Essays

I’ve been a blogger for a little more than 20 years and in that time I’ve written a little more than 20 books: novels for adults; novels for teens; short story collections; essay collections; graphic novels for adults, highschoolers and middle-schoolers; a picture-book for small children, and book-length nonfiction on various subjects. I’ve written and delivered some hundreds of speeches as well, for several kinds of technical and non-technical audience, as well as for young kids and teens. Over that same period, I’ve published many millions of words of work in the form of blog-posts. Far from competing with my “serious” writing time, blogging has enabled me to write an objectively large quantity of well-regarded, commercially and critically successful prose that has made many readers happy enough that they were moved to tell me about it — and to inspire some readers to rethink their careers and lives based on how my work made them feel. There’s a version of the “why writers should blog” story that is tawdry and mercenary: “Blog,” the story goes, “and you will build a brand and a platform that you can use to promote your work.” Virtually every sentence that contains the word “brand” is bullshit, and that one is no exception.

If you collected lists of techniques for doing great work in a lot of different fields, what would the intersection look like? I decided to find out by making it. Partly my goal was to create a guide that could be used by someone working in any field. But I was also curious about the shape of the intersection. And one thing this exercise shows is that it does have a definite shape; it's not just a point labelled "work hard." The following recipe assumes you're very ambitious. The first step is to decide what to work on. The work you choose needs to have three qualities: it has to be something you have a natural aptitude for, that you have a deep interest in, and that offers scope to do great work. In practice you don't have to worry much about the third criterion. Ambitious people are if anything already too conservative about it. So all you need to do is find something you have an aptitude for and great interest in. That sounds straightforward, but it's often quite difficult. When you're young you don't know what you're good at or what different kinds of work are like. Some kinds of work you end up doing may not even exist yet. So while some people know what they want to do at 14, most have to figure it out.

It’s tempting, as a venture investor, to back companies developing amazing new technologies. But this often doesn’t work out as well as investing in companies that are using existing technologies in a new way. New technologies have a larger long-term societal impact but new markets are better investments. Because new markets begin small and their impact is measured along a different metric than the one people are used to, they are often derided as “we wanted flying cars, we got 140 characters.” This exhortation disguised as an observation leads venture investors astray. 140 characters—a new market—was a great startup investment; flying cars—a new technology—has been a poor one. Take, for instance, new technologies most of us would much rather have exist than flying cars: cleantech. In 2007 legendary venture investor John Doerr said “Green technologies…could be the biggest economic opportunity of the 21st century” and he committed Kleiner Perkins to investing $200 million in cleantech. This is a perfect example of wishful thinking: of the $25 billion of investment in the sector between 2006 and 2011, only half was returned; a huge miss. What went wrong?

Strange things are happening to American democracy this week: An unelected tech billionaire appears to have somehow shredded any chance of a government funding bill being passed into law. Whether or not a new bill is introduced and lawmakers find a way to agree on how to keep the government open, watching some guy on Twitter essentially wield the power of an elected representative has been wild.

I made a prediction on Twitter on February 6th: If Millennials (b. 1980 – 2000) were the premium mediocre generation, Gen Z (b. 2000 – 2020) is going to be the domestic cozy generation. I was waiting for the perfect image to start blogging the idea, and last week supplied one: the Celestial Buddies plush toy that rode on the Crew Dragon test flight. The symbolism is perfect: an oddly satisfying little squeezable nugget of comfort within the disorienting, weird domesticity of a spaceship. Domestic cozy is in an attitude, emerging socioeconomic posture, and aesthetic, that is in many ways the antithesis of premium mediocrity. Unsurprisingly, it takes its cues from the marginal shadow behaviors of premium mediocrity.

What should an essay be? Many people would say persuasive. That's what a lot of us were taught essays should be. But I think we can aim for something more ambitious: that an essay should be useful. To start with, that means it should be correct. But it's not enough merely to be correct. It's easy to make a statement correct by making it vague. That's a common flaw in academic writing, for example. If you know nothing at all about an issue, you can't go wrong by saying that the issue is a complex one, that there are many factors to be considered, that it's a mistake to take too simplistic a view of it, and so on. Though no doubt correct, such statements tell the reader nothing. Useful writing makes claims that are as strong as they can be made without becoming false.

I grew up ski racing in Lake Tahoe. I was on the Squaw Valley Ski Team, and it was the center of my life for over a decade. At a conference a few months ago I was asked what skiing taught me about investing. This was on stage, where you can’t ponder your answer – you have to blurt out whatever you can think of. I didn’t think skiing taught me anything about investing. But one incident came to mind. “Well, let me take this to a dark and tragic place,” I said before telling a group of 500 strangers a story I hadn’t talked about much in almost 20 years. A dozen of us had grown up skiing together. Most had known each other since we were young children.

The most powerful force in social networks is their ability to tap into our fundamental human desire for status and recognition. TikTok's genius lies in its understanding and optimization of this core human drive.

The tech industry talks a lot about changing the world, but it works even harder to keep itself exactly the same. The pattern is clear: women are passed over for promotions, underpaid, and pushed out of jobs for speaking up.

Let me tell you the story of two investors, neither of whom knew each other, but whose paths crossed in an interesting way. Grace Groner was orphaned at age 12. She never married. She never had kids. She never drove a car. She lived most of her life alone in a one-bedroom house and worked her whole career as a secretary. She was, by all accounts, a lovely lady. But she lived a humble and quiet life. That made the $7 million she left to charity after her death in 2010 at age 100 all the more confusing. People who knew her asked: Where did Grace get all that money? But there was no secret. There was no inheritance. Grace took humble savings from a meager salary and enjoyed eighty years of hands-off compounding in the stock market. That was it. Weeks after Grace died, an unrelated investing story hit the news. Richard Fuscone, former vice chairman of Merrill Lynch’s Latin America division, declared personal bankruptcy, fighting off foreclosure on two homes, one of which was nearly 20,000 square feet and had a $66,000 a month mortgage. Fuscone was the opposite of Grace Groner; educated at Harvard and University of Chicago, he became so successful in the investment industry that he retired in his 40s to “pursue personal and charitable interests.” But heavy borrowing and illiquid investments did him in. The same year Grace Goner left a veritable fortune to charity, Richard stood before a bankruptcy judge and declared: “I have been devastated by the financial crisis … The only source of liquidity is whatever my wife is able to sell in terms of personal furnishings.”

In literature, as in life, the question of likability is a different one for women than it is for men. We have different expectations for women. We want them to be likable, to be nice, to be good.

We're entering a new economic age - the deployment age - where the key challenge isn't inventing new technologies, but deploying existing ones in transformative ways.

We float in and out of various temporalities, or differential zones of temporal experience. We are all in time, but our experience of time shifts and morphs, even within a given day. Sometimes we are rushed. Sometimes we are pressured. Sometimes the time can’t pass fast enough. From the time we were children, we knew that our experience of time could shift. We knew that time would pass much more slowly during certain periods: a long, uninteresting stretch of the school day as we awaited recess or the days leading up to a birthday or Christmas. Time on those occasions seemed to crawl. Then there were those moments of play and joy and companionship when we became unaware of the passing of time until those moments drew to a close and we wondered where the time had gone or how it had passed so quickly.

AI will create abundance. The price of goods and services will fall, and the world will enter a post-scarcity era. But this transition will require fundamental changes to our economic system.

Traditional planning assumes you can predict the future. Discovery-driven planning assumes you can't - and provides a systematic way to learn what you need to know to succeed.

Fortune favors the bold. Corporate comms, traditionally, does not. As an industry, we communicators are very skilled at being careful, measured, safe. These can be good things, but they stand in the way of great things. There’s a common belief that less risk equals less error. That’s wrong. When you avoid risks, you don’t make fewer mistakes — you make different mistakes. You make mistakes of omission. And for startups in particular, those are the worst kind of mistakes because your enemy is the status quo. When you only play it safe, you forfeit opportunities to define a new category, change people's minds, stoke an important debate, and maybe even change the whole trajectory of your company. Won’t taking risks also lead to mistakes? Yes, inevitably. But here’s the key: don’t do anything obviously dumb.

Executive communication isn't just about what you say - it's about understanding context, anticipating reactions, and choosing the right moments for key messages.

A well-respected figure in tech recently asked me if I might like to co-author a piece with him on the subject of diversity. As we sat down to brainstorm, he joked, as an almost apologetic preface: “Just to be clear, I haven’t sexually harassed anyone, so I’m not doing this to cover up for anything.” The possibility hadn’t been on my mind, but as soon as he named it, I was saddened by how plausible it could be. Time named its 2017 Person of the Year to be ‘The Silence Breakers’: the brave women and men who spoke up and unleashed that wave of reckoning. They were not the first to speak, but theirs were the voices that resonated and were able to break through, which is as much a statement about them as it is about the world that would finally hear them.

Stop, Game I don’t know what to tell you. Maybe I’ll tell you three stories. Here is a fundamental story. There’s a company called GameStop Corp. It sells video games at the mall. It has over 5,000 stores. For various reasons people do not buy a ton of video games at the mall these days. Two of those reasons are: People do not love going to the mall during a deadly pandemic, and people today increasingly buy video games by downloading them directly from online stores. Being a mall retailer of video games is not obviously a great business to be in, and this has been reflected in GameStop’s earnings and stock price. In 2011, GameStop reported net income of $408 million on revenue of $9.5 billion; in the last 12 months, it had a net loss of $275 million on revenue of $5.2 billion. GameStop’s stock traded as high as $62.11 per share in 2007; it got as low as $3.50 in March 2020. It closed at $18.84 on Dec. 31, 2020, for an equity market capitalization of about $1.3 billion.

Product management isn't about following a process - it's about understanding and applying fundamental principles. Here are the ten commandments that separate great product managers from good ones.

The hyperactive hivemind workflow - centered on ongoing conversation fueled by unstructured and unscheduled messages - is sabotaging our ability to think, create, and do meaningful work.

One of the most common types of advice we give at Y Combinator is to do things that don't scale. A lot of would-be founders believe that startups either take off or don't. You build something, make it available, and if you've made a better mousetrap, people beat a path to your door as promised. Or they don't, in which case the market must not exist. Actually startups take off because the founders make them take off. There may be a handful that just grew by themselves, but usually it takes some sort of push to get them going. A good metaphor would be the cranks that car engines had before they got electric starters. Once the engine was going, it would keep going, but there was a separate and laborious process to get it going.

Customer love, delight, superfan, promoter. No matter what you’re building, it’s tempting to aspire for your customers to love your product. We want them to be delighted, to endorse or recommend, to become a superfan or a promoter. And it’s not always realistic. Overusing “love” as a metric feels disrespectful to me. It’s ignoring the reality of how customers make decisions and how they talk with each other about the things they do and use. Words matter. When we ask the wrong question, we get misleading answers. Worse yet, we signal that we ‘don’t get it’ – that we are accidentally or willfully pursuing our goals over that of our customers.

This summer, Elon Musk spoke to the National Governors Association and told them that “AI is a fundamental risk to the existence of human civilization.” Doomsayers have been issuing similar warnings for some time, but never before have they commanded so much visibility. Musk isn’t necessarily worried about the rise of a malicious computer like Skynet from The Terminator. Speaking to Maureen Dowd for a Vanity Fair article published in April, Musk gave an example of an artificial intelligence that’s given the task of picking strawberries. It seems harmless enough, but as the AI redesigns itself to be more effective, it might decide that the best way to maximize its output would be to destroy civilization and convert the entire surface of the Earth into strawberry fields. Thus, in its pursuit of a seemingly innocuous goal, an AI could bring about the extinction of humanity purely as an unintended side effect.

So you want to write a book? Or you want to start a blog? Or your humble hope is simply to write better? If I got a nickel for every time someone told me with shining eyes about their writing dreams, I would be able to build a library vast enough to house every Great American Novel conceived but never written. And I get it. If you are reading this, you probably feel a certain fondness for words. You are probably the type of person who: Remained alert through decades of English classes Secretly hope text-based platforms like Substack (and maybe even Threads or Xitter) will succeed Are inundated by writers (like yours truly) waxing poetic about writing Consider writing like vitamins — generally beneficial for one’s life. But going from dreaming about writing to actually writing is its own version of crossing the chasm — easy to say and hard to do. I have a theory for why: we are confused about why we write.

If there was one course I could add to every engineering education, it wouldn’t involve compilers or gates or time complexity. It would be Realities Of Your Industry 101, because we don’t teach them and this results in lots of unnecessary pain and suffering. This post aspires to be README.txt for your career as a young engineer. The goal is to make you happy, by filling in the gaps in your education regarding how the “real world” actually works. It took me about ten years and a lot of suffering to figure out some of this, starting from “fairly bright engineer with low self-confidence and zero practical knowledge of business.” I wouldn’t trust this as the definitive guide, but hopefully it will provide value over what your college Career Center isn’t telling you. 90% of programming jobs are in creating Line of Business software: Economics 101: the price for anything (including you) is a function of the supply of it and demand for it. Let’s talk about the demand side first. Most software is not sold in boxes, available on the Internet, or downloaded from the App Store. Most software is boring one-off applications in corporations, under-girding every imaginable facet of the global economy. It tracks expenses, it optimizes shipping costs, it assists the accounting department in preparing projections, it helps design new widgets, it prices insurance policies, it flags orders for manual review by the fraud department, etc etc. Software solves business problems. Software often solves business problems despite being soul-crushingly boring and of minimal technical complexity.

In housing, almost every buy-vs-rent discussion concentrates on cost. Renters must consider losing out on equity and appreciation. Buyers must consider insurance, taxes, closing costs (both when buying and selling), repairs, etc. There are lengthy articles, discussions, and interactive calculators about this dilemma, but they’re fixated on an entirely economic calculus. If you are in a position to seriously consider the question (and are reasonably sure of your financial discipline and algebra skills), I think these resources are something of a distraction. Housing is an aesthetic question as much as it is an economic one. You are not selecting a financial vehicle, but how you want to live. For instance, you might value a kind of environmental permeability — ensuring it is very easy to go indoors and outdoors dozens of times per day. Perhaps you work from home and simply want to stroll in and out of nature. Perhaps you have a dog or a child who wants to do the same. I value this greatly: the number of steps from my kitchen or my studio to bare grass and flowers should be as few as possible. Rather than travel to a park, I can open a window and hear my children in the sandbox, while I continue working, cooking, or relaxing. There is a corresponding permeability to much city life: while you may not be able to step from an apartment door into quiet greenery, you can walk to stores, cafes, parks, etc much more easily. These are both luxuries (many places have neither feature), and they carry an expense, but they are not caught in the calculus of buy-vs-rent.

It’s been almost 20 years and I still remember the dread of Mile Day in high school gym class: four terrible loops around the track, greeted at the graceless end by the rest of the class long awaiting us, some of the cool popular athletic girls laughing in that mean girl way at the misery of the final finishers. Last week I went out with no particular training and hit an 11.5 mile rocky trail run through the desert, up 1600 feet of elevation gain. One thought kept drifting through my mind as I pushed through the sand and gravel and rocks: A mile on this run is so much harder, and in so many ways I didn’t even know it could be harder! than a mile on one of those synthetic rubber tracks, but damn am I feeling so much stronger and more powerful and yes it still sucks and I’m hurting but I’m going to make it. It reminded me of a cartoon I saw in a diversity & inclusion workshop a long time ago. There are two runners at the starting line of a race. One, to the left, is in his running uniform and cleats, sprint position, ready to tear down a smooth track lane. On the right is someone who doesn’t have proper athletic gear and is looking down a path that’s torn up, obstacles in her way, rain and weather adding insult and mockery to the course she’s about to run. Tell me, is it fair to compare their mile times?

When I read biographies, early lives leap out the most. Leonardo da Vinci was a studio apprentice to Verrocchio at 14 years old. Walt Disney took on a number of jobs, chiefly delivering papers, by 11. Vladimir Nabokov published his first poetry collection at 16, while still in school. Andrew Carnegie finished schooling at 12 and was 13 when he began his second job as a telegraph office boy, where he convinced his superiors to teach him the telegraph machine itself. By 16, he was the family’s mainstay of income. Readers (and some biographers) tend to fixate on the celebrity itself, the inflection point when people achieved fame. But their early lives often contain something more revealing than their successes. Before you grasp, you have to reach. How did they learn to reach? In my examples, the individuals were all doing from a young age as opposed to merely attending school. And while they may not have wanted to work, the work was nonetheless something that they, their families, and society felt was useful, purposeful, and appreciated. In a sense, they had useful childhoods. Do children today have useful childhoods?

Two people meet at some point in their 20s, fall in love, and for some reason — a job, a grad school opportunity, whatever — decide to move to a place where they know very few people. Maybe they make some friends immediately, but more likely: they don’t. Maybe they already have a kid, maybe they start trying to have one (or a second) shortly after they move. They’re relatively early in their careers and spending a lot of time trying to advance them, so have very little energy to allocate to cultivating friendships that aren’t ready-made, e.g., a school cohort or friends at work. Those friendships are nice but somewhat shallow, in part because these people spend most of their spare time with their partner, or working, or parenting. It’s hard to get a sitter and you don’t feel super comfortable just lugging your kid to other people’s spaces. It’s not that you don’t get out of the house; it’s just that when you do, it’s usually with your partner and kids. Meanwhile, maybe a parent’s health is deteriorating and you’re struggling to navigate care for them across the country. Or maybe you moved closer to your parents to relieve your overwhelming childcare needs….but now you realize your parents are your primary points of adult contact.

Strategy is stuck. For too long the business world has been obsessed with the notion of building a sustainable competitive advantage. That idea is at the core of most strategy textbooks; it forms the basis of Warren Buffett’s investment strategy; it’s central to the success of companies on the “most admired” lists. I’m not arguing that it’s a bad idea—obviously, it’s marvelous to compete in a way that others can’t imitate. And even today there are companies that create a strong position and defend it for extended periods of time—firms such as GE, IKEA, Unilever, Tsingtao Brewery, and Swiss Re. But it’s now rare for a company to maintain a truly lasting advantage. Competitors and customers have become too unpredictable, and industries too amorphous. The forces at work here are familiar: the digital revolution, a “flat” world, fewer barriers to entry, globalization. Strategy is still useful in turbulent industries like consumer electronics, fast-moving consumer goods, television, publishing, photography, and…well, you get the idea. Leaders in these businesses can compete effectively—but not by sticking to the same old playbook. In a world where a competitive advantage often evaporates in less than a year, companies can’t afford to spend months at a time crafting a single long-term strategy. To stay ahead, they need to constantly start new strategic initiatives, building and exploiting many transient competitive advantages at once.

The net of a thousand lies The most surprising thing about the rebirth of flat Earthers in the 21st century is just how widespread the evidence against them is. You can understand how, centuries ago, people who’d never gained a high-enough vantage point from which to see the Earth’s curvature might come to the commonsense belief that the flat-seeming Earth was, indeed, flat. But today, when elementary schools routinely dangle GoPro cameras from balloons and loft them high enough to photograph the Earth’s curve — to say nothing of the unexceptional sight of the curved Earth from an airplane window — it takes a heroic effort to maintain the belief that the world is flat. Likewise for white nationalism and eugenics: In an age where you can become a computational genomics datapoint by swabbing your cheek and mailing it to a gene-sequencing company along with a modest sum of money, “race science” has never been easier to refute.

The Company Is Father. The Company Is Mother. The slice of contemporary Japanese life of keenest interest to you is dominated by one particular relationship: that of the Japanese salaryman to his employer. If you understand this relationship, it is almost a Rosetta stone. You’ll immediately be able to predict true things about the world like “Japanese startups probably have huge difficulties in hiring.” (About which, more later.) A salaryman (transliterated from the Japanese which is itself borrowed from English), more formally a “full-time company employee” (正社員), is the local equivalent of a W-2 employee in America. This is roughly 1/3rd of the labor force in Japan, but it has outsized societal impact. Traditionally, salarymen (and they are, by the way, mostly men) are hired into a particular company late in university and stay at that company or its affiliates until they retire. There are other workers at Japanese companies — contract employees, who can be (and are) let go at will, or young ladies on the “pink collar” track who are encouraged tacitly or explicitly to quit to get married or raise children — but the salaryman/employer relationship is the beating heart of the high-productivity Japanese private sector. (The Japanese economy is roughly 1/3rd the public sector, 1/3rd low-productivity firms like restaurants or traditional craftsmen, and 1/3rd high-productivity household-name megacorps. Salarymen are mostly present in the last one, which happens to dovetail with your professional interests.) The salaryman/employer relationship is best characterized as “You swear yourself to us, body and soul, and in return we will isolate you from all risks.”