Mental Models

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

How to Retain Everything You Read

How to Retain Everything You Read

Pace is not something I am particularly reasonable about when it comes to reading. Rather than savoring a book, I get too excited and tear through it. While there are worse habits than voracious reading, it became increasingly difficult, if not impossible, for me to recall any information prior to the most recent books I had read.