1. The Laws of Human Nature by Robert Greene
Robert Greene is a master strategist—perhaps the best of our generation. This book is the culmination of his lifetime of work on power, influence, and mastery. It’s an instructive guide to human nature based on historical accounts and evidence, rather than a particular viewpoint or moral judgment.
As Greene, emphasizes throughout the book, a deep understanding of human nature is advantageous for countless reasons. It helps build you into a strategic observer, become a better judge of character, outthink malicious people, develop greater empathy, and realize your potential.
True to form, Greene pulls stories from both sides throughout history—those who have succeeded and those who have failed in spectacular fashion. It’s an incredible resource if you want to hone your strategic mind and will pay immediate dividends in your own life, no matter your position.
“And in life as in warfare, strategists will always prevail over tacticians.”
2. Creativity, Inc. by Ed Catmull
A modern case study of how to harness creativity and build a culture where the creative process can thrive. Catmull discusses the evolution of Pixar Animation, including the philosophies and strategies that helped establish them as a creative force in animation and storytelling.
Catmull emphasizes how the teams embrace years of ambiguity that are inherent to the creative process as stories evolve into their own. Instead of becoming attached to a single storyline or character, they seek out a deep truth at the core of the film—a guiding principle—and craft the story around that. Catmull also stresses the role of leadership in cultivating creativity. It starts with loosening your grip, accepting risk, trusting your people, and giving them space to do what they do best.
“Craft is what we are expected to know; art is the unexpected use of our craft.”
3. Range by David Epstein
In a complicated, competitive world, there’s a push to focus early and narrowly. Navigating life seems to demand specialization. And the stories told the loudest (Tiger Woods) push that narrative.
In reality, far more eventual top performers devote less time to deliberate practice early on and instead undergo a sampling period. This offers them an opportunity to learn about and discover their own abilities and inclinations. Only later do they focus on one specific area and ramp up technical practice (Roger Federer).
This book is a tremendous resource for generalists and those pursuing a multidisciplinary approach in life. It’s something that needed to be written and Epstein does a great job emphasizing breadth over depth, the dangers of specialization, and the importance of match quality along the way.
“We learn who we are only by living, and not before.”
4. Extreme Ownership by Jocko Willink & Leif Babin
One of the best books on leadership that I’ve ever come across. And this is one of those books that I happened to read at the perfect time when I needed these lessons the most. Willink and Babin, two Navy SEALs officers, recall their time leading the most highly decorated special operation unit of the Iraq War. Each chapter highlights one of their leadership principles in action before relating it back to the business world.
I found the most relevant section to be on the laws of combat: cover and move, simple, prioritize and execute, and decentralized command. If you want to win, teams must not only know what to do, but they must also know why. As a leader, your job is to ask questions until you understand why.
There are also great lessons in empowering yourself by accepting total responsibility—no matter your position—and the importance of being aggressive (not overbearing).
“There are no bad teams, only bad leaders.”
5. Skin in the Game by Nassim Taleb
One of the best things about Taleb is his eagerness to challenge standard conventions and long-held beliefs about a range of topics. Nothing is off limits. As a result, you’re guaranteed to walk away with a new perspective after reading any of his books. In Skin in the Game he picks apart the way we think about uncertainty, symmetry, risk-sharing, and rationality in complex systems.
Taleb emphasizes the importance of thinking in high dimensions and evolving beyond the shallow. He also digs into how acting by removing is more powerful and less error-prone than acting by addition. This has implications in terms of unnecessary complexity in both our lives and how we think about strategy.
But the core of the book focuses on ethics and morality. Skin in the Game is about putting yourself out there and taking risks of your own. It’s immoral to keep the upside and transfer the downside to others. Besides, it’s impossible to understand the world and develop your own abilities without putting yourself out there and taking risks of your own.
“The curse of modernity is that we are increasingly populated by a class of people who are better at explaining than understanding, or better at explaining than doing.”
6. Endurance by Alfred Lansing
A brilliant tale of survival that documents Sir Ernest Shackleton’s failed voyage to cross the Antarctic. Shackleton was a compelling, larger-than-life figure who offered lessons in leadership and strategy at each turn.
The book also contains one of my favorite passages. And it speaks directly to strategy and thoughtful action: “Whatever his mood – whether it was gay and breezy, or dark with rage – he had one pervading characteristic: he was purposeful.” If you want to sharpen your strategic mind, that’s what you’re after. Every action should have intention.
Shackleton’s most profound lessons are revealed in his ability to transcend the fundamentals and shift strategies as the situation required. There are few men who faced more dire circumstances than Shackleton and his crew, and who survived without any casualties. While you can’t separate luck, there was a strong level of strategy and leadership required to come out alive on the other side.
“Whatever his mood – whether it was gay and breezy, or dark with rage – he had one pervading characteristic: he was purposeful.”