Book Notes

Range – David Epstein

Range: Why Generalists Triumph in a Specialized World – by David Epstein
Date read: 7/25/19. Recommendation: 8/10.

In a complicated, competitive world, there’s a push to focus early and narrowly. Navigating life seems to demand specialization. And the stories told the loudest (Tiger Woods) push that narrative. In reality, far more eventual elites devote less time to deliberate practice early on and instead undergo a sampling period. This offers them an opportunity to learn about and discover their own abilities and inclinations. Only later do they focus on one specific area and ramp up technical practice (Roger Federer). Awesome resource for generalists and those pursuing a multidisciplinary approach in life. This is a book that needed to be written, and Epstein does a great job emphasizing breadth over depth, the dangers of specialization, and the importance of match quality.

See my notes below or Amazon for details and reviews.

My notes:

Illusion of Specialization:
In a complicated, competitive world, there’s a push to focus early and narrowly. Navigating life seems to demand specialization. And the stories told the loudest (Tiger Woods) push that narrative. 

In reality, far more eventual elites devote less time to deliberate practice early on and instead undergo a “sampling period.” This offers them an opportunity to learn about and discover their own abilities and inclinations. Only later do they focus on one specific area and ramp up technical practice (Roger Federer).

Specialization works in fields where massive amounts of narrow practice help with repetitive tasks: golfers, surgeons, poker players, chess-masters, accountants. Doesn’t apply as well to scientists, entrepreneurs, artists. But you need both. 

Breadth > Depth:
Earlier career specializers make more immediately out of college. But delayed specializers end up surpassing them by finding work that better fits their skills and personalities. 

Gathering experience in multiple domains is a force multiplier in creative endeavors (technology, art, etc.). Helps avoid “cognitive entrenchment.”

Standard advice cautions changing directions. That’s why so many people need to have their life choices affirmed by outsiders. 

“If you’re working on well-defined and well-understood problems, specialists work very, very well. As ambiguity and uncertainty increases, which is the norm with systems problems, breadth becomes increasingly important.” Andy Ouderkirk

In product management, you’re a “T-shaped person.” You’re the trunk connecting the “I-shaped people.” Mosaic building. Asking the right questions. Via Jayshree Seth (scientist at 3M). 

Breadth can often reveal itself in terms of genres: Nail Gaiman, Hayao Miyazaki, Jordan Peele. 

Dangers of Specialization:
Specialization has created a “system of parallel trenches” – everyone’s digging deeper but rarely standing up to look at the terrain. Result is that we end up missing systemic issues. 

“Man with a hammer” syndrome. Everything looks like a nail.

Competitive Advantage:
“The bigger the picture, the more unique the potential human contribution. Our greatest strength is the exact opposite of narrow specialization. It is the ability to integrate broadly.” DE

Spaced Repetition and Speed:
Space between practice sessions enhances learning. The struggle to retrieve information when it’s on the edge of your short-term memory ultimately improves retention (See Gabriel Wyner, Fluent Forever).

“Frustration is not a sign you are not learning, but ease is.” DE

The best learning is slow, no matter how tempting learning hacks might seem. Slow, deliberate learning is a struggle that improves performance later. 

“Learning deeply means learning slowly. The cult of the head start fails the learner it seeks to serve.” DE

Vincent van Gogh:
“He tested options with maniacal intensity and got the maximum information signal about his fit as quickly as possible, and then moved to something else and repeated, until he had zigzagged his way to a place no one else had ever been, and where he alone excelled.” DE

Dropped out of school at 15. Went to work full time at his uncle’s art dealership. At 22 he was transferred to Paris. Passed studios of brilliant artists and never made the connection. Instead, found a new obsession in religion and decided he would work towards becoming a missionary in South America. In the meantime, he went to work as an assistant teacher at a boarding school and then became a tutor, followed by time spent as a bookstore clerk. At 27, in despair, turned to the last thing he could think of…drawing. Enrolled in art school at age 33, dropped out after a few weeks after being ridiculed by judges in a drawing competition. One day he found an easel and oil paints and took it to a sand dune in a storm. Slapped on colors, squeezed paint straight from the tube onto the canvas and discovered he could paint. He emerged with a new art without formality that attempted to capture something infinite. Works he made in hours as experiments would later become some of the most valuable pieces in the world. 

Match Quality:
Seek the best match quality based on where you are in this moment…who you are, your motivations, what you’d like to do, what you’d like to learn. Use this as a filter for new opportunities. 

Learn about yourself through a discovery period or sampling period. It’s risky to make long-term commitments (law school, med school), before you know how it fits you. Most personality changes occur between 18 and late 20s. Specializing early means attempting to predict match quality for a person who doesn’t exist yet.

Michael Crichton went to Harvard Medical School out of fear of how little money writers made. But he was able to leverage medical knowledge in his novels and scripts (Jurassic Park, E.R.). 

Patrick Rothfuss, fantasy writer, studied chemical engineering in college and bounced between majors for the next nine years. After that he went to grad school and slowly started piecing together The Name of the Wind. Used his knowledge of chemistry throughout the book and the world he created. 

Chrissie Wellington, four-time Ironman world championship winner, didn’t get on a bike until age 27. She was working on a sanitation project in Nepal and found she could keep up with the Sherpas in the Himalayas. 

“Career goals that once felt safe and certain can appear ludicrous the examined in the light of more self-knowledge. Our work preferences and our life preferences do not stay the same, because we do not stay the same.” DE

“We learn who we are only by living, and not before.” DE

NASA Challenger Disaster:
Occurred because they failed to shift strategies when conditions changed (See Ernest Shackleton for a true master of shifting strategy). NASA failed to value both quantitative and qualitative data. Instead, there was an allegiance to hierarchy and procedure. Valued consensus over conviction. 

Not Everything Needs to Have a Point:
Exploration and curiosity are enough. Louis Pasteur experimenting on chickens with cholera led to lab-created vaccines. Einstein investigating what happens to time in high versus low gravity. 

Hyper-specialization is a push for efficiency. But experimentation and pushing the boundaries, by nature, is inefficient. 

Ten Caesars – Barry Strauss

Ten Caesars – by Barry Strauss
Date read: 7/20/19. Recommendation: 7/10.

Approachable introduction to the lives and reigns of ten Roman emperors, from Augustus to Constantine. It’s a great high-level overview that allows you to explore some of the most influential leaders of the Roman Empire. I enjoy books like these because they introduce different historical figures and help me find the most interesting ones who are worth exploring later, without investing 300 pages in a single person. There are some great lessons in power, strategy, ego, discipline, and philosophy. For the Stoics out there, the section on Marcus Aurelius is particularly insightful.

See my notes below or Amazon for details and reviews.

My Notes:

Augustus: The Founder
Empire: Augustus ended a century of revolution and replaced the Roman Republic with an empire that would last centuries.

Focus on internals: Lost his father at the age of four and one of his guardians plundered his inheritance. But he turned to the internal strengths in his life: his own resilience, his mother, and her family. One of his defining characteristics was self-control. 

Strategy: Turned pain into strategy and became one of the three most powerful men in the Roman Empire by age 20. He was master strategist, thought further ahead and in greater dimensions than everyone else around him. 

Gray area: Augustus ended a civil war, rid the sea of pirates and brought peace. But there were also murders, betrayal, and excess along the way. His successors would have trouble balance the competing (often contradictory) demands.

“Caesar and Augustus were two sides of the coin of Roman genius. Caesar was the god of battle who poured his talent and his ego into two literary classics. Augustus was the Machiavellian statesman who forged his power in blood and iron, and then went on to build a structure of peace and wealth that survived his passing for two hundred years.” BS

Nero: The Entertainer
Seneca (Nero’s tutor): Seneca was born into a wealthy, influential Roman family from Hispania. His father was a writer, his mother studied philosophy. Seneca rose in Rome as an orator, philosopher, essayist, and playwright. Argued that mercy should be the hallmark of Nero’s reign. Advocated eloquence and dignity. Nero would eventually order both Seneca and his mother’s deaths. 

Ego: For the first five years, Nero kept his promises and shared power with the senators. But he craved popularity above all else – he was insecure and vain. When he didn’t get his way, he sought vengeance.

Lack of discipline: Nero would often wander into the streets of Rome at night to party in taverns and brothels. Neglected his primary duties because he viewed himself first and foremost as an artist. 

Marcus Aurelius: The Philosopher
Meditations: Private journal (now best-selling book), where he documented his philosophy (Stoicism) and life. Saved complaints for his diary, never revealed them in public.

Justice and goodness: “As a general, he was conscientious rather than outstanding. And yet Marcus was great because, more than any other emperor, he ruled through a commitment to justice and goodness. He aimed at humanity, steered clear of cruelty, and frequently sought compromise.” BS

Challenges: Faced one of the most difficult times in the Roman Empire by inheriting wars on two foreign fronts, a smallpox epidemic (and shortage of labor that followed after millions died), natural disaster, and financial struggles. 

Preparation: Marcus didn’t come into power until age 40. He received top education in rhetoric and philosophy. His character was impeccable. Admired the philosophy of Epictetus (Stoicism) and achieving inner freedom. But the one thing he had never done, despite holding all the important public offices in Rome, was commanding an army. His principles, discipline, and sense of duty allowed him to rise to the occasion. 

Character: He was thoughtful, but not quick witted. Worked hard. Thrifty. Reputation for being firm but reasonable. Ruled in favor of slave’s freedom whenever possible. Respected the Senate and attended their meetings. Improved welfare for poor children. Carefully monitored grain supply. Cleaned and repaired the streets of Rome. Made gladiators use blunt swords. 

Diocletian: The Great Divider
Restoring stability: First great accomplishment in an empire trapped in violence. For the previous 50 years, 20 men were emperor (average reign < 3 years). “Diocletian was big, bold, brutal, and orderly. Finesse was not his way, but the times did not call for finesse. They demanded military muscle, a steel-trap mind, an iron will, and absolute self-confidence.” BS

Sharing power: Diocletian knew sharing power was the key to maintaining power. Knew it would discourage the ambitious and talented from revolting. Also kew that Rome’s problems were too big for him to handle on his own. Named Maximian co-emperor, and Constantius and Galerius as Caesars who played a military role, serving Diocletian and Maximian. Maximian and Constantius ran the West. Diocletian and Galerius ran the East. But Diocletian controlled overall strategy and had final decision. 

Military strategy: Made border forts smaller, thicker, and harder to access. Number of legions expanded from 33 to 50, but with fewer men per legion (similar to Genghis Khan’s strategy).

Taxation: Massive building campaigns and military budget demanded more money. For the first time in Italy’s history, it was no longer exempt from taxes. Even Rome and the senators had to pay. 

Retirement: First and only Roman emperor to retired. Lived in relative peace in his palace in Split, Croatia for 10 years. Knew it was better to go out on top than to linger and lose loyalty the moment he grew weak. “In victory, know when to stop.” 

Thinking in Systems – Donella H. Meadows

Thinking in Systems – by Donella H. Meadows
Date read: 7/9/19. Recommendation: 8/10.

Great introduction to systems thinking – the ability to step back and appreciate the complexity of the interconnected whole. Meadows emphasizes the dangers of generalizing about complex systems and explains the key elements of resilient systems. This includes feedback loops, self-organization, experimentation, and alignment. She also digs into concepts like the tragedy of the commons, bounded rationality, modeling, and how to avoid the pitfalls of each. The benefit of systems thinking is that is helps you avoid isolated, shallow decision-making. With this comes the ability to appreciate the complexity of large systems, their connections, and how to improve or redesign them, when needed. This is an important book for anyone who’s working on complex problems or wants to grow into a more strategic thinker.

See my notes below or Amazon for details and reviews.

My Notes:

The system lens:
Helps reclaim intuition about whole systems, hone abilities to understand parts, see interconnections, ask “what if” questions about future behavior, and be creative in redesigns. 

Ancient Sufi story about a king visiting a city of blind citizens on his mighty elephant. Each citizen touched a small part of the elephant (ear, trunk, legs) and drew false conclusions. Need a better understanding of the whole, not just the elements it’s made of. 

Questions for testing the value of a model:

  1. Are driving factors likely to unfold this way?

  2. If they did, would the system react this way?

  3. What is driving the driving factors?

Systems studies are not designed to predict, they’re designed to explore what would happen if factors unfold in a range of different scenarios. 

Dangerous to generalize about complex systems. 

Rich structure of many feedback loops allows a system to thrive in a variable environment. Similar to Taleb’s concept of anti-fragility.

Resilience is similar to a plateau that a system can play safely upon. The more resilient a system, the larger the plateau and the greater its ability to bounce back when near the edges. Less resilient, smaller plateau.

Awareness of resilience allows you to harness, preserve, or improve a system’s restorative powers. 

Self-organization is the strongest form of system resilience. System that can evolve can survive almost any change. That’s why biodiversity is so important.

“Insistence on a single culture shuts down learning and cuts back resilience. Any system, biological, economic, or social, that gets so encrusted that it cannot self-evolve, a system that systematically scorns experimentation and wipes out the raw material of innovation, is doomed over the long term on the highly variable planet.” DM

Experimentation is key to anti-fragility and innovation. But it’s difficult because this means giving up control. 

Antifragile: “In the end, it seems that mastery has less to do with pushing leverage points than it does with strategically, profoundly, madly, letting go and dancing with the system.” DM

DM: “Complex systems can evolve from simple systems only if there are stable intermediate forms.” Why they’re so common in nature. 

Hierarchies are system inventions – provide stability, resilience, and reduce the amount of information system needs to keep track of. Too much central control overwhelms and breaks a system. Unable to achieve more complex tasks. 

“Our knowledge of the world instructs us first of all that the world is greater than our knowledge of it.” Wendell Berry

Everything we know about the world is a model – languages, maps, statistics, mental models. Usually correspond well with the world (hints our success as a species), but will never fully represent the world with 100% accuracy. If they did, we would never make mistakes or be surprised. 

Mental flexibility = willingness to redraw boundaries.

Alignment + policy resistance:
Bounded rationality: People make reasonable decisions based on information they have about parts of the system they’re closest too. But they don’t have perfect information or ability to see more distant parts of the systems. This is why narrow-minded behavior arises. 

Policy resistance occurs when goals of subsystems are misaligned. Need an overarching goal to tie things together. Feedback loops should serve the same goal. Much of that is identifying what problem you’re trying to solve.

1967 Romanian government decided they needed more people so they made abortions illegal. Short term results saw birth rate triple, then resistance set in. People pursued dangerous abortion which tripled maternal mortality. 

Hungary, at the same time, was also worried about low birth rate. Discovered it was partially due to cramped housing so they incentivized larger families with more living space. Only partially successful because it was only part of the problem, but not a disaster like Romania.

Sweden was most successful because they recognized that the goal of population and government was not family size, but quality of child care. Birth rate has gone up and down since then without causing panic because they focused on long-term welfare and more robust goal, not a narrow, short-sighted goal. 

Silver Rule Example from Garrett Hardin (see Nassim Taleb, Skin in the Game): people who want to prevent other people from having an abortion aren’t practicing intrinsic responsibility unless they’re personally willing to raise the resulting child.

“If you want to understand the deepest malfunctions of systems, pay attention to the rules and who has power over them.” DM

The tragedy of the commons:
Result of simple growth in a system where a resource is not only limited, but erodible when overused. Selfish behavior more convenient and profitable than responsibility to whole community and shared future. 

E.g. uncontrolled access to national park (over-tourism) bringing in crowds that destroy park’s natural beauties.

Three ways to avoid the tragedy of the commons:

  1. Educate and exhort (moral pressure)

  2. Privatize the commons (makes direct feedback loop)

  3. Regulate the commons (mutual coercion agreements, i.e. traffic lights, parking spaces).

Turning Pro – Steven Pressfield

Turning Pro – by Steven Pressfield
Date read: 7/2/19. Recommendation: 7/10.

A solid follow-up to Pressfield’s earlier book, The War of Art. Short, concise, and relevant for any artist or entrepreneur. Highlights the difference between amateurs and professionals, and what it takes to reach the top of your craft. Pressfield discusses shadow careers, the power of concentration, navigating fear, and standing on your own. He also emphasizes that habits are the primary difference between amateurs and professionals. Professionals have better habits that help them simplify life.

See my notes below or Amazon for details and reviews.

My Notes:

Shadow Careers vs. Your Calling

  • Shadow career = metaphor for real career. Shape is similar but entails no real risk. No skin in the game. No consequences.

  • Pressfield’s version was driving trucks instead of writing…took pride in it, felt powerful + manly, the work was interesting, romance of being on the road.

Power of Habits

  • Habits are the primary difference between amateurs and professionals.

  • Professionals have better habits that help them simplify life.

  • “The Zen monk, the artist, the entrepreneur often lead lives so plain they’re practically invisible.” SP

  • Pros face just as much fear, but structure their day to confront and overcome it.

Overcoming Resistance

  • To overcome resistance, you need concentration and depth.

  • If you’re shallow and unfocused, you’ll never make it out.

  • The draw to failure or trouble is so strong because its incapacitating, let’s you off the hook.

  • What you’re must afraid of is what you must do.

Signs of an Amateur

  • Fear dictates decisions (fear of being different or rejected leads to inauthenticity, fear of solitude and silence).

  • Avoid resistance through drama, denial, distraction.

  • To combat this, you need self-awareness.

Signs of a Professional

  • Seek wisdom and instruction from masters without surrendering self-sovereignty.

  • Doesn’t sit around waiting for inspiration, acts in anticipation. Orderly, workmanlike in habits and routine.

  • Trusts and examines the mystery. “The place we write from (or paint from or compose from or innovate from) is far deeper than our personal egos. That place is beyond intellect. It is deeper than rational thought.” SP

  • “The best pages I’ve ever written are pages I can’t remember writing.” SP

Life is a Single Player Game

  • There is no tribe. The artist and the entrepreneur enter the arena alone.

  • “In the hero’s journey, the wanderer returns home after years of exile, struggle, and suffering. He brings a gift for the people. The gift arises from what the hero has seen, what he has endured, what he has learned. But the gift is not that raw material alone. It is the ore refined into gold by the hero / wanderer / artist’s skilled and loving hands.” SP

A Short History of Nearly Everything – Bill Bryson

A Short History of Nearly Everything – by Bill Bryson
Date read: 6/15/19. Recommendation: 10/10.

A Short History of Nearly Everything is one of the most important books on my shelf. After graduating from university, it’s the first book that reminded me how much I loved reading. It was the catalyst for me to begin building back up my reading habits and I’ve read it multiple times since. At its heart, it’s a book about science and some of life’s biggest questions. Bryson tackles everything from the cosmos and physics to ice ages and evolution. He’s a brilliant writer and storyteller, which helps make complex topics like particle physics more accessible and relatable for novices, like me. The pages are filled with jaw-dropping facts and stories of those enshrined in (or forgotten by) the annals of science. The amount of knowledge in this book is incredible. But the most important thing you’ll come away with is a renewed sense of perspective. It’s a great reminder of just how insignificant we are and how precious life is.

See my notes below or Amazon for details and reviews.

My Notes:

Newton, Principia, and Unlikely Inspiration:
In 1683, Edmond Halley, Robert Hooke, and Christopher Wren made a scientific wager on celestial objects. It was known that planets orbited in a particular kind of oval, but no one understood why. Wren offered a prize worth forty-shillings. Halley became obsessed with the problem and went to Isaac Newton, hoping he could help. Newton had already calculated the ellipse but couldn’t recall where he put the formula. Halley urged him to put it into a paper. The result was Newton’s crowning scientific achievement–Principia–which explained orbits mathematically, outlined three laws of motion, and, for the first time, identified gravity. Halley paid for the book’s publication out of his own pocket when The Royal Society backed out due to financial struggles. Impact of Newton’s laws is hard to overstate…explained ocean tides, motion of planets, the trajectory of cannonballs, why we aren’t lost to space as the planet spins beneath us. 

Lord Kelvin, Polymath, Master of the Long Game:

  • Admitted to Glasgow University at the age of 10.

  • Graduated from Cambridge, won top prizes for rowing and mathematics, launched a musical society.

  • At the age of 22, became professor of natural philosophy at Glasgow for the next 53 years. 

  • Wrote 661 papers, gained 69 patents, contributed to every branch of the physical sciences.

  • Suggested the method that led to the invention of refrigeration, created scale of absolute temperature, invented boosting devices to send telegrams across oceans. 

Radioactivity and Early Adopters:
Many assumed radioactivity had to be beneficial since it was so energetic. It wasn’t banned in consumer products until 1938. Up until that point manufacturers put radioactive thorium in toothpaste and laxatives. Until the 1920s the Glen Springs Hotel in Finger Lakes (NY) featured the therapeutic effects of its “Radioactive mineral springs.”

Early life revealed little of what was to come. Didn’t learn to speak until he was three. Failed college entrance exams on first try. 

Took advantage of being underemployed: 1902 took job at Swiss patent office and stayed for 7 years. Challenging enough to engage his mind, but not enough to distract him from physics. Here he produced the special theory of relativity in 1905.

Drawdown periods: For originality, tune out. Einstein’s “On the Electrodynamics of Moving Bodies” had no footnotes or citations. It was like he reached the conclusions by pure thought, without listening to outside opinion. 

Little recognition early on: As an outsider, he was largely ignored in the physics community, despite solving several of the deepest mysteries of the universe. Proceeded to apply and get rejected as a university lecturer and high school teacher.

Theory of relativity: Space and time are not absolute. They’re relative to both the observer and the thing being observed. Faster one moves, the more pronounced effects become. The faster we accelerate, the more distorted we are, relative to an outside observer. 

Spent the second half of his life searching for a unified theory of physics, but failed. Physics has two bodies of laws, one for the very small, one for the universe at large.

Discovery by Bridging Ideas
Georges Lemaître, a Belgian priest-scholar with a Ph.D. from MIT, was the first to suggest that the universe began as a single geometrical point, a “primeval atom” which burst into existence and had been moving apart ever since. Referred to this as his “fireworks theory.” It was the first hint at the Big Bang. Combined his knowledge of Hubble’s discovery of the universe expanding and increasing speed in every direction, and Einstein’s General Theory of Relativity. 

Plate Tectonics:
“Look at the globe and what you are seeing is really a snapshot of the continents as they have been for just one-tenth of 1 percent of the Earth’s history.” BB

“The history of any one part of the Earth, like the life of a soldier, consists of long periods of boredom and short periods of terror.” Derek V. Ager

Disasters + Extinctions:
Last super volcano eruption took place 74,000 years ago in Toba, northern Sumatra. It was followed by six years of volcanic winter. Carried humans to brink of extinction, no more than a few thousand individuals. Modern humans arose from a very small population (explains our lack of genetic diversity). Some evidence shows for the next 20,000 years, human population never grew beyond a few thousand at a given time. Huge amount of time to recover from our perspective of time. But not from Earth’s. 

 99.99% of all species that have ever lived are no longer with us. Average lifespan of a species is about four millions years.

 Permian Extinction: 245 million years ago, wiped out the dinosaurs and 95% of animals known from fossil records disappear. Closest we’ve come to total obliteration. 

Life is Precious: 
“From the bottom of the deepest ocean trench to the top of the highest mountain, the zone that covers nearly the whole of known life, is only something over a dozen miles–not much when set against the roominess of the cosmos at large.” BB

Excellent Location: “We are, to an almost uncanny degree, the right distance from the right sort of star, one that is big enough to radiate lots of energy, but no so big to burn itself out swiftly…We are also fortunate to orbit where we do. Too much nearer and everything on Earth would have boiled away. Much farther away and everything would have frozen.” BB

Earth would have been uninhabitable if it had been just 1 percent farther or 5 percent closer to the sun. Think about Venus (sun’s warmth reaches it two minutes before us).

“We are so used to the notion of our own inevitability as life’s dominant species that it is hard to grasp that we are only here because of time extraterrestrial bangs and other random flukes.” BB

“The one thing we have in common with all other living things is that for nearly four billion years our ancestors have managed to slip through a series of closing doors every time we needed them to.” BB

“If this book has a lesson, it is that we are awfully lucky to be here–and by ‘we’ I mean every living thing. To attain any kind of life in this universe of ours appears to be quite an achievement. As humans we are doubly lucky, of course: We enjoy not only the privilege of existence but also a singular ability to appreciate it and even, in a multitude of ways, to make it better. It is a talent we have only barely begun to grasp.” BB

The Power of Being an Outsider:
Watson and Crick (no formal training in biochemistry) beat out many top insiders as they worked to discover the structure of DNA. 

Alexander von Humboldt:
Observed that there are three stages in scientific discovery: first, people deny that it is true; then they deny that it is important; finally they credit the wrong person.

Five million years ago, Panama rose from the sea, bridging North and South America, which disrupted warmer currents between the Pacific and Atlantic, and changed precipitation patterns across 50% of the world. Africa began to dry out and apes climbed down from trees in jungles to find a new way of life in the savannah.

One million years ago, upright beings left Africa and spread across the globe. Averaging 25 miles a year. 

Modern human is still 98.4% genetically indistinguishable from the modern chimpanzee. More difference between zebra and horse. 

Bird by Bird – Anne Lamott

Bird by Bird: Some Instructions on Writing and Life – by Anne Lamott
Date read: 6/2/19. Recommendation: 8/10.

Hilarious, insightful resource for writers. Lamott discusses everything from intuition and finding your voice, to the writing process and its rewards. Along the way, she weaves in personal experience and reveals the harsh realities of writing and publication–all in good humor. It’s a call to begin writing, find meaning in the process, and trust your voice. Bird by Bird is a tribute to good writing and dedicated readers.

See my notes below or Amazon for details and reviews.

My Notes:

The Gifts of Writing:

  • Gives you an excuse to do new things, see new places, explore. Also, motivates you to carefully observe life.

  • “Writing can give you what having a baby can give you: it can get you to start paying attention, can help you soften, can wake you up.” AL

  • “Becoming a writer is about becoming conscious. When you’re conscious and writing from a place of insight and simplicity and real caring about the truth, you have the ability to throw the lights on for your reader.” AL

Quake Books/Writers:

  • Feeling you get when you come across a kindred soul who seems to speak for you. 

  • “For some of us, books are as important as almost anything else on earth. What a miracle it is that out of these small, flat, rigid squares of paper unfolds world after world, worlds that sing to you, comfort and quiet or excite you. Books help us understand who we are and how we are to behave.” AL

  • “You wouldn’t be a writer if reading hadn’t enriched your soul more than other pursuits.” AL

The Work Is its Own Reward:

  • The act of writing gives more and teaches more than publication. It is its own reward.

  • “It’s like discovering that while you thought you needed the tea ceremony for the caffeine, what you really needed was the tea ceremony. The act of writing turns out to be its own reward.” AL

  • “You are going to have to give and give and give, or there’s no reason for you to be writing. You have to give from the deepest part of yourself, and you are going to have to go on giving, and the giving is going to have to be its own reward.” AL

Good Writing:

  • “Good writing is about telling the truth” AL

  • “An author makes you notice, makes you pay attention, and this is a great gift. My gratitude for good writing is unbounded; I’m grateful for it the way I’m grateful for the ocean.” AL

The Process:

  • Start by writing really shitty first drafts. That’s the only way to get started. 

  • Writing a book in a single flash of brilliance is a fantasy of the uninitiated. 

  • First draft = down draft. Just get it down. Look for sentences or paragraphs where you’re on to something.

  • Second draft = up draft. Fix it up. Figure out how to better communicate what you’re trying to say. Strip away busyness. 

  • Third draft = dental draft. Check every tooth. 

Plot vs. Characters:

  • “Plot grows out of character.” Not the other way around. 

  • Determine what each character cares about most in the world – that’s what’s at stake. 

  • ABCDE (action, background, development, climax, ending)


  • Confidence and intuition come from trusting yourself. This is how you reach the art of relaxed concentration. 

  • Make space for intuition. Rely on it. Let it guide the way. Get your rational mind out of the way.

Writer’s Block:

  • Start by accepting it. Give yourself permission to be stuck. Accept that you’re not in a productive creative period. Once you do that, you free yourself to fill back up. 

Finding Your Voice:

  • What you bring: “Life is like a recycling center, where all the concerns and dramas of humankind get recycled back and forth across the universe. But what you have to offer is your own sensibility, maybe your own sense of humor or insider pathos or meaning.” AL

  • “You cannot write out of someone else’s big dark place; you can only write out of your own.” AL

  • Bring out what’s inside of you and you will be able to sustain that indefinitely. Try to bring out something else, it will destroy you.

Steal Like an Artist – Austin Kleon

Steal Like an Artist – by Austin Kleon
Date read: 5/27/19. Recommendation: 7/10.

Short read on creativity and the importance of your influences. It reminded me of Steven Pressfield’s The War of Art. Kleon discusses the creative struggle, where to find inspiration, and how to leverage influences. Anyone can imitate style on a surface level and copy what’s been done. But the most talented artists take it one step further. They steal the thinking behind the style–the mindset of their influences–to emulate and create something of their own. Great reference for smart creatives who want to hone their craft and build the endurance to play the long game.

See my notes below or Amazon for details and reviews.

My Notes:

Your Influences Matter:

  • “The only art I’ll ever study is stuff that I can steal from.” David Bowie

  • “We are shaped and fashioned by what we love.” Goethe

  • Start with a single thinker you love. Find and study three people that influenced them. Begin to build branches of your own.

  • “It’s not the book you start with, it’s the book that book leads you to.” AK

Ignore Style, Look Deeper:

  • “Don’t just steal the style, steal the thinking behind the style. You don’t want to look like your heroes, your want to see like your heroes.”

  • Similar to quote from Marcus Aurelius: "Take a good hard look at people's ruling principle, especially of the wise, what they run away from and what they seek out."


  • Imitation = copying. Emulation = one step further, creating something that is your own.

  • “It is our failure to become our perceived ideal that ultimately defines us and makes us unique.” Conan O’Brien

  • “Our failure to copy our heroes is where we discover where our own thing lives. That is how we evolve.” AK

Inspiration to Create:

  • Step 1) Wonder at something. Step 2) Invite others to wonder with you.

  • “Complain about the way other people make software by making software.” Andre Torres

Power of routine and systems: 

  • “Be regular and orderly in your life, so that you may be violent and original in your work.” Gustave Flaubert

  • Mark art your main relaxing activity (Derek Sivers). A day job gives you financial freedom, human connection, and routine. Use it to your advantage. 

Creativity is subtraction:

  • Limitless possibilities can be paralyzing, place constraints on yourself. 

  • “What we respond to in any work of art is the artist’s struggle against his or her limitations.” Saul Steinberg

  • “It’s often what an artists choose to leave out that makes the art interesting.” AK

Endurance – Alfred Lansing

Endurance: Shackleton’s Incredible Voyage – by Alfred Lansing
Date read: 5/18/19. Recommendation: 8/10.

A brilliant tale of survival that documents Sir Ernest Shackleton’s failed voyage to cross Antarctica from west to east. Shackleton often appears as a larger-than-life character, offering lessons in leadership at every turn. But Lansing balances this by bringing in the perspective of the other twenty-seven crewmen. It’s one of those true stories that you could never dream up. Lansing highlights the importance of meaning, self-reliance, and gratitude in extreme conditions (à la Tribe by Sebastian Junger or Man’s Search for Meaning by Viktor Frankl). It’s also beautifully written. I stopped multiple times to rewrite passages out of admiration, hoping to steal a touch of Lansing’s style.

See my notes below or Amazon for details and reviews.

My Notes:

Imperial Trans-Antarctic Expedition:
Goal was to cross the Antarctic continent overland from west to east. Set out on October 26, 1914 from Buenos Aires with 27 men and Sir Ernest Shackleton at the helm. On January 19, 1915 became trapped in icy wasteland of the Weddell Sea midway between the South Pole and nearest known outpost of humanity, 1,200 miles away. 

After initial departure: “And in the space of a few short hours, with a thousand petty problems, to one of the barest simplicity in which only one real task remained–the achievement of the goal.”

Purposeful, bold, neat. 

“But if it hadn’t been audacious, it wouldn’t have been to Shackleton’s liking. He was, above all, an explorer in the classic mold–utterly self-reliant, romanic, and just a little swashbuckling.”

“Whatever his mood–whether it was gay and breezy, or dark with rage–he had one pervading characteristic: he was purposeful.”

Intensely aware of those who might undermine unity of group. Knew overall energy and attitude could be difference between life and death. Shackleton made tent, job, crew, and rescue-team assignments based on personality and demeanor. He knew how to motivate each man and preserve the morale of the team. Feared demoralization more than the cold, ice, or sea.

Shackleton believed in his own invincibility. His confidence fueled his men and is what made him a great leader. But it’s also what blinded him to realities and led to occasional poor decisions. 

Plans changed constantly as they drifted one direction or another. But Shackleton always operated with conviction. Being a great leader isn’t about accuracy. It’s about conviction and adaptability (strong opinions, loosely held). 

Frozen in ice:
“Thus their plight was naked and terrifying in its simplicity. If they were to get out–they had to get themselves out.”

After the ship getting stuck (and knowing they were going to have to make it through an entire winter of polar nights), the men grew closer. Built camaraderie through regular social occasions–Saturday night grog, Sunday night music, a lantern chat with a slide-illustrated lecture (once/month), dogsledding, and hockey.

After nine months, abandoned the Endurance and made camp on a large floe. Men responded well because indecision and speculation were over. Knew what needed to be done. Shackleton knew not to let ambiguity linger for too long. Conviction > indecisiveness. 

Gratitude and meaning in extreme conditions:
“The rapidity with which one can completely change one’s ideas…and accommodate ourselves to a state of barbarism is wonderful.” Worsley

“They had been on the ice just a month. And for all the trials and discomforts, these weeks of primitive living had been peculiarly enriching. The men had been forced to develop a degree of self-reliance greater than they had ever imagined possible.” 
*See Tribe (Sebastian Junger) and Man’s Search for Meaning (Viktor Frankl)

“What an ingrate I have been for such jobs when done for me at home.” Macklin

“One of the finest days we have ever had…a pleasure to be alive.” Greenstreet

“In some ways they had come to know themselves better. In this lonely world of ice and emptiness, they had achieved at least a limited kind of contentment. They had been tested and found wanting.”

Boredom is a fiercer foe than hardship:
“The monotony of life here is getting on our nerves. Nothing to do, nowhere to walk, no change in surroundings, food or anything.” Greenstreet

Speed > preparedness:
When they abandoned ship, Shackleton urged the crew to leave behind anything that wasn’t absolutely essential for survival. To demonstrate this, he tore a page from the Book of Job in his Bible, set the book in the snow and walked away. In his studies of past expeditions, knew that crews who brought equipment for every imaginable scenario fared worse than those who sacrificed preparedness for speed. 

Ferocity of the sea:
“But the sea is a different sort of enemy. Unlike the land, where courage and the simple will to endure can often see a man through, the struggle against the sea is an act of physical combat, and there is no escape.”

It Doesn’t Have to Be Crazy at Work – Jason Fried and David Heinemeier Hansson

It Doesn’t Have to Be Crazy at Work – by Jason Fried and David Heinemeier Hansson
Date read: 5/7/19. Recommendation: 8/10.

The book outlines lessons from Basecamp and how to run a calm company. Refreshing resource, particularly for those who get caught up in the chaos of work. They discuss why calmness is a productive emotion and the work structure they use at Basecamp to help sustain that. Fried and Heinemeier Hansson also dig into work ethic, the danger of meetings, the importance of saying no, the myth of low-hanging fruit, why they ship before they test, and the rationale for why they only have a single product. It’s a great, short read that will help you challenge the status quo.

See my notes below or Amazon for details and reviews.

My Notes:

Calmness = productive emotion:
Goal at Basecamp is to be a calm company. Similar to Phil Jackson’s approach to pre-game speeches or halftime speeches. Remain calm and in control.

“Calm requires getting comfortable with enough.”

“Becoming a calm company is all about making decisions about who you are, who you want to serve, and who you want to say no to. It’s about knowing what to optimize for. It’s not that any particular choice is the right one, but not making one or dithering is definitely the wrong one.”

In victory, learn when to stop (Robert Greene, 48 Laws of Power)
Basecamp currently generates tens of millions of dollars in profit and they’re happy with that. Not obsessed with doubling or tripling market share. Focused on serving existing customers well. 

Example, they’ve kept fixed monthly fee instead of per-seat business model. Helps them avoid conflicts of interest where biggest customer holds power over the product and controls your time. 

Also, why they only have a single product. 

Work structure:
Projects are typically six weeks cycles, followed by two weeks to wander and decompress. 

Monthly “heartbeats” written by the team lead to summarize progress that’s been made. Boils key learnings down to essential points. Automatically removes the noise of the day-to-day by taking a broader perspective.

Work ethic:
Effectiveness > busyness.

Point of diminishing returns: “Creativity, progress, and impact do not yield to brute force.”

Make the best decision that you’re able to now and avoid indecision: “Accept that better ideas aren’t necessarily better if they arrive after the train has left the station. If they’re so good, they can catch the next one.”

Saying no and getting more done:
Say no, claw back time: “The only way to get more done is to have less to do.” (Similar to Nassim Taleb’s quote, “You want maximal free time, not maximal activity, and you can assess your own ‘success’ according to such a metric.”).

“No is no to one thing. Yes is no to a thousand things.”

“When you say no now, you can come back and say yes later.”

“No is calm but hard. Yes is easy but a flurry.”

Myth of low-hanging fruit:
The idea that you can instantly move needles because you’ve never tried before is delusional. Almost always requires difficult work.

Hiring and talent:
“Stop thinking of talent as something to be plundered and start thinking of it as something to be grown and nurtured.”

Ship it:
Simulated environments provide simulated answers. If you want to know the truth about your product, you have to ship it and see how real customers use it in their natural environment. 

Basecamp doesn’t beta test. They don’t put things in front of users before they’re ready for production. Slow and timid response to feedback might help them catch a few things, but they value speed and conviction over safety. 

Building a Story Brand – Donald Miller

Building a Story Brand – by Donald Miller
Date read: 4/25/19. Recommendation: 8/10.

I avoided this book for a long time, despite numerous recommendations, out of an aversion to marketing and branding. But I’m glad I finally read it. The heart of the book is about clarifying and simplifying your message. Miller presents his strategy in a seven-point framework which forms that foundation of all great stories. Whether an artist or entrepreneur, it’s a great resource to help you improve your communication. I’ve already used the framework to overhaul my own website and improve my messaging in the products I’m building at work. You’ll get the most value out of this book if you follow (and actually complete) the exercises, chapter by chapter.

See my notes below or Amazon for details and reviews.

My Notes:

Two biggest mistakes in marketing:
-Failure to focus on aspects of product that help people survive/thrive.
-Requires too much energy from customer to understand what’s in it for them. 

“Story is the greatest weapon we have to combat noise, because it organizes information in such a way that people are compelled to listen.”

The best products don’t always win. The best communicators do.

Say less and communicate clearly, otherwise customers will give up trying to organize and make sense of all the data.

Steve Jobs learned this through his experience with Pixar. In 1983, Apple launched their computer Lisa and took out a nine-page ad in the New York Times. When he returned to the company, took two words and put them on a billboard: “Think Different.”

Seven major elements, make up the SB7 framework:
Character, Problem, Guide, Plan, Call to Action, Avoid Failure, Success.

Three questions you need to answer to drive engagement:

-What do you offer? How will it make my life better? What do I need to do to buy it?

Above the fold: Promise an aspirational identity, promise to solve a problem, state exactly what you do.

Similar to: What is this? What’s in it for me? What do I do next?

1) A Character:
The customer is the hero, not you. What do they want?

Define something they want and open up a gap. 

Make it about survival. 

Make it a single focus.

2) Has a Problem:
Villain should be root source, relatable, singular, and real.

Three dimensions: external problems, internal problems, philosophical problems.

6) And Calls Them to Action
Major life decisions aren’t made until you’re challenged to do so. Must be challenged by outside forces.

Be bolder in calls to action. If they’re soft, they’ll be ignored.

If you don’t clearly invite customers to take a journey with you, they won’t. 

People are drawn to clarity. Have clear calls to action so they know what they need to do next. 

Transitional calls to action are different. Instead of “buy now” they allow you to establish credibility, create reciprocity, and position yourself as the guide (think free information, testimonial video, free trial period). 

7) That Helps Them Avoid Failure
If we don’t bring up the negative stakes early and often, story will fall flat.

What are you helping your customer avoid? What does failure look like?

8) And Ends in Success
Be specific – JFK didn’t say he wanted to build a “highly competitive and productive space program,” he said “we’re going to put a man on the moon.”

Identity transformation: From, To (anxious, glum to carefree, radiant).

The Little Book of Stoicism – Jonas Salzgeber

The Little Book of Stoicism – by Jonas Salzgeber
Date read: 4/16/19. Recommendation: 8/10.

Both a solid introduction to Stoicism for beginners and a great reminder for those already familiar with the philosophy. Jonas gives an overview of Stoicism, including its origins and most influential philosophers. But most importantly, he details what’s in it for you with a list of practices that range from visualizations and journaling to mindsets and lifestyle shifts. At this point, I’ve read 15+ books on the subject and I still felt this was well worth my time. It’s a great resource on the subject and offers a few new Stoic angles to approach your life with.

See my notes below or Amazon for details and reviews.

My Notes:

Become good with your inner daimon (inner spirit or divine spark). Live in harmony with your highest self.

Refers to to the overall quality of your life, rather than a temporary mood.

Seneca refers to this as tranquility – the inner peace that comes from a calm confidence in your path and trusting yourself. 

Eudaimonia encompasses three things: living with areté (expressing your highest self, virtue), focusing on what you can control, and taking responsibility. 

Emotional Resilience:
“To bear trials with a calm mind robs misfortune of its strength and burden.” Seneca

Not about repressing emotion, but about acknowledging, reflecting, and learning.

“We can train ourselves to act calm despite feeling angry, act courageously despite feeling anxious, and going east despite the wolf pulling west.” JS

“I buy tranquility instead.”

“If a man knows not which port he sails, no wind is favorable.” Seneca

“Most of what we say and do is not essential. If you can eliminate it, you’ll have more time, and more tranquility.” Marcus Aurelius

Via Negativa (Nassim Taleb): Acting by removing is more powerful and less error prone. 

“It is a continuous vigilance and presence of mind, self-consciousness which never sleeps, and a constant tension of the spirit. Thanks to this attitude, the philosopher is fully aware of what he does at each instant, and he wills his actions fully.” Pierre Hadot

Stimulus -> follow immediate impression -> impulsive, often irrational response.
Stimulus -> pause to evaluate, challenge initial impression -> rational decision.

Awareness robs negative emotions of their capacity to destroy.

“Character beats beauty.” JS

“If you want anything good, you must get it from yourself.” Epictetus

“What would have become of Hercules, do you think, if there had been no lion, hydra, stag or boar – and no savage criminals to rid the world of? What would he have done in the absence of such challenges?” Epictetus

Train yourself to do what others dread and resist what others can’t. 

The Stoic Archer:
Focus on the process – evaluate what’s within your control. Preparation, effort, then let the arrow fly. 

Focus on getting the conditions right (your intentions and actions). Remember, the ultimate outcome is often external. If you do the right things consistently over a long enough time frame, there will be an eventual payoff. Just don’t bank on it every time. 

“Know that sometimes things will not go your way even if you do your best, and regardless of whether you deserved it or not. Don’t confuse your aspirations with how the universe should turn out.” JS

Acceptance vs. Resignation:
Acceptance = making the most of it, overcoming challenges, seeing them as opportunities (the obstacle is the way).

Resignation = giving up and allowing apathy to dictate your life. 

Confident Data Skills – Kirill Eremenko

Confident Data Skills – by 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.

See my notes below or Amazon for details and reviews.

My Notes:

Data has always been out there. What’s changed in the past decade is our ability to collect, organize, analyze and visualize it.

Data = quantitative AND qualitative.

“Big data” is a dynamic term given to datasets that are massive in volume (too big), velocity (too rapid), or variety (too many different data attributes). Technology always being developed to improve this, that’s why what we consider “big data” is in constant flux.

Cloud = storage facility with a virtualized infrastructure. 

The Netflix recommendation is a great example of the power of data science. Netflix was able use viewing habits to create niche subcategories (Exciting horror movies from the 1980s). They were also able to see overlap in audience’s viewing patterns - identifying that people who enjoyed political dramas also enjoyed Kevin Spacey films, which led them to remake House of Cards.

One of the things that makes data science so powerful is the sheer volume it enables us to process. Can help support doctors in diagnosing patients. Doctor might have seen 5,000 patients in their career. Machine has accumulated knowledge of 1,000,000 cases.

Beneficial to have roots in a different discipline when you enter data science – gives you an advantage and helps you ask the right questions. 

The data science process:

  1. Identify the question

  2. Prepare the data (ETL - extract, transform, load)

  3. Analyze the data

  4. Visualize the insights

  5. Present the insights

Prepare the data:
-Extract the data from its sources – ensures that you aren’t altering the original source.

-Transform the data into a comprehensible language for access in a relational database. This step is about reformatting, joining, splitting, aggregating, and cleaning the data. 

-Load the data into the end source (warehouse).

Essential algorithms:
Three main groups – classification, clustering, reinforcement learning.

Classification – when you know the categories you want to group, or classify, new data points into (e.g. survey response to a yes/no question)

-Types of classification algorithms: decision trees, random forest, K-nearest neighbors (K-NN), Naive Bayes, logistic regression.

-Decision tree runs tests on individual attributes in your dataset in order to determine the possible outcomes. Questions are the branches, answers are the leaves. Better for smaller datasets.

-Random forest builds upon same principles as decision tree, it just uses many different trees to make the same prediction and averages the results from the individual trees. Every decision tree casts its vote, random forest takes most voted option. Better for larger datasets

-K-nearest neighbors (K-NN) analyzes likeness by calculating the distance between a new data point and existing data points. Deterministic model. Assumption it makes is that unknown features will be similar. 

-Naive Bayes allows new data points to be easily included in the algorithm to dynamically update the probability value. Probabilistic model. Good for non-linear problems where classes cannot be separated with a straight line on the scatter plot and for datasets containing outliers (other algorithms easily biased by outliers). Drawback: naive assumptions made can create bias.

-Logistic regression is good for analyzing the likelihood of a customer’s interest in your product, evaluating response of customers based on demographic data, specifying which variable is the most statistically significant.

-Simple linear regression analyzes relationship between one dependent and one independent variable.

-Multiple linear regression analyzes relationships between on dependent and two or more independent variables.

Clustering – when you don’t know the groups you want an analysis to place your data into (e.g. survey based on age, distance from company’s closest store). 

-Types of clustering algorithms: K-means, hierarchical.

-K-means discovers statistically significant categories or groups in a given dataset. 

-Hierarchical includes agglomerative (bottom-up, works from single data point and groups it with nearest data points in incremental steps until all points have been absorbed into single cluster, this is the most common) and divisive (begins at top, single cluster encompasses all data points, works its way down, splitting the single cluster apart in order of distance between data points), both recorded in a dendrogram. 

Reinforcement learning - a form of machine learning that leans on concepts of behaviorism to train AI. 

-Types of algorithms: Upper confidence bound, Thompson sampling.

-Upper confidence bound (UCB) is a dynamic strategy that increases in accuracy as additional information is collected. Deterministic. After a single round, use data to alter bounds of one of the variants. Good for finding most effective ad campaigns or managing multiple project finances.

The Culture Code – Daniel Coyle

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.

See my notes below or Amazon for details and reviews.

My Notes:

Foundations of culture:
1) Build safety: creates sense of belonging + identity
2) Share vulnerability: creates cooperation and trust
3) Establish purpose: creates shared goals + values

Building safety:
Belonging cues possess three main qualities: energy (invest in the exchange), individualization (treat the person as unique, valued), future orientation (signal relationship will continue).

Performance is more dependent on behaviors that communicate sense of safety and belonging than on words. 

Google AdWords: Jeff Dean, engineer at Google, took it upon himself to fix the AdWords engine in 2002. Up until that point any targeted ads were garbage. Dean didn’t ask permission or tell anyone, he just did it. As a result, Google ousted the largest payer in the game, Overture. Not because they were smarter, but because it was safer. Less bureaucracy, more autonomy. 

Gregg Popovich, coach of San Antonio Spurs, is one of the best at this. High trust, no bullshit, tells players/coaches the truth, and loves them immensely. 

Popovich methods:
-Personal connection: he cares about you (body language, attention, behavior).

-Performance feedback: telling the difficult truth and providing constructive criticism, emphasizes the high-standards of their culture.

-Perspective: regularly engages the team with person, direct questions focused on the bigger picture (politics, history, food) to emphasize that life is bigger than basketball and everyone is connected. 

Sharing Vulnerability:
Ask more uncomfortable/tough questions that generate vulnerability (e.g. “Is there something you’ve dreamed of doing for a long time? Why haven’t you done it?”). Reciprocity here is key, second person has to reciprocate to keep it going. 

Vulnerability precedes trust. And without trust, you can’t create cooperation.

Leader must be vulnerable first. Ask your people these questions:
-What is one thing I currently do that you’d like me to continue?
-What is one thing I don’t do frequently enough that I should do more often?
-What can I do to make you more effective?

Link discipline to reconnection:
When a player on the Chicago Cubs violates a team rule, Joe Maddon requires them to purchase a bottle of wine and uncork it with him and spend time together. 

At BrainTrusts (See Pixar) teams are only allowed to highlight problems (not suggest solutions). Facilitates candor - small, targeted, less personal but impactful.

Establishing Purpose:
Focus less on creating one big signal or speech, instead focus on communicating many small, clear signals that add clarity to a single vision.

Aim to be consistent instead of worrying about being inspiring. 

What type of performance are you after?
High-proficiency environments: defined, reliable performance.
-Create priorities, define key behaviors, lighthouse signaling purpose (e.g. New Zealand’s All Blacks).

High-creativity environments: help create something new.
-Less about guiding or steering, more about creating the right conditions/environment (See Ed Catmull at Pixar). 

High-purpose cultures (whether proficient or creative) are dynamic, allow them to evolve:

“High-purpose environments don’t descend on groups from on high; they are dug out of the ground, over and over, as a group navigates its problems together and evolves to meet the challenges of a fast-changing world.” DC

Skin in the Game – Nassim Taleb

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.

See my notes below or Amazon for details and reviews.

My Notes:

The core of the book focuses on four topics: a) uncertainty and the reliability of knowledge, b) symmetry in human affairs (fairness, justice, responsibility, reciprocity), c) information sharing in transactions, d) rationality in complex systems and the real world. 

Importance of skin in the game:
Necessary for fairness, commercial efficiency, risk management, but most importantly, it’s necessary to understand the world. It’s about the things that existential for humans (justice, honor, sacrifice).

Skin in the game means having exposure to the real world and paying a price for consequences, good or bad. Keeps human hubris in check.

Soul in the game: “If you do not take risks for your opinions, you are nothing.” NT

Natural filter: if you can’t put your soul into something, leave it for someone else. 

No skin in the game (keep upside, transfer downside to others): Bureaucrats, consultants, administrators, politicians, corporate executives.
*See diagram on page 47 for list of asymmetries.

Asymmetries in life come from agency problems – absence of skin in the game contaminates fields and produces distortions. Skin in the game demands symmetry. 

“The curse of modernity is that we are increasingly populated by a class of people who are better at explaining than understanding, or better at explaining than doing.” NT 

“Avoid taking advice from someone who gives advice for a living, unless there is a penalty for their advice.” NT

Thinking in high, not low, dimensions:
Many people struggle to understand multidimensional problems – cholesterol reading is a single-dimensional representation that isn’t necessarily representative of complex system of multidimensional health. Another extension of this problem, comparing actions of dictators in war torn countries to the prime minster of Norway, not the local alternative. 

The Silver Rule:
“Do not treat others the way you would not like them to treat you.” NT

Mind your own business, don’t try to decide what’s good for others (The Golden Rule). 

Via negativa:
Via negativa (acting by removing) is more powerful and less error-prone than via positiva (acting by addition).” NT

Don’t ever allow yourself to have an assistant, it hinders your natural filtering system. Without one you’ll only be able to do the things you truly enjoy. “You want maximal free time, not maximal activity, and you can assess your own ‘success’ according to such a metric.”

“Assistance moves you one step away from authenticity.” NT - for example, using Google Translate as opposed to learning the language through interactions with locals. 

Decentralization and fragmentation help stability and improve people’s connection to their work. In a way, preserves a deep sense self-sufficiency that we all crave.

Minorities, not majorities, rule:
All it takes to get a book banned is a few intolerant activists who create a fuss. In a way, the most intolerant minority rules.

Revolutions aren’t always favored by the majority, in fact they’re often driven by an obsessive minority. 

It’s okay to be intolerant with intolerant minorities. They’re violating the Silver Rule (see above). Can’t use “American values” when treating intolerant extremists who deny people’s right to their own religion. 

Cato’s injunction: he preferred to be asked why he didn’t have a statue than why he had one. One of the most important lessons I learned early on in life and helps demand far greater respect than people who overshare/overpromote and are focused on “personal brand.”

“A free person does not need to win arguments – just win.” NT

The Lindy effect:
Heuristic explaining that time removes the fragile and keeps the robust. If something is “Lindy” then it ages in reverse, life expectancy lengthens with time, conditional on survival. E.g., book with life expectancy of 100 years and has a future life expectancy of 100 more. 

There’s only one effective judge of things: time. 

“Burn old logs. Drink old wine. Read old books. Keep old friends.” Alfonso X

Summarizing Wittgenstein: knowledge is the reverse of an athletic contest. In philosophy, the winner is the one who finished last. 

An idea will survive the test of time not only if it does not harm, but also if it favors one’s survival. 

Paradox of Progress: Story of New York banker vacationing in Greece, talking to a fisherman. Consider Robert Green’s insight from The 48 Laws of Power, “In victory, learn when to stop.

“When the beard (or hair) is black, heed the reasoning, but ignore the conclusion. When the beard is gray, consider both reasoning and conclusion. When the beard is white, skip the reasoning, but mind the conclusion.” NT

The Gordian Knot:
Greek story about Alexander the Magnus untying a wagon with dozens of knots (oracle predicted that whoever did it would rule over all of Asia). Instead of overcomplicating the solution, drew his sword and cut the knot. Theme: what matters is not complexity of presentation but results.

Modern dilemma - patient shows up with a headache, much better to give him aspirin or tell him to get a full night of sleep than do brain surgery (even though it might appear more scientific)

You can criticize what a person said (more sensational) or what a person meant. Figuring out what a person meant requires you have a better grasp of the idea. Charlatan’s can be identified by their criticism of specific statements. 

Virtue signaling: exploiting virtue for personal gain, image, career, status. Immoral to claim virtue without living with its consequences. 

“Courage is the only virtue you cannot fake.” NT 

The Law of the Jungle:
The world belongs to the collaborative. Consider how few predators there are in comparison to collaborative animals (think of a watering hole). 

What you do, not what you think or what you believe. At it’s core, it’s rationality is about survival.

The Silk Roads – Peter Frankopan

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).

See my notes below or Amazon for details and reviews.

My Notes:

Intellectual center of the world:
Before the modern era, the Middle East and Asia were the scientific hub of the world (places like Iraq, Uzbekistan, Afghanistan). Center of logic, theology, mathematics, medicine, and philosophy.

At its peak, Baghdad was magnificent. Filled with parks, markets, mosques, bathhouses, schools, hospitals, palaces, kiosks, gardens. 

Silk Roads:
Linked the Pacific to Mediterranean, first major pathways that connected distant people and cultures. Carried goods, but also fostered intellectual and religious exchange. 

This is not a modern phenomenon. It was just as prevalent 2,000+ years ago with the expansion of China under the Han dynasty or Alexander of Macedon’s conquests of Persian territory. Each created its own opportunities, problems and technological advances. 

What we think to be uniquely modern problems are rarely that (with the exception of climate, obesity, and a few others). People have been outraged for the entirety of human history about certain things, particularly progress and change. Certain themes have remained present as far back as we can see – i.e. struggles between religions. 

“Two millennia ago, silks made by hand in China were being worn by the rich and powerful in Carthage and other cities in the Mediterranean, while pottery manufactured in southern France could be found in England and in the Persian Gulf. Spices and condiments grown in India were being used in the kitchens of Xinjiang, as they were in those of Rome. Buildings in northern Afghanistan carried inscriptions in Greek, while horses from Central Asia were being ridden proudly thousands of miles away to the east.” PF

The Mongols:
The Mongols rose to power and gained the largest land empire in history because of ruthless planning, streamlined organization, and a clear set of strategic objectives. Ability and loyalty > tribal background or status.

Mongols were not always seen as oppressors, invested in infrastructure, rebuilt cities, emphasized arts and production. Their reputation as bloodthirsty barbarians is due to histories written after the fact.

“This slanted view of the past provides a notable lesson in how useful it is for leaders who have a view to posterity to patronize historians who write sympathetically of their age of empire–something the Mongols conspicuously failed to do.” PF

The Plague:
Silk roads were the veins through which the plague devastated the world.

Social and economic change brought about in the west was significant. Shortage of labor helped increase its value and wages, enhanced negotiation power of lower classes. Also matched by weakening of propertied class with lower rents and falling interest rates. Wealth became more even distributed and resulted in a greater purchasing power and demand for luxury goods. Rise in wealth also brought about better diets and health. Post-plague populations were generally far healthier than before it struck. 

Great overview of the political struggles between faiths for much of human history. Puts the foolishness of religion and silly beginnings in perspective.

Eighth and ninth centuries, Muslims (in the east) were curious, tolerant, open-minded, focused on progress. Europe (the west) was filled with Christian fundamentalists who were the opposite. They were considered intellectual backwaters.

In the middle of the ninth century, the Khazars decided to become Jewish. Khazar ruler brought delegations from each faith to debate and present their case. He asked Christians whether Islam or Judaism was the better faith, they said the first was much worse. He asked the Muslims whether Christianity or Judaism was better and they ripped Christianity. Both had admitted Judaism to be better and so they converted. 

Shift in world's political and economic center of gravity:
Since Europe was at the far end of the Silk Roads, it was an afterthought for most of history. But in the 1490s, Christopher Columbus crossed the Atlantic and Vasco de Gama navigated the southern tip of Africa. Both opened new trade routes and shifted the center of world power. Europe took center stage as the midpoint between the east and the west.

Rise of Western Europe:
France, Germany, Austria, Spain, Portugal and England were irrelevant in the world of the ancient Greeks, and were largely peripheral in the history of Rome. But after Columbus and Vasco de Gama, this changed their course of history entirely.

England would eventually turn what proved to be its weakness (distant, isolated), to its strength and the tides shifted towards Western Europe.

Led to a massive redistribution of wealth. WWI bankrupted the old world and enriched the new. To finance food production, weapons, munitions, the Allies commissioned J.P. Morgan & Co., taking on huge debts. During the Great War, Britain went from being largest creditor in the world to being its largest debtor. World economy was left in ruins.

Genghis Khan and the Making of the Modern World – Jack Weatherford

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 the foundation for the modern world with free commerce, open communication, shared knowledge, secular politics, religious coexistence, international law, and diplomatic immunity.

See my notes below or Amazon for details and reviews.

My Notes:

Genghis Khan was born in 1162, unified all tribes on steppe and founded the Mongol nation in 1206. His life and character were shaped by rugged landscape on the Mongolian steppe.

Genghis Khan was self-made. Grew up in a world of violence (murder, kidnapping, enslavement), encountered no more than a few hundred people on the Mongolian steppe in his childhood, received no formal education. He showed remarkable instinct for survival and self-preservation.

Military Genius
Brilliant use of speed and surprise on battlefield. Perfected siege warfare, negating benefits of walled cities. Goal of every invasion was to frighten the enemy into surrendering before the battle began.

Turned massive populations against the places they invaded by terrifying peasants at the foothills and sending swarms of refugees into the cities which could not support them. 

Traveling lightly, quickly: Traveled without a supply train (waited until cold months so horses could graze, better for hunting) or siege engines and equipment. Instead, brought along a faster-moving engineering corps to build whatever they dreamed up or the situation required. Mobility boost from all cavalry (no marching infantry). 

“Victory did not come to the one who played by the rules; it came to the one who made the rules and imposed them on his enemy. Triumph could not be partial. It was complete, total, and undeniable – or it was nothing.” JW

In 25 years under Genghis Khan, the Mongol army conquered more lands and people than the Romans conquered in 400 years. 

Leveraged his own naiveté as a tool - did not grow up in cities of have access to antiquated tactics. Had to create his own, such as diverting a channel of the Yellow River to flood the fortified Tangut capital. 

Would often lure enemy away from battlefield in false retreat, drew enemy further away (in overconfidence) and exhausted them. Once enemies became disorganized and tired, Mongols would turn and shoot them down. (See example of Duke Henry II of Silesia and army of 30,000 knights, page 152). 

Benefits of Multiculturalism
“Genghis Khan’s army combined the traditional fierceness and speed of the steppe warrior with the highest technological sophistication of Chinese civilization.” JW

Each step of the way, combined new ideas and strategies he learned or discovered from different challenges or cultures. Always learning, experimenting, adapting, and revising. Never fought the same war twice. 

Genghis Khan sought talented men as his closest advisors, no matter their origin.

“Whether in their policy of religious tolerance, devising a universal alphabet, maintaining relay stations, playing games, or printing almanacs, money, or astronomy charts, the rulers of the Mongol Empire displayed a persistent universalism. Because they had no system of their own to impose upon their subjects, they were willing to adopt and combine systems from everywhere. Without deep cultural preferences in these areas, the Mongols implemented pragmatics rather than ideological solutions.” JW

Arbitrary Authority
Distrust of arbitrary authority – Championed individual merit, loyalty, achievement and smashed feudal system of aristocratic privilege and birth.

Killed all aristocratic leaders (rich and powerful) in each conquered land to decapitate social system of enemy and eliminate future resistance.

Inspired deep loyalty in his people by taking conquered people into his tribe (sans aristocrats) as equal members in good standing who could share fairly in future prosperity. This helped unite his future empire.

Second-order thinking: When looting, ordered a soldier’s share for each widow and orphan of anyone killed in the raid. Main benefit was to avoid temptation to rush looting without complete victory. Also, inspired soldiers who knew he would take care of their families.

In six decades, none of his generals deserted him. He also never harmed or punished a single one of them. Unrivaled fidelity among all great kings throughout history. 

Organized warriors across different tribes and kin into units of ten (arban) who were to fight and live together as loyally as blood. Helped unite tribes and people across the empire.

Sought to remove all animosity/dissension within the ranks of his followers: Forbade the enslavement of any Mongol, declared all children legitimate, forbade selling of women into marriage, outlawed adultery, punished theft of animals, forbade hunting of animals during breeding times (March-October), decreed complete and total religious freedom. 

First to connect China and Europe with diplomatic and commercial contacts–opened the world to new commerce in goods, ideas, knowledge. Unrivaled carriers of culture. 

Literacy and the number of books increased drastically during the Mongol dynasty.

First in history to decree compete religious freedom for everyone in the empire. Recognized the disruptive potential of competing religions.

After initial destruction and shock of conquest in each country the Mongols set foot in, unprecedented rise in cultural communication, expanded trade, improved civilization. Mongol influence, in many ways, led Europe to the Renaissance.

“Without the vision of a goal, a man cannot manage his own life, much less the lives of others.” GK

Fostered exchange of medical knowledge by establishing hospitals and training centers, bringing together the best doctors of the time from India and the Middle East with Chinese healers.

Set foundation for modern world with free commerce, open communication, shared knowledge, secular politics, religious coexistence, international law, and diplomatic immunity. 

Khubilai Khan
Lacked military skills of Genghis, but also recognized he couldn’t conquer China by mere force. Combined brilliant ideas with great implementation with allowed him to manage his territory and its expansion south. 

Commissioned Chinese-style imperial capital which grew into modern capital of Beijing. 

Previous dynasties had tried to unite Chinese states, but Khubilai was the first one to pull it off. Accomplished this by empowering Peasants by giving them responsibility in local community (acting as local governments), public schools, education, literacy. “The greatest legacy of the Mongol Empire bequeathed to the Chinese is the Chinese nation itself.” Hidehiro Okada

Downfall of the Mongol Empire
The plague cut off each part of the Mongol Empire (Persia, Russia, China) from the other and interlocking system collapsed. Depended on quick, constant movement of people and information. During the plague, various parts of empire were either decimated or isolated themselves for survival. 

1492, more than a century after the last khan ruled over China, Christopher Columbus set off to revive lost contact with Mongol court. Reached United States thinking it must be southern neighbors of Mongols in India (hints naming, “Indians”).

The Tigress of Forlì – Elizabeth Lev

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.

See my notes below or Amazon for details and reviews.

My Notes:

Renaissance Italy’s Most Courageous and Notorious Countess, Caterina Riario Sforza de’ Medici

Legacy: Ingenuity, boldness, cunning, astute strategies, and iron determination. Fended off her husband’s assassins, the French Army, and Cesare Borgia.

Warrior: Grew up learning to bear and wield arms in the tradition of her warrior family. Her family emphasized training of female children along males the use of weapons, riding and hunting. Gave her an unusual advantage and first-class education in the fundamentals of military leadership. 

Galeazzo Maria Sforza
 (father, Duke of Milan): Admired his boldness, warrior nature that he blended with his love for the arts. He turned Milan into an intellectual rival to Florence. He defined Caterina’s ideal of bravery and elegance.

Bona of Savoy (Galeazzo’s second wife, not Caterina’s biological mother): After Galeazzo was murdered, she transformed from a quiet, patient mother and wife, into a competent head of state, dealing with threats and taking on all responsibility. Safely transported Caterina to join her husband (Girolamo Riario) in Rome after her father’s death.

Defying Expectations:
Throughout her life, powerful men viewed her as a pawn on the chessboard of Italian politics, to be used and sacrificed at will. They doubted her ability to rule and never took her seriously. She would prove this to be foolish, time and time again. 

Brutally realistic expectations set by early marriage (at age 10) to a foolish, self-indulgent husband (Girolamo) and the murder of her father forced her to build deep well of fortitude and resilience.

She was held in high-esteem, her intelligence, manners, and sense of fashion were widely admired. While Girolamo was holed up, wary of strangers, she would take to the streets to walk among her subjects and actively engage the citizens. Even when the bubonic plague hit, she would visit the poorest quarters, tend to the ill and bring food/medicine.

Girolamo’s missteps:
Caterina was constantly helping to negotiate her husbands errant moves, whether failed assassination plots, greedy exploitations, his fear of combat, or his antagonization of powerful families in northern Italy. Girolamo lacked substance and intelligence. She never complained, but she took a more active role after the first couple years. She didn’t want to sit idly by as her husband squandered the family name and the children’s inheritance. 

Upon Pope Sixtus’s death:
 mobs raced to the Riarios’ house in Rome and tore it down in pent up rage towards Girolamo. Caterina and Girolamo were safe in Forlì, but instead of hiding behind her husband’s forces, she jumped on a horse (seven months pregnant at the time) and rode to Rome. She seized the papal fort of Castle Sant’Angelo and turned the cannons towards all access roads around the Vatican to cut off the cardinals. She single-handedly held the College of Cardinals at bay for eleven days and negotiated that her family retain the lands of Immola and Forlì.

Dimensional thinking - there’s a time for patience and there’s a time for boldness. Caterina knew how the balance the two.

Girolamo’s Death: murdered in his palace, Caterina immediately jumped into action, barricading the the room that she and the children were in to buy herself time. She immediately issued instructions for a messenger to send for her allies (and her brother, the duke of Milan). Once captured, she was brought to her castle, Ravaldino, to negotiate its surrender. She devised elaborate schemes to buy time, negotiating the castle’s surrender, plotting with Tommaso Feo (the guardian of the castle and who she was supposed to be negotiating with). After one negotiation session, he claimed to take her captive and locked out her kidnappers (the Orsis). The kidnappers brought her children out front and threatened their lives in front of Caterina. She was able to think strategically, as she knew her children, being the nephews of the duke of Milan, could not be killed without retaliation. She also knew that surrendering would give her no advantage–her family would likely be poisoned or imprisoned–so she held her position and strode to the edge of the ramparts with daggers drawn. She held the castle for 13 days until reinforcements arrived. Preserving Forlì and her family.

Cesare Borgia’s Invasion of Ravaldino:
December 19, 1499, Borgia began his siege. Caterina embarrassed and befuddled him. Frustrated by her resistance, raised the bounty of her head to ten-thousand ducats, but no one inside the fortress was willing to betray her. She commanded a deep loyalty. People flocked to Forlì to witness her defense and fearlessness against the most cruel man in Italy. The longer Borgia was stalled by a woman, the weaker he seemed in the eyes of his adversaries. On January 12, he threw everything he had at the fortress and broke in. Caterina fought on the front ranks for two hours, side by side with her men against Borgia’s soldiers. She was the equal of any man on the battlefield. She was eventually captured, but did not go quietly.

Legacy – James Kerr

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.

See my notes below or Amazon for details and reviews.

My Notes:

Personal Discipline:

  • Post-game the All Blacks debrief and everyone is given a chance to speak. Once they break, something unexpected happens, two players grab a broom and begin sweeping the sheds, cleaning up after themselves. 

  • No one looks after the All Blacks, they look after themselves. They don’t expect someone else to do their job or things to be handed to them.

  • Strong personal discipline translates to discipline on the field.


  • “Only by knowing yourself can you become an effective leader.” Vince Lombardi

  • Self-knowledge helps develop character and integrity. Character and integrity help develop leadership.

  • “What is my job on the planet? What is it that needs doing, that I know something about, that probably won’t happen unless I take responsibility for it?” Buckminster Fuller


  • Force multiplier: Any lasting organization has a fundamental set of principles…a values-based, purpose-driven culture. Challenge is to bring that to life and into the lives of those on your team.

  • “My army won because they knew what they were fighting for and loved what they knew.” Oliver Cromwell

  • Establish a higher culture than your opposition and you’ll win.

  • “It’s better to have a thousand enemies outside the tent than one inside the tent.” Arab proverb

  • Multiculturalism - ever-changing sense of what it means to be a New Zealander or an All Black: “Successful cultures are organic and adaptive, they change and flow, yet always just under the surface is a bedrock of values, smoothed by the current above, but unyielding.” See Shane Parrish interview with Shopify founder Tobi Lütke.


  • Sigmoid Curve: Learning, growth, decline.

  • Outwitting inevitability and hijacking the curve: “The key, of course, is when we’re on top of our game, to change our game; to exit relationships, recruit new talent, alter tactics, reassess strategy.” JK

  • Growth comes from allowing yourself, your skills and your sense of authenticity to evolve. Tiger Woods changing his golf swing. Bob Dylan altering his sound. 


  • Leaders create leaders.

  • “Move rapidly into a commanding position, assess your unfolding options quickly and clearly, attack with absolute and ruthless commitment – assess, adjust and repeat.” JK

  • Empower your people: “The competitive advantage is nullified when you try to run decisions up and down the chain of command…Once the commander’s intent is understood, decisions must be devolved to the lowest possible level to allow these front line soldiers to exploit the opportunities that develop.” General Gordon R. Sullivan

  • “Leaders are teachers – our job is to lead people through uncertainty and confusion into self-knowledge and self-possession.” JK

Power of Storytelling:

  • “Using vivid storytelling techniques, including themes, symbols, imagery, rituals, mantras and metaphor, and bringing them to life with imagination and flair, leaders create a sense of inclusion, connectedness, and unity.” JK

  • “We learn best – and change – from hearing stories that strike a chord with us…Those in leadership positions who fail to grasp or use the power of stories risk failure for their companies or themselves.” John Kotter

  • “Metaphors are where we recognize ourselves in stories.” JK

  • “The greatest thing by far is to have a command of metaphor. This alone cannot be imparted by another; it is the mark of genius, for to make good metaphors implies an eye for resemblance.” Aristotle

Authenticity + Integrity:

  • “Authenticity allows us to author our own lives; to make our own original imprint and to write our own story in a voice that is true to our values.” JK

  • Integrity means being able to count on yourself (and others being able to count on you) to deliver. It’s about honoring your word. 


  • Red head: tight, inhibited, results-oriented, anxious, aggressive, over-compensating, desperate.

  • Blue head: loose, expressive, in the moment, calm, relaxed concentration, clear, accurate, on task.

  • “In the heat of battle, the difference between the inhibitions of the Red and the freedom of Blue is the manner in which we control our attention.” JK

  • To get out of your own head, shift your attention to something external. 


  • Whakapapa - Maori term for genealogy, our place in the ascending order of all living things. Sun slowly moves down this chain of people, signifying life. When the sun is on us we inherit the tribe’s stories, values, transitions. We help advance that, then pass it on to the next person in the chain.

  • Whakapapa is similar to the Stoic term sympatheia (interconnected whole). 

  • “What you leave behind is not what is engraved in stone monuments, but what is woven into the lives of others.” Sean Fitzpatrick

  • “A society grows great when old men plant trees whose shade they will never see.” Greek Proverb

  • “Character is also the mark left on you by life, and the mark we leave on life.” JK

  • “If we value life, life values us.” JK

Creativity, Inc. – Ed Catmull

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. See my notes below or Amazon for details and reviews.

My Notes:

Problems are the rule, rather than the exception. Even at great companies.
Mentality at Pixar is that they will always have problems, many of them hidden. But they work hard to uncover them, embrace the discomfort, and band together to solve them.

“The desire for everything to run smoothly is a false goal–it leads to measuring people by the mistakes they make rather than by their ability to solve problems.” EC

Blending Art + Technology
Walt Disney embraced new technologies…he would incorporate it into their work (blue screen matting, multi-plane cameras, xerography) and talk about it on his show to highlight the relationship between art and technology.

Catmull and Pixar took the same approach, blurring the lines between disciplines. Result was Toy Story, the first computer animated feature film.

Goal is to enable people to do their best work. That means more creative freedom (autonomy + empowerment), less tightening your grip.

The best leaders all have a single trait in common – self-awareness.

People > Ideas (because ideas come from people)
Always try to hire good people who are smarter than you. Then figure out what they need, assign them to projects that match their skills, and ensure they work well together.

“It is the focus on people–their work habits, their talents, their values–that is absolutely central to any creative venture.” EC

Bet on Yourself
George Lucas, instead of demanding higher salary after success of American Graffiti (the norm in Hollywood, bump up your quote), skipped the raise and asked to retain ownership of licensing and merchandising rights to his next film, Star Wars.

Ed Catmull felt like a fraud in his early years as president of Pixar. He didn’t share the aggressive tendencies of other flashy leaders. Imposter feeling finally went away after years later after repeated experience of weathering failures, watching films succeed, building Pixar’s culture, and developing relationships.

“As long as you commit to a destination and drive toward it with all your might, people will accept when you correct course.” EC

Make your best guess and go with it. Decisions can be made far faster (product development) if you assess them in terms of how reversible they are (*See Shane Parrish’s interview with Shopify’s CEO, Tobi Lütke).

Avoid the temptation to oversimplify (and overcomplicate)
In early days of Pixar while Catmull was selling the Pixar Imaging Computer to make money, he sought advice of experienced professionals because he was unsure and stressed. Simple answers were seductive and prevented him from asking more fundamental questions.

Many leaders assume too much credit in their successes and ignore the role of randomness and luck.
*See Nassim Taleb’s Fooled by Randomness + Occam’s Razor

Important to acknowledge role of randomness and luck, because this allows you to keep an open mind, check your ego, and make rational decisions. Not everything you did was a stroke of genius.

Make room for the unknown in creativity. It can bring inspiration and originality. Not everything needs to have a point or be about productivity/efficiency.

Thinking Fast vs. Slow
Steve Jobs would often shoot down Ed Catmull’s arguments when they disagreed because he was a much faster thinker. Catmull would wait a week, collect his thoughts, deliberate, then state his case. Jobs always kept an open mind.

Candor and Trust
“A hallmark of a healthy creative culture is that its people feel free to share ideas, opinions, and criticisms. Lack of candor, if unchecked, ultimately leads to dysfunctional environments.” EC

Without candor, you fail to establish trust. Without trust, creative collaboration becomes impossible.

You are not your idea. If you emotionally invest and overidentify with your idea, you’ll become defensive when challenged or given feedback.

Guiding Principles
The search for a story is the search for a guiding principle. This allows Pixar’s films to evolve drastically from their original treatments. Once they find the guiding principle, easier to build the characters, storyline, settings to better communicate that.

Don’t become emotionally attached to a single character or storyline, become emotionally attached to the guiding principle. Look for deep truths and build from there.

“Originality is fragile. And, in its first moment, it’s often far from pretty. This is why I call early mock-ups of our films ‘ugly babies.’ They are truly ugly: awkward and unformed, vulnerable and incomplete. They need nurturing–in the form of time and patience–in order to grow.” EC

Pixar’s use of “guiding principles” could be interchangeable with “vision” in product development. Don’t get attached to a single feature. Invest in the vision.

Experimentation and Failure
“Experiments are fact-finding missions that, over time, inch scientists toward greater understanding. That means any outcome is a good outcome, because it yields new information.” EC

Animated shorts are Pixar’s version of prototypes. Relatively inexpensive way to test the waters and see if they’re onto something.

Make it safe to take risks: “Rather than trying to prevent all errors, we should assume, as is almost always the case, that our people’s intentions are good and that they want to solve problems. Give them responsibility, let the mistakes happen, and let people fix them...Management’s job is not to prevent risk but to build the ability to recover.”

Constraining creativity is a steep price: “The cost of preventing errors is often far greater than the cost of fixing them.”

“We all know people who eagerly face the unknown; they engage with the seemingly intractable problems of science, engineering, and society; they embrace the complexities of visual or written expression; the are invigorated by uncertainty. That’s because they believe that, through questioning, they can do more than merely look through the door. They can venture across its threshold.” EC

“Creativity has to start somewhere, and we are true believers in the power of bracing, candid feedback and the iterative process–reworking, reworking, and reworking again, until a flawed story finds its through line or a hallow character finds its soul.” EC

“Craft is what we are expected to know; art is the unexpected use of our craft.” EC

Learn the fundamentals and key players (the map), then rip it up and make your own way (*See Bob Dylan, Chronicles). At its core, creativity is about embracing ambiguity and discomfort.

“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.” EC

“Unleashing creativity requires that we loosen the controls, accept risk, trust our colleagues, work to clear the path for them, and pay attention to anything that creates fear.” EC

When Disney acquired Pixar, Catmull helped run both animation departments separately. Wanted each to have their own identities and be able to differentiate themselves, as long as they shared a sense of personal ownership and pride in the company.

Tobi Lütke, CEO of Shopify, has a similar approach. He encourages each group within the company to establish their own culture. He doesn’t try to impart a single homogenous culture across the entire organization.

Inspired – Marty Cagan

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.

See my notes below or Amazon for details and reviews.

My Notes:

The best product teams share three main principles:
1. Risks tackled up front (value, usability, feasibility, business viability)
2. Products are defined and designed collaboratively
3. Focus is on solving problems, not implementing features

Product/market fit: smallest actual product that meets needs of a specific market of customers.

Product Manager key responsibilities (all focused on evaluating opportunities and determining what gets built):
1. Deep knowledge of customer (issues, pains, desires)
2. Deep knowledge of data and analytics
3. Deep knowledge of all aspects of your business (stakeholders, finance, marketing, sales, legal, technical capabilities, user experience)
4. Deep knowledge of your market and industry

Successful product people are a combination of smart, creative, and persistent.

VPs of Product should have these four key competencies:
1. Team development
2. Product vision
3. Execution
4. Product culture

How to organize teams:
1. Alignment with investment strategy
2. Minimize dependencies
3. Ownership and autonomy: build teams of missionaries (they’re force multipliers), not mercenaries
4. Maximize leverage: establish a balance with shared services
5. Product vision and strategy
6. Team size: 3-10
7. Alignment with architecture: otherwise dependencies, slow pace
8. Alignment with user or customer: team focused on buyers should be different than the team focused on sellers
9. Alignment with business

Management’s responsibility is to provide product teams with business problems, objectives, and vision (NOT solutions). Let the team figure out the best way to solve the problems.

Product Discovery:
Collaboration between product, UX, and engineers to tackle risk before writing production-quality software. Outcome is a validated product backlog.

Purpose is to address value, usability, feasibility, and business viability risks.

Goal is to gain deeper understanding of customers and validate product ideas (qualitatively and quantitatively).

Dedicating time to framing the problem and communicating this can make significant difference in results.

“But one of the most important lessons in our industry is to fall in love with the problem, not the solution.” MC

Opportunity Assessment Technique:
What business objective is this work intended to address?
2. How will you know if you succeeded?
3. What problem will this solve for customers?
4. What type of customer are we focused on?

Customer Letter Technique:
Product manager writes an imaginary press release or letter from hypothetical perspective of a customer talking about how it has improved their life.

Product Opportunities:
Assess the market and pick lucrative areas where pain exists. Or look at what technology enables and match that up with a pain point. Or encourage customers to use products to solve problems other than what you planned for.

One of biggest innovations at eBay was watching how customers used platform to sell things the team never would have imagined (concert tickets, fine art, cars). Built capabilities to facilitate these types of transactions after demand was established.

Customer Interviews:
Always be working to understand if your customers are who you think they are, if they really have the problems you think they have, how they solve the problem today, and what would be required from them to switch.

Provide the ability to learn at much lower cost (time and effort) than building the full product.

Always ask, “what’s the fastest way to learn this?” MVP should be a prototype, never an actual product.

Benefits of prototyping: forces you to think through the problem at a deeper level, team collaboration, quickly assess one or more of the product risks.

A/B Testing:
Optimization A/B testing: Small changes, different calls to action, colors, fonts. 50/50 distribution. Conceptually similar.

Discovery A/B testing: Big differences, different concepts. Live-data prototype shown to 1% of users or less.

Necessity leading to invention:
In the early days of Netflix they had the same model (pay per rental) as Blockbuster. One of the many tests they ran was to assess customer interest in a subscription service (monthly fee for unlimited movies). They generated significant interest but created more problems in the process of bringing it to life. Most people wanted to rent the newest films which was prohibitively expensive. Netflix needed to get people to ask for a blend of old/new (inexpensive/expensive) titles. This was how the queue, rating system, and recommendation engine were born.