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

The Difference Between Lifelong Learners and Pretenders

There’s an underlying difference between lifelong learners — smart, intellectually curious thinkers — and those who use obscure knowledge as social collateral. Often it’s the first visible symptom of misplaced motivation and a shallow foundation of ideas — overidentification.

We all know someone who overidentifies with each book, documentary, or source of information they come across. They regurgitate the ideas and arguments presented, ad nauseam. There’s no room for personal interpretation. They seek a source that fits neatly into their existing worldview and repeat it for weeks as if it’s their own.

In contrast, the smartest minds allow themselves to sit in the gray area. They don’t overidentify with any single source of knowledge. Instead, they give themselves time to distill information and ideas into their most useful components.

The pretenders take the opposite approach. It’s all or nothing. They fail to grasp that you don’t have to adopt 100% of the arguments presented by a public voice — author, filmmaker, thought leader, etc. But a single idea you don’t identify with doesn’t negate the overall value of their work.

At its core, this mindset is often rooted in the promise of some external reward. When your desire to learn is fueled by ego, approval, attention, or recognition, overidentification is the obvious end result. You’re not truly committed to learning. You’ll stop when you come across the first idea that appears satisfactory, perpetuating your own confirmation bias.

Although, it’s not always a conscious decision. It’s easy to overidentify, especially early in life with limited perspective. You have fewer reference points. As a result, when you find an influencer who you admire, you naturally gravitate towards all of their ideas.

But the more you read and the more you learn, the more aware you become of just how wide the spectrum of opinions is.

It’s a strange feeling. We’ve all experienced a strong desire to identify with the entirety of the views from those we respect. It would certainly make things easier and eliminate most of the painstaking introspection required on our part. Who wouldn’t want a definitive, personal guide to entrust with navigating life’s uncertainties on our behalf?

Unfortunately, there’s no neatly packaged manual for our individual lives.

Have the moral courage to live in the gray, sit with uncertainty but not in a passive way. Live the questions so that, one day, you will live yourself into the answers.
— Jacqueline Novogratz

Part of a self-sufficient mind is being able to sift through facts, opinions, and interpretations to piece together your own cohesive worldview. You’re allowed to, and should, borrow ideas from multiple sources. But that means you’re going to have to put in the work.

There’s not a single person who has been right about everything. And there’s not an intelligent, enlightened thinker who has gone their entire life without changing their mind about something.

There are many people committed to learning and developing the most informed view on a specific subject. But that doesn’t mean they have every right answer. Most people are just doing their best to figure things out.

You should still maintain a zero-tolerance policy for deception or pure ignorance. If someone is unable to accept empirical facts or universal laws, it’s probably not worth investing the time to consider their ideas further. By refusing to operate with any sort of foundation in science or reason, it shows an unwillingness to enter a neutral arena. It’s the easiest way to distort reality and manipulate the field.

No one said it was going to be easy. The true litmus test of your critical thinking skills is how well you hold, assess, and incorporate new ideas into your own worldview. Is it a free for all? Or is it a careful examination and contemplation of the ideas that check out and resonate strongest with you?

Lifelong learners embrace ambiguity. They resist the urge to immediately adopt or discredit someone’s point of view based on a single interpretation or opinion. The deeper your well of knowledge, the better you’re able to balance multiple viewpoints, and the more rational your perspective.

Allow yourself to live and learn in the gray area.

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.