Reading List

The 5 Best Books to Sharpen Your Strategic Mind

WANT FREE COPIES OF THE BOOKS IN THIS ARTICLE?

As a thank you for my newsletter subscribers, I’m currently giving away FREE copies of all five books featured in this article (giveaway ends 11/15). Enter for your chance to win here.


Ever wonder if you’re focused on the right things? This fear defined my first five years out of college. I was mainly reacting to the things happening around me, bouncing from one distraction to the next. I tried to be purposeful but I had no sense of direction and failed to grasp the nuance of the long game. In other words, I failed to recognize the importance of strategy. 

At their core, strategies are the frameworks you stack to help advance your principles, move you closer to your goals, and realize your aspirations. Strategies sit above tactics, but below guiding principles. They pave the way forward and help create momentum.

A strong strategy helps to direct your focus and anticipate the obstacles or adversaries standing in the way. This requires long-term thinking – an ability so see multiple moves ahead and an understanding of the interconnected whole. But it’s also about knowing what you’re working towards and what’s within your control. 

This story will be familiar to those who have read my new ebook, 7 Strategies to Navigate the Noise. It’s all about connecting your guiding principles with your day-to-day. Life gets easier when you develop a stronger sense of strategy and are able to take thoughtful action. 

Over the past ten years, I’ve faced this question day in and day out, pouring over hundreds of books in an attempt to figure it out. In 7 Strategies to Navigate the Noise, I recommend twenty-two different books to improve your strategic mind. I’ve narrowed that list to the five most influential books on strategy to get you started.

Each book offers something of its own and was a major influence in helping me develop a stronger sense of strategy and self-sufficiency. If you’re struggling to determine whether or not you’re focused on the right things or need help sharpening your strategic mind, these books should provide a solid starting place.

1) The Laws of Human Nature by Robert Greene

Robert Greene is a master strategist in his own right and 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 you grow 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 it will pay immediate dividends in your own life, no matter your position. 

2) The Tigress of Forlì by Elizabeth Lev

The biography of Renaissance Italy’s most courageous countess, Caterina Sforza. Her tale is one of clever strategy, boldness, and determination. Sforza’s entire life reads like a storybook, as she fights off her husband’s assassins, the French Army, and Cesare Borgia. 

Sforza is an archetype of a dimensional thinker who was able to consider second and third-order consequences at every pivotal moment. And this was how she fought her way through life, outthinking and outmaneuvering every adversary and obstacle she came across. 

Throughout her life, powerful men viewed her as a pawn on the chessboard of Italian politics. They doubted her ability to rule and refused to take her seriously. She would prove this to be foolish, time and time again. It’s a fascinating and inspiring biography one of history’s most underrated strategic leaders. 

3) Meditations by Marcus Aurelius

A cornerstone of Stoic philosophy. At its core, it’s about the art of living. This is the true value of practical, functional philosophy. And there’s no better starting place than Marcus Aurelius. 

If you want to be more strategic, you need a bedrock of principles that you can call upon at any moment. You must also have a strong understanding of your sphere of influence – what’s within your control, what’s beyond, and what falls in-between. Stoic philosophy and the frameworks emphasized in Meditations are one of the best places you can start. 

4) Endurance: Shackleton’s Incredible Voyage 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 required to come out on the other side. 

5) Skin in the Game by Nassim Taleb

One of the great things about Taleb is that he challenges standard conventions and long-held beliefs about a range of topics. As a result, you’re guaranteed to walk away with a new perspective. Here he picks apart the way we think about uncertainty, symmetry, risk-sharing, and rationality in complex systems.

In terms of strategy, 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 strategic abilities without putting yourself out there and taking risks of your own. 

The best strategic thinkers have grown from the chaos they’ve faced and developed resilience. Strategy isn’t about accruing power and sitting back while others take the risk. It’s about using long-term thinking to improve your position and build your capacity to give more back to the world. At its core, strategy is about taking calculated risks for the things you care about most – thoughtful action. 


Want free copies of the books in this article?

As a thank you for my newsletter subscribers, I’m currently giving away FREE copies of all five books featured in this article (giveaway ends 11/15). Enter for your chance to win here.

The 5 Best Books to Help You Create More

Perennial Seller – Ryan Holiday

A useful starting place to understand the entire creative journey–from sitting down to create, through positioning, marketing, and building a platform. Holiday pulls dozens of examples from creative minds throughout history to uncover tactics and best practices. But the underlying strategy consistent throughout the book can be summed up as playing the long game. If you want to create something of lasting value, there are no shortcuts or paths to immediate gratification. Dedicate yourself to your creative process and put in the work.

To create something is a daring, beautiful act. The architect, the author, the artist–are all building something where nothing was before.
— Ryan Holiday

Grit – Angela Duckworth

In any creative endeavor, you’ll need both direction and determination–what Duckworth defines as “grit”– if you want to make meaningful progress. The book emphasizes the importance of deliberate practice, purpose, and stamina over intensity. The best thing about Duckworth’s writing is that she makes it real. It’s not about a magical experience that leads you to your passion, purpose, or life’s work. Instead, this comes through a discovery period–often messy, serendipitous, and inefficient–followed by years of refinement, and a lifetime of deepening.

Passion for your work is a little bit discovery, followed by a lot of development, and then a lifetime of deepening.
— Angela Duckworth

Atomic Habits – James Clear

Once you have a sense of direction, you need to build the creative habits to put things into action. The concept behind Atomic Habits is that by stacking tiny habits over time you can achieve compounding, remarkable results. Your creative results, as Clear suggests, are the lagging measure of your habits. He offers great insight into nonlinear growth (breakthrough moments), identity, discipline, and environmental design. The importance of building better systems is hard to overvalue. There’s room for everyone to improve in this capacity, and if nothing else it’s a refreshing reminder: “Does this behavior help me become the type of person I wish to be? Does this habit cast a vote for or against my desired identity?"

It is only by making the fundamentals in life easier that you can create the mental space needed for free thinking and creativity.
— James Clear

Creativity, Inc. – Ed Catmull

One of the best modern examples of the impact that comes from harnessing creativity and building a culture where the creative process can thrive. Catmull discusses the evolution of Pixar Animation, including the philosophies and strategies that have established them as creative force. Most notably, the team at Pixar embraces the years of ambiguity inherent to the creative process as a story evolves into its own. Instead of becoming attached to a single storyline or character, they seek out a deep truth at the core of the film–the guiding principle–and craft the story around that. Catmull also emphasizes 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.

There is a sweet spot between the known and the unknown where originality happens; the key is to be able to linger there without panicking.”
— Ed Catmull

Leonardo da Vinci – Walter Isaacson

Throughout history there have been more profound, practical thinkers than Leonardo. But there’s never been anyone as creative as he was across so many different fields–art, science, engineering, technology, the humanities. If you’re hoping to improve your own creativity, you can do worse than studying the life and work of the person who became history’s archetype of the Renaissance Man. The depth of his curiosity and imagination are something to behold. What makes Leonardo such a powerful influence is that he was relatable and not some distant, untouchable figure. His creative genius was self-made, built from personal experience, experiments, and dedication to his craft.

Be open to mystery. Not everything needs sharp lines.
— Walter Isaacson

And One More…

If five books isn’t enough, check out Mastery by Robert Greene. It’s a comprehensive guide to living a creative life, and one of my favorites. Greene starts with the essentials–discovering your art and immersing yourself in the mindset of an apprentice–and tracks the journey through building creative strategies and, ultimately, mastery.

The 5 Best Books I Read in 2018

Each month I send out a newsletter featuring the best books I’ve worked my way through (I filter out the stuff that sucks). But that list grows quickly and I know it can be tough to decide what to read next. The degree to which a book resonates with you depends largely on the timing of when you read it–what obstacles you’re facing, what skills you’re trying to develop, what your current priorities are.

To provide a more useful starting place, I’ve reflected on the past year and narrowed down my top recommendations to just five books. These are the books that resonated strongest with me at different points in the year and whose lessons remain just as relevant today.

I hope you find something awesome. You can’t go wrong with any of these books. Each is profound and insightful in its own way. If you want to check out my notes before you dive in, click on the book title to see more. Keep up the good reading.

1. The Messy Middle – Scott Belsky
More than a business book, and that’s what I loved about it. It’s about embracing the long game and leading through ambiguity. Whether you’re an entrepreneur or artist, you’ll find relevance. Belsky details the endurance that it takes to bring an idea to life. It might not be as pretty as the beginning or end, but the middle is worthy of equal attention since it’s where most of the journey takes place. Overall, it's a great resource for those who are guiding others (or themselves) through uncertainty. Check out my notes or Amazon for details and reviews.

Curiosity is the fuel you need to play the long game.
— Scott Belsky



2. The Invention of Nature: Alexander von Humboldt's New World – Andrea Wulf
The story of one of the most profound polymaths you've never heard of. Humboldt was a Prussian explorer, writer, geographer, and naturalist born in 1769. He revolutionized the way we view the natural world by making connections and framing nature as a unified whole. He viewed everything as reciprocal and interwoven, challenging the human-centered perspective that ruled up until that point in time (i.e. 'nature is made for the sake of man').

His work also influenced generations of scientists and writers including the likes of Charles Darwin, John Muir, and Henry David Thoreau. It's easy to see why Humboldt was so influential–the stories Wulf tells of his expeditions and adventures well into old age are fascinating. Check out my notes or Amazon for details and reviews.

Nature everywhere speaks to man in a voice familiar to his soul.
— Alexander von Humboldt



3. How to Change Your Mind – Michael Pollan
A look into the renaissance of psychedelics and how a new generation of scientists are testing their potential to improve mental health, including depression, anxiety, trauma, and addiction. Pollan is a brilliant writer, offering a healthy dose of skepticism throughout the book, which helps add a voice of reason to an often fanciful topic. He acknowledges the provocative, often uncomfortable frontier of psychedelic therapy, which sits somewhere between science and spirituality.

True to form, his deep interest in the natural world comes through, specifically as it relates to psilocybin. He also digs into the broader cultural and historical significance, detailing the stories of each influential character involved. But the best parts of the book are when Pollan examines ambiguous, difficult concepts such as consciousness, spirituality, and ego dissolution. Whether you're interested in better understanding the science, potential benefits to mental health, or a new lens through which to view the world and your own experience, this book makes significant contributions to furthering each. Check out my notes or Amazon for details and reviews.

For me, ‘spiritual’ is a good name for some of the powerful mental phenomena that arise when the voice of the ego is muted or silenced.
— Michael Pollan



4. The Inner Game of Tennis – W. Timothy Gallwey
I'm usually skeptical of anything that resembles sports as a metaphor for life, but this a tremendous read. It's less a book about tennis (although there are a few sections) and more about the art of relaxed concentration. It's a simple but profound concept that suggests the secret to performing your best is in developing a quiet confidence, and most importantly, not trying too hard.

Gallwey draws a line between Self 1–the conscious teller, and Self 2–the doer. He advocates developing greater trust in Self 2, which helps to cultivate effortless concentration (flow), instead of a more tense, overly controlled approach which creates an unnecessary obstacle. Gallwey also offers an insightful perspective as he digs deeper into concepts including judgment, ego, and mindfulness, which adds another dimension to the book. Check out my notes or Amazon for details and reviews.

The player of the inner game comes to value the art of relaxed concentration above all other skills; he discovers a true basis for self-confidence; and he learns that the secret to winning any game lies in not trying too hard.
— W. Timothy Gallwey



5. Leonardo da Vinci – Walter Isaacson
The amount of information in this book is incredible (biographies by Walter Isaacson are not quick reads). Throughout the book, I marveled at not only Leonardo, but also Isaacson’s ability to aggregate so much information and tell a compelling story. He’s brilliant at drawing out subtle themes that help tie everything together. Leonardo feels relatable and human in that his genius was self-made, built from personal experience/experiments and dedication to his craft(s). But he feels simultaneously distant in that the breadth of his abilities across disciplines, obsession with detail, and ability to bridge observation and imagination seem otherworldly.

This book is an investment, but you’ll walk away with a reenergized curiosity and a newfound appreciation for the finer details in life. That’s what makes books like this worth it–the message resonates far stronger than what you might get out of a 200-page popular nonfiction title. Check out my notes or Amazon for details and reviews.

“Vision without execution is hallucination...Skill without imagination is barren.”
— Walter Isaacson