2023 Reading Update

So far in 2023, I’ve read 24 books and gave up on 7. I would have written about all these awesome books earlier, but writing on my new personal finance blog has taken up more of my time than previously.

If you’ve read any good nonfiction books, please pass the recommendations my way. I’m always looking for new material!

★★★★★ Chip War

If you read one book this year, I would recommend this one. The creation of microprocessor chips isn’t just important to techies and nerds anymore. The country that can produce more and better chips will prevail over all other countries. Miller not only describes the incredibly fascinating way in which chips are made, but makes a compelling argument about the hot topic of chip dominance between China and the US. I couldn’t put this one down and now really want to take a tour of a chip fab if I ever get the chance.

★★★★★ The School of Life

The School of Life doesn’t get everything correct, but there’s enough really good wisdom in here to make it a must read. This was initially hard for me to get into because it’s so thoroughly unscientific. At no point does this devolve into the popular science trope of citing social science research. You’re never asked to believe in the outcomes of a study conducted at such and such university that proves that love is real. But I think that’s the key part of the charm: it’s direct and even when it misses, it’s still thought-provoking.

★★★★★ Immune

I remember taking biology 120 in college: it was a big, long, and somewhat boring lecture series. This book is the opposite of that. Philipp Dettmer does an incredible job of making the specific mechanics of our immune systems accessible and fascinating. There’s so much detail in here that I almost immediately forgot most of it, but I came away with a deep, abiding understanding of the absolutely absurd level of complexity built into how our bodies keep us healthy.

★★★★★ The Fall of Robespierre

In my opinion, this is history writing at it’s finest. Rather than describing the events of the French revolution at a high level (booooorrriinnng), he zooms in and tells the deeply human, messy, and interconnected history of how a seminal historical event actually unfolded. What is often described in history textbooks in a couple of sentences and comes across as dry and predetermined here comes alive with ambiguity, reversals of fortune, random strokes of good luck, and human tension. I wish that I was taught this sort of history during my time in school.

★★★★☆ The Making of the Atomic Bomb

This would have gotten 5/5 stars, but good lord does Rhodes take a long time focusing on the history of physics. Easily the first half of the book is just focused on the extremely detailed history of the physicists and experiments that led up to what the title promises: the creation of the atomic bomb. And I get it, the title is about the making of the bomb, but I would have appreciated a longer epitaph about what some of the key figures did after the Manhattan Project. I was especially curious to learn what many thought about their contributions decades later.

★★★★☆ Chaos Monkeys

This one won’t change the way you see the world in a fundamental way, but good lord is it entertaining and accurate. Martinez was a couple of years ahead of me going through YCombinator and working at Facebook. But our experiences overlapped so closely that I feel like I am in a unique position to judge the accuracy of this book. And it is 100% accurate. If you ever wanted to know what it’s actually like to be funded by YC, work at Meta, or just be a techie in Silicon Valley, look no further.

★★★★☆ Barbarians at the Gate

This one deserves it’s reputation as a classic among business books. It’s well-researched, readable, and interesting at a human level. Personally, I think the people most likely to benefit from reading this book are younger people who don’t have a lot of working experience yet. It does a really good job of explaining how business at big corporations is really conducted. Obviously, the cast of characters here were chosen because they are almost caricatures of themselves, but if you’ve worked in corporate America long enough, you’ve met every single person described in these pages.

★★★★☆ Preparing for War

Onishi might be wrong about his primary thesis, but it is at least consistent and may answer a question that’s been on my mind for the last 8 years: why is conservative political ideology so nonsensical? His theory is that most conservative rhetoric is an intentional misdirection from the real truth that the only consistent Republican system of belief is white supremacy. That’s almost certainly an oversimplification for any one conservative person’s system of beliefs, but the shoe does seem to fit the party’s direction at the national level. At the very least, I’d encourage you to read it and make your own assessment of his hypothesis.

★★★★☆ Entangled Life

I had actually been avoiding this one despite the insanely positive reviews. I mean, c’mon, how much is there to know about mushrooms? But I was wrong and the reviews were right: this one really is insanely interesting. If, like me, you thought that fungi were only just mushrooms then you should do yourself a favor and read this book. It was so good that I found myself spontaneously gushing about it to coworkers.

★★★★☆ The Secret Life of Groceries

This book could have easily devolved into another Supersize Me, editorialized expose about grocery stores, but it rises above that. I learned a lot about why Trader Joes is so likable, why it’s nearly impossible for good food to be sold at large box stores, and why the food we eat is neither so terrible as journalists would have you believe or as good as food marketers claim it is.

★★★★☆ John Adams

I love the musical Hamilton. The show briefly covers the Adams administration, but I realized recently that I didn’t really know much about him nor his work. And of course, David McCullough is a nonfiction legend. I’ve read most of his books, and they’re all great.

This might have scored higher with me if I hadn’t accidentally downloaded the abridged version of the audio book. So, don’t do that if you actually want to learn about Adams. Otherwise, I really enjoyed refreshing my knowledge on the founders. I came away thinking that Hamilton was probably the lesser of the two men, but the musical is still great.

★★★☆☆ Dead in the Water

I have a fascination with large boats. I have no idea why. But if you’re like me and maritime shipping and boats are at all interesting to you, this one will definitely keep your turning the pages. It’s about what is probably the largest known maritime insurance fraud that occurred about 15 years ago. It’s got everything you want in a story: a bad guy, a good guy, murder, fraud, extortion, and … big boats.

★★★☆☆ The World in a Grain

I was worried that this book would fall into the category of pop-sci books that became a fad in the mid 2010s. They all follow the same pattern and pitch: Simple Noun: How Simple Noun is Important to Every Person That Has Ever Lived and May Have Killed Your Parents. I’ve read a couple books in this genre and they can be pretty cloying in their fascination with their subject. But this one is significantly better than the rest of it’s ilk. For one, I think Beiser’s point about the importance of sand to the modern world is actually accurate. From concrete to glass to silicon chips, we really do depend on sand quite a bit. And I knew next to nothing about it prior to reading this fun book.

★★★☆☆ Trust the Plan

Given how unhinged the political right has become in the US and the visibility of this particular conspiracy theory to adherents of that ideology, I felt I needed to better understand what QAnon really is about. It turns out it’s even more insane and vapid than I had assumed. I had thought that perhaps, due to the relatively high profile this particular conspiracy theory had attained, there would be more to it than random posts on 4Chan, but …. nope. Having read it, I feel equal parts dismayed and educated.

★★★☆☆ Uneasy Street

I love reading about how people think about and understand money. And this book does a good job of accurately representing how wealthy people understand and cope with their own wealth. This one didn’t cause me to fundamentally reevaluate my life or anything, but it was a fun read and I think Sherman did a good job avoiding the popular “eat the rich” narrative.

★★★☆☆ The Skeptics’ Guide to the Universe

I want my kids to read this when they get a bit older. Novella’s commitment to skeptical thought is a breath of fresh air. It’s deeply entertaining to read. It’s like a written version of MythBusters but with a lot less filer. My only gripe is one inconsistency in his approach. He really dives into and tears apart most folk beliefs, but seems to make an exception for theories that surround the AI singularity. I think that AI doomerism casts a spell on many hyper-intelligent rationalists and I wish he’d taken off the proverbial gloves and asked harder questions on this topic.

★★★☆☆ The Perfectionists

This was a fun read and I loved that Winchester organizes the book by measures of precision. I didn’t learn anything earth-shattering here, but it was entertaining and I learned lots of factoids along the way. I also came away with a better understanding of just how imprecise most human-made objects are.

★★★☆☆ Rise of the Robots

You’ll be unsurprised to learn that AI is going to steal your job and probably cause the collapse of our society. So, you know, not much to see here.

★★★☆☆ Rise and Kill First

Okay, the premise here is really fascinating. I knew nothing about Israel’s explicit policy of assassination as a tool of the state. From there, I assumed that Mossad and other associated defense agencies must be hyper-competent killing machines. And certainly they have killed a bunch of people, but I came away from the book reaffirmed in my belief that almost all spycraft and covert military stuff hews closer to the depiction of the CIA in Burn After Reading than any Tom Clancy novel.

★★★☆☆ The Wager

Who doesn’t love a good adventure/survival porn book from the age of discovery? That’s right, nobody. If Scorsese and DiCaprio ever actually release a movie based on this material, I’ll definitely watch it.

★★★☆☆ Endless Forms

I hate wasps. And I actually mean to use the word “hate” here. It probably has something to do with the fact that I’ve been stung repeatedly by them over my life and even sent to the hospital due to an allergic reaction. If they at least had the good manners to die when they sting, this penchant for stinging all the time could sort of be forgiven, but no, they aren’t even polite enough for that.

So I was interested to see if Sumner could convince me to abandon my well-deserved dislike of these murder flies. The short answer is no, they’re still beastly and awful. But they are at least more interesting than I had previously understood. Also, most of the wasps you actually see aren’t the aggressive, social species that would actually sting you. So there’s that I guess.

★★★☆☆ Who Gets In and Why

College admissions is pretty borked. This book is probably not worth reading unless you have a kid that’s college-bound, but it' is interesting to get a glimpse at just how subjective the process really is. Also, I’ll be curious to see how long we keep pretending that essays are a valid way to communicate anything of value in a post-ChatGPT world.

★★★☆☆ The Great Displacement

I had hoped that Jake Bittle would go beyond what I had already learned about how climate change would affect people’s lives here in the US. He did add a little color around the edges, but he didn’t try to do any advanced modeling or make any specific recommendations, which was a bit of a letdown. Basically the south and west are pretty much doomed due to desertification, drought, and increasing temperatures. So, nothing new here.

★★★☆☆ The Escape Artist

This was a good read on a topic that I already knew a lot about. I do hope that this book is incorporated into school curricula, though, because it tells a far more nuanced historical account of the Holocaust than is typically discussed.

Didn’t Finish

★★☆☆☆ The World

I wasn’t even able to make it through the introduction. Too long-winded! Get to the point.

★★☆☆☆ All That Moves Us

I thought this one would something akin to Complications, but this wasn’t as well-written and tended towards saccharine, feel-good stories.

★★☆☆☆ Cobalt Red

I’m a jaded, cynical bastard, but I find it completely unsurprising that big western hardware companies exploit other people in the world and that their suffering is exquisite and completely unnecessary. If you haven’t read about this sort of thing before, this is worth reading about, but I just found it sad to reflect on yet more senseless misery.

★★☆☆☆ The Last Days of the Dinosaurs

I was hoping for lots of science and disaster porn, but instead, got lots of poetic descriptions of late-Jurassic landscapes.

★★☆☆☆ Last Call at the Hotel Imperial

You know that corny 1920s radio announcer voice? Yeah, kinda what it’s like reading this book. I don’t mean that the narration of the audio book sounds like that, but the personalities here are so larger-than-life and so much of their time, it was too much.

★★☆☆☆ The Lessons of History

First, the audio book version of this was ruined by a poorly-recorded interview with Will Durant that’s borderline un-listenable. Second, if you read history or nonfiction books, you’ve probably already figured out most of the lessons they cover.

★★☆☆☆ There Are No Accidents

Felt like an overly-long Atlantic article. The world is unfair and people get hurt as a result of it.

★★☆☆☆ Infinite Powers

If you like math, you’ll probably really like this one. I hated Calculus and I still made it through about halfway, which is a huge vote of confidence. But, at the end of the day, this is a book about math and it’s never been my passion.

The Top 10 Nonfiction Books I Read in 2022

This year I read 21 books. Here are the best 10. For more on the 11 books I didn’t include, you can check out my Q3 Book Review and my recent Q4 Book Review posts:

★★★★★ The Betrayal of Anne Frank

I first read The Diary of Anne Frank in middle school and I didn’t really understand it. I don’t mean that I didn’t comprehend the facts. I read it and learned about Anne and her family and what they went through in the Second World War.

But it wasn’t until I had kids that I felt like I was able to actually understand the tragedy and heartbreak of their experiences. And until I saw this book on Audible, I had simply assumed that nobody knew who had tipped off the Gestapo to their presence in the annex. I think I had actually gone one step further and made the assumption that it would be impossible to figure out the mystery after so many intervening years.

I was wrong. This book isn’t fascinating because it purports to answer an international mystery known to millions of people. The book is fascinating because of the way in which it does so. I learned a bunch of incredible details about life in Amsterdam in the waning months of WW2 that I had never thought to consider. And that’s ultimately what good history is all about: connecting modern readers to what it was like to be alive at a particular moment in the past with all the mundane, beautiful, and horrific details.

★★★★☆ The Psychology of Money

My rationalist friends hate me for this one, but I think this book is a great set of easy rules of thumb for using money to get what you want out of life. The fundamental premise that Housel takes is that humans are not inherently rational and most of us don’t actually like to think about money all that much. Despite this, almost every living adult has to deal with money. And not just in a transactional should-I-buy-this-book-right-now sort of way, we have to make long-term decisions about how to invest our money, how to care for our aging parents, and how to save for our children’s education.

If you are the sort of person who doesn’t particularly enjoy doing rationalist thought exercises to uncover your terminal beliefs, calibrating the accuracy of your future predictions with statistical models, and better understanding how Monte Carlo simulation work, this book is a great way to develop a healthy relationship with money. Personally, I kinda enjoy all that nerdy stuff, but even I have days when I feel tired and the lessons in this book are good first-approximations of monetary wisdom.

★★★★☆ Allow Me to Retort

Equal parts informative, depressing, and hilarious, Mystal’s analysis of the US Constitution is a great read, especially for folks like me that aren’t steeped in legal history. His central premise is that the US Constitution was an amazing piece of law that worked very well to create one of the most prosperous and enduring democracies the world has ever seen. But it was also written by racist slaveholders that were explicitly not interested in creating a country of equal rights for its citizens. And insofar as we want that kind of a world to exist today, it’s a pretty garbage place to start.

I was raised to revere the US Constitution, and as a snapshot of historic intent that was successful beyond any of it’s writer’s wildest dreams, it’s pretty amazing. But as the founding fathers themselves believed, no single legal document should be expected to endure for centuries without major overhauls and re-writes. Mystal’s suggestions for making those revisions seem appropriate given our current political moment.

The only reason I didn’t give this one 5/5 stars is that Mystal’s writing style is pretty monotonous. I binged this one pretty hard, and I think I just got burnt out on that particular style of delivery.

★★★★☆ How to Be Perfect

As I get older, I find myself thinking more about philosophy and it’s implications for my life. But reading most philosophy books is an exercise is protracted self-punishment. You could be doing something fun, like having your toenails pulled out, but instead you’re stuck trying to figure out what the actual heck Heidegger is trying to communicate.

This is where Michael Shur comes to the rescue. As the author of the wildly funny TV show The Good Place, he takes a hilarious and light approach to the most weighty questions of what it means to be alive. Not only did I laugh most of the way through the book, I actually came away with a functional understanding of the major western philosophical disciplines and how my own personal beliefs adhere to or diverge from those approaches.

This book is like an intro to philosophy lecture and a standup comedy routine rolled up into one. The reason this didn’t get 5 stars is that it didn’t fundamentally change my perspective on life, the universe, and everything. Which is a pretty tall order for any single book.

★★★★☆ The Alchemy of Air

This one details how modern humanity is able to feed all ~8 billion of us. It’s a fascinating story that involves an ardently nationalism German Jew, a savvy industrialist and inventor, and Hitler’s Third Reich. Along the way, I learned about fascinating side topics like how humanity used to rely on bird shit to feed ourselves and how an enormous factory in eastern Germany was briefly the allies’ most important bombing target in the waning months of WW2.

Underneath the historical details, Hager proves himself to be a compelling storyteller and historian. Not only is the book deeply-researched and accurate, he does that rarest of things for a nonfiction writer: he only tells you the most interesting stuff.

★★★★☆ Empires of Light

Before reading this one, I would have told you that I knew a fair amount about how electricity was discovered and commercialized. But to quote George R.R. Martin, “you know nothing, John Snow.” I didn’t realize that Tesla was such a bad businessman. Like, I knew he was no Edison, but wow. And I hadn’t realized that George Westinghouse was such an important and pivotal figure in the story of how we got electric lights. The only reason this one didn’t get the final star is that I feel like I’ve been reading too much about the late 19th century recently and so some of the ancillary topics just didn’t feel as fresh.

★★★☆☆ The Last Pirate of New York

This book won’t redefine how you perceive the world or shake the foundations of your reality, but it’s a damn good book filled with interesting historical details about the city that never sleeps. I learned about the origins of the word “Shanhai’d,” I learned a lot about how murder investigations were run decades before forensic techniques were discovered, and how worldly the past really was. At the end of the day, though, you shouldn’t read it to learn any one particular thing, you should read it because it’s just a great story.

★★★☆☆ Einstein: His Life and Universe

Maybe it’s a bit unfair for me to rate this a 3/5. I knew it couldn’t be a 5-star review because I was already so familiar with Einstein’s achievements and contributions to science. But I felt that I just didn’t know as much as I should about the details of how he came about those achievements. The story of his life is more interesting than I expected and Isaacson does a good job of retelling his major life events with a balanced hand. The one place where I think he came off as being a bit too soft on the man was in the way that he underplayed how hurtful he was to those directly around him. His infidelities were legion and Isaacson brushes them off a bit too gently in my opinion.

★★★☆☆ The Storyteller

I hadn’t realized just how much of the music I grew up on was either directly created by or heavily influenced by a single man: David Grohl. From Smells Like Teen Spirit to Everlong, this guy’s songwriting and musical prowess practically defines a generation. And as you might expect, the stories he has to tell about his life and career are pretty damn entertaining. He’s met every amazing musical artist, he’s performed to tens of thousands of people, and as the title suggests, he’s pretty good at telling interesting stories about it all.

There were two reasons I gave this one 3/5 stars: first, the end of the book is quite a bit weaker than the start. I’m guessing the editor pushed Grohl to hit a certain word count, but that meant including some less-than-riveting stories at the end that kinda devolved into Hollywood-style hero worship. Second, there’s only so much you can rhapsodize about metal/rock music and avoid jumping the shark.

★★★☆☆ The Facemaker

I didn’t know much about reconstructive surgery. I didn’t even know that the term “plastic surgery” doesn’t refer to the material we know today by that name. It was originally used to describe materials like wood and rubber that were “plastic” in that they could be shaped by doctors to replace parts of the body. If you were alive in the 1730s, for instance, getting a wooden peg leg would have been considered “plastic surgery.”

Okay, that’s a fun little trivia tidbit, but the real reason I would recommend this book is that it tells a story that has largely been lost to modernity about what injuries meant to the soldiers who served in World War I.

Conclusion

I’m looking forward to reading more books in 2023. If you have any great recommendations, send them my way. And if you enjoyed this, you should follow me on:

  • Substack - where I summarize the stuff I learn from books like these into 3 minute reads.

  • Twitter - thoughts about economics and technology.

  • LinkedIn - what I’ve learned from being a YC founder and being a PM at Facebook and Google.

Q4 2022 Book Review

Here’s what I read in Q4 2022.

★★★★☆ The Alchemy of Air

This was a really, really good book. The only reason it didn’t get 5 stars is that it didn’t fundamentally change the way I view the world. But it is everything else you’d want from a great nonfiction book: fascinating characters, counter-factual revelations about important events in history, and chemistry. What’s not to like? My wife has gotten tired of me talking about this one, it’s that good.

★★★★☆ Empires of Light

Before reading this one, I would have told you that I knew a fair amount about how electricity was discovered and commercialized. But to quote George R.R. Martin, “you know nothing, John Snow.” I didn’t realize that Tesla was such a bad businessman. Like, I knew he was no Edison, but wow. And I hadn’t realized that George Westinghouse was such an important and pivotal figure in the story of how we got electric lights. The only reason this one didn’t get the final star is that I feel like I’ve been reading too much about the late 19th century recently and so some of the ancillary topics just didn’t feel as fresh.

★★★☆☆ The World For Sale

A decent summary of the world of asset trading. I didn’t know much about the industry prior to reading the book. Going in, I thought that perhaps asset trading was somehow different than other sorts of financial trading, but was disappointed to realize that it’s 99% identical. If you’ve seen The Wolf of Wall Street, you’ve basically read this book already, except that rather than scamming people in the US, asset traders were doing dubious business in developing nations instead. There are some interesting portraits of savants and hucksters in here, which kept it readable.

★★★☆☆ The Storm of Steel

War is hell, but for Ernst Junger, it’s clear that war is also deeply meaningful and important. I found myself more fascinated by Junger than his retelling of his experiences in the trenches of the first World War. He was a decorated German soldier and hard right nationalist, but he didn’t support the Nazis. He was explicitly spared deportation and other depredations by the Nazi leadership because of his stature as a writer and social icon. He wrote scores of books in his lifetime and was a polarizing figure until the day he died. I liked My War Gone By, I Miss it So more as a recounting of someone who finds a home in the experience of war.

★★★☆☆ The Order of Time

I feel pretty confident that I just wasn’t smart enough to really understand whole swaths of this book. Something something the scale of organisms determines how they perceive time’s movement? I think? After reading Einstein’s biography and re-familiarizing myself with his theories of relativity, I think I understood more of the ideas in this book, but it was touch and go for at least 30% of the content. I’d love to discuss this book with someone that’s far better at physics than me to see if I even understood the big points correctly.

★★★☆☆ The Last Pirate of New York

This book won’t redefine how you perceive the world or shake the foundations of your reality, but it’s a damn good book filled with interesting historical details about the city that never sleeps. I learned about the origins of the word “Shanhai’d,” I learned a lot about how murder investigations were run decades before forensic techniques were discovered, and how worldly the past really was. But again, it’s just a great story.

★★★☆☆ Einstein: His Life and Universe

Maybe it’s a bit unfair for me to rate this a 3/5. I knew it couldn’t be a 5-star review because I was already so familiar with Einstein’s achievements and contributions to science. But I felt that I just didn’t know as much as I should about the details of how he came about those achievements. The story of his life is more interesting than I expected and Isaacson does a good job of retelling his major life events with a balanced hand. I think he underplayed how hurtful he was to those directly around him, but I’m just intrinsically judgmental about infidelity.

Getting to Base Camp is Skill, Getting to the Summit is Luck

“Mild success can be explainable by skills and labor. Wild success is attributable to variance.” -Fooled by Randomness, Nassim Taleb

Most types of achievement I have observed follow a power law. 

You see this pattern in lots of highly-visible areas of life: wealth, power, followers, attention, income, and corporate titles to name just a few. As technology becomes increasingly pervasive and people have more access to world markets, talent pools, and social circles, this trend will continue to accelerate. Taylor Swift briefly holding every spot in the billboard top 10 is not an anomaly: most types of success are being concentrated in ever-greater quantities in the hands of a dwindling number of humans. 

But I’m not interested in rehashing my very long series on income inequality, I’m interested in some observations that I’ve made about how people traverse this curve and achieve greater things. If you are all the way out on the far right-hand side of the curve, how do you move to the left? Frame this in whatever way is personally relevant for you: maybe you are a deeply-passionate musician, novelist, teacher, or farmer. It’s natural to want to sell more records, write more books, teach more students, or increase per-acre yields.

Climbing Mountains

I like climbing mountains. When you are planning a hike up a big mountain, there are two categories of logistics you plan for: 

  1. Getting to a place on the mountain where you can make a summit attempt.

  2. Making a summit attempt.

Preparing for the former is often 90% within your control. You carefully inventory your gear, check your permits, and drive to the trailhead early in the morning.

But getting up that last little bit of the mountain to stand on the summit is mostly about playing the odds. If you want to climb Denali, for instance, the best thing you can do to increase your odds of actually doing it is to block off a couple weeks (preferably a whole month) so that you’ll be there when the weather is just right. You can always try to force it, of course, but that carries the very real threat of injury or death. And in case you think that never actually happens, 96 people have died on Denali since 1903. [source]

The Determinism Tree Line

What I’ve been describing is a system where the inputs and outputs have a discrete discontinuity. If that language sounds fancy, there’s a good hiking metaphor here too. On a big mountain, there is a point in the ascent where the trees suddenly disappear. The vegetation is discretely discontinuous at a certain elevation. Below that elevation and you’re hiking through a thick forest, above it, there’s nothing but sky, rocks, and some small shrubs. 

For many important deterministic systems, inputs and outputs are deliberately transparent and predictable. The most ubiquitous of these systems that I’ve come across is education. In the US public school system, things are predictable: you memorize the things the adults tell you to, you write the memorized stuff down, and you are rewarded for it. This is predictable because we have a lot of control over the inputs: ourselves! You see the same thing in other systems built for young people: internships, apprenticeships, and entry-level jobs are built to make it clear that taking a desirable action results in desirable results and vice-versa. 

And this is where a lot of smart people get lost and confused. After spending twenty-some odd years in artificial, deterministic systems where inputs and outputs are prescribed, measured, quantified, and transparent, they make the mistake of assuming that other important dimensions of life are similarly predictable. They try to apply the tool set that made them successful in deterministic systems to systems that are increasingly random. They try to ascend Mt. Everest wearing the light pants they wore while hiking to the base of the Khumbu Glacier.

But the way that you get an entry-level job is very different from the way that you become the CEO of that organization. The way that you learn to run a small diner is very different from the way that you become a multinational franchise owner. 

Tactics for Managing Randomness and Reaching the Summit

Just because systems become less deterministic as you level up in your chosen pursuit doesn’t mean that you lose all ability to influence them. But that wording is important: for most stuff in life, the older you get, the more you work within systems where your desired outcome can only be influenced, not directly controlled.

The rational thing to do is to start treating the things you want to achieve in terms of probabilities. Rather than taking direction from peers and superiors and assuming causal relationships between the directions and outcomes, you must formulate guesses about what relationships exist between your actions and the things you want. You then test those relationships and then invest your time in the activities with the highest correlation. 

In my career so far, I’ve identified a number of things that seem to be strongly correlated with outsized returns: network size, generalist skill sets, intellectual leverage, and sustainability.

  1. Maximize for professional network size. One of the best ways I know of to increase the odds of experiencing unprecedented good luck in your career is to build a very large and very high-quality network of peers. This is what MBA programs are actually good for: introducing you to a lot of really hard-working, connected, ambitious people. But for folks that don’t want to spend 2 years of your life schmoozing your peers or for folks like me who are too old to get the benefits from such a program, when a career decision comes up, you should always choose the option that allows you meet and work with large groups of other bright and ambitious people. This means switching companies, teams, or projects regularly. It also probably requires you to work at one or two really big companies where you can meet a lot of people rapidly.

  2. Don’t over-specialize. If you’re already at base camp, you probably have enough specialist skill that you’ll hit strong diminishing returns if you keep investing. Early in your career, it makes lots of sense to go deep and become an expert at a couple of skills, but by the time you’re mid/senior in your discipline, you’ll find that people are rewarded not for deep specialization, but for modest specialization and the ability to spot patterns and create solutions across disciplines. Avoiding over-specialization also helps the first goal by forcing you to meet all sorts of different people working on different problems.

  3. Learn to clone yourself. Invest in skills that increase your leverage instead of increasing your deliverables. Writing is a good way to clone yourself. As you read this post, you’re engaging with words and ideas that I wrote at some point in the past, but you are still engaging with me, George Saines from across space and time (hello by the way!). Responding to questions on Quora or Stack Overflow has the same effect: you get to multiply your presence. The more “surface area” you have, the more likely that you’ll be considered for the lead role in that new broadway play about one of the American founding fathers (who is Alexander Hamilton anyways?). You’ll be more likely to be invited to be employee #5 at the next Facebook. You’ll be front of mind when a seasoned angel investor is syndicating a financing round for the next Uber. 

  4. Avoid burnout at all costs. It’s fine to work intensely. It might even be fine to work intensely for a substantial period of time, but avoid burnout at all costs. If you burn out, you risk being incapable of making a summit push if the opportunity presents itself. As Nassim Taleb discusses in Black Swan, if you burn out (he uses the phrase “blow up”), the game is over and you lose all the leverage you’ve carefully built up. The way this has worked for me is that if I find myself in a role where I’m having to work nights and weekends, I give myself a deadline. It’s an up or out system: if I hit my deadline and I haven’t achieved my goal, I leave the role, quit the company, work for a different manager, etc. It takes discipline to see the pattern and commit ahead of time, but avoiding burnout is worth the effort.

You might look at this list and think “George, that stuff is super boring. Don’t you have any better advice that can get me to VP in the next 6 months?” And the answer is “not really.” If you think this stuff is boring, you’ll be disappointed to learn that climbing huge mountains is much the same. You take seriously all the boring, mundane, everyday logistics of getting to basecamp. Then you give yourself as many opportunities as possible to seize the first 3 clear days to touch the heavens.

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