Tag: Writing

The Sleeper Agent at Chipotle

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The goal of the game is to notice when you’re being played.

In December of 2008, I unwrapped a burrito-based scheme.

My local Chipotle had a promo: buy a $20 gift card, get a coupon for a free burrito. I asked the cashier what the gift card could be used for. “It’s as good as cash.”

I paid $20. They handed me a $20 gift card and a coupon. I asked for another. I handed them the $20 gift card; they handed me a functionally-identical card and a second coupon. I did this four times. The cashier said she might need to check with her manager. I smiled and said I was done, leaving with my four burritos, $20 gift card, and twenty fewer dollars in my pocket.

Chipotle ran this same promotion every December and May through 2011. I always had a $20 gift card on me, ready to use it to buy another. I ate essentially free burritos for three years. Even as a high schooler, I couldn’t eat them fast enough.

I was very proud of myself.

I hadn’t been to Chipotle in years. Today, they had a two-for-one deal – officially for the start of the Stanley Cup Finals (and coincidentally on the biggest stoner holiday of the year). 

I ordered. And, like a just-activated sleeper agent, the skills came back.

Bowl, not burrito – they fill the bowl more.

Say “extra [item],” then pause. Wait until they finish scooping. Once you give them the next task, they will stop the previous one. Wait until they finish and you’re sure to have extracted the maximum.  Ask for half-and-half meat. They always overshoot; you end up with closer to two-thirds and two-thirds. (Combine this trick with the pause for even more.) 

Sour cream on the side. Guac on the side. The containers hold more than the spoon puts on the bowl.

I watched myself do it. Pause after “extra cheese”. Sour cream on the side. My bowl came out about 30% fuller than Partner’s order of the same item. The skills were still there, fifteen years later, like riding a bike.

Here’s the thing I didn’t see in 2008.

Chipotle ran those gift card promotions for three years. If exploiting them had dented the company, they would have stopped after year one. Instead, the promotion kept running. The fraction of people who figured out the loophole was, presumably, priced in. (Or maybe only my Chipotle failed to stop this loophole. As Partner’s mom says, “It’s better to be lucky than smart.” Unfortunately, I’m usually smart.)

I thought I was beating the system. The system was too big to care. 

Today is even funnier. Chipotle is doing two-for-one on 4/20. Their margins on a 30%-overfilled bowl are fine – the whole promotion exists because they must make more than 50% margins on food sales. The tactics I was proud of – pause-after-extra, half-and-half, sidesies – if everyone did them, Chipotle would be ecstatic. My “exploits” meant I ate at Chipotle when I otherwise wouldn’t have. And as long as I do that, they win. 

It’s like the credit card companies with their 5%-cashback offers. They’ve run the math. They’re making profit. Go ahead and max out the offers: That just means you’re playing the game. 

Being Wise to the game sometimes means: 

  1. Noticing that winning the game means you’re playing; and sometimes playing itself is losing.  
  2. Making games that entice others to play, and where any play is a win for you. In casino parlance, this is being The House. In Chipotle, it means having such high margins that a 50%-off deal plus customers bowlmaxxing still leads to a profit. 

And, fine: sometimes a teenager actually does beat the house. I did. Sorry, Chipotle.

Still, that nostalgia brought me back to Chipotle today, over ten years later.  

On long enough timelines, with large enough groups, The House always wins.

Game on. Or maybe: Got played.

Who’s the Muppet Now?

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The goal of the game is to play. You play by entering their world. 

Two exes have independently called me a muppet.
Today I meandered through Central Park with a literal muppet.
She didn’t have fur or someone’s hand up her backside.
But she voiced a muppet in the 70s and became one of the most in-demand voice-over artists in the country.

Partner and I met her at a Burning Man-esque immersive theater event. She and Partner exchanged numbers. We met at noon today. She has white hair and takes stairs slowly and always with a handrail. She mentions her sciatica. Thrice over the next 90 minutes, she slips into a character voice. The first: a high-pitched mocking childish sing-song, context-fit for parodying the president. Second: Italian, to correct my poorer accent. Third: I can’t recall. 

We started at the Museum of Natural History. By the time we entered the Shakespeare garden a block or two away, an hour had passed in our minds. In reality, under ten minutes. 

There’s a time dilation that happens with some people. Where they keep saying “Look at those flowers!” so you do. And when you’re looking at the bright purple of a cherry blossom, you lose yourself. Floating away, endlessly, somewhere into an abyss you didn’t recognize existed, let alone could be accessed at any second… where 90 minutes could have been 3 or 4 hours… you move slower, your internal monologue slows, but you don’t mind. The same place you’ve been a half-dozen times, but this time you enter it in a new way.

It’s not new. You’re new. The collective you is new. 

This experience happens more with artists. With creatives and children too. You spend an hour or a day or the rest of your life studying the veining in one perfect leaf. 

Suddenly, she’s apologizing on the phone. “Lunch Saturday? Wasn’t it Sunday? I’ll be right there.” She’s sure they agreed Sunday, but won’t leave her friend alone at the restaurant.

Then you leave and you return to the honking cars and the car exhaust fumes and the hot dog vendors and the rest of the dragnet made out of always-fraying sinew that yanks us all forward. 

You asked how she does the voices. She said, “They just come to me. They always have.” Your father has said you do voices well — but each time he says it, you’ve thought, “I know people far better.” Having gone beat-for-beat with a real character, you know this to be true.

So you return home, where you wonder about what you have to Give. What naturally comes to you the way voices do to her? Then you shake your head because mulling and musing and obsessing and ruminating never got anyone anywhere. So you smile, because you finally met a real-life muppet. 

I’ve been a muppet to others. This is a muppet to me.

Wise to the Game

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A relaunch.

I’m most alive when I’m playing games.

A few months ago, my sister asked me about an unspoken rule in her business culture – an implicit game. I told her about games where explicit acknowledgment of the rule breaks the rule, and pointing that out is also against the rule. She thanked me and said I should write about the philosophy of games.

I’ve been thinking about that ever since.

Near the end of my senior year of college, I ushered my father into a room above the library and drew three circles on a whiteboard: writing, philosophy, and befriending eccentric people. In the middle I wrote the question that would pick my profession: “in what areas am I in the top 5% of my classmates?” 

The answer that fell out: befriend eccentric people, then write their philosophy.

Not wanting to be a starving writer, I asked one follow-up: who in that circle has money? Growing up in Silicon Valley, the answer was tech founders. I spent the next six years building that business and rose to the top of the technology ghostwriting industry. It was fun while I was growing. It’s not fun anymore. The game is too easy. 

So today I ran the exercise again, with the ikigai framework:

  • What do I love? Games. Learning new things. Befriending eccentric people.
  • What am I paid for? Writing.
  • What does the world need? Play. Whimsy. Fun.
  • What am I good at? Making complex things clear.

The answer that fell out is games, which makes sense: games are a bounded, examinable instance of the thing the world needs more of. If the world needs more play, games are where play can be examined. I learned this at clown school: the first course isn’t about humor or fun or jokes; it’s about games. 

The three pillars of this publication, going forward:

  1. Games.
  2. Eccentric people.
  3. Practical philosophy.

Writing is the medium. Speaking, eventually.

The new name is Wise to the Game. (My last name is Wise. It’s a pun. A double-pun? No: a triple-pun. Try to keep up.) 

More tomorrow.

The Sum

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The goal of the game is to keep the sum. You keep the sum by noticing who’s low. 

Partner and I play a game: we try to keep our sum competence level the same.

On a normal day, she’s the one who tells strangers their dog isn’t actually a schnauzer — it’s just cut like one. She’s the one who’d google the laws on dog-deterrents in the tree box, to get the annoying ones removed.

Today we met with a doctor, and afterwards she wanted to curl up in a ball. So she went to our cave of a bedroom, where she either napped or fiddled on her phone. And today I was the one who googled the dog-deterrent laws. I didn’t spot the schnauzer — I didn’t know to look. But the gym got visited, and we got fed. The sum held.

It goes the other direction too. Yesterday I noped out of what I usually handle — navigating, picking the food place — and she took us to Whole Foods where we bought my favorite oranges.

I don’t think this is an accident (at least on my side). When she’s doing well, we’d both rather I spend my attention elsewhere. When she’s doing worse, it’s worth the effort. 

One question this raises: if one of us is very competent, is it worthwhile for the other to be negative? 

I assume no, but let’s investigate. 

What’s the benefit to un-competence? Not merely the lack, but the negative. 

One piece is fun. Competence is goal-oriented. Un-competence is expansive, innovative, novel. Competence lifts the weight and puts it back down, thereby strengthening the muscle. Un-competence learns there is such a thing as standing on one’s head. 

Sometimes standing on one’s head raises new understanding of human biology. Sometimes un-competence creates a new joke. 

I wonder if other people play a similar game in their relationships. Or if it’s just me — if I’d do this with anyone.

It doesn’t strike me as a bad approach. If anything, it’s quite elegant. 

Game on.

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

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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)

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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.

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

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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….

Everyone Starts a Stranger (Apr 11 2026)

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In which, new friends.

“And thanks for inviting two strangers into your house,” the six-foot-six south Indian computer scientist/theater double-major said just before leaving. 

Later, Partner and I laughed at this comment. We don’t even think of such an invitation as odd. We didn’t invite strangers into our house. We invited new friends. 

We talk to strangers. It’s a chosen relationship (and future family) policy. We met this pair at a NYC alumni event for my high school on Thursday. The conversation flowed smoothly; they seemed like fun, smart, and pleasant chaps. We exchanged contact information. I input mine with a funny contact photo of myself. Later, he texted me a picture of himself mimicking that photo. 

Today we learned they don’t even know each other very well: they met a few weeks ago and became rock climbing buddies. (How droll: one brought the other to a highschool reunion without even knowing him well!)

We had them over today for lentils and conversation. The night ended with a game of Mario Party. 

The value of talking to strangers cannot be overstated. The humor – to me – of two people meeting two other people and it being *surprising* when one pair invites the other pair over for dinner… prompts a little sadness in me. While I am undoubtedly top few percentile in frequency of meeting strangers and inviting them to events, at least one of those two found the concept foreign. Pleasant, but foreign. Two college grads from last year, have they not socialized in this way? Had I, when I was in college, gone to others’ house for dinner? 

Yes. Or some facsimile. 

I remember my now-fiancée and her then-roommate (and bestfriend) inviting me to their off-campus house for drinks. She texted to ask what my drink of choice was. I replied, “whiskey sour”. I will always remember her stirring the simple syrup on the stove, explaining how it was becoming a super-saturated solution. 

Most of all, I remember the kindness of her acquiring the items to make my favorite drink. That, and her laugh. What a blessing that I may have that laugh with me forever. 

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

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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. 😌

On Occupation (April 8 2026)

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Not the military type. 

My recent activity has all but concluded.
Six months of hiring.
An important job.
Hiring, negotiating, structuring, whittling.
And now I have a contractor. 

My plans are submitted.
So, may god’s love be with me! 

Now,
I want a job. 

Sure, I spent 6 months working on key life projects (purchasing an apartment; hiring contractors).
Now I’d like to return to work.
It’s a weird experience for someone who
has only ever run his own business.
(Sure, there was a year-long stint as chief of staff to the ceo of a tech company.) 

I’ve only ever gotten jobs from referrals.
And most of those are self-directed. 

Now,
I seek something stable.
I’d love a remote job with clear deliverables.
What are my skills? 

  1. Writing. Blog posts, website copy. I’ve done lots of reliable work here. (Earlier this decade, I was the most sought-after ghostwriter in the Bay Area tech scene!)  
  2. Fundraising pitches. I’ve raised $1.5M for one startup and $800k for another, both by rewriting and workshopping their pitches (and the former by actually doing the pitching). 
  3. CEO whispering. I navigated one company through a cofounder split-up, served as chief of staff to the ceo of another, and helped a third rewrite her sales contracts and sales calls, tripling her ARR in 2 months. 

What else? 

  • I do good work, turn it in on time, and my coworkers generally like me. That’s worth something too. 

I feel this odd sense of loss. Of distance from myself. As though I wish for this situation – this need for occupation – to be solved. But also, a reticence to exist in a box where it is solved. 

I’d enjoy this occupation because the rest of my activity is more lax.
The books I’ve written; the apartment I’m remodeling; the weird medical and legal systems I’m working through: all would be improved if my head were also often somewhere else. 

And also, it would be nice if that somewhere else also gave me money.