Cone-Eyes

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 !!!”

Budapest: Scams and Porn

How porn, scams, and power fantasies feed each other

[Day 2 in Budapest. Written from a downtown bar.] 

In Budapest, there’s a classic tourist scam. The kind of scam that’s so common you learn about it from Rick Steves. A beautiful woman approaches you on the street, flirts, suggests a drink at a bar she knows. You go. The menu has no prices. You order a round. The bill comes: $500 for two glasses of champagne. A very large man near the door makes clear: this is not negotiable.

The scam works because the mark doesn’t expect it. He thinks he’s lucky. 

And the reason he thinks he’s lucky traces back through Soviet history.  

Here’s the loop, roughly:

1. Post-communist economic disparity creates a visible gap between local women and Western tourists with money.

2. Sex tourism follows: Guys pay for sex.

3. Some of them film it. A whole genre emerges — the “meet a girl on the street in Eastern Europe” category. The premise: “this just happens! You walk around Prague or Budapest, and beautiful woman will come home with you.”[1] 

4. Enough men absorb this trope from porn as a realistic model of how Eastern Europe works. They arrive pre-loaded with the belief that beautiful women approach foreign men on the street.

5. Scam operators notice this. They don’t even need to be aware of the porn. They just notice this story works. A woman approaches, flirts, leads the guy to the scam bar. He doesn’t question it because it matches the script he’s already running.

The porn normalized the scenario. The scam monetized the same scenario from another direction.

I like comedy, so let’s look at this from a recursive, self-parody perspective: 

Once enough guys get scammed and tell the story online (forums, Reddit, travel warnings, the Rick Steves travel guide) the scam itself becomes a known thing. It enters the cultural awareness. And what does entertainment do with any known phenomenon?

It digests it back into fantasy.

My predicted next genre: porn where the guy gets taken to the clip joint, sees what’s happening, fights the bouncer, and the girl is so impressed she actually sleeps with him. The humiliation gets rewritten as a test. The mark becomes the hero. The audience gets to engage with the anxiety of being scammed abroad, but instead of worry it gets transmuted into a power fantasy.

Reality creates the fantasy. The fantasy creates the vulnerability. The vulnerability creates the scam. The scam gets folded back into the fantasy. Someday maybe people will want to be scammed by the beautiful woman as they’ve gotten off on it so many times. 

This structure isn’t unique to Budapest. Casting couch porn followed the same loop. The real casting couch was an open Hollywood secret (producers leveraging access for sex). Exploitative, coercive, career-ending for the women who refused. Then the genre emerged: the “audition” scenario, repackaged as the fantasy itself. The power imbalance turned from a social bug into the pornographic product.

The pattern repeats because it works. A real dynamic involving real exploitation gets turned into content, and fed back to an audience that is now one step further from seeing the thing clearly. Nobody plans the full loop. Each actor in the chain is just optimizing locally — the pornographer for clicks, the scammer for cash, the next pornographer for a fresher scenario. The loop runs itself.

The economic loop feels no different from the gentrification loop seen in Brooklyn, Berlin, and Budapest: down-trodden area → cheap real estate for bars or clubs → yuppies who want to be near artists → cafes → expensive real estate 

It’s an economic loop. You’re living inside thousands every day. Try not to get fucked by them. [1] Budapest actually produces a lot of porn, and this “meet a strange woman and bring her home” is a common genre, featuring the beautiful city architecture

Top-Secret Games: Airport Edition 

Serious places make the silliest games

Airports pretend they’re fancier than bus stations. Some games to remind them of their silliness

Packing

  • Try “onebagging”: no matter how long the trip, pack everything in a personal-item-sized backpack. Partner and I traveled through Europe for 4 months with one 20L backpack each. Benefits include: 
  1. Less to lug
  2. Recognize how little you actually need. 
  3. Save $50+ per budget airline flight (which charge for carry-ons). That $50 (or $75!) could go toward a new shirt or hat or socks or whatever-you-neglected-due-to-your-limited-space-and-probably-won’t-need-anyway. 

Checking in

  • Snap a picture of the airplane seatmap. This may come in handy. 

TSA Checkpoints

Which line?

Most people choose by line length. But length is often less important than throughput speed. At a fork, neither line is likely to be 25% longer. But one TSA agent often is 25% slower. 

Free Awkward Massage

When you’ve arrived to the airport with ample time to spare, tell the TSA agent, “I’d like to opt out of the body scanner”. 

They’ll summon an agent who aligns with their perception of your gender appearance (androgynous people: I have no idea). 

That person will blandly-and-with-dead-eyes presage the next two minutes of your future. Their articulation will be simultaneously formal (“I will first pat down your upper body, then your lower body…”) and ridiculous (“When I get to your sensitive areas, such as the waistband, I will use only the back of my hands”). 

The experience feels like a procedural drama crossed with a lazy streetwalker naming service prices. You know it’s pointless and dumb. They know it’s pointless and dumb. And now they’re obligated to touch you. 

For an added joy, leave something innocuous in your pocket: your passport or a few coins or a used dental flosser. 

While they’re performing this intimate massage, try not to laugh. 

Or guffaw at their pointlessness. 

Or lean on them while they’re bending over to pat you. 

On a societal level: there’s no winning. It isn’t a game. It’s a farce.

In the Lounge

0. Play credit card games to acquire lounge access. (These games are pre-preparation.) 

  1. Before leaving the lounge, choose between Future Fueling Level 1 (stuffing your backpack with canned drinks to go), and Future Fueling Level 2 (squirreling food into the ziplocs you brought). I play level 1; Partner Level 2. 

At the Gate

  1. If it’s your birthday, tell the counter check-in people it’s your birthday. (Most of their work is dealing with annoyed travelers, so they really love this refreshing opportunity!) 
  2. If it’s not your birthday, ponder the ethics of telling them it’s your honeymoon. (Decide against it as your partner doesn’t have a ring and you really don’t want them to ask, plus lying to win games is cheating.)
  3. Ask the gate agent whether the airplane is full. If it’s not, ask them if they could move you to better seats. Do not pay for the change: that’s how the terrorists win. 

When lining up for budget airlines with your Onebag®, do the following:

0. Have a bag that, if need be, is small enough to fit in the sizer if you put on all your layers and jam your pockets full. (The first step to winning is choosing a game you can win.) 

  1. Seek the person who is least interested in doing their job correctly. 
  2. Position your body to hide your bags. 
  3. Upon approaching the desk, ask them a question that distracts them without increasing their engagement, something like “Have you been to [destination city]? It’s my first time.” Be kind and friendly and light. You’ll know you’ve succeeded when their dead eyes shift energyless to the person behind you. 

Boarding the Plane

  1. If the plane has open seating, board earliest. See the “final note” (below) for methods to keep your neighboring seat empty. 
  2. Board last. If the agents ask, tell them it’s because “Boarding last is lucky!” And it is! The last person on the plane gets to see what seats are available before taking theirs.
    1. This approach enables the harnessing of what million milers call “poor man’s first class” (an open row).

Final Note 

  • Throughout this experience, if you ever want to repel someone’s attention (maybe your bag is slightly too big; maybe the plane is open-seating and you want the open seat beside you to remain), make a grotesque face and pick your nose. (Only pull this trick if you want to distract their attention and don’t have to interact with them. If the interaction is mandatory, this move can be dangerous.) Really get into it. Remind yourself, “No one expects a nose-picker to be strategic. Some people actually look like this or pick their nose like this. I wouldn’t want to interact with them, either!” 

“Yes, And” in The City.

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

“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.

There’s a Fine, Fine Line Between Campy & Bad

Bad + heightened + self-aware = camp. Bad + heightened – self-aware = bad.

Can you discern between campy acting and bad acting?

On Thursday, I watched a play. Half the actors performed camp; the other half were unskilled. Camp is the mimicry and affectionate mockery of bad. There’s a fine, fine line between them: to the untrained observer, camp could appear as bad.

Thus, the performers must train the observers.

What’s in a Play?

A skilled actor who cannot entertain is not a skilled actor. However, in this situation, I do not think the actors are entirely to blame. An actor in an uncurated environment can only do so much.

The director is responsible for show cohesion, just as a coach is responsible for team cohesion. (A football player can reasonably say, “I played my role perfectly; today’s loss is not my fault.”)

Thursday’s show presented individuals but lacked a bigger picture. Every actor played according to their ability. Some of those abilities were poor. The director failed to account for this gap. Again, I think this is a coaching issue. Plenty of highschool sports teams have bench warmers and waterboys. Plenty of highschool plays contain “tree #1”. (And New York City theater likely has far more people auditioning than available roles.)

Just as a comedian must wink at the audience lest we think him a liar, this play needed a wink. The play was a small-theater (but professional) production of A Funny Thing Happened on the Way to the Forum, a musical containing archetypes — archetypes that, as over-the-top portrayals, may not be authentic. Inauthentic acting done well may be camp. Done poorly? Amateurish.

When the actors first entered the stage, playing mock-audience members, one could have said, “This is going to be campy.” A director’s note in the printed programs could have said, “We lean into the camp.” Instead, the performances fell into the uncanny valley.

A Holistic Hole

A basketball coach must do more than ensure each teammate performs their role. They must ensure the team gets the ball into the basket. Otherwise, you end up with beautiful acrobatics but complete strategic failure.

Or, in this case, a play that audiences did not want to watch.

In Favor of Race-Ism

Not that kind; the playful kind. 

Two days ago, Partner asked, “Are most games races?” 

As a lover of games and bad puns, I present to you: 

RACE-IAL DYNAMICS: a taxonomy of games if we assume all games are races.

Why Touch Upon Race? 

Race is a touchy subject. Why perform this taxonomy at all? 

Story structures come from games. Flirting often mimics tag. Political jabs often mimic “I’m not touching you”. 

Separating the races allows us a clearer vocabulary about the different race mechanics found in a game. 

If you’re playing game A, which has race dynamic Alpha, would the game be better with race dynamic Beta? 

What’s in a Race? 

A “race” is approximately a competition involving time. Common words/constructions include: 

  • “First to X” 
  • “Most Y in [time]” 

RACE-ISM is the categorization of games by their races. (People who subscribe to 

this categorization are therefore RACE-IST.) 

Segregating the Races

Some races are pure: reach the victory condition before the opponent. Most games contain some amount of RACE MIXING (the incorporation of different race-like components, which tends to create stronger games, as we’ll get into later). Let us attempt for a moment to see the races in their purest forms. 

Who’s Racing, How & When? 

  • SIMULTANEOUS RACE
    • “I race while you race” 
  • SEQUENTIAL RACE
    • “I race, then you race” 
  • ASYMMETRIC RACES
    • “Can I X before you Y?”
  • ANTIPARALLEL RACE
    • “You want to go in one direction; I want to go in the other” (e.g. tug of war). 

Race Physiognomy 

  • RACE-RACE
    • “First to X”. 
  • SLOW RACE
    • “Who gets there last?”
  • SCORE RACE
    • “Most points wins” or, for golf “least points wins”
  • QUALITY RACE
    • “Best X within [time]”, where X is about quality traits, not numerical (e.g. the Great British Bake-off or gymnastics.) 
  • ENDURANCE RACE (or SURVIVAL RACE)
    • “Who quits last?”

Race Ends

The word “end” can mean either culmination (“the end of my work shift”) or goal (“you are working to what end?”). As this piece contains copious puns, I shall employ the word to mean both. 

  • RACE CULMINATIONS
    • TIME-ENDED RACES
      • A clock concludes the race 
    • PLAY-ENDED RACES
      • A player action concludes the race
  • RACE OBJECTIVES can be
    • the SAME
      • (“first to touch the tree”)
    • DIFFERENT INSTANCES OF THE SAME
      • (“first to checkmate the opponent’s king”)
    • DIFFERENT
      • (“can I tag this runner before they get to the base?”)
    • SUBJECTIVE
      • (“most satisfying to X person”)
    • OBJECTIVE
      • (“Highest measurable count of X”) 

Race Mixing

Most people only watch footraces at the Olympics once every four years, which implies we find them less interesting than other sports. Football, for example, contains:

  • An antiparallel asymmetric race
    • (offense vs defense) 
  • with mini asymmetric antiparallel races
    • (cornerbacks guarding wide receivers; offensive line protecting the quarterback while the defensive line attempts to pressure and/or tackle the quarterback), 
  • with multiple race ends and sub-ends
    • (the game itself concludes after the clock runs out of time (time-ended race), but the clock can pause due to various in-game mechanics)
    • (the number of downs is a play-ended race, influenceable by both teams) 

Football’s different races require different skills: speed, strength, and hand-eye coordination of course, but also time management, rapid-fire decisionmaking, and balance of risk-taking. Since games parallel the skills we use in the rest of our lives, the simple ones tend to be less generally valuable, just as the ability to perform one simple task (picking up a pencil) is less valuable than performing a more complex task (writing a biography). 

Inferior Races 

There are no inferior races. RACE-IAL PREFERENCE is a matter of taste. 

For example, my favorite type of race happens in cooking: One person speeds to finish the rice before another person can toast the marshmallow, all before the oven is pre-heated. As an added benefit, at the end we enjoy a tasty race krispie treat.

Consistency, Consistency, Consstncy

“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.) 

    Four Umpires

    Games require fairness. Fairness requires… Umpires?

    Bottom of the ninth, tie game, runners on first and third, the coach signals for a new pitcher.

    The Away team choruses from the first-base dugout: “You got this, Julian!” “Go get ’em, Julian!” (No relation.)

    The new pitcher takes the mound. He has the wispy, windswept hair of an early-2000s teenage heartthrob, and just enough muscle to suggest he started working out when puberty hit a couple years ago. 

    Julian throws his first warmup pitch.

    A player walks from the third-base dugout to behind home plate. Maybe 15 years old. He accuses a woman old enough to be his mother: “Are you taking videos?” 

    “No,” she replies. “You guys were [doing something she found objectionable].”

    Julian throws his second warmup pitch. The boy continues the accusation: “Were you taking videos?” 

    “No, just pictures.” She continues her explanation. 

    “I don’t care.” The boy stomps back to third base. 

    A third warmup pitch. The umpire calls the game back in play.

    Julian straddles the mound. His neck swivels, unable to see the opposing players on first and third at the same time. The previous cheers have gone silent. Julian twitches his knee. Something catches his eye near first. He looks over at it.

    “Bawk!” yells someone from the third base dugout. 

    “Bawk!” the umpire agrees like a chorus of chickens. “He lifted his knee and put it back. That’s a bawk.”

    “What’s a bawk?” Partner asks me. I start laughing. 

    “What’s a bawk?” she repeats. 

    “It’s…” I begin.

    Suddenly, everything is happening at once. The umpire clears the path between third base and home, like he’s making way for prince Ali. The player touches home. His friends cheer. A tall man says “Excuse me” to someone beside us; he removes a sun-shaded phone from the fence, where it was probably recording or livestreaming the game. The umpire walks over to the Away team to explain the rule violation. A younger looking boy has both palms against his cheeks and mouth agape like a real life Scream. Someone says, “At least we gave them a hard fight.”

    I turn to Partner and explain. “Basically, the pitcher isn’t allowed to trick the base runners. So there are a lot of very precise rules about what he can and can’t do. I think I’ve heard my father say ‘breaking the plane of the knee’ at some point, meaning you have to pitch immediately when you do that. If you break the rule, as punishment for your shenanigans, the players are awarded a free base.”

    “And that’s called a bawk?”

    “Yep. Spelled B-A-L-K.”

    “Ballk.”

    “Yeah, but pronounced like what a chicken says. Rhymes with ‘walk’.”

    “Bawk.”

    Fifteen minutes earlier, Partner and I arrived to the baseball fields. Four fields, spread out in this grassy oasis one third of the way from the top of Central Park.

    Over the next hour, we will watch four ball games. The most notable play in every game will be by the umpire.

    More Like Guidelines

    The first players are either middleschool or highschool kids. Brown jerseys for the pitching team. No one on base. 

    The pitcher throws a warm-up pitch. The ball bounces three feet before home plate; the catcher tosses it back.

    The batter approaches the plate. The pitcher throws. This ball bounces too. “Ball,” says the umpire.

    Partner and I watch eleven subsequent pitches. Some fly high, into the chainlink fence behind the catcher. Most bounce, like the first two. None cross home plate between the batter’s knees and shoulders. 

    Dutifully, on each pitch, the umpire says “Ball” and the corresponding number.

    One at a time, players populate the bases. After all twelve pitches are thrown, the bases are full.

    The pitcher begins his windup. The batter steps out of the box. The pitcher stops. 

    “That’s a balk!” the umpire shouts at the pitcher. “You can’t [I stop paying attention].”

    “Let’s go to that game,” I say, gesturing across the field.

    “Walk around or through?” Partner asks.

    The umpire is walking back his previous position, calling it a “No pitch.” 

    “We can walk through. He’s not going to throw anything hittable.”

    Partner and I walk behind the third-base fence, then skirt into the outfield in foul territory. As we pass the left fielder, I notice the players on each base slowly advancing one base.

    When a child has thrown twelve balls in a row, are you really going to call him out for a balk? Sometimes the spirit of the game calls for bending the rules. If a child pitcher can’t throw a single strike, that sounds like a rule problem. I’m reminded of the problems I experienced playing pony baseball: Stealing is legalized before any catcher has the arm to throw out the runners. A runner on first is effectively a runner on third. 

    We walked to the baseball field where Julian would soon bawk, then continued toward the softball games.

    The Competent Umpire of Slow-Pitch Softball

    The softball game on our left looks competitive. The game on our right, less so. We go left.

    The cocky third baseman nabs a line-drive one-handed. “Out.”

    Partner and I walk behind home plate, where the umpire is chatting with an off-duty ump.

    This umpire wears no mask nor padding. No padding for the catcher. Nor helmet for the batter. I learn something new about slow-pitch softball.

    The next batter hits a ground ball toward third base. The third baseman fields the ball mid-stride and throws off-balance, clearly showing off.

    The umpire calls “out,” then turns three-quarters of the way toward the fence behind him.

    “I coulda played at Arizona,” the umpire continues. “A-S-U. Got a full ride. Said no. What did I know? I didn’t want to go to Arizona.”

    He turns back to the game: “Ball.” 

    He turns back to his friend: “I played everywhere. Puerto Rico, Dominican Republic…” Returning to the game: “Strike.” Returning to his friend: “Hawaii.”

    I’m impressed by how he can both continue the conversation and accurately referee the game.

    A batter waits just outside the batting box.

    “Can we go?” asks the pitcher.

    “I’m waiting for you,” the ump responds.

    “I’m waiting for you,” says the batter.

    “No you ain’t,” the ump responds.

    As an unbiased observer at this game, I can confidently say: they were not, in fact, waiting for the umpire.

    That Ain’t the Rules

    Partner and I approach our final softball game of the day.

    Ten kids in ragtag outfits and red pinnies, aged between 22 and 25, versus ten older guys, between 30 and 40, in matching jerseys.

    The pinnies are having a blast — yelling and hollering, cheering among themselves.

    The pitcher throws. Ball. Strike. The inning ends.

    The pinnies take the field. I count ten players and seven gloves. 

    “Don’t you have gloves?” the umpire says.

    Someone shouts back, “No.”

    Someone else says, “But it’s okay. We don’t need ’em.”

    “You need gloves,” says the umpire.

    I turn to Partner. “You definitely don’t need gloves. Gloves were only an early 1900s thing. I’m pretty sure they’re not required.”

    Partner: “Might be a beer league thing.” (According to Partner, beer league is a type of casual softball where players drink beer in their dugouts between fielding.)

    The older team lends three gloves to the pinnies.

    Partner and I watch an inning or two. It’s riotous, raucous fun — all hijinks, everybody trying their best, but no pressure on winning.

    One pitcher throws a ball that arcs around 13 feet high. The ump calls “strike three.” The batter taps the top of his head.

    “That’s too high,” I say to Partner. “If it’s above 12 feet, it’s a ball.”

    The ump says, “It bounced before the line. That’s a strike.”

    The batter is out.

    The game rapidly evolves into “Who can throw the highest pitch that still lands short of the line?” Some are clearly over 15 feet, landing at the front of the plate, and still being called as strikes.

    I pull out my phone. In under ten seconds, I read aloud to Partner: “Four-to-ten-foot arc. Any pitch too high or too flat is a ball, unless the batter swings.”

    The players are now chopping at pitches coming down above their heads. The game looks less like softball and more like swatting flies.

    Yet, somehow, no one seems to mind.

    Partner is getting cold. We’ll watch this final inning.

    The pinnies are batting. Runners on every base.

    The umpire yells something to one of the baserunners. Another pitch. “Ball.” Then the umpire yells, “He’s out! Three outs!”

    I walk over to the third-base dugout. I ask one of the kids in pinnies: “How did that inning end?”

    He tells me: “The ump said no leading off.” He gestures toward second base. “He wasn’t on the base, so he called him out.”

    “And what about the pitches. Don’t they have to be under ten feet?” I ask.

    “I don’t know. I don’t know the rules,” he tells me.

    “How did you guys get to be here?”

    “We went to college together. Seemed like a fun thing to do.”

    I wonder what it would be like to play a game without knowing such fundamental information as What counts as a strike? and I should bring a glove.

    Walking home, I give Partner my shirt to stay warm, and I’m struck by how much more fun the pinnie team was having than any other team we watched that day.

    They don’t know that the ump ruined their game. So maybe… he didn’t.

    Working to Win the Lottery

    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.