Books

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

Top 6 Books for Better Mental Models (<200 pages)

Many of the smartest minds throughout history–those who have demonstrated mastery in their respective fields and contributed something meaningful to the world–have favored a multidisciplinary approach over specialization. They’ve recognized that the more flexible and wide-ranging your mental models, the stronger your cognitive abilities, and the less rigid your thinking. At an individual level, it’s not only more effective but also more fulfilling.

A multidisciplinary approach leads to resourcefulness, ingenuity, and resilience. It better prepares you to develop each of these skills, navigate inevitable obstacles, and build your own momentum. It’s the antithesis of confining yourself to a single discipline with a shallow skill-set and isolated mental models.

In fact, the defining feature of a multidisciplinary approach is its dynamic latticework of mental models. This is achieved by broad exposure to a range of subjects, which allows you to leverage and connect the most relevant knowledge from each. By positioning yourself at the intersection of multiple disciplines, you cultivate the ability to tie together seemingly unrelated concepts in a way the vast majority are incapable of. It’s here where the most creative, innovative ideas are discovered.

Last year I wrote an article on the beginner’s guide to a multidisciplinary approach and recommended four books for building better mental models. It resonated with quite a few people who were looking for an introduction to this concept. In revisiting this theme, I’ve wanted to provide a new reading list that’s even more accessible–each book is under 200 pages.

While this is in no way comprehensive, it is my hope that this will help you begin building your own framework across multiple disciplines. If you’re up for a short read, dig in.

1) The Obstacle Is the Way — by Ryan Holiday

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 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.”

Talent is not the most sought-after characteristic. Grace and poise are, because these two attributes precede the opportunity to deploy any other skill.
— Ryan Holiday

2) The Geometry of Wealth—by Brian Portnoy

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 on the path towards adaptive simplicity in investing, he also digs deeper into its importance in our broader lives, offering an enlightened discussion of experienced vs. reflective happiness, expectations, and human nature.

The ‘good life’ is not the tweak of ephemeral pleasure, but the engagement with more meaningful, virtuous pursuits. Momentary pleasures are distinct from the enduring gravity of meaningful experience.
— Brian Portnoy

3) The Bed of Procrustes — by Nassim Taleb

Great introduction to Taleb’s ideas on uncertainty, which he discusses in detail in his other books that make up the Incerto series: AntifragileFooled by Randomness, and The Black Swan. This book offers a succinct look into how we deal with what we don’t know. Taleb considers our tendency to package and reduce ideas into neat narratives that fit within the constraints of our limited knowledge. I would argue that he’s one of the most original, brilliant minds of our time.

Knowledge is subtractive, not additive–what we subtract (reduction by what does not work, what not to do), not what we add (what to do).
— Nassim Taleb

4) Real Artists Don’t Starve — by Jeff Goins

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. 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.

Thriving Artists don’t just live off their art. Like good investors, they keep diverse portfolios, relying on multiple income streams to make a living. Rarely do they go all in on any single area of work. The challenge, then, is knowing what investments to make and when.
— Jeff Goins

5) The Inner Game of Tennis — by W. Timothy Gallwey

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.

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

6) Tribe — by Sebastian Junger

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.

Human beings need three basic things in order to be content: they need to feel competent at what they do; they need to feel authentic in their lives; and they need to feel connected to others.
— Sebastian Junger

Top 4 Books for Better Mental Models

In a world of specialization, mental models are the most powerful argument for adopting a multidisciplinary approach. The concept behind mental models is that broad exposure to a range of subjects enables you to leverage the most useful knowledge from each and make better decisions.

When you position yourself at the intersection of multiple disciplines, you develop the ability to connect seemingly unrelated dots in a way that the vast majority are otherwise incapable of discovering. It’s here where true creativity and the most innovative solutions are found.

Charlie Munger coined the term “latticework” of mental models–which is exactly what you’re aiming for. The models you pick up should be intertwined with one another, as well as with your personal and vicarious experience. The more connections, the faster you’ll be able to navigate the latticework of your mind, and the stronger your cognitive ability.

You can begin building better models by going straight to the source. If you read and study those who have demonstrated mastery over their specific fields–regardless of industry–you can improve your decision-making ability considerably.

Over the past year, I’ve read (and reread) over 70 books in search for the best systems. These have served as the foundation for improving my own mental models. I’ve distilled what I’ve found to be the most important methods and strategies down to just four books. Each documents real models from some of the most intelligent, imaginative minds in history.

While these are in no way comprehensive, it is my hope is that they will provide a useful starting place to build your own latticework.

1) Mastery — by Robert Greene

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 and models from some of the greatest masters in history–Leonardo da Vinci, Benjamin Franklin, Charles Darwin, Albert Einstein, Paul Graham, and dozens more.

“The pain and boredom we experience in the initial stage of learning a skill toughens our minds, much like physical exercise. Too many people believe that everything must be pleasurable in life, which makes them constantly search for distractions and short-circuits the learning process. The pain is a kind of challenge your mind presents–will you learn how to focus and move past the boredom, or like a child will you succumb to the need for immediate pleasure and distraction?”
— Robert Greene

2) Tools of Titans — by Tim Ferriss

A collection of interviews with hundreds of the most talented entrepreneurs and thought leaders consolidated into their most useful sound bites. It follows the same format as his popular podcast. Ferriss lays the framework for building better, more productive mental models. Rather than suggesting a checklist of X-Y-Z required to set yourself apart, he emphasizes strategies and tactics which can be applied more broadly. 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–especially when I’m in need of a new perspective.

Most people think they can wait around for the big moments to turn it on. But if you don’t cultivate ‘turning it on’ as a way of life in the little moments–and there are hundreds of times more little moments than big–then there’s no chance in the big moments.
— Josh Waitzkin

3) Antifragile — by Nassim Taleb

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–the key to personal growth. 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 models.

With randomness, uncertainty, chaos: you want to use them, not hide from them. You want to be the fire and wish for the wind.
— Nassim Taleb

4) The Daily Stoic — by Ryan Holiday and Stephen Hanselman

I’ve found Stoicism to be the most effective philosophy for modern life. If you’re unfamiliar with Stoicism, you’re probably operating under the misconception that it’s synonymous with a lack of emotion. In actuality, it’s a school of philosophy focused on cultivating an unwavering sense of focus, appreciation, and rationality. The Daily Stoic is a great introduction to some of the most memorable Stoic philosophers and their models for living a better life, including Epictetus, Seneca the Younger, and Marcus Aurelius. The book offers daily wisdom–366 short sections–focused on the most important Stoic themes. This is not a philosophy textbook filled with abstract concepts. It’s an accessible overview of Stoicism and its emphasis on the art of living.

Take a good hard look at people’s ruling principle, especially of the wise, what they run away from and what they seek out.
— Marcus Aurelius