Here's my reading list with ratings and detailed notes. You can read more about my reading and note taking system here.
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Confident Data Skills – Kirill Eremenko
Date read: 3/29/19. Recommendation: 8/10.
Great resource for those wanting to learn the fundamentals of data science. It’s particularly relevant if you’re looking to better leverage data in your existing job (as I am in product management) or explore a new career path in data science (huge opportunities here, in case you’ve been living under a rock). Eremenko does a great job breaking down the data science process for beginners and explaining the essential algorithms. Case studies from Netflix and LinkedIn, help bring these concepts to life.
The Culture Code – by Daniel Coyle
Date read: 3/24/19. Recommendation: 7/10.
Short read discussing the foundations of great culture. Coyle references some of the world’s most successful organizations and leaders, including Pixar, Google, New Zealand’s All Blacks, Gregg Popovich, and the Navy SEALs. Each remarkable culture shares three key elements–building safety, sharing vulnerability, and establishing purpose. It’s worth skimming through for the few important takeaways and examples he shares.
Skin in the Game – by Nassim Taleb
Date read: 3/21/19. Recommendation: 9/10.
True to form, Taleb challenges standard conventions and long-held beliefs about a range of topics including uncertainty, symmetry, risk sharing, and rationality in complex systems. Skin in the game means having exposure to the real world and paying a price for consequences, good or bad. He explains that it’s necessary for fairness, commercial efficiency, and risk management. But most importantly, it’s necessary to understand the world. Taleb digs into real-world applications of his ideas and explains important heuristics like the Lindy effect. This will give you an entirely new lens to view the world and open your eyes to things you might never have questioned before. I cannot recommend his books enough, this is as great of a starting place as any. Love him or hate him, he’s one of the most original minds of our time.
The Silk Roads – by Peter Frankopan
Date read: 3/5/19. Recommendation: 7/10.
A comprehensive world history from the perspective of the East. The entire book is an important reminder that before the modern era, the Middle East and Asia were the scientific hubs of the world. Places like Iraq, Uzbekistan, and Afghanistan were the centers of logic, theology, mathematics, medicine, and philosophy. The Silk Road allowed ideas and goods to spread, connecting distant people and cultures, from the Pacific to the Mediterranean. For most of history, Western Europe was an isolated, intellectual backwater. Frankopan details all of this and how the world’s political and economic center of gravity eventually came to shift West in recent centuries. It’s a great resource if you want to challenge your Western-centric view of history (it could also double as religious studies course).
Genghis Khan and the Making of the Modern World – by Jack Weatherford
Date read: 2/15/19. Recommendation: 8/10.
An intriguing look into the life of Genghis Khan and the far-reaching impact of the Mongol Empire that continues to be felt in the modern world. Genghis Khan’s life and character were shaped by the rugged terrain of the Mongolian steppe. He faced a bitter fight for survival from the moment he entered the world. He would take the harsh lessons he learned from an early age to unite warring tribes on the steppe and inspire a deep loyalty in his people. In 25 years under Genghis Khan, the Mongol army conquered more lands and people than the Romans conquered in 400 years. But his most significant contribution was that he set foundation for the modern world with free commerce, open communication, shared knowledge, secular politics, religious coexistence, international law, and diplomatic immunity.
The Tigress of Forlì – by Elizabeth Lev
Date read: 2/7/19. Recommendation: 8/10.
The story of Renaissance Italy’s most courageous countess, Caterina Sforza. Her tale is one of clever strategy, boldness, and determination. Sforza’s life reads like a storybook as she fights off her husband’s assassins, the French Army, and Cesare Borgia. Throughout her life, powerful men viewed her as a pawn on the chessboard of Italian politics. They doubted her ability to rule and never took her seriously. She would prove this to be foolish, time and time again. Fascinating, inspiring biography.
Legacy – by James Kerr
Date read: 2/1/19. Recommendation: 7/10.
A detailed look at the principles and strategies of history’s most successful rugby team, New Zealand’s All Blacks. There are some great quotes in this book and at its core, it’s all about leadership. Kerr examines the things that set apart the All Blacks, including: discipline, self-awareness, culture, adaptation, storytelling, and purpose. It’s an insightful read that will provide immediate takeaways which you can use to become a better person and a better leader.
Creativity, Inc. – by Ed Catmull
Date read: 1/22/19. Recommendation: 9/10.
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.
Inspired: How to Create Tech Products Customers Love – by Marty Cagan
Date read: 1/9/19. Recommendation: 7/10.
A valuable resource for technology teams that’s tailored to product management. Cagan discusses the principles of strong product teams and breaks down the individual roles–product managers, designers, engineers, product marketing, and other supporting positions. He also discusses the process of getting to the right product through discovery, ideation, prototyping, and testing. At times it can be a bit prescriptive and could use a few more stories to illustrate the concepts and techniques. But overall, worth the read for entrepreneurs operating in this space or those looking for an introduction to technology product management.
The Laws of Human Nature – by Robert Greene
Date read: 1/1/19. Recommendation: 10/10.
As close to perfection as a book can get. This is the culmination of Greene’s lifetime of work focused on power, influence, and mastery, brought together in a single text focused on the truths of human nature. It’s an instructive guide to human nature and people’s behavior, based on evidence rather than a particular viewpoint or moral judgment. As Greene emphasizes throughout the book, understanding human nature in a deep way is advantageous for countless reasons. It helps you become a strategic observer, better judge of character, outthink malicious people, motivate and influence those around you, alter negative patterns, develop greater empathy, and recognize your true potential. True to form, Greene pulls stories from both sides throughout history–masters and those who have failed spectacularly–to breathe life into each law. I cannot recommend this book highly enough. It’s an incredible resource and an investment that will pay dividends for your entire life. The sooner you read it, the better.
Man’s Search for Meaning – by Viktor Frankl
Date read: 12/14/18. Recommendation: 9/10.
Frankl documents his story of survival in Nazi concentration camps during World War II. His experience at Auschwitz reinforced one of his key ideas: life is not a quest for pleasure or power, but a quest for meaning. Throughout the book, he reflects on Nietzsche’s insight that, “He who has a why to live for can bear almost any how.” Frankl suggests that there are three primary outlets to instill life with meaning: courage during difficult times, relationships, and creativity. I drew strong connections between this and one of my favorite books, Tribe by Sebastian Junger, which spotlights veterans and the struggle to find loyalty, belonging, and meaning in modern society. Man’s Search for Meaning is profound and a catalyst for insightful discussions on the importance of meaning and the role of suffering in our own lives.
Make Time: How to Focus on What Matters Every Day – by Jake Knapp and John Zeratsky
Date read: 11/28/18. Recommendation: 7/10.
Strategies and tactics for creating more time to focus on the things you care about. It’s not about productivity, it’s about setting your own priorities. Similar to Sprint, they offer a framework to assist in the process: Highlight, Laser, Energize, Reflect. The real value of the book comes from the individual tactics they suggest, such as creating a distraction free phone, differentiating between “fake” and “real” wins, and bucking cultural norms. It’s all about becoming more intentional in how you spend time and allocate your energy. If you want to work on improving your own priorities and ability to focus, this is a solid resource.
Chronicles: Volume One – by Bob Dylan
Date read: 11/23/18. Recommendation: 8/10.
Dylan’s career is a master class in embracing the impermanence of identity and authenticity. The fragments of himself that he brought to life shows he understands this in a deep way. Dylan resonates with people because his songwriting tracks his own development as a human being. His songs reflect who he was–his observations, experiences, and imagination–and who he refused to be at each point in time. In Chronicles, it helps to be familiar with Dylan’s work since the chapters jump between different points of his career and he name-drops dozens of obscure folk artists. If that’s not your thing, it’s still worth reading. Just don’t get hung up on the dense sections. Dylan, full of complexity and brilliance, offers insight into creativity, identity and human nature. Chronicles will challenge the way you think and force you to consider things through a new lens–perhaps the highest compliment a book can receive.
Atomic Habits – by James Clear
Date read: 11/4/18. Recommendation: 8/10.
The idea behind Atomic Habits is that by stacking tiny habits over time you can achieve compounding, remarkable results. Your outcomes, as Clear suggests, are the lagging measure of your habits. He offers great insight into nonlinear growth (breakthrough moments), identity, discipline, and environmental design, as it relates to behavior change. The models used throughout the book help make each concept relatable and are something I will come back to for years to come. The importance of playing the long game and building better systems is hard to undervalue. 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?"
Grit – by Angela Duckworth
Date read: 10/30/18. Recommendation: 8/10.
A detailed look at what sets apart highly successful people. Top performers, as Duckworth suggests, are unusually resilient and hardworking. But they’ve also developed something else–a deep awareness of what they want. Grit is this combination of direction and determination. She discusses the importance of effort, deliberate practice, purpose, and stamina over intensity. The best thing about the book and her 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, she emphasizes that this comes through a discovery period–often messy, serendipitous, and inefficient–followed by years of refinement, and a lifetime of deepening. It’s not going to happen overnight. You have to figure out what you’re working towards and what you can sustain indefinitely.
The Manual – by Epictetus
Date read: 10/24/18. Recommendation: 8/10.
Enjoyed the Ancient Renewal translation by Sam Torode. I’m always eager to read any new or updated translation of the classics. I’ve always found Epictetus to be one of the more inspiring Stoic philosophers. This is a great introduction to Stoicism for those interested in the philosophy. It’s also a great refresher for those already familiar. He discusses themes of impermanence, substance, expectations vs. reality, mental toughness, and authenticity.
The Messy Middle – by Scott Belsky
Date read: 10/20/18. Recommendation: 9/10.
More than a business book, and that’s what I loved about it. It’s a book about embracing the long game and leading through ambiguity–whether you’re a founder, entrepreneur, or artist, you’ll find relevance. Belsky details the endurance it takes to bring an idea to life. It’s not always 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. As a product manager, I found the book to be particularly insightful for my daily work and career. The next time I’m asked for a great product book, I’ll be recommending this. But again, the beauty of this book is that it’s relevant for anyone who’s building something from nothing. Those who are leading others (or themselves) through uncertainty will benefit greatly from it. Far from a generic business book with the same recycled ideas, it’s original, practical, profound, and one of the best books I’ve read all year.
Leonardo da Vinci – by Walter Isaacson
Date read: 9/29/18. Recommendation: 9/10.
The amount of information in this book is incredible–biographies by Walter Isaacson are not quick reads. Throughout the book, I’d marvel at not only Leonardo, but also Isaacson’s ability to aggregate so much information and tell a compelling story. He’s brilliant in 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 also 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.
Your Move: The Underdog’s Guide to Building Your Business – by Ramit Sethi
Date read: 9/20/18. Recommendation: 8/10.
Ramit Sethi is one of my favorite humans and writers (I Will Teach You to Be Rich is a gem, if you haven’t read it). He’s someone who gets it. Whether it’s finance, or in this case business, he’s always focused on the things that matter and assigning things their proper weight. In Your Move he offers insight into handpicking customers, being more selective about who you target, and why that’s fundamental to success. He emphasizes authenticity and crafting a message that resonates with your target audience’s hopes, dreams, pain points, and fears. It’s a book that should be able to point you in the right direction whether you’re struggling with your initial idea, defining your audience, or putting yourself and your product out there. There’s actionable insight for each.
The Consolations of Philosophy – by Alain de Botton
Date read: 9/8/18. Recommendation: 7/10.
An introduction to some of the greatest thinkers including Socrates, Epicurus, Seneca, Montaigne, Schopenhauer, and Nietzsche. Botton wraps each philosopher in the context of consolation for a different human struggle (Seneca = consolations for frustration). If you’re already into philosophy, it’s an interesting format you’ll find both strange and engaging. If you’re not, it provides an accessible introduction to the subject without requiring a college course on abstract thought.
Everybody Writes – by Ann Handley
Date read: 9/3/18. Recommendation: 8/10.
Handley’s background in marketing differentiates this from other ‘how to write’ books. She remains focused on how to write better and the rules of writing, but there’s an emphasis on measurable results. It’s a solid resource for any writer or content creator. It’s a great reminder (and guide) to cut the unnecessary, be more direct, and improve readability. All of which are important because they help you not only capture initial attention, but also preserve/build that momentum between sentences and paragraphs. The end goal is creating something that resonates with your audience and enriches their lives.
The Invention of Nature: Alexander von Humboldt's New World – by Andrea Wulf
Date read: 8/18/18. Recommendation: 9/10.
The story of one of the most profound polymaths you've probably 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'). Humboldt's fascination with nature brought together art and science, combining exact observation with painterly descriptions, which helped make science far more popular and accessible. 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 both fascinating and inspiring.
Rework – by Jason Fried and David Heinemeier
Date read: 8/4/18. Recommendation: 8/10.
Relevant to anyone building, running, or growing a business. Fried and Heinemeier offer valuable first-hand experience that goes against conventional, mediocre business advice. They discuss the approach and tactics they've used to grow their own software company, Basecamp, to reach over 3 million people around the world. Much of their advice centers around remaining small, frugal, and profitable. They caution against business plans, workaholics, and ramping up as an end goal. Instead favoring adaptability, hiring people who have lives outside of work, and simplicity. They even encourage letting your customers outgrow you, rather than altering your product to add complexity. Keep it simple and build something that makes it as easy as possible for new people to get on board (that's where the continued growth lies).
Benjamin Franklin: An American Life – by Walter Isaacson
Date read: 8/1/18. Recommendation: 9/10.
A brilliant look at the multi-disciplinary life of Benjamin Franklin. As a scientist, inventor, diplomat, writer, business strategist, and political thinker, it's fascinating how many pivotal moments of early American history he was involved in. In each aspect of his life, he prided himself in practical solutions that served the common good. As Isaacson suggests, Franklin was the first great American exemplar of the Enlightenment and the Age of Reason–as defined by an emphasis on reason, education, and a distrust of arbitrary authority. He was unapologetically self-taught and self-made. Isaacson doesn't shy away from Franklin's complexities and does a great job explaining how his legacy has shifted over time, reflecting the values of different eras. There's a reason he's held in such high esteem by some of the most brilliant minds of our time.
The Geometry of Wealth – by Brian Portnoy
Date read: 7/4/18. Recommendation: 9/10.
A look into the relationship between money and meaning. Portnoy suggests that wealth and investing are about funding contentment and underwriting a meaningful life, as defined by you. Not about getting rich, having "more," and losing yourself on the hedonic treadmill. He explains that simplification is the path towards effectively managing expectations in money and life–and the trajectory of a happy life is shaped by expectations. The Geometry of Wealth is as practical as it is philosophical. À la Charlie Munger, Portnoy emphasizes individual behavior, mainly self-control and self-awareness, as the most important factor in investment success. He suggests we focus on being "less wrong" over being "more right," in the sense that asset allocation is far more important than security selection and market timing. But he also takes a deeper look at experienced happiness, reflective happiness, expectations, and human nature, which adds an entire extra dimension to this fascinating book.
Real Artists Don't Starve – by Jeff Goins
Date read: 6/8/18. Recommendation 7/10.
Practical and refreshing resource for smart creatives and entrepreneurs. Goins picks apart the myths surrounding the Starving Artist and offers an improved alternative of the Thriving Artist. There are dozens of useful rules of thumb you can apply to your own position, no matter where you are in the journey. Thriving Artists build their creative dreams step by step (not overnight). They focus on rearrangement and building upon the work of those who have influenced them (not obsessing over originality). They leverage their existing jobs for resources (not quitting too early and without reason). They recognize the value of a multidisciplinary approach and multiple revenue streams (not mastering a single skill and risking it all on a single bet). Goins follows this same pattern throughout the book, detailing the difference in mindsets, how to position yourself in the market, and how to make a living. It's a modern-day guide for living a better, more creative life, without struggling for the sake of struggling.
The Four Tendencies – by Gretchen Rubin
Date read: 5/29/18. Recommendation 7/10.
Rubin details four main personality tendencies–upholder, questioner, obliger, rebel–that we all gravitate towards based on how we handle internal and external expectations. It's an interesting look into human nature and quite valuable when considering how we should motivate, persuade, or navigate conflict with ourselves and others. There's no one-size-fits-all. She details each of the four tendencies in depth, while conceding that there are an enormous range of personalities, even among people with the same tendency. This dramatically influences how each of the tendencies are expressed. The goal of the book is to help us better understand ourselves and those around us by building greater self-awareness and acknowledging our differences. That way we can leverage our strengths, navigate our weaknesses, and build lives that work better for us.
How to Change Your Mind – by Michael Pollan
Date read: 5/25/18. Recommendation 9/10.
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 (mushrooms). 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 moments when Pollan examines ambiguous, difficult concepts such as consciousness, spirituality, ego dissolution, and the ineffability of his own psychedelic experiences. 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.
The Inner Game of Tennis – by W. Timothy Gallwey
Date read: 5/1/18. Recommendation: 9/10.
I'm usually skeptical of anything that remotely 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, awareness, ego, and mindfulness, which adds another dimension to the book.
Enlightenment Now – by Steven Pinker
Date read: 4/28/18. Recommendation: 8/10.
As the title suggests, Pinker makes the argument for reason, science, humanism and progress–the four themes that tie together thinkers of the enlightenment. He focuses on all the ways the world is improving, stating the case for optimism in a similar vein as The Rational Optimist (Matt Ridley) and The Moral Arc (Michael Shermer). It's a refreshing dose of perspective in a world that seems increasingly convinced that the end is near. Using statistics to back his position, Pinker tackles a range of subjects including inequality, political ideology, wealth, happiness, morality, and religion, to name a few. All this is not to suggest that progress is utopia, we should always strive to improve, but we should also appreciate how far we've come. The only drawback to the book is its density, which makes its ideas less accessible than I had hoped.
The War of Art – by Steven Pressfield
Date read: 4/15/18. Recommendation: 8/10.
Worth the investment for any creative. It's a short read and a manifesto that many hold dear. Pressfield cuts through excuses which embody what he defines as Resistance. He offers blunt advice to eliminate distractions and get on with the work you should be doing. The only thing that matters is sitting down and putting in the effort, every single day. The more you're able to remove your ego from that equation, the less interference there will be. We've all struggled with Resistance in some form–procrastination, fear, low self-confidence, rationalization. The War of Art is a call to overcome that and move yourself into a higher sphere by dedicating uninterrupted time to your craft.
When: The Scientific Secrets of Perfect Timing – by Daniel H. Pink
Date read: 4/11/18. Recommendation: 6/10.
Easy read with a few interesting takeaways regarding the science of timing. You'll get most of the value this book has to offer within the first 50 pages. Pink details how everyone experiences the day in three stages–a peak, trough, and rebound (not necessarily in that order). Each has a unique impact on our cognitive abilities. The key is to develop a greater awareness of when we should perform certain tasks by identifying our own personal chronotype – individual biological clock that affects performance and mood. Anyone who's dialed in to their own mental and physical abilities has likely built a natural awareness and routine around this, but it's always worth the reminder.
Quiet: The Power of Introverts in a World That Can't Stop Talking – Susan Cain
Date read: 3/27/18. Recommendation: 8/10.
Quiet is a bible for introverts. Cain struck a chord with a massive, often overlooked audience, with an insightful look into the place of introversion in our culture that has come to hold extroversion as the highest ideal. But it's an important book for introverts and extroverts alike. For introverts, it offers a resource and the reassurance to be authentic, put yourself in the right lighting, and use your natural strengths. Cain also digs into concepts like restorative niches, soft power, self-monitoring, and deliberate practice–all familiar concepts to introverts. She also gets a bit more granular and discusses the difference between temperament and personality, nature vs. nurture, and the evolutionary benefits to each personality type. As Quiet suggests, the goal is to identify your own preferences along the spectrum introversion/extroversion so you can spend more time in your sweet spot and get the most out of your life.
How Google Works – by Eric Schmidt and Jonathan Rosenberg
Date read: 3/11/18. Recommendation: 9/10.
Fascinating read and tremendous resource for anyone working in a startup and/or the tech industry. How Google Works offers an insightful look into all the elements that have contributed to Google's success in recent years, as well as the initiatives that have come up short. The core tenets of the book emphasize the importance of creating great products, attracting smart creatives, and cultivating an environment where you can succeed at scale. Many of these contradict the way massive corporations work–Google values user experience over revenue, transparency at all levels, less ego, more freedom, fewer meetings, and smaller teams, to name a few. As a side note, make sure you grab the latest edition of this book, as it contains an interesting addition that discusses how Alphabet (Google's parent company) works.
10% Happier – by Dan Harris
Date read: 2/27/18. Recommendation: 8/10.
If you're skeptical of meditation and mindfulness, this book was written for you. Harris questions everything and cuts through the inane and fanciful self-help industry–including the likes of Eckhart Tolle and Deepak Chopra. Instead, he focuses on practicality and offers a more rational approach. Harris entertains through his personal narrative, while discussing the importance of concepts like impermanence, insecurity, and the power of negative thinking. Each of these elements play a role in cultivating mindfulness–an ability to recognize what's happening in your mind right now without getting carried away by it. For Harris, despite his skepticism, this was the difference in becoming a less stressed, and more secure, collected version of himself.
The Black Swan: The Impact of the Highly Improbable – by Nassim Taleb
Date read: 1/28/18. Recommendation: 9/10.
A strong case could be made that Nassim Taleb is one of the most original minds of our time. It's well worth reading every book of his Incerto series, which includes: Antifragile, The Black Swan, The Bed of Procrustes, and Fooled by Randomness. Taleb defines Black Swans as events with the following three attributes: rarity, extreme impact, and retrospective (though not prospective) predictability. He discusses how the root of our inability to understand Black Swans lies in mistaking a naive observation of the past to be representative of the future. The book details specific themes that arise from our blindness to the Black Swan, including: confirmation bias, narrative fallacy, human nature, silent evidence, and tunneling. Taleb sets out to make us more aware of the biases in our logic as it relates to Black Swans so that we might better embrace our own humanity (that's part of it!) and avoid large-scale harmful predictions that might hurt our future. He advocates the "barbell" strategy and positioning ourselves to take advantage of positive Black Swans (lose small to win big) and situations where favorable consequences are much larger than unfavorable ones.
A More Beautiful Question – by Warren Berger
Date read: 1/19/18. Recommendation: 8/10.
I first heard Warren Berger on The Knowledge Project podcast, then purchased this book in an effort to improve my own questioning ability. While it is a great resource for asking better questions, this book offers so much more than that. It's an insightful look into the role of inquiry in modern life. Berger suggests that as the world becomes more complex and dynamic, questions become more valuable than answers. He offers a framework to formulate and ask better questions. But he also digs deeper into topics such as the age of adaptation, design thinking, our education system, and the reasons people avoid fundamental questioning. As an added bonus, there are some brilliant questions Berger challenges us to consider for ourselves along the way.
Zero to One – by Peter Thiel & Blake Masters
Date Read: 1/12/18. Recommendation: 8/10.
I had high expectations for this one, considering it has become a sacred text for many startups and entrepreneurs. But Zero to One did not disappoint. The core of the book emphasizes that there is no single secret to innovation and entrepreneurship. But Thiel explains that if we want to to create a better future, we can't wait around, we have to go out and actually build it. He touches on concepts like vertical progress, opposite principles, monopolies, luck, venture capital, and the importance of getting the founders right when launching a new startup. The first half of the book is particularly brilliant. If you're an entrepreneur or working in technology, there's a reason this book is so highly rated.
The Inevitable: Understanding 12 Technological Forces That Will Shape Our Future – by Kevin Kelly
Date Read: 12/27/17. Recommendation 7/10.
Kelly is a great teacher when it comes to helping others think beyond the realm of current possibilities. I often find myself fighting the inertia of the way things currently are, instead of looking at the inevitable trends and determining what's next. The specific forces he outlines become a bit repetitive, as there is significant overlap to each. But as a whole it's a great exercise in reminding yourself to take your thinking to the next level. Kelly is also refreshingly optimistic about the future of technology. He suggests that while we have little control over the inevitable technological forces on the horizon, we do have influence over their character and how symmetrical those relationships end up being.
Tribe of Mentors – by Tim Ferriss
Date Read: 12/20/17. Recommendation: 8/10.
Tribe of Mentors is built around a set of 11 questions that Tim set out to answer for himself by asking some of the most brilliant people (100+ in this book). Most of the questions are the same as the rapid-fire questions he uses in his podcast, "what book have you gifted the most?" and "what new belief, behavior, or habit has most improved your life?" There are a few nuggets of eye-opening wisdom, but the brevity kept things fairly shallow for me. I prefer Tools of Titans which covers a wider range of ideas in greater depth, and includes more of Tim's own notes and insights. For me, the most valuable part of Tribe of Mentors was its wealth of book recommendations
The Undoing Project: A Friendship That Changed Our Minds – by Michael Lewis
Date Read: 11/26/17. Recommendation: 9/10.
A fascinating look into the unlikely relationship and original contributions of two Israeli psychologists, Daniel Kahneman and Amos Tversky. Together they examined how people make decisions and predictions, and uncovered the systematic bias and errors that are inherent to each. They found that the human mind replaced laws of chance with rules of thumb–what they referred to as "heuristics," including availability, representativeness, anchoring, and simulation. Each heuristic reveals itself in the form of a cognitive bias (hindsight, recency, vividness, etc.). The papers of Kahneman and Tversky have had widespread positive implications, helping to educate experts in various fields (economics, policy, medicine) of their own biases, and ultimately leading to the creation of "behavioral economics."
The Airbnb Story – by Leigh Gallagher
Date Read: 11/15/17. Recommendation: 7/10.
Essentially a giant case study of Airbnb and its founders–Brian Chesky, Joe Gebbia, and Nathan Blecharczyk–which documents the evolution of their initial concept through its unprecedented growth. With regard to each of the founders, it was interesting to hear about their backgrounds and a great reminder that there's no one-size-fits-all approach to launching a company. Chesky and Gebbia were resourceful and got things off the ground without the traditional "technical DNA" that most investors in Silicon Valley obsess over. Their art-school background ended up being an asset that helped set them apart from competitors (better user interface), along with a perfect wave of external factors including timing, price, and a shift in consumer preferences towards artisanal experiences. Gallagher also does a great job remaining objective and presenting both sides of the story–as Airbnb hasn't come without controversy. It's one of the most engaging success stories of recent years.
Hooked: How to Build Habit-Forming Products – by Nir Eyal
Date Read: 11/11/17. Recommendation: 6/10.
Examines how to engineer user behavior, the moral implications, and how to leverage those findings to improve people's lives. Eyal documents each step of the "hook model," consisting of a trigger, action, investment, and variable reward. It's a short read and doesn't advance much past the basics, but if you're looking for an introduction to the startup mindset and how to begin building a product or service of your own, it's worth your time.
Poor Charlie's Almanack – by Charles T. Munger & Peter D. Kaufman
Date Read: 11/1/17. Recommendation: 9/10.
This is one of those must-read books because Munger's concepts are foundational to so many other authors and their ideas. To set expectations, the book is a monster. It took me months and multiple attempts to get through because there is so much there. It's comprised of 11 speeches given by Munger over the years. He details his now-popularized concept of "multiple mental models" and building a latticework of these models to improve cognition. Munger explains that adopting a more multidisciplinary approach is critical to achieving this, and cites Keynes when he suggests that it's better to be roughly right than precisely wrong. He also outlines "sit-on-your-ass investing" and the general approach that led to his success alongside Warren Buffett at Berkshire Hathaway. Poor Charlie's Almanack is one of those that you should sit with and reflect on so you can take it all in.
The Lessons of History – by Will & Ariel Durant
Date read: 10/22/17. Recommendation: 7/10.
A high-level look at the major lessons and themes throughout human history. The Durant's discuss race, religion, economics, capitalism, socialism, war, progress, and heritage, to name a few. They offer some interesting insights that are particularly relevant in today's politically-charged climate. They tackle the concentration of wealth, value of free enterprise, and increasing complexity of the economy. The Lessons of History also wisely reminds us to maintain a healthy level of skepticism as, "history is so indifferently rich that a case for almost any conclusion from it can be made by a selection of instances."
Principles – by Ray Dalio
Date read: 10/14/17. Recommendation: 8/10.
Dalio offers a detailed analysis of his principles for life and work, which have led him to become one of the most successful investors of our time. He offers these lessons with a refreshing dose of humility–not what you'd expect from the founder of one of the world's largest hedge funds. I gravitated towards his life principles where he champions truth, the value of painful mistakes, and the importance of looking beyond first-order consequences. His work principles also offer great insight into human relationships, conflict resolution, and the importance of building a culture of transparency.
Mastery – by Robert Greene
Date read: 9/30/17. Recommendation: 10/10.
You would be hard-pressed to find a more profound, relevant book, no matter your position in life. If I had to recommend a single book of Greene's to get you started, this would be it. He begins by defining mastery as the sensation we experience when we feel that we have a greater command of reality, other people, and ourselves. The book offers a deep dive into every element of mastery–including insight for those just starting out and searching for their life's task. True to form, Greene also provides detailed accounts from some of the greatest masters in history–Leonardo da Vinci, Benjamin Franklin, Charles Darwin, Albert Einstein, Paul Graham, and dozens more.
The 50th Law – by Robert Greene
Date read: 9/12/17. Recommendation: 8/10.
Greene pairs up with Curtis Jackson (50 Cent) to offer a real-world look into the laws of power and perseverance. He details stories from Jackson's rise and dissects how he was able to evolve and create momentum to escape dire circumstances. The more interesting sections of the book examine the underlying themes in Jackson's stories, such as fearlessness, self-reliance, and persistence.
Fooled by Randomness – by Nassim Nicholas Taleb
Date read: 8/28/17. Recommendation: 8/10.
Deep dive into the role of luck in the financial markets and life. Taleb emphasizes how we tend to only accept randomness in our failures, never in our successes. He discusses concepts like Monte Carlo math, Russian roulette, the Pólya process, nonlinearity and the human brain, and Buridan's donkey. Our tendency to favor the visible, narrated, and neat models, leads us to being fooled by randomness. He summarizes best by suggesting we are all idiots who are mistake prone, but only a handful of us have the rare privilege of knowing it.
The Bed of Procrustes: Philosophical and Practical Aphorisms – by Nassim Nicholas Taleb
Date read: 8/18/17. Recommendation: 9/10.
Great introduction to Taleb's take on uncertainty, which he discusses in detail in his other books that make up the Incerto series: Antifragile, Fooled by Randomness, and The Black Swan. This book offers a succinct look into how we deal with what we don't know. Taleb examines our tendency to package and reduce ideas into neat narratives that fit within the constraints of our limited knowledge.
On Writing Well: The Classic Guide to Writing Nonfiction – by William Zinsser
Date read: 8/14/17. Recommendation: 8/10.
An essential for nonfiction writers. This is the only book I keep within reach as I'm writing. Zinsser advocates a lean, direct writing style. He outlines strategies for crafting a more effective story that resonates with readers. This includes how to cut down first drafts, rewrite, organize the flow of an article, develop your own voice, address your audience, handle humor, and avoid the danger of clichés. There's also a practical style guide for reference that addresses everything from the use of qualifiers (rather, quite, very) to specific punctuation marks (dash, colon, exclamation point). Every writer will be better for picking this up.
Perennial Seller – by Ryan Holiday
Date read: 8/6/17. Recommendation: 9/10.
You can't go wrong with any of Holiday's work. His latest is a great read for anyone who considers themselves creative, and particularly insightful for writers and entrepreneurs. If you're thinking of writing a book or bringing an idea to life, start here and save yourself a few headaches. He outlines best practices for the creative process, along with the importance of positioning, marketing, and building a platform. The most important advice 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. Put in the work.
The Rational Optimist – by Matt Ridley
Date read: 7/29/17. Recommendation: 8/10.
I read this book to combat confirmation bias. I tend to romanticize the past and idealize the simple living we associate with the hunter-gatherer era. As such, I read a lot of books that fall in line with that interest. Ridley makes the argument that we're currently living in the best period of human history (which we are). He credits this to the free exchange of ideas and knowledge, which breeds even more innovation and knowledge. He details the driving factors of dynamic change, bottom-up innovation, and how the specialization of talents has led to mutual gain for everyone involved. It's a dense book but Ridley offers brilliant insight, which should give you a much needed boost of optimism for the future.
I Will Teach You to Be Rich – by Ramit Sethi
Date read: 7/22/17. Recommendation: 9/10.
The most accessible, practical book I've read on personal finance. Sethi dismisses trendy advice, such as cutting back on lattes, and instead emphasizes saving on the big purchases that really matter. And he's hilarious. This book is all about optimizing your strategy, prioritizing what matters most, and making money work for you (instead of obsessing over the minute details). This is a must read for anyone in their 20s or 30s, and should be a required reading for all who can still take advantage of the most valuable asset in investing: time.
If You Can: How Millennials Can Get Rich Slowly – William J. Bernstein
Date read: 7/15/17. Recommendation: 7/10.
An easy-to-read overview of the topics covered in his earlier book, The Investor's Manifesto. I prefer the depth and detail of the latter. But if you're looking for an introduction to investing in low-cost index funds and the importance of developing a financial strategy at an early age, this is a good starting place.
The Investor's Manifesto – William J. Bernstein
Date Read: 7/5/17. Recommendation: 8/10.
Champions an investment strategy focused on low-cost index funds that track the market, rather than attempting to guess on individual stocks. This is a must-read when it comes to investing. And it's not a massive encyclopedia. Bernstein offers a more rational approach to investing by detailing historic returns of various asset classes, the importance of diversification, and why you must play the long game if you have any hopes of coming out ahead.
Growth Hacker Marketing – by Ryan Holiday
Date read: 7/2/17. Recommendation: 9/10.
Flips traditional marketing (and ad agencies) on its head in favor of the growth hacker mindset. Growth hacking still requires pulling customers in but it favors a more innovative, effective, and cheaper method of reaching the target audience. Holiday emphasizes the importance of Product Market Fit and building a product that generates explosive, contagious reactions from those who first see it. Great foundation to have in place before building any product, service, or following. Digs into real examples of some of the most successful startups in Silicon Valley (Airbnb, Twitter, Dropbox, etc.) and how they were able to adapt, optimize, and make themselves indispensable in the process.
How to Be a Stoic – by Massimo Pigliucci
Date read: 6/24/17. Recommendation: 4/10.
New addition to my library of Stoic philosophy. I didn't feel like it brought enough original ideas to the table, based on the books already out there. It's essentially a walkthrough of Epictetus. If you're looking to get into Stoicism, check out A Guide to the Good Life, Ego Is the Enemy, or The Obstacle Is the Way. Or go straight to the source and read Seneca or Marcus Aurelius.
Live Your Truth – by Kamal Ravikant
Date read: 6/19/17. Recommendation: 6/10.
Not a book I would typically read, but there are a few hidden gems in its passages. If you're looking for inspiration, it's an easy read that you can get through in a day. Ravikant's handful of original, eye-opening insights make it worth it. Most of the book is focused on tapping into yourself and living an authentic life.
Homo Deus: A Brief History of Tomorrow – by Yuval Noah Harari
Date read: 6/11/17. Recommendation: 8/10.
Follow-up to Harari's critically acclaimed Sapiens. Whereas Sapiens is focuses on humanity's history, Homo Deus examines on humanity's future. Compelling book in its own right and worth reading. Guaranteed to expand your perspective and worldview. He discusses how Homo sapiens came to dominate the world, imagine and assign meaning to life, and what our current trajectory looks like.
The Time Paradox – by Philip Zimbardo and John Boyd
Date Read: 6/3/17. Recommendation: 9/10.
Fascinating look at how the way we regard time influences the course of our lives. Zimbardo and Boyd discuss six distinct time perspectives and illustrate how they are a reflection of our personal attitudes, beliefs and values. Great insight into the future-oriented world we live in and what that means for those who are more present-oriented. Also offers an interesting examination of various religions and their effect on individual time perspectives and behaviors.
Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days – by Jake Knapp
Date read: 5/28/17. Recommendation: 8/10.
Targeted to those working in technology, but useful lessons that can be applied more broadly. The authors pioneered their own rapid sprint process at Google Ventures. The book documents, step-by-step, the best way to examine, prototype, and test new ideas with customers, in a single week. The faster you can test out a new idea out and gather real feedback, the better. Great framework for creative problem solving, no matter what project or initiative you're working on.
Walden – by Henry David Thoreau
Date read: 5/21/17. Recommendation: 8/10.
Another classic. Thoreau documents his two years of simple living in a cabin near Walden Pond outside Concord, Massachusetts. He discusses themes of minimalism and self-sufficiency. Along the way he emphasizes the value of reconnecting with the natural world, and hints at stoic themes with his disdain for modern luxuries and comforts. His motivation for the book? Ensuring he was not wasting his life on trivialities, and instead living in a more deliberate, meaningful fashion.
The Art of Travel – by Alain de Botton
Date read: 5/15/17. Recommendation: 6/10.
Interesting book that feels like a series of essays. Dissects why we travel, the inspiration for doing so, and contemplates the experience of traveling abroad in a way that resonates with any seasoned traveler. In certain sections the language gets a bit too abstract and flowery for my taste. But if traveling is a large part of your identity, you'll appreciate de Botton's ideas.
A Guide to the Good Life: The Ancient Art of Stoic Joy – by William B. Irvine
Date read: 5/8/17. Recommendation: 9/10.
There's no better modern introduction to Stoicism. Contrary to today's understanding of the term as a lack of outward emotion, it's a life philosophy which cultivates rationality, appreciation, and joy. Irvine discusses the practicality of Stoicism, how it applies to our every day lives, and the importance of adopting a coherent philosophy of life that suits us as individuals. He hits on key concepts in Stoic philosophy and wraps them in a modern, logical context. I originally read this book over a year ago, and almost every single word struck a chord with me. It was one of my first encounters with Stoicism and I was surprised to find it matched almost identically with my existing worldview, which I had pieced together over the years.
On the Shortness of Life – by Seneca
Date read: 5/4/17. Recommendation: 9/10.
If you're looking to dive deeper into the works of Seneca, this is a great follow up to Letters from a Stoic. I read the Penguin Great Ideas edition. It's a collection of three essays filled with plenty of brilliant insight that Seneca is so well known for.
The 48 Laws of Power – by Robert Greene
Date read: 4/17/17. Recommendation: 10/10.
This took me months to read because there's so much to it. Perhaps the most detailed, convincing book I've ever read. Greene sets forth the individual laws of power and offers countless historical examples of each in practice. Not a book you're going to finish over the weekend, but a very important book and investment. Greene makes the argument that it's not a question of ethics, the game of power is inescapable, even in our daily lives. We might as well learn the game and master the laws of power so we're more aware, less distracted, and better able to negotiate situations in our favor.
Meditations – by Marcus Aurelius
Date read: 4/5/17. Recommendation: 10/10.
A cornerstone of Stoic philosophy, along with Letters from a Stoic by Seneca. It's critical which interpretation you read. I highly recommend the Modern Library version with an introduction by Gregory Hays. It's a short read with some of the most useful insights and aphorisms that money can buy.
Antifragile - by Nassim Nicholas Taleb
Date read: 4/1/17. Recommendation: 10/10.
Taleb introduces his concept of antifragility, which explains that certain things (including us) benefit from a degree of randomness, chaos, and disorder. While comfort, convenience, and predictability, breed the opposite–fragility. He presents this as part of what he calls 'the central triad' which ranges from fragile to robust to antifragile. As he explains antifragility, he discusses the value systems that hold us prisoner, ancestral vs. modern life, and Seneca's version of Stoicism. It's a dense read, but worth it for a glimpse into the originality of Taleb's ideas.
Check out my notes or Amazon for details and reviews.
The Daily Stoic – by Ryan Holiday & Stephen Hanselman
Date read: 3/29/17. Recommendation: 9/10.
If you're this far along in my reading list and you're on board with Stoicism, you'll enjoy this book. The greater your interest in Stoic philosophy, the more you're going to get out of the book. It's a tremendous resource. There's also a daily newsletter that offers brief overviews of many topics covered in the book. I don't normally recommend signing up for mailing lists, but this one is worth checking out. It's a great daily reminder and a solid introduction to Stoicism if you're looking for a place to start.
Sapiens: A Brief History of Humankind – by Yuval Noah Harari
Date read: 3/21/17. Recommendation: 10/10.
This is my favorite nonfiction book, hands down. It's one of the most important books you'll read and tackles some of the biggest questions we face. Harari tracks human evolution and the implications of the cognitive revolution through the agricultural, industrial, and scientific revolutions. There's a reason it's so popular and highly regarded. Just read it.
The Antidote: Happiness for People Who Can't Stand Positive Thinking – by Oliver Burkeman
Date read: 3/11/17. Recommendation: 9/10.
Rejects the self-help industry and the "power" of positive thinking. One of my favorite books that I've read this year. Burkeman sees the obsession with positive thinking and attaining happiness as counterproductive, and the very thing that makes us unhappy. There are great chapters on Stoicism and negative visualization, meditation and non-attachment, resourcefulness and the myths of goal setting, as well as impermanence and the pitfalls of seeking safety above all else. Makes the case that living meaningfully starts with the negative path to happiness–one which embraces uncertainty, insecurity, and the realities of every day life–so you can better appreciate when things go right. Unrealistic positive expectations are not only ineffective, they're often counterproductive.
Talk Like TED – by Carmine Gallo
Date read: 3/5/17. Recommendation: 7/10.
Gallo dissects the most popular TED talks and discusses the nine elements they all have in common. Great resource if you're hoping to improve your public speaking, presentation, or storytelling skills. The most engaging speakers elicit a set of common themes grouped as emotional, novel, or memorable. If nothing else, these lessons will help you become a better communicator.
Letters from a Stoic – by Seneca
Date read: 2/13/17. Recommendation: 9/10.
Introduction to Penguin Classics edition. Perhaps the most highly regarded/referenced work of Stoic philosophy along with Meditations by Marcus Aurelius. Go straight to the source. It's a classic and one of the most important works you'll read.
The Obstacle Is the Way – by Ryan Holiday
Date read: 1/30/17. Recommendation: 9/10.
One of the most accessible modern introductions to Stoic philosophy. Holiday examines the inevitable obstacles we all face in life, how to better frame them as opportunities to practice virtue, and how to harness them to create momentum of our own. He structures the book around the three interconnected disciplines required to overcome any obstacle: perception, action, and will. There's an incredible amount of knowledge packed into these 200 pages. No matter what challenges you face or where you're trying to go, it's a great resource for fine tuning your attitude, strategy, and mental toughness. Inspired by Marcus Aurelius, "The impediment to action advances action. What stands in the way becomes the way."
The Subtle Art of Not Giving a Fuck – by Mark Manson
Date read: 1/17/17. Recommendation: 8/10.
One of the most entertaining writers you'll find. Essentially a deep dive into one my favorite articles from his blog. The core of the book focuses on allocating more time and energy to what matters most (the appropriate allocation of fucks). Instead of over-investing in trivial, superficial things (the inappropriate allocation of fucks). He criticizes our culture's obsession with unrealistically positive expectations and the sense of inadequacy that it provokes. Life is a struggle, we should instead determine what we're willing to struggle for.
Tools of Titans – by Tim Ferriss
Date read: 1/14/17. Recommendation: 9/10.
If you're a fan of the Tim Ferriss podcast, you'll enjoy this book. It's a collection of all his interviews, distilled into their most useful bits of information. Ferriss offers insight into the habits and mental models of top performers across every industry, from fitness to Silicon Valley. This book is a gold mine for thought provoking quotes. A few of my favorite sections feature Naval Ravikant (entrepreneur/investor), Josh Waitzkin (chess prodigy), and Alain de Botton (philosopher). There are sure to be a handful of ideas that will resonate with you and help improve your own mental models. It's a book I revisit with regularity.
Tribe: On Homecoming and Belonging – by Sebastian Junger
Date read: 1/9/17. Recommendation: 10/10.
Clear, concise, and thought-provoking read that examines the struggle to find loyalty, belonging and meaning in modern society. Junger spotlights military veterans and the growing rates of post-traumatic stress disorder, but he also takes a step back to examine the human condition at large. He discusses hardship, raw experiences, social bonds, community, mental health, and what we can learn from tribal societies. Tribe explains that there are three essential needs that must be met if we wish to feel content–the need to feel competent at what we do, the need to feel authentic in our lives, and the need to feel connected to others. Junger considers the effects of their absence and makes a compelling case that we should strive to rediscover and prioritize their importance.
Ego Is the Enemy – by Ryan Holiday
Date read: 1/5/17. Recommendation: 10/10.
My favorite Ryan Holiday book. If you haven't read any of his work yet, start here. It's a great look into how–in an effort to nurse our ego–we often act in opposition to our best interests. He discusses how to leverage ideas from Stoic philosophy, the pitfalls of self-narrative, and the importance of being a lifelong learner. Numerous life lessons and productive mental models packed into a quick read. Along with Tribe by Sebastian Junger, this is the book I've gifted the most in the past year.