Up in the Air

Most people hate flying. And they’re right – air travel largely sucks. You’re jammed into a tiny space, treated like a head of cattle, essentially just riding a bus in the sky.

That may all be true. But it’s also true that planes are my happy place. Up in the air, I’m free.1


I spent several years taking 50+ flights per year, both for work and pleasure. Leaving is always crazy: do laundry, then pack my clothes, make sure I haven’t forgotten anything.2 But once I get to the airport, all of that changes.

Little perks make flying alone as stress-free as possible. Airline status. TSA PreCheck. Lounge access. You can play the credit card game to get these benefits for free.

Walk to the gate just before they close the door to the flight. (Of course you want to maximize lounge time.) And you don’t want to be trapped in that metal tube with the masses for any longer than necessary.

The real magic occurs once we’re airborne, though. I have no WiFi, no communication with the outside world. I’m untouchable.

I get my best work done on airplanes. I can actually focus on writing.3 I have the willpower to sit down and read a book without checking Twitter. I’ll become engrossed in a movie.

Over the past decade or so, I’ve felt my attention span drastically shortening. The inside of an airplane is one of the last refuges from distracting interconnectivity. Much of modern-day knowledge work is simply being a human router. But our best work requires deep focus and solitude; flights provide that environment, allowing us to execute.

Cal Newport describes this phenomenon in his book, Deep Work:

As a popular speaker, Shankman spends much of his time flying. He eventually realized that thirty thousand feet was an ideal environment for him to focus. As he explained in a blog post, “Locked in a seat with nothing in front of me, nothing to distract me, nothing to set off my ‘Ooh! Shiny!’ DNA, I have nothing to do but be at one with my thoughts.” It was sometime after this realization that Shankman signed a book contract that gave him only two weeks to finish the entire manuscript. Meeting this deadline would require incredible concentration. To achieve this state, Shankman did something unconventional. He booked a round-trip business-class ticket to Tokyo. He wrote during the whole flight to Japan, drank an espresso in the business class lounge once he arrived in Japan, then turned around and flew back, once again writing the whole way—arriving back in the States only thirty hours after he first left with a completed manuscript now in hand. “The trip cost $4,000 and was worth every penny,” he explained.

I’m missing those long solo flights. I’ll use my miles for a round-trip to Japan once I get a book deal. 😛


  1. Obvious reference to the movie Up in the Air. I’m not sure why it was so celebrated by frequent fliers, though. It’s a good movie, but it doesn’t extol travel so much as abase it. 

  2. Back when I lived in New York, before departure I’d also clean my apartment to prepare it for Airbnb guests. I’m still mad at that guy who stole my shoes. 

  3. Coding can be tough without the internet, though. 

Book Review – Barbarian Days

I am an obsessive person. Throughout life, I’ve had various passions – chess, boxing, travel, options trading – some more serious than others.

I’ve long wondered: “What if I were to pursue one of these passions to the absolute limits of my abilities…even if it meant the utter and deliberate neglect of every other area of my life?”

William Finnegan’s Barbarian Days: A Surfing Life is a 447-page meditation on this sort of devotion: a life designed around chasing the evanescent moment just before the crash of a wave.



William Finnegan grew up in the post-World War II boom of Southern California. He lived a typical suburban Los Angeles life, with the exception of a couple of short stints in Hawaii, where his dad worked on site as a film producer.

The stories from Hawaii were by far the most interesting part of his adolescence. His childhood, like the childhoods of many Baby Boomers, seemed to be defined by violence. Upon arriving at the rough-and-tumble Kaimuki Intermediate School, Finnegan is regularly whacked over the head with a two-by-four during shop class. He becomes acquainted with festive Hawaiian celebrations such as “Kill a Haole Day”, in which any white person was fair game to be beaten up.

My orientation program at school included a series of fistfights, some of them formally scheduled. There was a cemetery next to the campus, with a well-hidden patch of grass down in one corner where kids went to settle their differences. I found myself facing off there with a number of boys named Freitas—none of them, again, apparently related to my hairy tormentor from wood shop. My first opponent was so small and young that I doubted he was even at our school. The Freitas clan’s method for training its members in battle, it seemed, was to find some fool without allies or the brains to avoid a challenge, then send their youngest fighter with any chance at all into the ring. If he lost, the next biggest Freitas would be sent in. This went on until the nonkinsman was defeated. It was all quite dispassionate, the bouts arranged and refereed by older Freitases, and more or less fairly conducted.

With this backdrop of violence in an antediluvian Hawaiian paradise and post-modern Southern California suburbia, surfing is both a respite from – and a part of – the pressures of adolescence.

But surfing always had this horizon, this fear line, that made it different from other things, certainly from other sports I knew. You could do it with friends, but when the waves got big, or you got into trouble, there never seemed to be anyone around.

Everything out there was disturbingly interlaced with everything else. Waves were the playing field. They were the goal. They were the object of your deepest desire and adoration. At the same time, they were your adversary, your nemesis, even your mortal enemy. The surf was your refuge, your happy hiding place, but it was also a hostile wilderness—a dynamic, indifferent world. At thirteen, I had mostly stopped believing in God, but that was a new development, and it had left a hole in my world, a feeling that I’d been abandoned. The ocean was like an uncaring God, endlessly dangerous, power beyond measure.

And yet you were expected, even as a kid, to take its measure every day. You were required—this was essential, a matter of survival—to know your limits, both physical and emotional. But how could you know your limits unless you tested them?

Surfing Hawaii

The opening of this book dragged a little, but served to establish Finnegan’s origin story:

My father liked to tell a story about a day when I got discouraged. From the warmth of the car, he had been watching me flounder—I imagine him smoking his pipe, wearing a big fluffy fisherman’s sweater. I came in, my feet and knees bleeding, stumbling across the rocks, dropping my board, humiliated and exhausted. He told me to go back out and catch three more waves. I refused. He insisted. I could ride them on my knees if necessary, he said. I was furious. But I went back out and caught the waves, and in his version of the story, that was when I became a surfer. If he hadn’t made me go back out that day, I would have quit. He was sure of that.

From a young age, Finnegan is independent and stubborn. As he becomes a teenager, he also becomes more withdrawn. He regards himself as somewhat of a reclusive romantic, using surfing as a vehicle to reach a higher spiritual plane.

What could rightly have worried my dad about me and surfing was the special brand of monomania, antisocial and ill-balanced, that a serious commitment to surfing nearly always brought with it. Surfing was still something that one did—that I did—with friends, but the club thing, the organized-sports part, was fading fast. I no longer dreamed about winning contests, as I had dreamed about pitching for the Dodgers. The newly emerging ideal was solitude, purity, perfect waves far from civilization. Robinson Crusoe, Endless Summer. This was a track that led away from citizenship, in the ancient sense of the word, toward a scratched-out frontier where we would live as latter-day barbarians. This was not the daydream of the happy idler. It went deeper than that. Chasing waves in a dedicated way was both profoundly egocentric and selfless, dynamic and ascetic, radical in its rejection of the values of duty and conventional achievement.

In his late teens, Finnegan takes a break from surfing to become a bit of a hippie. Channeling his inner Kerouac, he embarks on a cross-country road trip with his friend Domenic. They have teenage adventures – drinking in bars, dropping acid in New York City, ironically choosing not to make the trip to Woodstock:

It was 1969, the summer of Woodstock, but the flyers for the festival plastered around Greenwich Village mentioned an admission charge. That sounded lame to us—some kind of artsy-craftsy weekend for old people—so we skipped it. (My newsman’s intuition, never great, was then unborn.)

He also backpacked around Europe with his first serious girlfriend, Caryn, who is portrayed as his “true love” throughout the book. In his travels and relationship with Caryn, Finnegan’s restlessness and selfishness is apparent.

We had started to quarrel, Caryn and I, and we didn’t fight well. On the road, moreover, I turned into a tyrant, setting a merciless pace as we bummed around Western Europe, living on crackers and fresh air, sleeping under the stars. There was always someplace new, someplace better, we had to be. I dragged her on grueling pilgrimages to rock festivals (Bath) and surf towns (Biarritz) and the old haunts (and graves) of my favorite writers. Caryn, less callow, did not see the reason for all the hurry. She pressed dried flowers in her journal, went to museums, and, already fluent in French and German, undertook to learn each language we encountered. She finally dug in her heels on the western Greek island of Corfu after I announced that I had a burning desire to see more “Turkish influence.” I could go hunt for Ottoman minarets on my own, she said. And so I up and left her on the remote, mountain-backed beach where we were camping au naturel. Neither of us, I suppose, believed I would really do it, but I had become adept at, if nothing else, moving quickly through strange territory at low cost, and within a week I was in Turkey itself, newly intent on traveling overland to India. Motion, new companions, new lands were my drugs in those days—I found they did wonders for the adolescent nerves. Turkish influence fascinated me for about half an hour. Then only Tamil influence would do.

Holy shit. Finnegan abandons his 17-year-old girlfriend on a Greek island because he wants to see Turkey. Eventually, a few weeks later, he goes back for Caryn and finds her in a campground south of Munich. When he reunites with Caryn, he writes only, “She seemed fine”, and the two resume their travels.

Later, as a college dropout, he convinces Caryn to move with him to Hawaii so that he can chase waves. Here, Bill’s manipulative charm is in full force:

Caryn did have one motive that was her own for agreeing to come to Maui. Her father was reportedly there. Sam had been an aerospace engineer before LSD came into his life. He had left his job and family and, with no explanation beyond his own spiritual search, stopped calling or writing. But the word on the coconut wireless was that he was dividing his time between a Zen Buddhist monastery on the north coast of Maui and a state mental hospital nearby. I was not above mentioning the possibility that Caryn might find him if we moved to the island.

Eventually, Caryn puts her food down and they break up. Good for her.

By the age of 25, Finnegan has lived many lives. After his travels and his time living in Hawaii, he returns to California and graduates from college. He then gets a job as a brakeman on the railroad. This part of his life he glosses over in his memoir – I would have loved to see a lot more written about this.

The story picks up with him and his friend Bryan embarking on a round-the-world trip in pursuit of waves.

I had five thousand dollars in the bank, by far the most I had ever saved. I was twenty-five, and I had never been to the South Seas. It was time for a serious surf trip, an open-ended wave chase. Such a trip felt strangely mandatory. I would go west forever, like Magellan or Francis Drake—that was how I thought of it. In truth, difficult as it was, pulling up stakes was in many ways easier than staying. It gave me an excellent excuse to postpone mundane but frightening decisions about where and how to live. I would disappear from the overdetermined, underwhelming world of disco-dulled, energy-crisis America. I might even become another person—someone more to my liking—in the Antipodes.

A good memoir makes you reflect not only on the life of the person who wrote the book, but on your own life. I saw a lot of myself in this section of the book. A scary amount. Or at least, the part of me from my early 20s that thought traveling the world would provide a sense of meaning in my life.

Like Finnegan, I spent half a decade flying around the world in search of novelty, looking in hostels in South America or Southeast Asia for the answer to a question that I had never defined.

What was different for Bill, however, was the surf-centricity of his trip. As a surfer, he has a higher calling (cue eye roll from the rest of us) than the other backpackers he encounters.

Surfing, under the circumstances, was a godsend. It was our project, why we got up in the morning. After we ran across a group of Western backpackers in Apia, I grumbled, according to Bryan, that they “were nothing but goddam sightseers.” I didn’t remember saying that, but it was in fact how I felt. We did plenty of palagi looking-looking-looking ourselves, and there was something obscene about that, but at least we had a purpose, an objective, however fleeting, pointless, idle, and silly it might seem to anyone else.

Throughout this time, he and Bryan are reading and writing, which becomes apparent in reading the multi-page descriptions of a wave that Finnegan surfed 40 years ago. He captivates you with the romantic natures of becoming one with the ocean: the moment of encountering the divine in the barrel of the wave. He talks about finding the perfect wave on a desolate island – Tavarua, Fiji. He and Bryan camp there for a week, avoiding the snakes that blanket the island, surfing the perfect wave day after day. At the time, perhaps 10 people in the world knew about that wave.



I first read this book having never surfed, yet I was spellbound. It is clear how much Finnegan is devoted to the pursuit.

Finnegan prioritizes surfing and his own ego above all else. He shows flashes of self-awareness, but throughout the book his narcissism is unparalleled. He leaves behind a string of girlfriends that he either abandons to travel – or worse, takes with him to live in squalor on remote, inhospitable islands, all in the pursuit of waves.

Was “surfing” even what I was doing? I chased waves instinctively, got appropriately stoked when it was good, got thoroughly immersed in working out the puzzle of a new spot. Still, peak moments were, by definition, few and far between. Most sessions were unremarkable. What was consistent was a certain serenity that followed a rigorous session. It was physical, this postsurf mood, but it had a distinct emotionality too. Sometimes it was mild elation. Often it was a pleasant melancholy. After particularly intense tubes or wipeouts, I felt a charged and wild inclination to weep, which could last for hours. It was like the gamut of powerful feelings that can follow heartfelt sex.

Later in the book, when he and Bryan recollect their travels, Bryan seems bothered by how they, as two relatively rich Westerners, took advantage of their hosts in the South Pacific. Bill isn’t nearly as troubled:

He [Bryan] once wrote that he had just realized that the hospitality we received back in 1978 from Sina Savaiinaea and her family in Samoa had cost them a lot of money, relative to their wealth, and that we had repaid them with trinkets rather than the cash that they desperately needed and were expecting but were too polite to mention. He was so horrified he couldn’t sleep. And I wasn’t at all sure he was wrong.

Many of us have a small voice inside calling to us to abandon any pretense of a normal life and live like a drifter. And isn’t life fleeting? Why not choose to live as a latter-day barbarian, surfing in tropical locales?

So this section of the book was alluringly romantic. It calls to us, reminiscent of the Choose Life monologue from Trainspotting, which argues there is no real difference between the hedonistic pursuit of pleasure through drugs and the rat race of chasing job promotions and the materialistic trappings of everyday life.

I get it! Bill isn’t hurting anyone. But don’t we have a greater responsibility to the world than this? Even Bill was full of self-doubt:

But I did wonder what I was doing with my life. We had been gone so long now that I felt unmoored from all possible explanations for this trip. It was certainly no longer a vacation. What was I vacationing from? I had wangled a one-year leave of absence from the railroad, which had run out while we were in Kirra. Officially resigning my job as a trainman, and my precious seniority date—June 8, 1974—had been unexpectedly difficult emotionally. I still believed I would never find another job so satisfying and well paid. But it was done. I panicked sometimes, convinced I was wasting my youth, aimlessly wandering on the dark side of the moon while old friends, classmates, my peers, were building lives, careers, becoming adults back in America. I had wanted to be useful, somehow, to work, to write, to teach, to accomplish great things—what had happened to that? Yes, I had felt compelled, almost required, to take a big surf trip. But did it really need to last this long?

As my partner put it: “This book was about his relationship with surfing. His wife, his daughter, friendships – they were only mentioned in relation to the ways that they interfered with his surfing. He’s obviously a smart guy – if he had spent half of his effort on something worthwhile rather than surfing, he could have cured cancer.”

After several years of travel, Finnegan eventually settles in apartheid South Africa and becomes a schoolteacher. Here, I think he first grows a conscience and realizes that the world is bigger than himself.

I had no right to judge how South Africans, black or white, dealt individually with their extraordinary situation, but working on the Cape Flats, seeing the workings of institutionalized injustice and state terror up relatively close, was deeply affecting me—was making me impatient with, among other things, myself. There was simply no escaping politics, and I found no common political ground with any of the surfers I met. So I chased waves alone.

Finnegan, ever the rebel, ignores orders to teach a curriculum that complies with the government regime. He does what he can to help his black students. While his efforts come from the right place, as an outsider they are noticeably ham-handed. One example: he begins a career-counseling project for his students, trying to get them permits to attend formerly all-white colleges. In doing so, he wades into a morass of politics, not knowing that applying for a permit was extremely controversial as it served to perpetuate the system of inequality.

In the end, I came to see my careers program as an enormous American folly, even in some cases quite destructive, where it encouraged false hopes or encouraged kids to defy boycotts that I knew nothing about.

Yet at least Finnegan is thinking of people other than himself. He beings to take his career as a writer much more seriously:

At the end of the school year, I found myself vowing to take no more day jobs. I would write for a living, period. I started writing essays, short features, for American magazines. I wrote nothing about South Africa—though I had a pile of overflowing notebooks. I yearned to go home—wherever exactly that might be. I clung to a line in one of Bryan’s letters. He had moved back to Missoula. There was a spot on the softball team for me, he wrote. A spot on the softball team.

Big Waves, Big Egos

From South Africa, Finnegan moves to San Francisco to pursue a career in journalism in earnest.

San Francisco is not particularly known for its surfing. In fact, most people don’t realize that people surf in the city. Most can’t. But if you’re willing to brave 40 degree water and 20 foot waves, you can shred some serious gnar in the shadow of the Golden Gate Bridge.

I once read an interview of a war reporter who said that the military is one of the only places where men can express love 1 for one another. That society has so stunted men emotionally that they need the trials of war to tell their friends that they care about them.

I think that you can extend this – at least for those of us who have not been on the battlefield – to sports. For what are sports if not men playacting war? In the case of surfing, you risk death by drowning every time you’re out there. In this chapter of the book, surfing is the vehicle in which male friendships and emotions are explored.

Surfing San Francisco

In the big waves of San Francisco, big personalities come out. In particular this chapter highlighted two larger-than-life characters.

  1. Doc (Mark Renneker), a brash doctor who broke every rule of surfing etiquette and was the most polarizing surfer in San Francisco, either loved or reviled by every other surfer in the city.
  2. Peewee (Bill Bergerson), a local carpenter who was extraordinarily reserved, down-to-earth, and best introduced by the following story:

    Once, on a crowded day at VFW’s during my first winter in San Francisco, a local surfer was behaving badly—stealing waves, jumping the queue, and threatening anyone who objected. Peewee warned him once, quietly. When the guy kept it up, then nearly decapitated another surfer with a clumsy pullout, Peewee invited him to leave the water. The miscreant snarled. Peewee knocked him off his board, turned his board over, and, with small, sharp blows with the heel of his hand, broke off each of his three fins. The guy paddled in. Years later, Ocean Beach regulars who hadn’t seen this incident were still asking those who had to tell it again.

Doc was famously committed to surfing big waves. While he lived with his long-term girlfriend, he refused to get married, because once you get married (and especially after you have kids), you become too risk-intolerant for massive swells.

“The rule about guys getting married: their readiness to ride big waves goes down one notch immediately,” he liked to say. “And it goes down another big notch with each kid. Most guys with three kids won’t go out in waves over four feet!”

Mark had a commitment to surfing that makes Finnegan look positively listless.

Recalling his L.A. youth, he told me, “Among my friends, there was a strong belief in the surfer’s path. Most people swerved from it sooner or later.” For his models for aging well, he looked to older surfers—he called them “elders.” Doc Ball, a lifelong surfer and retired dentist in Northern California, then in his eighties, was a favorite. “He’s still stoked,” Mark said. “He still skateboards!”

Peewee, on the other hand, struck me as preternaturally wise, at least if I were grading on curve for surfers.

“It’s such a great sport it corrupts people,” he said. “It’s like drug addiction. You just don’t want to do anything else. You don’t want to go to work. If you do, it’s always ‘You really missed it’ when you get off.” As a carpenter, Peewee said, he had some job flexibility, and he tried to take a month off each year to go surfing someplace else, like Hawaii or Indonesia. But there was no way that he could surf as avidly as he had surfed while growing up—not without risking dereliction…

He was equally closemouthed on the subject of big waves. He preferred them to small waves, he said, because they were uncrowded. “Crowds can get tense,” he said. “In big waves, it’s just you and the ocean.” Peewee was known around Ocean Beach for his iron nerves in big surf, but it took him a number of years, he said, to build up to facing very big waves. “Each new wipeout makes you realize, though, that you’re actually safer than you thought. It’s just water. It’s just holding your breath. The wave will pass.” Did he never panic? “Sure. But all you have to do, really, is relax. You’ll always come up.” In retrospect, he said, the times when he had thought he was drowning were not in fact such close calls.

How the World Goes On

After San Francisco, Bill moves to New York where he becomes a staff writer for The New Yorker. Still, he manages to surf nonstop. He makes annual pilgrimages to Madeira, in Portugal, where he encounters harrowing waves.

There was another one [wave]. It was bigger than the others. But the important thing about it was that it sucked all the water off the shelf. Boulders started surfacing in front of me, and then I was standing in a field of rocks in rushing, waist-deep water. I did not understand where I was—a field of rocks had risen out of the ocean, quite far from shore, at a break I thought I knew. In a lifetime of surfing, I had never seen anything like this. The wave mutated into a hideous, boiling, two-story wall of whitewater almost without breaking—it had run out of water to draw from. I had a moment in which to decide what to do before it hit me. I picked a fissure in the wall and threw myself up and into it. The vague hope was that if I wriggled in deep enough, the whitewater might swallow me rather than simply smash me to pieces on the rocks. Something like that occurred, apparently. My feet were sliced up from the leap, but I did not hit the bottom as I rag-dolled shoreward in the bowels of the wave. And when I next surfaced I was in deep water, in the channel east of Pequena, safe…

That night, back in Jardim, I lay in the dark on a lumpy cot thinking about quitting surfing. The southeast wind groaned in the eaves of the old house where I was staying. Various parts of me hurt. My left eye was weeping from too much sun and saltwater. One hand throbbed from a gash received trying to get ashore at Madonna. The other hand throbbed with urchin spines picked up in a collision with the reef at Shadowlands the week before. Both feet ached with infected cuts. My lower back felt like I had spent the month digging a ditch. I truly was too old for this. I was losing my quickness, my strength, my nerve. Why didn’t I just leave it to guys in their physical prime, like André? Even the guys my age who still tried to ride serious waves—guys in their forties, even fifties—managed to get in the water two hundred, three hundred days a year. Who was I kidding, trying to skate by on a small fraction of that? Why not walk away while I could? Would quitting really leave such a big psychic hole?

For the rest of the book, Finnegan makes the excuses of an addict. Well into middle age, he constantly takes the risks you’d expect from an 18-year-old. He has a wife and child, yet goes out in waves alone that all other surfers are content to watch from shore.

I found myself getting more reckless, even before my parents died. In Dubai, chasing a story about human trafficking, I stepped on the toes of Uzbek slavers and their local protectors and had to leave the emirate in a hurry. Reporting on organized crime in Mexico, I edged further into the lion’s den than I should have. This was the sort of work I had sworn off when Mollie was born. The same impulses were showing up in my surfing. I went to Oaxaca to ride Puerto Escondido, which is generally considered the heaviest beachbreak in the world. I snapped two boards and came home with a perforated eardrum. I wasn’t turning into a big-wave surfer—I would never have the nerves for that—but I was pushing into places where I did not belong. On the bigger days at Puerto, I was the oldest guy in the water by decades. What did I think I was doing? I liked the idea of growing old gracefully. The alternative was, after all, mortifying. But I rarely gave my age a conscious thought. I just couldn’t seem to pass up even a slim chance of getting a great wave. Was this some backward, death-scorning way to grieve? I didn’t think so. A few weeks after my sixtieth birthday, I pulled into two barrels, back-to-back, at Pua‘ena Point, on the North Shore of Oahu. They were as deep and long as any tube I had ridden since Kirra, more than thirty years before. Both waves let me out untouched. Being adjacent to that much beauty—more than adjacent; immersed in, pierced by it—was the point. The physical risks were footnotes.

He’s condemned by self-love. He’s entirely full of himself. But at least he is self-aware enough to recognize all of this.

Despite how hard I’ve been on Bill throughout this review, I absolutely loved this book. I read it for the first time in the summer of 2019, in a surf-themed bar on the Lower East Side. I re-read it in San Diego, where quotes from the book bounced around my head while I paddled out into waves. The writing in this book is beautiful – I hope that my liberal sampling of quotes does it justice.

While William Finnegan is not exactly a sympathetic character, that is in part because he has lived a life that induces envy, one that most of us could only dream of. He ends his memoir recounting a surf session in Tavarua, which has been turned into a luxury surf resort:

The waves kept pouring through, shining and mysterious, filling the air with an austere exaltation. Inia was on fire, as a surfer, as a preacher. Did I still doubt? “We will not fear, though the earth give way and the mountains fall into the heart of the sea, though its waters roar and foam.” I continued to doubt. But I was not afraid. I just didn’t want this to end.

That’s exactly how I felt reading this book.


  1. Philios, to be precise. 

How to Buy a Car

I never thought I’d own a car.

I’ve always lived in cities and had access to public transportation and ridesharing, so historically this has been relatively easy. I prided myself on not having a car given its economic rationality and the slight sense of moral superiority I got by not risking others’ lives in getting behind the wheel.

Then COVID hit, and quarantining in a one-bedroom apartment highlighted all of the negatives of living in New York City that I previously was able to overlook. So I left New York, bought a car, and started driving it around the country.


Dreaming of the open road

Buying a car was the worst consumer experience of my life by an order of magnitude.

For my entire life, people had told me how awful the experience of purchasing a car is. I didn’t believe them: I’m a good negotiator and can handle high-pressure sales tactics. What I neglected to consider, however, was how different negotiation is in one-shot vs. repeated games. You need to approach a negotiation where you’ll never see your counterparty again (e.g., car-buying) in a fundamentally different manner than one in which you want to have a good future working relationship with your counterparty (e.g., salary negotiation). But I’m getting ahead of myself.

I wrote this guide in the hopes that others will have an easier experience than I did.1


The first step of the process is to determine the exact make, model, and trim of car that you want.

You’ll have to determine what the most important factors are for you in a vehicle. Safety? Reliability and warranty? Off-road capabilities? Ability to transport heavy-duty machinery? Being competitive in the Cannonball Run?

You’ll also need to set a budget. A car is pure consumption: don’t view it as an investment.


Which way will your doors open?

With these factors in mind, you should be able to determine the class of car that you want: truck, SUV, sedan, etc. From there, look up the rankings for your given class of car. Consumer Reports is a good resource – you may be able to get a free subscription from your local public library. Kelley Blue Book and other sites also compile car reviews from professionals and consumers.

When I started this process, I didn’t realize that the exact same make and model of car can vary in price by $10,000+ depending on the color and any options added on (trim). Look at the difference between the different trims and determine which features (if any) are worth paying for. Personally, I just wanted an affordable car that got me from Point A to Point B reliably and safely, so I chose the base trim.

Once you land on a 1-3 cars that fit your criteria, visit a dealership and give them a test drive. If you have exactly one car in mind, this is to ensure that there are no red flags and that you like it inside and out. If you are choosing between a couple, this can be the factor that separates one from the rest.

Secure Financing

At this point, you know the exact make, model, and trim of car that you want. You need to determine how you will pay for the car before you go to the dealership.

If you have the cash on hand to buy the car, great. You may need a cashier’s check from your bank. It is doubtful that the dealership will take a personal check or allow you to put the majority of your car purchase on a credit card.

Likely, you’ll finance your car purchase. Assuming you have decent credit, you can get a loan from any bank. I plugged my information into a few banks’ car loan portals (Bank of America, Chase, etc.). As a very rough estimate of the car price to plug into the site, take the MSRP of the car you’ve researched + 10%. You should end up paying much less than this.

Given current interest and inflation rates, it may make sense to take out a car loan, even if you can afford to pay in cash. For context, in June 2020 I was able to get a 48-month car loan at a 3.19% APR (with a 0% down payment) from Bank of America.

The result of your work will be a form that you’ll take to the dealership that shows you have a loan lined up for the vehicle.

You’ll also need insurance. Luckily, I was able to use my parents’ insurance agent to handle this process, so I don’t have much to add on this topic. Again, Reddit is your friend here.

Contact Dealerships

With a car in mind and funding secured, you’re ready to start negotiations.

Visit individual dealerships’ websites to look at the pricing for the exact car that you want. The pricing on the website may be directionally accurate, but in my experience it is completely divorced from reality. Often, the listed prices will be inclusive of all discounts and rebates (which you may or may not qualify for) and will not include not only tax, title, and license, but $1,000+ charges that the dealership will try to add to your bill when you get there.

You care about the “out-the-door” price. This is the amount that will be on the check that you deliver to the dealership: the price of the car (inclusive of all eligible rebates and offers), plus tax, title, and license.

Email dealerships asking for the out-the-door price of the car. Many will say that they can’t give you a written quote and will try to call you or tell you to come into the dealership. Ignore this – insist on a quote via email.2 You may have to go back and forth a few times. A good script that worked for me is:

Hi – I am interested in the red 2020 Kia Soul LX listed on your site (VIN XYZ). I am buying with cash and want to make a purchase today based on price alone. What is the best out-the-door price that you can offer?

Obviously, insert the exact color, make, model, trim, and VIN that you have determined in your research. To the dealership, you’re paying in cash since you have financing secured from a bank already.

Email a few dealerships, get their lowest offers, then email them all back to see if they can go any lower. Make them compete against one another for your business. You should let them know that you have a better offer – a line that worked well for me was:

My current best offer is $X out-the-door. If you can beat that, I will come in today to buy.

Note that $X may be your actual best offer, or it might be a couple hundred dollars below that number. 😉

For context, I negotiated a $17,663 out-the-door price for a 2020 Kia Soul whose MSRP was $20,355.

Some things that may help lower the cost:

  1. Buy a common car. The Kia Soul is not a luxury vehicle – you have much more power to negotiate on a car where dealers are looking to move volume.
  2. Be flexible with trim and color. I would have preferred a burnt orange or yellow Soul. Was I willing to pay $2,000 more for that? Hell no.
  3. Buy at the end of the year. (Or buy last year’s model.) I bought my 2020 Soul just two weeks before the 2021 model came out, meaning the dealer wanted to move the 2020 inventory.
  4. Buy at the end of the month. Some car dealerships get a monthly volume bonus from the manufacturer based on the number of cars that they sell. If they are close to the sale threshold to receive that bonus, they may be willing to give you a better deal on your car.3

Be the Hammer, Not the Nail

The car dealership will likely try to fuck you. I visited several dealerships where salespeople didn’t honor negotiated prices, intentionally ganged up on me, and tried to confuse, berate, and belittle me into purchasing a vehicle. Here is your game plan to avoid as much angst as possible.

Walk into the dealership with:

  1. A friend
  2. Your financing letter
  3. Your negotiated price in hand (a printed out version of the email with your final price circled).

At this point, you hand your email to the salesperson and say:

I’ve negotiated the price with your internet salesperson for a red 2020 Kia Soul LX (insert relevant color, year, make, model, and trim here). I am ready to buy. Let me know if you will honor this negotiated price (pointing at the price) and I will purchase the car today. If not, tell me now so that I can walk out the door.

This is aggressive! But you need to be aggressive in this situation so as not to be taken advantage of.

At this point, the salesperson will likely hem and haw that the price you’ve negotiated is for “well-qualified buyers” who are eligible for all rebates or some such nonsense. Insist on the price that you’ve negotiated – you have already established the price you’ll pay based on your exact qualifications in your email exchange, which is conveniently printed out and now sitting in the salesperson’s hand.

Now, the salesperson will either (begrudgingly) agree to sell you the car for this price, or will not honor your written agreement – in which case you’ll walk out the door. When they start to draw up the paperwork, take the car for a test drive to make sure that there are no issues or surprises with the exact car that you’re purchasing.

Remember that you are in an adversarial interaction in enemy territory! You brought your friend to keep a clear head and pull you out of the situation if the sale begins to go poorly.


A rare image of a car salesperson

Assuming there are no issues with the car, the dealership will likely try to get you to finance through them. You can entertain this offer – it may be lower that what you’ve negotiated with the bank. Make sure that there are no hidden fees associated and that you are comparing the APRs of the offers, not only the monthly payments.

I ended up keeping my Bank of America financing because it was cheaper than what the dealership could offer. At this point, you will need to sign a bunch of paperwork to get your car, as well as prove that you have insurance. You will probably need to call the loan officer listed on your financing letter and get them to send a check to the dealership. This will happen either before they give you the car, or within 1-2 days of you receiving the keys. I found the loan officer to be incredibly helpful – a notable contrast with the car salespeople.

Make sure that everything looks right on the paperwork before signing. The final cost should match what you agreed upon via email. If anything looks or feels off during your visit to the dealership, slow down, talk to your friend, and don’t be afraid to walk out the door.

Here are some tricks that various Kia dealerships and salespeople tried on me:

  • Told me with a straight face that the total amount that I’d be paying was $18,000, when in fact the paperwork indicated it was $23,000 ($18,000 financed plus a $5,000 down payment today). When I pointed out this fact, they told me that since I’d be paying $5,000 today, that portion “Didn’t count”.
  • The same salesman told me that the price indicated on the website only applied if you lease a car (this made absolutely no sense).
  • Tried to add $2,500 to the final sale price for absolutely no services rendered because “This is a standard charge for all of the cars that we sell”.
  • Took the printed email with the final out-the-door price circled and gave it to the financing manager who spent two hours shuffling papers in the office doing absolutely nothing (I watched). The financing manager then charged me $200 more than he should have on the final paperwork hoping that I was worn down and wouldn’t notice.4

Hopefully, you avoid the majority of these issues by negotiating your final out-the-door price via email. Again, if the dealer tries to do anything shady or if anything seems off, slow down and talk to your friend to get a second opinion, stand up for yourself, and walk out the door if necessary.


You’ve purchased a new car without excessive wailing and gnashing of teeth. Hold on to it as long as you can so that you can put off this awful process for as long as possible.


Or, just buy a Tesla. I’ve got my eyes on the Cybertruck.


  1. I bought a new car – this guide assumes that you are doing the same. Many of my learnings were drawn from this great Reddit post

  2. I made the mistake of getting a price via phone, then having a dealership try to charge me $1,000 more than the agreed-upon price when I came to buy in person. I walked out the door, but it was a huge waste of time. 

  3. See also: the dealer’s true cost, how car dealerships really make money

  4. This ended up being the car that I bought – of course I also had the email exchange on my phone and sent him back to get the negotiated price. 

On Boxing

Boxing Ring

"Once that bell rings you’re on your own. It’s just you and the other guy." – Joe Louis

The Struggle

Most adults don’t challenge themselves: physically, mentally, or emotionally. Once we move up Maslow’s hierarchy and have a stable career and decent relationships, it’s all too easy to fall into a pattern of either throwing ourselves into a bullshit job or clocking in at work and living through escapist hobbies and our children.

Being a kid is in many ways much harder than being an adult. Looking back on childhood, it’s easy to forget how much we struggled and sucked at new things: how many years it took to become competent readers, writers, or athletes.

I’m convinced that this struggle, the discomfort that comes with being awful at something (not neural plasticity or any other convenient excuse), is what separates children from adults when it comes to learning new skills. Children don’t have expectations of competence, so they are willing to struggle to become good. Adults give up during the pain period.1

Personally, it has been easy for me to slip into this rut athletically. I was a good football player in high school, played for a year in college, and have always gravitated towards weightlifting as opposed to any endurance sport. Essentially, I have the perfect body for lucha libre.

Lucha Libre

You may not like it, but this is what peak performance looks like.

After several years of on-and-off strength training, I was knocked down by an appendectomy. That experience – the realization that, contrary to the popularly-held belief of all men in their 20s, I was not invincible – spurred me into action. Unless I got my ass into motion, this would be my athletic pinnacle. I only have a few years left for any big athletic accomplishments.

Armed with this new humility, I walked into Trinity Boxing Club, an old-school, no-nonsense boxing gym in Lower Manhattan. I was craving the physicality of sport that I had missed out on since I had quit playing football. I also had an unspoken pipe dream of competing in the Golden Gloves.

I only trained hard for about six months before COVID shut down the gym, putting my plans on hold. But even in that short time, I fell in love with boxing. Here’s what I learned.

Just Show Up

Showing up is 80% of the battle. Even on days that you don’t feel like training, you need to drag yourself to the gym. There’s no substitute for putting in those reps.

Natural ability is just a starting point. After that – whether it’s boxing, learning to code, entrepreneurship, relationships, you name it – you need to put in focused hours to become a champion.

Control Your Emotions

The difference between children and adults is that children are controlled by their emotions, but adults are in control of theirs. By this definition, most people never become adults.

Through boxing, you learn how to control your emotions. The first time that I stepped into the ring to spar, my adrenaline was pumping so hard that I was gasping for air after just 15 seconds. Over time, with more reps (see Just Show Up), I learned to calm down. My fear and anxiety were biological suggestions – not imperatives.

Boxing is pain. In a fight, the best case scenario is that you keep your hands up so you don’t get punched in the face…so then your body gets destroyed. Every part of training sucks. You’re gasping for air, your muscles are screaming.

But you learn to embrace this grind. You push on despite your pain. You laugh at it. In boxing, as in life, growth comes not despite pain, but because of it.

Boxing is Pain

"Everybody has a plan until they get punched in the face." – Mike Tyson


In individual sports like boxing and chess, there are no teammates to lean on. There are no excuses for why you didn’t win, no one else to blame when things go wrong. You are the man in the arena.

So when you step into the ring to square off against someone bigger and stronger than you for the first time, it can be terrifying. But you will survive it. And suddenly, your problems at work don’t seem so big. When you’ve faced your anxieties in the ring and lived to fight another day, you are better prepared to face them in other areas of your life.


Paradoxically, boxing also causes you to lose your ego. You will be awful at first. Everyone is. When I stepped into the gym for the first time, I thought I knew how to throw a punch. I didn’t.

You’ll see guys who you think you should be able to knock out with one punch ruin you with technique. You’ll find out how out of shape that you are. And until you put on the gloves to spar, you’ll realize you had no idea just how long three minutes could be.2

Nobody cares what brought you to the gym. Girlfriend dumped you? Lost your job? Good. It doesn’t matter what color your skin is or whether you put on work boots or a suit in the morning. Everyone is there to work hard and improve; that’s all that matters.

Men Need to Fight

Men have a biological need to fight and physically compete. When I played football, the thing that gave me the most joy wasn’t having the ball in my hands or even scoring a touchdown, but rather a big hit: physically imposing your will on another man. There is something primal in this, reminiscent of the Greek thumos.

I’ve argued that society is experiencing a crisis of masculinity. Physical sports like boxing help to counteract this. They provide a healthy outlet for male aggression – an enviornment where we can punch one another in the face and then grab a beer afterwards.

Boxing Glove

I hated every minute of training, but I said, “Don’t quit. Suffer now and live the rest of your life as a champion.”
– Muhammad Ali


  1. Here is a germane language-learning example

  2. If you’d like to improve your mental state, though, sparring does wonders. Having done both, I can tell you that three minutes in the ring is better than three months of therapy. 

Your Life as Financial Derivatives

Over the past several months, I’ve watched the price of Bitcoin increase 400%, the price of Ethereum increase 1,000%, and the price of Dogecoin increase 5,000% (in bubble driven, then deflated by Elon).

I’ve been kicking myself for standing on the sidelines through all of this. I’ve been researching crypto since 2013, work at a cryptocurrency analytics company, and made some money trading in the 2017 crypto bull run. Yet I’ve had a lot of FOMO as it seems like everyone except me is making money.1

To the Moon!

To the Moon!

However, there’s a strong argument to be made that I shouldn’t be investing in crypto at all. If you analyze the net present value of my future cash flows, by far my biggest portfolio position – my salary, stock options, and the expertise and personal capital I build through the work I do for 10 hours per day – is long cryptocurrency futures. If I get rich due to crypto, it will be because of TRM stock options, not because I made an early bet on Bitcoin or Ethereum.

This is the smart decision! I shouldn’t be investing in crypto for the same reason that you shouldn’t invest in your company’s stock. Sure, you may think that Apple stock will continue to increase in value (I do), but if a Black Swan event occurs and you’re laid off, you don’t want your retirement account to evaporate as well. See Enron.2

So how I spend the majority of my waking time can be represented as a call option on cryptocurrency and blockchain adoption.

What other areas of life also contain hidden derivatives?3

  1. Mortgages. When you take out a mortgage in order to buy a house, you are placing a levered bet on the future of the local labor market. Ask my family who lives in Detroit how that worked out when the auto companies left.
  2. Relationships. Staying single is holding a call option on your future attractiveness in the dating pool. Assuming a heterosexual relationship, theta is higher for women than for men. Conversely, being in a relationship is selling that call. You earn premium up front, but may miss out on gains.
  3. Learning. Being a lifelong learner and building a marketable skillset is a hedge against competition in the global labor market. If you’re not continually learning or building your comparative advantage, you have taken a short position on globalization and are not concerned with the risk of educated, motivated people in lower-cost countries abroad taking your job.
  4. Parties. Attending a cocktail party is spending your time on a far out-of-the-money call option. You may meet someone or be presented with an opportunity that changes your life.4
  5. Hobbies. Odds are that few will read this post. But each time I write and publish online, I pay a small premium (time) for a call option that my writing will lead to opportunities that I wouldn’t get otherwise. Any time spent creating as opposed to consuming is not only buying this call option, but also serves to increase the portfolio diversification of your future earning potential.
  6. Cryonics. Being cryogenically frozen is a call option on the future of science, as well as being a hedge against death. Pascal’s wager for the 21st Century.


  1. It’s especially humbling (and infuriating) when you understand something and know you’re smarter than people who are making money hand over fist in that area.

  2. If a significant portion of your compensation is in RSUs or stock grants, the same logic applies. You should sell immediately. 

  3. Many people intentionally pursue optionality in their careers, often to their own detriment. Here, I explicitly look for the inverse: areas where people don’t think they are placing bets, but nevertheless are. 

  4. I believe this idea comes from Nassim Taleb in The Black Swan