 10” books that have enthralled me this year — some old, some new. All incredibly valuable to me, and hopefully to you.

Make 2020 an incredibly rich and prosperous year!

- Matt

Stillness is the Key (Ryan Holiday)

This one was my favorite. Holiday analyzes a wide variety of philosophies and religions, spanning thousands of years, and he highlights their commonality: our desperate search for stillness. Drawing on epic stories and some of the world’s greatest thinkers (Nietzsche, Seneca, Confucius, and more), he shows how it’s a necessary way of living. As we fight the assault on our attention in today’s digital world, that same pressure for self-mastery, peace, and focus has long confounded humans for thousands of years. In this book, Holiday highlights some practical approaches for finding stillness in life. We can all learn from this text. (Note: I had the pleasure of meeting Ryan at his live podcast book launch in NYC in October with James Altucher. Photo below. Great experience!)

Range: Why Generalists Triumph in a Specialized World (David Epstein)

Malcom Gladwell, trumped! You’re likely familiar with the “10,000 hours rule” — the method espoused by Anders Ericsson and made famous in Gladwell’s Outliers. In this stellar piece, Epstein brings important research to the forefront and completely invalidates this theory. He argues that instead of spending all our time getting great at one thing, we should cultivate “range” — dancing in and out of different disciplines, learning and practicing different skills. The top performers in the world (with few exceptions) don’t get locked in to early specialization, but instead embrace the generalist mentality, allowing them to “go deep” later in life in the thing they really become well known for. Fascinating and motivating.

The Laws of Human Nature (Robert Greene)

Robert Greene is a master at researching and crafting epic books. Ones that cut to the heart of our humanity, often in a dark and blunt manner. We’re all social animals, guided by a set of underlying “laws” that we’re generally unaware of. So, Greene unpacks ancient wisdom and philosophy in this book to explain why we operate the way we do. Pulling from the likes of Martin Luther King Jr, Queen Elizabeth I, and Pericles, Greene shows us how to master our emotions and thoughts, and helps us gain clarity on our higher purpose.

The Systems View of Life: A Unifying Vision (Fritjof Capra & Pier Luigi Luisi)

I won’t mislead you — this is a true textbook. I took two months to thoroughly digest this piece, but it was wonderful. Capra and co have spent the better part of three decades shedding light on a new way to view life: as a system that’s highly interconnected, like an ecosystem. Ecology and related disciplines can effectively guide so much of how we understand and interact with the world if we let it. The book starts with a “knock” on Descartes and Newton, showing how their mechanistic thinking, while great in many respects, has severely limited our thinking over time (e.g., in healthcare, psychology, and law). In many respects, this book is a revolutionary text which shows how social networks, dissipative structures, and a systemic understanding of evolution can greatly aid problem solving in today’s highly-complex and interconnected world.

Side note: this book inspired some fun conference presentations I did this year on cyber security, where I dug deep into philosophy. You can find some of that thinking in this podcast interview I did.

The Ride of a Lifetime: Lessons Learned from 15 Years as CEO of the Walt Disney Company (Robert Iger)

I bought this one on a gamble. After reading Walt Disney’s bio last year, the company has always intrigued me. At first glance, I thought this was going to be a formulaic and ghostwritten piece by a CEO looking to capture some attention at the high point of his career. Thankfully, I was wrong. It was really entertaining, getting to see (a) how Iger navigated four decades of leading media conglomerates and (b) seeing how Disney restored its greatness. I was particularly surprised by Iger’s close friendship with Steve Jobs and how Pixar came fully into the Disney family after some tense times. I also appreciate how Iger carefully layered in some leadership themes he’s learned along the way, and expounded upon them through some revealing experiences he’s had over his career. Truly a great biography.

How to Think Like a Roman Emperor: The Stoic Philosophy of Marcus Aurelius (Donald Robertson)

Ah, so cool! Marcus Aurelius is my favorite Stoic philosopher, and getting to “peer in” to his life was so insightful. The Meditations was his personal journal, and it survives to this day as one of the most important self-help classics ever. In this book, cognitive psychotherapist Donald Robertson weaves the life and philosophy of Marcus Aurelius together in a way that provides a compelling, modern-day guide for how we can adopt Stoicism for greater emotional resilience and fulfillment. From Marcus’ early days as a philosophy student at the court of Hadrian through his unlikely but highly successful reign as emperor of Rome, Robertson shows how Marcus relied on philosophical doctrine to endure incredible adversity, and even how his writings inspired Cognitive Behavior Therapy today.

Trillion Dollar Coach: The Leadership Playbook of Silicon Valley’s Bill Campbell (Eric Schmidt, Jonathan Rosenberg, & Alan Eagle)

Did you know a football coach propelled some of the biggest tech companies to life? Google, Apple, Intuit, and a host of others all greatly benefited from the coaching and mentorship of the legendary (but not widely-known) Bill Campbell. Eric Schmidt and co gather together in this book to honor Campbell and articulate how Bill’s coaching — focused on empathy, valuing people, and doing what’s right for the long-term — unlocked some of the greatest potential in Silicon Valley and made it real. In this delightful yet short book, they’ve codified and packaged much of his wisdom for us to learn from, even if Bill (now passed) wouldn’t have wanted that attention.

The Icarus Deception: How High Will You Fly? (Seth Godin)

You know the ancient story of Icarus? His father made him wings and told him not to fly close to the sun. As you might know, he said “screw off” and he plunged to his doom. The lesson: play it safe and follow the playbook. Industrialists loved this, because they needed people behaving like machines. And this is the message we all grew up with. But we also forget that Icarus’ father said “don’t fly too low, because seawater would ruin his wings. Flying too low is even more dangerous, because it feels deceptively safe. In this stellar read, Godin does it again. He pushes us outside of our comfort zones and makes clear how being part of today’s connection economy necessitates that we make art. Seizing new ground, being bold, and making a ruckus are the only choices we have today. So go on, be an artist. Never let anyone talk you down.

American Caesar: Douglas MacArthur 1880–1964 (William Manchester)

A few years ago, I watched Emperor with Tommy Lee Jones, starring as General Douglas MacArthur. I got an inkling then that maybe this general was a little pompous — possibly a great man, but full of himself. But holy shit. After reading this epic biography by Manchester, I believe MacArthur really did view himself as the next incarnation of Caesar. No doubt, he had a super-impressive career well into his 70s, and was one of only five men in history to have achieved the rank of General of the United States Army (five-star). He was a stupendous paradox of a human being. He served in WWI, WWII, and the Korean War, and people literally worshipped him. Especially the people who he fought for in the Pacific. What I took away is that, despite his self-obsession, he was a very caring individual and greatly respected the many cultures he came across in his life. He fought hard to preserve the goodness of conquered peoples, while also seeking to make their lives better (using an American lens).

Gridiron Genius: A Master Class in Winning Championships and Building Dynasties in the NFL (Michael Lombardi)

Written by maybe the second-most famous Lombardi in the NFL, we get a sneak peak at what makes NFL franchises dominate year after year. Informed by 30 years of intimately supporting three coaching titans (Bill Walsh, Al Davis, and Bill Belichick) — Lombardi provides the framework for what makes a successful organization work. We see that the smartest leaders script everything, they always think about the entire “system”, and they’re relentlessly focused on everyone “doing their job” at every moment. A really entertaining and enlightening read, with great lessons for sports, business, and life in general.

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