Tag: Life

Lost and Found

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To win, be kind. To be kind, break the rules.

I twice lost faith in humanity today. Once, I got it back. The rules cost my faith. People breaking them gave it back. 

Three airport snippets and a meander: 

1. The bag with no status (lost #1)

At Houston Hobby Airport, I entered my information into my airline’s bag-check kiosk. It told me to see an agent. I approached one at an empty desk. She asked if I had status. I said the machine sent me to you. She asked if I had status. I said no. She told me to go to the info desk around the corner. I told her the kiosk sent me to her. She asked again if I had status. I have the right credit card and a bunch of points, so I shrugged and said yes. She asked what I needed. I said I’d like to check a bag. She checked the bag. Then she told me I didn’t have status, so next time I’d have to go to the other desk. Her questioning about my status took longer than the bag check, and it ultimately didn’t matter. The rules may be dumb. But at least they’re poorly enforced. 

2. Carousel 5 says Denver (lost #2)

Landing at LGA, I went to carousel 5, where the flight attendants said our bags would be. The sign over it said “Denver.” I had flown from Houston. Houston is not Denver. I asked the agent standing there. He said all the Houston bags were out; if mine wasn’t, I should go to the office. I went to the office. I gave the office agent my flight number. She asked for my claim check. I told her I’d left it on the plane. She tutted, found my information anyway, and told me to go back to the carousel. I went back. My bag was there. The agent at the carousel told me he’d tried to shout for me to come back the moment he realized he’d been wrong. He might have been wrong. But at least he tried to fix it, however poorly. 

3. The green bag (regained)

When the plane landed, the woman beside me turned around and said, “My bag’s in the overhead of row 13, five rows back. Green bag. Could you pass it up?” And people did. A wheely bag, no less. At least 6 strangers joined the mission. Great move. I’m surprised it worked. Well played. 

Keeping the Faith

In downtown Houston, I yelled “Praise the Lord!” Two women on the street ahead of me turned around. In New York, where I live, and Chicago, where I’d spent the last 5 days, strangers don’t look at crazy people. In Houston they do. Maybe Houston keeps its crazy people off the street. In 24 hours downtown, I didn’t see any.

I wondered if Houston just removes them. I looked it up: it’s a mix. Houston housed a lot of its homeless, Texas bans public camping, and a city built for cars has fewer sidewalks to be seen on anyway.

About 18 hours later, I boarded a Houston tram. A man with wild eyes came to the door, clasped his hands, and started begging a being only he could see. No one moved away from him. Back home we’d have given him a wide berth. Here, the crowd understands him.

Houston gives a pass for praying.

Why Do People Live Here?

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To win, position well. To position well, realize it’s a choice. 

“Why do people live here?”

It’s a common refrain when I travel. And I travel a lot.

Between 2018 and 2025, I lived in a van, driving around the U.S. and Canada. For 4 months in 2022, I lived in Australia, New Zealand, Japan, Indonesia, and South Korea. And most places make absolutely no sense to me.

New Orleans, New York, San Francisco: I get. Austin, Seoul, Paris, Tokyo: totally. But Chicago? Kansas City? Cleveland? Dallas and Houston? Those tiny towns in Nevada and Colorado and Oregon with more elevation than people?

I’m in Chicago for a friend’s wedding. A surprise thunderstorm shook our windows. Two years ago when I visited, I heard a siren. I asked my friend: “What’s that siren for?” He said it’s a weather warning: we were about to be cold enough to be deadly.

The trains run above ground (terribly noisy), and most don’t even run all night. The weather is always either too hot or too cold. The theater and art are good, but not as good as New York or L.A. The food is tasty, but overwhelmingly unhealthy. Maybe it’s the sports?

I don’t buy that most people intentionally choose where to live based on their values and preferences.

Where & why? 

Ask people why they live where they live (I do, constantly) and most people give one of 4 answers:

  1. They were born there. (This is Partner’s most frequent response when I pose the question.)
  2. Work or school took them there.
  3. A lover took them there.
  4. It’s the nearest city to where they were born. (Partner grew up in the “big city” for her area, because it had a Walmart. This “big city”: 16,000 people.)

Who’s the actor here? 

Every answer describes something that happened to the person. Born there: the game placed you. Work took you: the company (or admissions committee) chose. A lover took you: the lover chose (or their company did). Nearest city: the game placed you, plus a radius.

Where you live is one of the biggest decisions in your life. It decides your environment, your friends, your culture, your wages, your rent, and your weekends. And it’s a rare big game where most players never even realize they’re playing. The board hands them an opening setup, and they just accept it.

I can count on one hand the friends who chose their place to live by auditioning and deciding.

Reality & possibility

How many people decide where to go? Between 18 and 30, do you explore while you can (no mortgage, no kids, career still portable)? After your kids leave home, do you think about moving?

Money, visas, family gravity: there are good reasons to stay where you live. But a lot of it strikes me as activation energy. You’re a distinct person with individual tastes. And you just happen to have been born in exactly the right place? 

I’ll take the other side of that bet.

French Security: Worse Than Nothing

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Whatever they’re trying to do, they’re failing.

French security sucks. It’s worse than nothing. At least nothing wouldn’t delay tourists.

I approach the metal detector. I hand the officer my backpack. I walk through the detector. He hands me my backpack. Sounds like a normal security process. Except he never looked inside my bag.

Same thing yesterday at the Paris catacombs: at the end, a man seated at a desk with a sign saying open your bags so we can ensure you’re not stealing bones. But he doesn’t open your bags. He doesn’t even wave you on. He just plays on his phone.

Three months ago at a Parisian rugby match: the security officers pat down every entrant. Partner stayed in my line. The officer gestured her to a line with a female agent. Partner walked past him. He let her go.

At Orly Airport, you must navigate through all of the stanchions in sequence, even if the line is 0 people. An extra 60 meters of walking per person. One white-haired woman ducked under the rope. The officers yelled at her. She said, “I’m old, it’s hard to walk!” They demanded she go back.

The Louvre was heisted last October. Has nothing changed? Do none of the workers know the point of their jobs? Do none of them believe in their work? Are they too snoozy from the fondue lunch? (Author’s note: fondue is Swiss. But it does make me snoozy.)

What game is this?

The goal of the game is to win. I say that a lot. Sometimes too much. The goal of the game is to win; you win by doing X. But it’s pretty fundamental: if you’re not trying to win, what are you doing?

Sometimes the goal is different. Sometimes it’s to not-lose. Sometimes it’s to survive. Sometimes it’s to tie. But this security bullshit? Whatever it is, it’s not achieving it.

Even some contrived goal, like “create a specific form of job stability for a certain number of people in France without disrupting the general French living and working systems”, couldn’t you do that better? And that’s already super contrived.

The best rebuttal: fake security still deters. Which is fair. True. Like the faux eyes on the wings of a moth, the mere existence of security may prevent me from attempting to sneak a gun into the [insert grand French monument].

But fake security works when it appears real. If the moth has a sign saying “These are just mock eyes; I’m actually a helpless moth, teehee”, that bug is getting nommed. And today, at the Palais de Justice, a guard waves visitors through a body scanner. The alarm went off on the visitor behind me. The guard ignored it, clicked “Ok,” and waved the woman through. You can’t advertise the fakeness! Bluffing is one thing! This is bluffing while turning your cards face up!

Even I get it!

I don’t like security. I’m fully anti-TSA. Considering the rate of deaths by terrorist attack vs the rate of deaths by automobile crashes, I’m even pro-shrug-it-off re 9/11.

But even I understand the point of security. I get why we have it. I just think it’s dumb.

This version of security is the worst version! Not only does it have no impact; it also wastes people’s time! What the hell are you doing, France?!

Do you want to get invaded by the Germans for the fourth time in 160 years? Because you’re sure acting like it!

Cone-Eyes

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The goal of medicine should be optimal health. You can achieve optimal health through all sorts of pathways.

Tomorrow, they will slice into my eye (graphic representation). I’ve been eagerly awaiting this day for years.

Fifteen years ago, I learned I have keratoconus, a degenerative eye disease that prompted my sister to nickname me “cone-eyes.”

I first wore glasses at ~12, contacts at ~15. Hated both. The etiology is unclear: maybe the growth plates that jammed in my cheeks as a child; maybe eye-rubbing caused the mis-shape; maybe the mis-shape caused the eye-rubbing. By the end of one’s twenties, the cone generally stabilizes.

Most people avoid elective medical interventions. As my mother likes to say: “You only get one body.” That logic explains why most people stop at the first reasonable doctor, take the standard recommendation, and live with whatever they’ve been handed.

I know at least three ways to play this game better. You can hire the world’s best, every time (expensive, not always available). You can take what’s offered, set low expectations, and hope (cheap, sometimes works). Or you can attack the doctors until you find one who doesn’t buckle. 

I do the third.

For my eyes, one optometrist wanted me to harden my corneas. Standard of care. I declined for my case. Another doctor, in southwestern Spain, wanted to harden them and then install hard plastic lenses. Closer.

Now, in Paris, I’ve found the Center for Keratoconus and the Cornea. The practice literally says “keratoconus” in its name. This specific surgeon looks at eyes like mine all day, every day. 700 of these surgeries; 0 major complications. Of the ~2 million performed worldwide, the number who have gone blind doesn’t appear in the literature. I believe it’s either 0 or close to it.

The risks:

  • The lens rotates (a second procedure is then needed to re-seat it).
  • If my vision deteriorates, I will need to replace the lenses. (The lenses won’t cause this deterioration: it’s just a natural occurrence for some people as they age.) 
  • A punch to the eye becomes a much bigger problem.
  • Worse night vision.
  • Infection (very unlikely with proper care).

The benefits:

  • Perfect vision, no glasses.
  • Perfect peripheral vision. Today, to look at something off the edge of my vision, I turn my whole head. The edges of my glasses cap my field. After tomorrow, just my eyes move.
  • Better at sports.
  • A weirder benefit: I’m less anxious without glasses. Legally blind without them, but calmer. I don’t know why. After tomorrow, I won’t have to choose.

I already spend most of my life attempting not to be eye-gouged. After tomorrow, that preference intensifies. In exchange, the head-swivel stops.

Today, walking through the park, I removed my glasses and looked at them. Despite the humorous engraving on the side[1], I’ve never liked them. I hope tomorrow evening to jump up and down on them in glee.

I feel nervous. That’s why the surgeon gave me xanax. That, and he’ll be operating on my eyes while I’m still using them. 

Will it go well? We’ll see, I hope. 

[1] It reads “HURRR DURRR !!!”

“Yes, And” in The City.

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To find your people, yes-and. To yes-and, be the offer.

Humans sense intention.

In college, the art student I was dating saw scribbles on a whiteboard in my dorm room. They connected the lines into a picture. They saw the noise as marks of humanity. They recognized this humanity and added their own.

Improvisational theater dubs this move “yes, and.” When someone makes an offer (a line, an emotion, a mimed hat), you accept it (“yes”) and add (“and”). 

The game feels deeply respectful: honoring others’ contributions while adding your own. You can’t yes-and into a vacuum. Someone has to move first, even if only The First Mover. 

When you yes-and readily, the world yes-ands you back. 

Yesterday, the world yes-and-ed me four times.

Business Advice

Two people texted me yesterday asking for business advice. 

Partner’s friend asked about negotiating a role with a CEO I used to advise. He didn’t know I knew the CEO. He generically knew me as a CEO whisperer and good at creatively evaluating contracts.

Another friend asked for advice negotiating his boyfriend’s equity compensation package. I shot back 13 points of commentary. He replied: “Julian, babe, wow!!!! Thank you SO much for this!!!”

My initial offer in these exchanges was a reputation built over years. My friends’ yes-es were recognizing the mark. Their and-s were the specific questions.

Small World

My former college roommate brought a friend to play cards til midnight. When the new guy mentioned he was a debater, I ballparked his age and asked if he had known my brother-in-law.

He said: “Oh yeah, he was a legend. Is he still very stoic?”

My offer: hosting an invented cooperative poker game.

His “yes”: joining. His “and”: sharing about himself.

My “yes”: piecing together the traits. My “and”: asking the precise follow-up.

His “yes”: acknowledgement. His “and”: mentioning my brother-in-law’s reputation.

We snapped a selfie to send to brother-in-law. After this connection, our poker-game riffing increased. 

On the Train

A woman in her mid-fifties boarded the 6 train at 42nd Street Grand Central. She commented on my fun hat and asked what I was reading. 

My initial offer: being legible, plus an emotional openness to interaction that I learned at clown school.

Shortly after studying in France, I noticed myriad people wanting to interact with me. Turns out: you can teach charisma.

The exchange:

“It’s called The Grasshopper.”

“Is it about grasshoppers?”

“It’s about philosophy of games.”

“Are you a philosophy major?”

“I was a philosophy major.”

“Do you still work in philosophy?”

“In a manner of speaking.”

She smiled. “What do you write about?”

“I run a publication where I write about games, and I ghostwrite for tech people.”

“I’ve been looking for a ghostwriter.”

We exchanged information. We’re scheduled to talk Monday.

My offer: the book and the hat. Her “yes”: the engagement. Her “and”: the question chain.

Our conversation yes-and-ed back and forth.

Independently, Marketing discovered this move: make deliberate choices that legibly convey the desired information.

Yes-and has the same rule.

“No, But…” 

Partner and I visited a bathroom showroom.

For our two bathtubs, the “bathroom expert” recommended a 15.5″ deep bathtub for the larger space. We had told him we wanted that one to be maximally deep. (I found a 17.5″ deep bathtub after five minutes of searching. In a brand he represents.)

His response rejected our initial offer.

I told him we were unlikely to support his other recommendation either. We had asked for a bathtub. His recommendation was only 8” deep. (Partner’s comment to me, after the fact: “That’s not a bathtub. That’s a sink.”)

The salesman: “But it’s good for washing children.”

He didn’t ask why we disliked the depth. He didn’t interrogate enough to understand our preferences.

This was a “but.”

When someone “no”s or “but”s you, you question if they’re values-aligned.

This “no” will prompt me to check all his other work.

New York

New York is a city of infinite possibilities.

My rate of random encounters has skyrocketed over the last 4 months.

  • Met new friends at an alumni gathering. We’ve since played board games four times.
  • Met a ghostwriting client at a tech-incubator brunch.

The hard part has always been noticing the games. Yesterday I noticed four.

Moving to New York was a “yes.” When I’m living in alignment with my preferences, the city hollers back “yes” every day.

And its millions of people add a booming “AND!!!!!!!!!!!!!!”

People can sense agency. The more you enact change on the world, the more you attract people to you. 

You yes-and the world; the world becomes more yes-and-able for you. 

Take it from a better clown than me: Life has been created for you to enjoy, but you won’t enjoy it unless you pay for it with some good, hard work. 

Score is the Thief of Commerce

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“To win, score the most. To score the most, stop keeping score.”

Last week, after three days in my metaphorical writing cave, I hollered to Partner, “I know I haven’t been doing dishes. I owe you.” I caught it immediately: “Actually, I think keeping score is bad practice. I take it back.” She laughed and continued on with her day.

I like scores. Keeping score is a clear and straightforward way to understand and compare performance. But sometimes, keeping score can be actively harmful.

Macro scoring enables comparison between multiple options. Micro-scoring corrodes as it leads you to optimize the wrong things. As my family motto goes (it’s intentionally too long for comedic effect), “Before you hyper-optimize a process, be sure you’re optimizing for what you actually want and not a correlate.”

The Bad (Reflexive Scoring)

Should I owe Partner dishes? I was heads-down on work because I spent the previous three weeks coordinating medical appointments for Partner and renovation work for our apartment.

As Middle East history teaches: if you dig back far enough, you can find huge grievances on all sides. Without touching on rightness or wrongness (as I do not have a sufficiently long stick with which to touch), this process does not seem to form stability. And stability is something I would like in my partnership.

Simply: if Partner feels I’m not doing dishes enough, she will say so. If I feel I’m not washing dishes enough, I should wash more dishes.

Score-keeping as a way of digging yourself out of a hole will often lead to resentment of the scorekeeping mechanism (or participants, which is even worse).

The Good (Reflective Scoring)

I once heard a successful startup founder describe his romantic check-ins. He and his wife divide his work into four categories: money earner, father, lover, friend. Rating each on a 1–10 scale, so long as his overall score achieves more than 25 points, he passes. For this partnership, this calculation may solve a real problem: it recognizes a person’s contributions despite changes over time.

This scoring process is a feedback instrument, driven by deliberate weighing of details — not a reflex prompted by momentary discomfort.

The Bridge (Incentive Alignment)

Hourly work misaligns incentives. This structure causes less efficiency and innovation: working faster costs the worker money!

I realized this structure with my $16/hr marketing internship after my sophomore year of college. I automated all my work, and all the other interns’ work. My superior said, “Sit tight and read.” I arrived to work early and left late because they paid me hourly. I was always there to do work if they wanted to give me work. (Now, I would take a slightly different tack: raising this lack-of-work to my boss’s boss. But at the time, I thought arriving early and staying late to maximize my dollars was the standard way to play the game.)

Even if your boss is your best friend, the hourly contract puts you in opposition. The score isn’t a personality conflict; it’s a contract feature. No amount of scorekeeping can account for misalignment.

The Ugly (Anti-Commerce)

Some work should be 90%–10%. In my partnership, Partner captains cooking 90% of the time; I captain travel logistics and social plans 90% of the time. I’m sufficiently capable to create edible food. Partner is sufficiently capable to book flights and schedule with friends. We simply enjoy it less (and are less skilled).

Micro tit-for-tat prevents specializing and trading, which is the fundamental lesson of commerce. So long as we both share the common knowledge that we’re both helping the team, the score is anti-helpful.

When partners are aligned on what they’re moving toward, the allocation can skew without it mattering. Some weeks she does more; some weeks I do. The “oxygen mask before helping others” frame applies: feeding yourself, whether literal food or via nurturing work, isn’t a withdrawal from the partnership — it’s a contribution to it, because your effectiveness is shared.

The reflex inside an aligned partnership imports structural-scoring logic into a relationship that thrives on more flexibility than scoring provides.

The score is the thief of commerce.

The Reckoning (Trust)

Would you rather employ someone values-aligned and unskilled, or skilled but misaligned? For piecework, I think skilled but misaligned. For a teammate, values-aligned. (That said, I am historically incompetent at working with unskilled people.) But I guess that’s still better than someone who will sabotage, even if they do it unknowingly.

Alignment produces trust. A scorecard substitutes for trust, poorly.

Last night, Partner asked me to do the dishes.

Consistency, Consistency, Consstncy

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“Every Day” means Every Day! means ¿Every Day? 

I have a motto: Seven days a week means seven days a week. (Except when it means five.) 

I have three categories of “Every day”: 

1. Religious Commitments 

If lightning struck me and I awoke in the emergency room, I would still write every day. 

The commitment is inflexible. The details are wishy-washy. Sometimes “day” stretches into the early morning hours of the next day. Sometimes “writing” means a scribbled sentence onto a post-it note reading “I don’t want to write today.” When I was writing two pages per day for my first book, many days started with writing “I don’t want to write today… I don’t want to write today…” until I got in the groove and shifted to the topic. Most days, I pen and publish a brief essay. 

When I injured my back, I performed a prenatal core workout as my daily 5 minute abs. 

This “every day” works because the requirement is rigid but the goal very easy. 

2. When 7 = 6 

    I lift weights every day. 

    (Except for ~2 days per week.) 

    I tell myself I lift weights every day. Sometimes this approach is honest: Over the last two months, some weeks, I lifted 7/7 days. 

    The issue: Weightlifting relies on unpredictable activities. How well will I sleep? How recovered will I be? Sometimes, I need a rest day to prevent injury. 

    7 days per week therefore becomes 6. But if I aimed for 6, 6 becomes 5… and 5 becomes 4…  and very soon I’m watching cartoons with Dorito dust on my chest

    This “every day” works because the requirement is flexible but the goal very intense. 

    3. The Failure of Flossing 

    Jeff Foxworthy’s dentist asks, “Have you been flossing every day?” 

    “Not every day…” Jeff admits. “The last time I flossed… You did it!” 

    Most people don’t floss. I don’t brush my teeth in the morning. (I only brush at night.) 

    Turns out I brush in the morning every day the way most people floss every day. 

    Default to Yes

    I experience a large mental cost oscillating about action. 

    Writing 5 days per week is somehow more difficult than 7. If I give myself an out, I consider and negotiate. Instead, I commit and know my category. 

    Seven days a week means seven days a week.

    (Except for the contexts where it should mean five.)

    (Or zero.)

    (Or negative one.) 

    Working to Win the Lottery

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    Sometimes, the safe play is the lottery.

    “I’d rather be working for a paycheck than waiting to win the lottery.”

    —Bright Eyes, “First Day of My Life,” I’m Wide Awake, It’s Morning

    There’s a difference between waiting to win the lottery and working to win the lottery.

    Waiting doesn’t make sense: the lottery is a losing proposition. But working to win the lottery? If you can skew the odds in your favor, you can win.

    Upon graduating from college, I reasoned: “I could get a job at a Big Tech Company that pays $60k/year, this year, or next year, or in ten years.” So I started my own business doing what I wanted to be doing.

    I know of two strategies: working for a paycheck, and working to win the lottery. (By “lottery” I mean asymmetric upside, where one hit pays for many misses.) Most people, Partner included, are wired for the paycheck. I’m wired for the lottery. Both can win.

    Most people think of the lottery as riskier. I disagree.

    Here’s the move that separates my thinking from everyone else’s: the safer path is concentrated. You work for a company; that company goes under, you’re screwed. You find a similar company. But what happens when the whole industry goes under? The skills you’ve built might be useless worldwide.

    The skills I’ve built? Not so much — because I’ve had the ability to choose what skills I build. The employee path is actually a concentrated bet on the need for similar skillsets. My portfolio is which skills to build. That, for me, is diversification.

    The risk actually shows up at the intersection between the operator and the game. For me, this isn’t risky. I have savings discipline, deal flow, and a fitting temperament. For someone without those, it would be. We think of risk as the variance in an activity. On the meta-level, it’s more about being fit for the game and playing enough times to outlast the variance.

    Two Paycheck Jobs

    In my life, I have worked two standard, 9-5, knowledge-work paycheck jobs.

    The first: I interned at a marketing agency in NYC the summer after my sophomore year of college. I automated all of my work, then all of the other interns’ work, then my direct superior’s work. When I asked my superior for more work, he said, “Sit tight and read.” So I played games on my computer, peaking at 120th in the world at a card game I liked.

    The second was at a fintech. $175k cash per year. Predictable.

    My first month working there, my monthly burn was 3x what it was the month before. I had been earning $100–150k with my own business.

    It wasn’t the money. It was the perceived predictability.

    The three most addictive things in the world are:

    1. Methamphetamine
    2. Nicotine
    3. A steady paycheck

    What can I say: I wanted to try the drug. I just got my fix and got out.

    The Math

    I keep my costs low. I don’t get much more value from the $50 Chinese restaurant over the $5 basement dumplings. Most of life’s joy comes from experiences and removing friction. I therefore spend money on travel and life infrastructure.

    I lived in a van while building my first business.

    The math: ten months of San Francisco rent = one van. After ten months of rent, you have nothing. After ten months of van, you have a van. (Also nice that I bought it for $12,500 and sold it 3 years later for $19,500. Taught me a lot about macroeconomic waves, too: the van market went crazy during COVID.)

    While living in the van, I squirreled money into early-stage tech companies.

    Natural aptitude matters. If none of my bets had paid off, I would have switched plans. But four $25k bets is only $100k. Which, if you’re making $150k per year and spending $30k, is only 1 year of work to find out whether you have a skill (in my case, the skill is betting on people).

    Bet on People Who Will Win

    I once asked Ann Miura-Ko (a Midas List member and board member of Lyft) whether there was more to investing than finding competent and trustworthy CEOs. I had a hunch that was the whole game. She agreed: yes. But she added that doing it well is not trivial.

    Fun for her to confirm my approach.

    So that’s been my approach. I haven’t bet on technology or the future. I’ve bet on individual people.

    My company was a ghostwriting business. I spent a lot of time living in experts’ heads. Bylines included:

    • Justin Kan (founder of Twitch)
    • Sam Altman (then of Y-Combinator)
    • Ellen Pao (CEO of Reddit)

    During this investing, I also dabbled with crypto. I took the advice of friends, but those friends didn’t have control over the asset. They were speculators. With a private company, I’m betting on actual leadership. Leadership controls the outcome. They’re responsible for everything.

    The lesson: bet on people who control the outcome. Or bet on no-one (the index). Don’t bet on people without control.

    In a gambling sense: I’ve placed four bets on startups, where variance is high and likelihood is low:

    • 1 failed
    • 1 is planned to IPO this year
    • 1 is going gangbusters
    • 1 (the one that prompted this musing) just received a term sheet at 2.5x what I bought in

    When Partner learned that my ~$15k investment was now worth ~$37.5k, she told me: “You’re like an odd sort of couch.” Apparently, most people find coins in the couch cushions, not tech company stock that they haven’t thought about in months.

    It’s the same way I play poker: I find a spot where I have an edge, and I hammer it over and over and over again. Eventually, if I bet the same amount into ten different companies, and a successful company will more than 10x my money, I need to be right more than 1/10 times. (And, of course, not run out of money.)

    Most people either don’t have the resolve or aren’t right more than 1/10 times.

    Different Risk Profiles

    Graduating university, Partner was saving 75% of her paycheck. She didn’t know many people didn’t save at all, and most financial experts only recommend around 15%. She thought what she was doing seemed logical.

    We are FIRE sort of people, just with different risk profiles. Partner enjoys working for a paycheck. I work to win the lottery.

    These mutually-balanced approaches are part of what makes us a good team. When we need to invent something out of nothing, I’m usually team captain. When a problem needs debugging, she’s in command.

    After reading a draft of this article, Partner had this to say: 

    “I think this last part might warrant slightly more space. You’re hedged in a way most people don’t get to be. 

    It’s one thing to take big bets when you’re young and have no responsibilities. It’s that people tend to get addicted to the paycheck when they set their lives up in ways where they feel the need to have stability. They may miss out on being able to use those skills in big-bet ways as they don’t want to risk a loss. It’s also hard to have the mental space and discipline to self-hedge.

    I’m your hedge so you can chase the upside.” 

    One day, my ship will come in. And if not, we’re still happy.

    The Hand of My Dreams

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    If the logic doesn’t follow, keep going. Don’t go back.

    This actually happened earlier today: 

    The Setup

    Two guys had run out of money in the poker game. One of them – the host – had lost angrily. He was displeased with two other people at the table, and responsible for the other broke-guy’s buyin. The host said, “And if we’re down by $54 and we send $50, what will you do…” 

    Then he told us, “You’ll take it and be grateful and not hound us for the other $4.” 

    A while later – minutes or hours, I don’t know – the final three of us were playing double-handed omaha. 8 cards per person, split into two hands. The board was A99Q. I had AAxx in one hand for the over-full: the second-best possible hand. Even better: my two aces were both spades. 

    The Opponents

    The woman on my left – an Asian girl from my highschool – had KKxx for the kings-over full house. (The board now contained A99QK, with still the final card to be dealt.) In her other hand, she had 99xx for quads, but also definitely did not have quads. 

    The woman on my right – a different Asian girl from my highschool – had 8cTcJc spread across her 8 cards, which went with the 9c, Qc, and Kc on the board to make a straight flush. Fortunately for me, the cards were separated across her hands so she didn’t actually have a straight-flush despite having the cards. 

    The Accounting

    We were already all in. I performed the accounting. The hundred-dollar chips were exhausted, so we used the silver bracelets each valued at $200. 

    The pot totalled around $1500. We hadn’t all contributed equally. I wasn’t concerned since I had so much equity. 

    The Broken Protocol

    We agreed to run the river three times. 

    We clicked my computer mouse to run the first river. It dealt an entire new board. We tried again. Same issue. I suggested we should use the same physical deck we were already playing with to run the river (duh!). 

    The Showdown

    I awoke.

    A Game You Can’t Decline

    JulianLeave a comment

    The goal of the game is to play well. You play well by knowing you’re playing.

    Last night, friends came over. They’d baked cookies. They brought the cookies in a Tupperware container. As they were leaving, Partner went to retrieve the Tupperware and hand it back at the door.

    I winced internally. I should have said something. 

    Here’s the game I saw and Partner didn’t: you don’t return the Tupperware at the door. You keep the Tupperware. Eventually, you need to return it – which means you’ll see them again, which means there’s an open thread between you. The Tupperware is a mild promissory note. Yes, we’ll have you over, or you’ll invite us, or we’ll see you at the thing – because also, here’s your Tupperware.

    Returning the container at the door closes the loop transactionally. Everyone walks away even. But the loop is what builds the relationship. Even is not what you want when starting a relationship if the other person would find you returning the tupperware weird.

    When I mentioned it to Partner afterward, she got it instantly. She’d just never thought of it that way. We also agreed that it isn’t logical. Of course they want their Tupperware back. The whole thing is illogical. Most social dynamics games are.

    I’m reminded of a buddy of mine this past summer. A woman had stayed over at his apartment. Now, she wanted her ring back. He told her to retrieve it from his roommate. No, buddy! She left it so you have to see her again! 

    I once had a 9 AM appointment with a doctor. Due to a series of errors made by his office and lab, my appointment ran until 2:30 PM. Around noon, I mentioned wanting to grab a sandwich. He gave me cash and offered to pay for mine as well.

    Something felt wrong. I bought both sandwiches and gave him the cash back.

    I suspect he didn’t even register the move. But Partner had the same instinct I did when I told her: pay for his sandwich, refuse the cash. The discomfort was real and shared, even if neither of us could immediately articulate why.

    Here’s why: the cash created an obligation flow that didn’t match the relationship. He had spent five and a half hours of my day on his office’s mistakes. The appropriate flow was him owing me. His offer to buy me lunch was a way to pay down his debt of guilt. But not an appropriately-sized one.

    Buying the sandwich, refusing the cash, was the right move. It accepted the kindness implicit in offering food while refusing the implicit power-move. Imperfect, but instinct steered correctly. 

    And as we left his office, he apologized at least 8 times for the delay. By the end, he said, “I’m done apologizing. If I apologize again, hit me.” That’s the appropriate obligation for someone who’s wasted 5 hours of your day. 

    Recently, I made a friend who pocket-vetos any activities that are emotionally intense for him. He only plays the games he wants to play, in the ways he wants to play them.

    It’s no surprise this correlates with power and resources. As friends have gotten more powerful, more of them have developed this stance. No explanation, no apology, no negotiation. Generally no answer, not even a “No”. 

    If you’re young and broke and unattractive and awkward, you can’t pull this off. People stop inviting you. Every social interaction has to be navigated, every gift has to be reciprocated, every obligation has to be honored. The poverty of optionality forces you to play every game offered. 

    As you accumulate power and resources, you can decline games without consequence. People still invite you. People still want you around. They accept this trait because you’re still worth it. Like the celebrity who’s notorious for being prickly in interviews, the rudeness becomes a feature: a filter mechanism.

    Three observations: 

    1. Refusing to play is itself a move. 

    • A recurring claim of this blog. It holds here.

    2. Not-playing a game requires winning sufficiently in other games, or people will stop playing games with you entirely. 

    • The friend’s pocket-vetos work because the rest of his social game is in order. He’s not refusing because he doesn’t understand the games; he’s refusing because losing this game doesn’t matter for him anymore. If Warren Buffett never set a schedule, only meeting with people willing to show up at his offices in Omaha, people would still gladly sit in his office for hours, waiting for the possibility to talk with him. 

    3. Winning generally comes from choosing which game is being played and at what level. 

    • Most of us learn how to act in specific spots in specific games. That’s a fine level one, but it misses out on level two (shifting the odds in your favor) and level three (dictating the battlefield). 

    One more thing: the move I should have made about the Tupperware was overruling Partner in real time. I saw the game. I knew the right move. I let her make the suboptimal one because I didn’t want to interrupt.

    That’s a habit of mine – letting people make moves I see as wrong, then discussing afterward if it matters. The discussion-afterward version doesn’t recover the move. It just generates retrospective alignment for next time.

    Sometimes the right move is to interrupt. Saying wait, I’m gonna eat all those in the moment would have been weird. It also would have been the right move. Weirdness is sometimes the price of playing well.

    [It’s late. I’ve read this one too many times to like it. The daily-publishing game is hard tonight. I hope I like this post in the morning. Sigh.]