On Skillful Calibration (and Safely Pokin’ Gators!)

To improve, calibrate. To calibrate, employ expected value calculations (which is more fun than it sounds).

Two years ago, a friend passed on the opportunity to invest in Anthropic. He now regrets passing.

This friend prioritizes calibration. Yesterday I learned why he generally avoids risks. When viewing a risk, he considers only the magnitude, failing to also include the risk’s probability.

Expected value is one of game theory’s most powerful calculations: 

  • Probability × Magnitude = Expected Value. 

My friend is not unique: people often drop one of the two terms. Include both in your simple math; your outcomes will be better calibrated. (And it only takes a second!)

Magnitude-Only: Frozen From Fear

Considering only the downside magnitude over-biases against action. This heuristic will keep you alive but not enable you to thrive.

This example occurs whenever somebody says, “But what if it fails?” as a conversation ender. Slap a probability on that bad boy and you’ve got an EV.

Probability-Only: Missing the Magnitude

A friend once described why they don’t vote: “the likelihood I’ll have an impact is near-zero.” Ah, but tomes have been written about the enormous magnitude.

When someone says, “It probably won’t happen,” or “it’s a drop in a bucket,” check they’re also considering the size of the bucket. If the impact is large enough, the low likelihood that your single drop makes it overflow may be enough.

EV → More Fun

During my all-time favorite date, Partner and I hooted & hollered at an alligator.

Twenty minutes earlier, we strolled down a path through a Louisiana swamp. Partner meandered toward some tall grass. I said, “I wouldn’t do that.” Partner was surprised because her self-preservation instinct usually eclipses mine. I mentioned alligators, and said: in this circumstance, the magnitude is very bad (being eaten by a gator) and the probability much higher than usual (Louisiana swamps contain alligators, and Pokémon has taught me to beware tall grass).

Compare that moment to later: on a bridge 10 feet above an alligator. The magnitude is still very bad, but the likelihood de minimis. (Teehee, alligators can’t jump 10 feet!) 

Since we knew ourselves to be safe, we could poke the gator with our metaphorical stick.

When something seems scary, investigate the probability. E.g. “I can’t miss work to see my child’s school play: I could lose my job.” 

This concern is well-founded, but misses two elements: the likelihood of losing your job (probability) and the fact that you can influence that likelihood via other actions (malleable probability). (I’ll write more on malleable probability another time, especially as it relates to luck.)

Expanding your Vocabulary

Expected Value is a core step, but it is only the first step.

Error bars can make this topic tougher. The question “How likely is extra-terrestrial life to exist in our universe?” prompts wildly different outcomes whether you include the error bars.

So even if you do the EV calculation, you’ll still be wrong sometimes, you’ll still lose sometimes, and there’s still more calculation to do. (For a fun example, see Pascal’s Mugging.)

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.) 

    A Game You Can’t Decline

    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.]

    The $10.125 Sandwich

    The goal of the game is selling sandwiches. You sell sandwiches by making it fun. You make it fun by taking fun seriously. 

    I bought a sandwich today. The sandwich shop offers a cute promotion: from 3 to 6 pm, if you call a coin flip correctly, you pay half price. 

    It’s fun, it’s attractive, and they net 75% of the normal retail price. 

    But the experience is broken. 

    First, you don’t pay until after the flip. So I, who sees loopholes without trying, am instantly aware that I could order the sandwich, flip the coin, and walk if it lands the wrong way. How would they even develop a process to stop me? I pay full price and then the flip determines my refund?

    Second, the coin. It’s some B.S. commemorative coin — one side is the restaurant name, the other the logo — where neither side is obviously heads or tails. So the cashier has to tell me, and presumably every patron between 3 and 6pm, “this side is heads.”

    Third, the flip. Less a flip than a half-spin. He calls it whichever way it lands in his hand. Not even the catches-it-and-slaps-it-onto-the-back-of-his-other-hand move that’s standard on any schoolyard.

    What happened to the good ol’ quarter?
    Why are we making this more complicated than it needs to be?
    Why can’t the customer flip the coin onto the counter, where it would be easily visible?
    Why not call the sides “name” and “logo” instead of heads and tails? 

    The sandwich was good. It satisfied my basic need – fuel after the gym so I’m not grumpy. It wasn’t $13.50 good. It’s definitely $6.75 good. It’s probably also $10.125 good (the expected cost). 

    Here’s what bugs me. The promotion could have been theater. A customer walks in, gets drawn into a small moment of drama, calls it in the air, wins or loses, laughs either way, tells their friends. Instead it’s a transaction with a dice roll bolted on. The cashier is phoning it in. The coin is wrong. The flip is wrong. The ritual isn’t a ritual.

    The fun version costs them nothing. Same margin, same coin-flip odds, same sandwich. Just a real coin, a real flip, and a cashier who understands he’s running a tiny game show for thirty seconds a day. 

    And sure, if there are people in line behind me, by all means do the quick version. But the main reason they’re doing this promotion at all is because they don’t have many patrons between 3 and 6pm. 

    If they fixed it, I’d come back. If they fixed it, I’d bring people. The half-time half-price is nice; the experience could also have value. 

    Also, I called heads and it landed tails. 

    Know what you’re hiring for (Apr 15 2026)

    As long as you do your job 🙂 

    My contractor is excellent. Exquisite. Delightful. Perfect for the price point. 

    His project manager is new.
    Not in a bad way.
    In a just-moved-to-the-U.S.-from-Pakistan-where-he-used-to-be-an-architect way.
    In a living-with-eight-relatives-out-in-the-boonies way.
    In a this-is-his-first-project-at-his-new-job-in-a-new-country way.
    In a hungry way. 

    Yesterday, he sent me a long email saying we need to stick to timeline.
    I replied appreciating him for his work and telling him, respectfully, that the delays have all been on his side.
    I also texted the contractor to follow up about a question he and I had discussed thrice, but that the project manager had a different conclusion on.
    I received a reply that included both the answer I expected and a note that he was looking forward to seeing me tomorrow.
    I replied: tomorrow? That works, but did we have a scheduled appointment? 

    And at 8:36am, Partner prods me in my half-torporious slumber to say that project manager is en route.
    I check my email. At 5am, the project manager emailed to say we were meeting at 9am. 

    The amusing part is: this is actually fine. None of these minor hiccups have actually been problematic for the specific job I want him to do.
    And also, if his timing is a bit slower because he’s green, we’ve signed a sufficiently solid contract to be okay in that eventuality. 

    I’m still very sure that the project manager is a good fit, and that the contractor is excellent.
    I’m also suspicious that the project manager might have been up all night working on my project. (He said he had sent the 5am email “last night” and I’m not sure when he slept before taking the metro north train in.)
    And that he dresses differently depending on whether he is going to meet designers (black turtleneck on one occasion, stylish black t-shirt on another) or subcontractors (blue jeans and a baseball cap).
    Lol.
    Keep up the good work! 

    Vandals & Volition (Apr 14 2026)

    Why can’t we all want the same things? 

    Just outside our apartment, walking to The Park, Partner & I spotted a man kick a trash can. The can fell on its side, languishing in the street. 

    Despite having an appointment in 40 minutes and Google Maps informing me the walk would take 38 minutes, I stopped to right the can. I lifted first its outer shell, plopping it back in its rightful place on the sidewalk, then its inner catching chamber, inserting this chamber into the shell. 

    Walking away, I felt both smug and nervous. I caught myself sneaking glances at the vandal who had tipped it over. Will he notice? Come after me? Have I regressed the impact of his righteous fury, thereby inspiring it against myself? 

    Just as I entered the park, he looked back toward the can, object of his anger. Noticing it was tipped, he crossed back across 7th avenue, re-set himself in the same position, and kicked it over again. 

    And I, already too far and with other things to do, continued on with my day. 

    Three hours later, I returned to find the can replaced in its proper location, save for the lid slightly open. Some other Good Samaritan must have contributed to the fight against entropy. 

    But I’ll always remember the kicker’s determination. How inspiring it must be to have a clear, defined purpose. 

    I found it: the best article ever written in America. I laughed. I cried. I hungered. I grew. Deeply worth the experience, especially for those of us who care about the journey of food and the food of journeying.

    https://www.theatlantic.com/magazine/2026/05/best-free-restaurant-bread-america/686582/

    And a quote from April 8th: 

    “How come you’re incredibly detail-oriented when reading a contract?” – Partner, fishing out an egg from the pot of eggs I sous vided last night and clearly just missed one when I put them away.

    Selections & Sewage (Apr 13 2026)

    In which Our hero explores options. 

    Click here for the accompanying video. 

    Today, Partner and I visited an appliance showroom. Here’s what we learned: 

    • Shower heads come with flow rate limiters. The national legal maximum is 2.5 gallons per minute. You can remove your flow rate limiter, as the salesman at the showroom once did. His shower subsequently shot water with such force that it knocked the shower door clean off and flooded his bathroom. 
    • If you buy a thermostatic shower handle, you can have infinite separate shower heads all pointing at you. The shower heads are each limited at 2.5 gallons per minute. The thermostatic valve caps out at 14 gallons per minute. So even with three shower heads you won’t lose water pressure! All you have to do is ensure you’re shipping the showerhead to a state that does not have more restrictive requirements (California and New York both cap showerheads at 1.8 gallons per minute)
    • Some faucets cost $150. Some cost $800. Some cost $2400. They all dispense water. The $800 vs $2400 is cosmetic. The $150 vs $800 can be functional. 
    • The cheapest toilets and the expensive toilets both will ultimately contain sewage. The cheapest toilets don’t have glazed piping, so over time the sewage will accumulate in the pipe. The mid-range vs expensive toilets are functionally equivalent, just with different aesthetics and different ease of cleaning the part that doesn’t touch sewage. 
    • No one makes a bidet seat in black. 
    • Everyone likes a toto toilet, especially if you’re getting one with a bidet. I’m not convinced. I enjoy a vigorous stream when shooting water around my anus. The toto toilets I have used are disappointing in this context. 
    • Linear drains (long, thin rectangular ones) in New York City are much more expensive than normal, square drains since they must legally be made of more expensive materials. 
    • Steam showers cost $5k, minimum. 
    • Neither Partner nor I like rain head showers. Our dislike, according to the showroom attendant, is a common perspective. 
    • I will likely be able to realize my dream of three showerheads all at once. Bully for me! 
    • One model of toilet costs just over $26,000. It is not made of gold. I did get to sit on it.

    The empty longing of a holding pattern. (Apr 12 2026)

    In which Our Hero yearns. 

    When a plane doesn’t yet have a safe runway available, the control tower tells the captain to “go around again”. The captain circles and circles, awaiting the change in this external event that will enable the hundreds of passengers to continue on with their lives. No one enjoys a holding pattern. Quite the opposite: it is during these unenjoyable intervals that we find ourselves “killing time”. 

    The last few weeks have been versions of this activity. I’ve forwarded key aspects of incredible importance (my eye surgery; Partner’s jaw surgery complications fixing; Partner’s medical malpractice case; apartment renovations; my work). Yet we – Partner and I – are not living the lives we wish. 

    We lift weights more days than not. We amble through the most beautiful park in the greatest city in the world. We cook and eat food that we enjoy. We watch Jeopardy over lunch or dinner, shouting out the answers we know (and a roughly equal number that we don’t). 

    But still, we wish for more community. 

    We moved into this apartment with the intent of living with others. Now, 2.5 months in, renovations have not started. They might not for another month. Then add 4 months for the renovations themselves. And it could be – probably will be – over half a year before we live with roommates we like, hosting weekly dinners and playing board games and shouting out Jeopardy answers with more than just ourselves. 

    This period – this holding pattern – weighs on me. 

    There’s no point establishing clear patterns and habits and routines when they will all change in a month. No point improving the infrastructure or systems in a home that will literally have different walls. No reason to stabilize on processes of engagement with my roommate (Partner) when we’ll need to live elsewhere for a while and then return to a different home. 

    So we set ourselves on a month-long horizon. We establish temporary patterns. We work, and lift weights, and reach out to friends. We enjoy what we can. 

    But still, each day, I want more. 

    I want what we’re building. I want at least 5 people living here. I want to cook meals with others, to establish a weekly “Come over for dinner on Tuesday!” that invites a half-dozen people. A board game group and a poker group. I miss those activities. I miss them, though I’ve never had them. 

    And that weight – the weight of wanting what I don’t have – is a heavy burden

    for at least the next month. Or two. Or four. Or six. Or….

    A Small Change’s Gonna Come (Apr 10 2026)

    You can’t always get what you already don’t like having

    Steven Jobbers (the famous fruit vendor) once said (or at least I remember hearing of him saying it) that he tracks whether his days are good and if he ever has too many not-good days in a row, he makes a change. 

    Yesterday, I made a change. 

    This change: 

    Walking up 7th avenue, roundabouts 26th street, I saw all the negatives. Everything sucked. So I switched it. I saw that woman’s hat. That’s a good hat. Then the windowpane. That’s some straight-up magic. Then the fact that Partner enjoys hanging out with me, even when I’m a grumptastic grumplestiltskin. That’s nice. 

    I did this over and over – saw the positive, the good, the bright thing. 

    Often that’s how I get dragged into the doldrums: seeing the problem, the issue, why it wouldn’t work. I avoid that, resist it, run from it. 

    That’s how Partner engineers. She sees the problem, the issue, the way it won’t work. I find that demotivating. She finds it comforting. 

    Today, Partner worked from a coffeeshop. I worked from home, leaving three hours before I woke up. A good day is one where you sing to yourself in the morning, then only put on pants around noon. I completed around 7 administrative tasks, only one actually for me. Then, at 1pm, Partner came back. How nice it was to see her after a few hours away! 

    I like working alone. I like the emptiness. The lack of seen-ness. The feeling and knowledge that no one’s paying attention to whatever-the-hell I’m doing. Writing with a witness is a nightmare. 

    She likes coffeeshops.
    I can’t stand them.
    Two nice

    tiny

    significant

    shifts. 

    Ahhh. 😌

    Alums, Assembled. (Apr 9 2026)

    If you can’t return to the school, the school will return to you. 

    “I was just talking about you. I was telling him about your underground gambling ring in highschool.” 

    My reputation left an impression. 

    “If the administration found you, they would have expelled you!” 

    Oh, come on. Do you know how hard it was to get expelled from that school? Dealing drugs to other students or cheating on an exam, sure. Or, like, punching someone. But gambling? 

    “Julian Wise! I know that name.” –two women from the grade below me. They recognized my name. I sure didn’t recognize them. 

    My highschool had an alumni gathering in New York City earlier tonight. I ran into some old friends and met some new friends. This is why I live in New York: the serendipitous activities; the always-on; the my-highschool-was-on-the-west-coast-but-of-course-there-are-enough-people-in-New-York-for-an-alumni-gathering. 

    I feel sad. Sad that it’s over. Sad that I can’t ride that social high. Missing it already. 

    I miss that event more than I miss most of the activities I did in highschool. 

    Improv, some theater, bumming around with friends. ..
    I don’t miss having been there.
    New York seems to have been in hibernation mode.
    And now, finally, it opens.