1. Get paid $250,000 by a prestigious fellowship to drop out and build (you’re not exactly sure what yet)

2. Do Y Combinator with a few classmates—no need to drop out, thanks to their new “Early Decision” track, borrowing the language of college and aligning itself with it

3. Sign a return offer with Anthropic, OpenAI, or the frontier lab of your choice for $300k+ for your first year post-grad

4. Go to class, learn, finish your degree with grace and uncertainty of what follows

Twenty years ago, this would have been a trick question—only Option 4 existed in earnest, and being at an institution where these options are available today held the equivalent street cred of the other three. Today all four options are theoretically attainable, funded by real and moving dollars, and actively competing for the same twenty-one-year-old’s mindshare. The Atlantic recently published “The Stanford Freshmen Who Want to Rule the World,” a piece about venture capitalists “grooming” (article’s verb choice, not mine) teenagers with pre-idea funding and yacht parties. The Atlantic excerpt is drawn from a forthcoming book by a Stanford senior, already optioned for a film. [Thank you, Blake W. for the share!]

I read the piece from the bougier side of campus. I am no freshman being courted, but as I sit at Coupa’s GSB outpost writing this, I am vicariously experiencing a familiar venture capitalist cycle through my classmates in thirty-minute intervals at a nearby table. Their loyal associate (me, in a past life) furiously scribbles notes about each classmate’s what, how, why, and most importantly, where…did you go to school? In a not-so-distant parallel life, I am the founder being interviewed, part of a broader, engineered, frictionless pipeline, designed to incentivize one thing: starting.

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Starting has never been faster (thank you, AI), cheaper (thank you, VCs), or more culturally validated (thank you, Silicon Valley wealth spiral), and yet starting is still not the same thing as committing.

There are amazing ripple effects of the abundance of capital on Stanford’s campus—I’ve compared being here to Renaissance Florence, where the Medici commissions made it possible for artists to take risks that still define the celestial limits of human potential. (I chastise myself for the apologia in my comparison and wonder: what if cultural production were still the measure of a society’s competitiveness?)

Sarah Guo visited my class last week and described the ecosystem she’s helping to build: the Thiel Fellowship, Y Combinator, and her own fund’s Embed program create prestigious spaces where even failure has a buyer. This off-ramp allows people to take risks in a more structured, ironically fail-safe way. (Silicon Valley loves to credit its embrace of failure as the reason behind its innovations and successes; but if failure has an underwritten back-up plan, is it even failure anymore?) She shared that one of her favorite things about startups is that they force people to do myriad activities that have little to do with their backgrounds, and that, in successful cases, people grow enormously as leaders as a result.

Yet even the Medicis demanded commitment in exchange for patronage. Brunelleschi got money to build a specific dome—not to explore whether or not he was a “dome guy.”

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I had coffee last week with a Stanford undergrad who’s deciding between a spicy return offer at Meta and starting a company with a classmate. That these two options exist in the same breath surprises me and provides further motivation to write this piece. The options comprise vastly different risk profiles that require radically different lifestyles—different relationships to identity, uncertainty, prestige, purpose, all things no twenty-one-year-old should be expected to have already figured out but nevertheless should matter in considering where to begin one’s adult life. Similarly, a friend in the business school is debating between applying to incubators with her startup idea and following her compatriots to Anthropic. To me, you have to be a fundamentally different person to choose each path, and still no one is safe—that the bubble makes one look as easy—or as interchangeable—as the other is, I think, the point.

So what is the question we are not asking ourselves?

I think…it’s what we actually care about.

A startup is much more about the commitment, the keeping it up, than the starting. As an investor, my favorite question to ask founders was: what about this problem keeps you going after it stops being fun? Or: why do you believe you’ll want to work on this for the next 10+ years?

As a person, I am trying to learn how to answer these questions myself, about my own life. I love to start things. Céline and I started Artificial Whimsy because the way people wrote about tech felt like death by a thousand LinkedIn cuts. I started this piece six times with six different theses—one of them, God help me, about the privileged paralysis of limitless optionality. My fear is that my mirror reflects someone who moves on after the quick dopamine hits of starting down a path and receiving validation, but when the going gets tough, who will not be there in the end. I worry, constantly, that I have become so delusionally good at selling my potential that I will forget how to choose to be evaluated on my own results.

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I know it’s not just me. The bubble selects for people who are dazzlingly charming in thirty-minute intervals. Venture capital is a market that prices potential—a check a token of conviction that a person will convert potential energy into kinetic. But in 2005, the original information asymmetry of venture was knowing a person was sacrificing something irreplaceable, a safety net credential, by dropping out to take your fellowship money and start a company. The signal lay in the magnitude of the risk undertaken. An investor did not need a back-channel reference to know the founder was serious and committed, because the founder had torched plan B, had burned the boats. Today, dropping out is not so risky as predictable, another prestigious path to choose, next to your offer in [Big Tech, Big Three, Big Whatever].

Do not forget that the lowest-risk asset carries the lowest return.

We also know the lowest-commitment decision carries the lowest satisfaction. A study from Harvard and MIT asked photography students to choose prints to keep—one group could swap their choice, while the other was stuck. Both groups initially preferred the option of being able to swap, but the group that could swap ended up liking their prints less. The researchers found that people prefer to make changeable decisions rather than unchangeable ones because they do not realize they may be more satisfied with the latter. Read that again.

The implications stretch further than startup funding or career decisions—they exist in a context where career decisions are proxies for our identities. Your job is both the answer to “what are you up to post-grad” and, whether you like it or not, the way many will define your worth.

We enjoy being many things at once. There is a tradition at the GSB called TALK, in which two students share their life stories every Wednesday with the rest of the class. If I had a penny for every TALK that mentioned duality, or existing across the many multitudes of self, I’d be fucking rich in pennies. I like the version of me that people meet and can’t place in a box—student, sister, lover of words and tiramisu, occasional beat-boxer, extremely serious sobber and psychotically happy Cheshire cat. There is real joy in plurality, and the audience’s eyes widen with awe, sometimes judgment, upon realizing that I contain more than they expected.

But I am starting to wonder whether the pleasure is in being many things or in never having to be just one. Plurality, like optionality, like the option to switch photo prints, like the $250,000 dropout fellowship…feels like freedom. Kierkegaard called anxiety “the dizziness of freedom,” the vertigo of standing above the abyss of possibility, knowing that the moment you choose, you murder every other version of yourself. Plath likened wanting to preserve optionality to never wanting to pluck figs off a tree and losing them all in the ineluctable passing of time:

One fig was a husband and a happy home and children, and another fig was a famous poet and another fig was a brilliant professor, and another fig was Ee Gee, the amazing editor, and another fig was Europe and Africa and South America….I saw myself sitting in the crotch of this fig tree, starving to death, just because I couldn’t make up my mind which of the figs I would choose. I wanted each and every one of them, but choosing one meant losing all the rest, and, as I sat there, unable to decide, the figs began to wrinkle and go black, and, one by one, they plopped to the ground at my feet.

Choose or don’t. Either way, certain options will inevitably recede.

This is why, in spite of the cost of risk having never been cheaper, the experience of taking risk has never felt worse.

What I keep forgetting (and maybe you do too) is that every time I’ve actually closed a door and forced a step forward, life got bigger, not smaller. I left trading and found a profession that paid me to meet inspiring people. I came to business school with no plan and built a community I care about more than anything on my résumé. Letting the other versions of ourselves go, in front of everyone, full fanfare, without knowing the one you choose will be enough—that is the open door I choose, and that open door tastes like freedom, the most expensive thing we can have.

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weekly whimsy

• What we’re watching:

  • Both: BEEF Season 2

• What we’re using:

  • Danielle: the duality of Wispr Flow on solo Dish walks, and Physical Phones and

  • Celine: the Oxford English Dictionary. I am a purist about this and will not use any other dictionary for all of my dictionary needs (and I have many). Have I been gifted a subscription before for Christmas? Yes, yes I have.

• What we’re wearing:

  • Celine: not Reformation—private equity has ruined it, I swear; please send recommendations my way because my whole wardrobe is propped up on this stock, and the bubble has burst!

  • Danielle: another plug for my Thousand Fell sustainable sneaks (size up!)

Written by: Danielle Zhang
Edited by: Céline Vendler

It arrived by way of someone I knew in college—a place where, for context, I could be found loafing about in a rickety old wooden clapboard building that belonged to the literary magazine, discussing poetry while my even-artier friends chainsmoked around me, joking, occasionally, that one day a cigarette butt would bring the end to a 150-year-old tradition that counts the likes of T. S. Eliot and E. E. Cummings in its membership, and leaving, invariably, my hair perfumed with the stale, acrid, stubborn fumes.

She had posted a screenshot of one of the questions, asking readers to choose the passage they like best, between the opening of Elizabeth Bishop’s “The Fish,” one of the great 20th-century poet’s more famous poems, and some bad poem, if you can call it that, by Anthropic’s Claude, Opus 4.5. She had, of course, answered correctly (it should be clear that by this I mean she chose Bishop), noting in the caption how obvious it was; besides the masterful construction and stunning emotional arc of the poem, Elizabeth Bishop is one of the most anthologized poets of her generation, and if you know her, you probably know “The Fish.”

I chuckled smugly at the absurdity of the exercise, paying hardly any attention to the AI-generated “poem” beside the masterpiece. Who needed to? “The Fish” is instantly recognizable.

I hadn’t noticed, in the fine print revealed underneath the passages, that only 52% of readers had chosen one of my favorite poems of all time as their champion in the human-vs-AI writing face-off. This, obviously, depressed me.

I have asserted before, in this newsletter, many times, that human creativity will prevail over generative AI. Our very first post, in fact, is titled “Nevertheless, Creativity Survives,” a nod to Marianne Moore’s poem “Nevertheless,” about the resilience of life, the victory of survival. I am an English major, the daughter of an English major, the granddaughter of an English professor, and it goes on. I quote poems as some do scripture. If I believe in one thing, it is human expression:

• From our first post: “I suspect that those who try to erase and replace [human art] will find public disillusionment at the end of the road as people discover that AI is but another ‘mechanical trick’ [a borrowing from One Hundred Years of Solitude], no substitute for human expression. I also suspect that they will fail—that human art will persist, will wriggle its way through the concrete.”

• And from The Whimsical Guide to Writing Well: “But our bots do not write, or speak, or mean. They mimic symbolic patterns, convert those patterns into phonemic ones, and produce something that ‘means’ something only in the sense that it has semantic meaning….To convey meaning is at once a practical act and a metaphysical one….No matter how advanced the models become, they will always remain just that: models. Representations. Replicas. Forgeries. Frauds.”

Here, however, was hard, crowdsourced data from the newspaper with the largest digital readership in the country, suggesting that readers could not distinguish between human writing and AI writing—and could even prefer the latter.

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Indeed, Bishop’s was no exceptional case; other human writers faced a similar fate. In the genre of literary fiction, the results were split 50/50 between the human passage and the AI passage. In fantasy, human writing won by a razor-thin margin of two points. In science writing, readers overwhelmingly preferred the LLM’s writing, with only 35% of readers choosing the human-written text. Historical fiction fared the best, with the human excerpt winning 56% of votes. And then there was the narrow victory of Elizabeth Bishop, a disconcerting 52 to 48. While, on the whole, readers preferred human writing over AI writing, the odds were little better than a coin toss.

Now, it’s not as though a New York Times quiz is exactly the gold standard in research, so it’s important not to credit it unduly. Unfortunately, the results broadly mirror what Jeff Hancock, Harry and Norman Chandler Professor of Communication at Stanford, and his colleagues found in their study, “Human heuristics for AI-generated language are flawed,” where they had subjects distinguish between human and AI-generated self-presentations across different interpersonal contexts: professional, hospitality, and dating. The subjects’ accuracy rate was similar to that of the New York Times readers: 50-52%.

Why humans are unreliable AI detectors, they found, stems from our default tendency to trust others and our use of heuristics in determining whether or not to trust others, such as the use of first-person pronouns, informal language like contractions, and the topic of family. Basically, if it walks like a human and talks like a human, who’s to say, with any reasonable confidence, that it isn’t a human?

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AI writing is optimized to blend in: to construct a sentence, as probabilistic machines trained on vast swaths of human communication over time, LLMs generate a string of words that are statistically likely to precede and follow one another. There’s something inevitable about AI-generated sentences, like water circling down a drain: the words go that way, converge to that point, read simply and smoothly if they don’t leap off the page, appearing there, on your screen, for your easy consumption; and we are not surprised, since it was the most likely thing to happen.

Nestled in the center of the bell curve, its deceptiveness hides in plain sight.

Were my paragraphs extolling human creation more prayers than claims, then? I reluctantly remember that my Instagram bio reads, quoting Charlotte Brontë’s Jane Eyre, “& what I believed in I wished to behold.” Have I just been speaking into existence what I wish to behold, clapping my hands and shouting “I do believe in human writing! I do! I do!” so that fucking Tinker Bell doesn’t die? Is the belief in the triumph of human writing over AI slop just another form of magical thinking? Another humanistic, faith-based tradition that’s about to be discredited by advancements in science and technology?

I wouldn’t have it. I do believe in human writing. I do, I do.

I decided to take the quiz.

(You should too, here, and we’ll compare notes in our next piece.)

TO BE CONTINUED…

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weekly whimsy

This week, we’re back from our very whimsical business-school break. Céline grinded away on her top-secret job search (more to come to light on that when more has come to fruition on that) and still found time to sunset longboard in San Onofre because: touch grass (or ocean, or whatever your preferred ecological feature). Danielle drove up and down the California coast (edit: DJ’ed from the co-pilot seat) and had her first experience “roughing” it in an RV. She devoured arugula the size of her face in Mendocino and journaled by the moonlight in Bodega Bay.

• what we’re watching/reading:

  • Céline: Paired watch/read – Train Dreams and “Amends” by Adrienne Rich

  • Danielle: Invincible, a superhero story with all the gore and moral wreckage, little of the glory

• what we’re listening to:

  • Danielle: Syd Taylor’s After the Fact

  • Céline: If you want a good, juicy cry, Adele’s 30, particularly the opening and last two songs

• what we’re wearing:

  • Céline: Just got new Rainbows after wearing my last pair to smithereens, a staple in my shoe rack for the last 15+ years

  • Danielle: my silver Thousand Fell Driver sneakers from Kendall and Chloe Songer! (size up!)

  • Both: Whimsy merch coming soon… 👀 👀

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Written by: Céline Vendler
Edited by: Danielle Zhang

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Last week I had an admittedly wild conversation with my partner, who, for the record, is more AI-pilled than I am. I had a dream of connecting all of my favorite apps—GCal, Granola, Gmail, Notes—into one priority list and dashboard to rule them all. He looked at me as if I had built an elaborate Rube Goldberg contraption with the sole purpose of serving myself a single peanut.

“What’s the problem?” he asked.

“I can’t remember all the things I need to do.”

“So write them down.”

“That’s too much work.”

“Isn’t that,” he asked, “the one kind of work you shouldn’t leave up to AI??”

I built the tool anyway. This is, I’ve come to understand, a very GSB thing to do.

At risk of projecting, the specific texture of our current moment at Stanford is dread wearing enthusiasm’s clothes. There is the usual—relatively justified, absolutely out of touch—job anxiety that perennially plagues the class of people who have worked their asses off all their lives to score above the 97th percentile. There is also the usual “new thing” enthusiasm, now channelled into vibe-coding workshops with overflow rooms, AI speakers every week, and experiential classes that credentialize your harassment of 100 strangers to “build” your next big stealth idea. But this enthusiasm only thinly masks deeper anxieties: of being left behind, of obsolescence, of destitution.

Will the category of job you trained for not exist by the time you graduate, leaving you stuck in what the internet has taken to calling “the permanent underclass”—capitalism’s version of hell? Be wary of excess enthusiasm: does it come from love, or might it come from fear—the ingratiating behavior of a people terrified of their incoming ruler?

At dinner last week, the question (which, at this point, surfaces every day) came up again: “Do you know what you’re doing after school?” One of my closest friends—charming and brilliant, who operated at three startups in four years before she came here—looked up and said, somewhat to herself, “What job can I even do?”

This is a story about people who have felt wanted and needed, by society if not by someone, for possibly their whole lives, now at one of the most well-resourced institutions in the world, where the opportunity cost of not starting a company is higher than that of starting one.

This is a story about people who were born or fought their way into the elite and want, very much, to stay there.

The implicit contract was that judgment alone—hard skills aside—has been, and will continue to be, the ticket in. Is that contract reaching the end of its enforceability?

Two weeks ago, a piece of financial fiction—a Substack memo written from June 2028, explicitly labeled a scenario, not a prediction—sparked a software sell-off, manifesting a speculative future just by speaking it into existence. My friend texted the group chat: “rn I’m in an AI doom spiral tho.” The reassurance came immediately— “you’re better equipped than 99% of the world!!”—and dissolved just as fast, not knowing which side of the 99% bifurcation we will actually land on. The New Yorker recently named this fear: that AI automation will upend the labor market and produce a new permanent underclass, a rebooted Marxist lumpenproletariat with nowhere to climb and no recourse.

What is dissonant about this particular moment, at this particular school, is that the people who have historically seen themselves above the bifurcation are not quite behaving like they believe it. In the same breath, a private equity guy will sign his return offer and wonder if the vertical SaaS companies his firm has been double, tripling down on for the last decade are going to get annihilated, wiped out by AI like the rest of us. He’ll sign because, up until now, everything has been okay: people said knowledge work would be automated, and here we still are. The dread is as present as the counterevidence, which makes it so hard to act on.

The career advice that’s been dispensed at conferences this year has converged on a single instruction. Sanjay Nadhavajhala from AI finance company F2 said, “I think analysts are going to operate more like VPs, and VPs are going to operate more like MDs. I think everyone levels up.”

“So what happens to the MDs?” the moderator asked.

“That’s the big question.”

Another panelist said to find the fastest-moving water with the highest talent density (what does that even mean in plain English? Is the talent salmon?). A nonetheless reasonable bet in uncertain waters. These are not bad instructions, but they are execution instructions. We are told to “build something” to prepare for non-technical role interviews, we nod, and then we go home and open Claude Code to “allow” “allow” “allow” our way into building something we’re not sure we need. Ask me on a given day and I’ll tell you that, like half our class, I, too, am recruiting to plumb the toilets at Anthropic, at least angling for physical adjacency. (Their own labor market research suggests this instinct is not entirely irrational.)

I don’t know if living inside the AI bubble makes us better at knowing when not to use it or just more comfortable on crutches. The MIT researchers studying cognitive debt would say the latter, that outsourcing erodes capacity for discernment, the same way Botox renders a muscle inert. My foray into LinkedIn experimentation would say the former—posts I write without AI perform better than the ones I write with it, likely because no prompt I’ve written has mastered the inscrutable design of my intrusive thoughts.

I also don’t know what the end state of continuous bifurcation is. The consulting layoffs will come, in my opinion—for the research, the slide work, the framework production—because AI can approximate the output cheaply enough that the premium disappears. And then the person who walks into the room, or the implementation team, that’s valuable now—or is it? Because that layer gets thinner too, as AI gets better at cleaning messy GTM data and pattern-matching across implementations. Enterprise salespeople exist because trust and negotiation are structural necessities, but for how long, and at what scale?

All this to ask: what do I actually have that increases in value over time?

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“Build something” isn’t a terrible place to start, so long as it’s not conflated with “build anything.” Our classmate, Celeste Bean, who runs AI workshops at GSB, has a framework for determining whether or not a product is worth building:

• Will you need this output next week?

• Do other people use it with their own data?

• Should it run automatically?

• Does it need to connect to other apps?

• Do you have a specific picture of how it should work?

The more yes answers, the more the build is justified. The framework forces the questions: what’s the actual problem we’re trying to solve, and does our solution replicate or innovate on previous ones? The framework can’t tell you that. Only you can tell you that. Celeste is co-founding an AI consultancy to help execs figure out what AI means for them. The business model is, essentially, being the person who asks these questions.

There’s also a prior question. Before you open Claude Code, before you plumb, ask yourself:

When do I reach flow state?

What have I avoided, that I love, because I think it’s “silly” or “beneath me”?

These are questions worth sitting with before you build anything, 1) because AI will lower the barrier to whatever you build next, and 2) what makes you you is what AI can never replicate. But only you can decide if it’s worth building to you. We wrote about learning how to listen to that answer.

And then go swimming once in a while. No, not in high-density, fast-moving waters. Take one day away, sans optimization, and honor the opinions of your nervous system. My brain needs that kind of inference time, and I suspect yours does, too.

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New section alert—back by popular demand!!

you asked, we listened. bringing back our favorite parts of our original format, with a twist:

• what we’re reading/watching:

  • Danielle: Rudyard Kipling’s “If” and revisiting oldie-but-goodie “How to Do What You Love” by Paul Graham

  • Céline: Speaking of permanent under/overclasses…Reading Aldous Huxley’s Brave New World in conjunction with watching Pluribus (yes, I know I’m late to the party, on both counts) is kind of a trip!

• what we’re listening to:

  • Céline: Been listening to a lot of Goldie Boutilier lately. And for an IRL experience, she’s playing in SF on March 29!

  • Danielle: Cobra Man’s lo-fi punk sound and this Chinese internet folk/classical crossover 芒种

• what we’re munching on:

  • Danielle: The new Zaytinya in Palo Alto (go via inKind for $$ off) and a crispy sweet potato omelette that has changed my mornings

  • Céline: And speaking of my techno-overlords, I caved to the algo and bought Ka’Chava shakes. I’m typically extremely skeptical of “Instagram brands,” but it has good ingredients and tastes yummy. And lord knows my gut/brain axis needs all the help it can get. Recommend the chocolate and strawberry, not so much the matcha.

This week’s poll

🎁 Gift box winner: Kaci!

• Kaci found us through LinkedIn (proof that occasionally LinkedIn delivers!) and is currently building Cimu, an at-home tailoring service for New Yorkers who don’t have time to deal with a tailor. Go check it out at shopcimu.com.

pls write back—we reply!

Love,
Céline and Danielle ♡

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Written by: Danielle Zhang
Edited by: Céline Vendler

We started Artificial Whimsy because we were tired of tech content that made us…ahem…hate ourselves.

We figured a few friends out there in the world might feel the same way. Apparently, over 1,000 of you do, which is both comforting and perhaps a sign that the tech industrial complex is an unavoidable part of our lives.

We write from the heart, but we want to write for you too—and we can’t do that while guessing, but not knowing, who you are.

Take the survey

We made a ~4 minute survey that we promise will be far more fun than some employee survey your Slack bot keeps pinging you about. And as a small token of whimsy for your time, we’re doing a lottery for a curated book bundle & AMC gift card. We’ll announce the winner in our next issue.

Thank you, genuinely, for your readership. We love writing, and the fact that ~60% of you open our emails is not lost on us.

Love,

Danielle & Céline
Artificial Whimsy

Over Instagram, one of my long-distance best friends sent me a meme “about how difficult everything is rn.” It took as its premise the adage “Life is full of ups and downs” and depicted a boy, shocked and dismayed, protesting, “You guys are having ups?”

“ME,” my friend messaged.

“LOL, been there dude,” I replied.

No more was divulged; no more was asked. I envision our hands vanishing into the water.

Let us make you smarter

As much as my best friend and I know about each other, we know little more from this exchange than the TLDR: we are both getting beat up in our (late, don’t talk to us about it) twenties at a time when social media has bent the vernacular towards viral meme-speak.

Memes can be a consolation, their millions of likes a palliative reminder that someone has felt this way before. At the same time, a generic image overlaid with a slapstick joke is hardly a just rendering of our intricate emotional landscapes—the Sparknotes to our living novels. Meme-speak, I’m convinced, offers but a glint of intimacy, like a sun that doesn’t warm.

Don’t get me wrong: I love a good meme. I send memes to my favorite people daily, and my day brightens when my favorite people send me memes in return. The human act of sending memes has been analogized to the penguin practice of “pebbling,” by which certain types of penguins present each other with pebbles in an act not only of courtship, but also of homebuilding. When I send you a meme, I am presenting you with a small token of affection, one building block for our friendship fort.

And the mechanisms by which memes forge bonds are rooted in human-–not just penguin—psychology. The exchange of memes or meme-speak can be a kind of “collective effervescence,” a term coined by the French sociologist Émile Durkheim describing how shared rituals and synchronized emotional experiences foster feelings of belonging and oneness. Through a combination of sardonic humor and collective effervescence, memes help us to cope and to connect.

Memes are silly, yes, but they’re also true. My recent trail of memes depicts a satirical, simplified, yet reasonably accurate portrait of an elder Gen-Z woman, in business school despite being an English major, who craves fulfillment in her career and—in the wake of daylight savings—time in bed:

Yet still I, Céline Vendler, in all of my depths and idiosyncrasies, in all of my inflamed heartaches and invisible pains, in all of my unique branches of self-doubt and self-worth am not captured in the above tetraptych of memes.

Hundreds of thousands of people have liked—in other words resonated with—these images. Represented by these images alone, I could be one of a million people—rather than one in a million people. Memes are inherently copies, designed to be infinitely copiable by others; the word “meme” comes from the Greek “mimēma” (like “mime” and “mimetic”), meaning “that which is imitated.” Individuals, and their particular stories, are the originals.

Behind each of these images is a story of my own. Take the second image—a variation on the popular meme-format of “Born to…Forced to…”—for example. It’s immediately relatable to women in corporate settings who like to read, which is to say: a lot of women. What I feel—but don’t narrate—when I send the meme, however, is much more specific. I am one of two English majors in my business school class; rounded to the nearest whole percentage, we comprise 0% of the class. Every day on campus I feel like a scuba diver, navigating thick waters that I can’t breathe, my oxygen tank heavy, awkward, and drained by the time I get home. In my accounting class last year, I wanted to understand why we amortize intangible assets but depreciate tangible ones—not on a conceptual level, but rather on an etymological one (to “amortize” literally means to “put to death,” but to “depreciate” means only to “make less precious”—is it because intangible assets can dissipate into the ether whereas tangible assets remain in this physical world, always with some salvage value? How is this not interesting?).

My accounting professor had no answer—said that’s just the way it is.

I quote poetry in the classroom far more than one would think possible at a business school (and more, perhaps, than my classmates would prefer). None of the conventional careers in finance, big tech, and consulting appeals to me. Even one of the career advisors agreed with me that I may not be in the right place. Behind the jocular meme, then, is the acute story of my out-of-placeness, of my loneliness and of my grief, and of my relentless pursuit of air that I can finally soak up and up and up. Life is too hard to live incongruently. One must do what one was born to do; one must, so the Hopkins poem I love so much goes, “Ac[t] in God’s eye what in God’s eye he is.”

The story is not unique in theme—it can be boiled down to a meme—but don’t you know me better now that I’ve told it, in my own words?

Memes play an important role in the American zeitgeist, but when we turn to memes as our default mode of communication, we lose the rich, textural detail that makes self-disclosure so powerful. In social psychology, social penetration theory posits that intimacy is created, in part, through reciprocal, progressive self-disclosure—the operative term here being progressive. If we remain forever in the meme-plane, and never progress further into the narrative plane, we will constrain our closeness. Indeed, not all self-disclosure is created equal: what is uttered, how it is uttered, and how much is uttered all contribute to the impact of any given disclosure.

Psychological distance theory offers language as a measure of distance: we use abstract language when talking about remote ideas, and we use concrete language when talking about proximate phenomena. And yet we use generalized memes to express some of our most intimate feelings—perhaps to protect ourselves with this very distance. “It be like that sometimes” is less evocative than “I am having a difficult week and could use your support.” Similarly, “That feeling when you…” is less revealing than naming your actual feeling. Memes, much like clichés, are inherently psychologically distancing: they typically speak in the indefinite “you” (or at best the interchangeable “me”) rather than the definite “I,” and they present abstractions of the human experience rather than singular narratives.

These theories are academic concepts, but they echo what intuition might tell you. You might have heard of or even tried the New York Times’s “The 36 Questions That Lead to Love,” founded in research conducted by the psychologist Arthur Aron (et al.) and practiced in organizational behavior classrooms like ours. In keeping with social penetration theory, the questions start out benign (“What would constitute a ‘perfect’ day for you?”) and progressively become more personal (“Of all the people in your family, whose death would you find most disturbing? Why?”). And to reduce psychological distance, every question requires you either to reveal a specific part of yourself or to engage with a specific part of your partner—detail is ineluctable.

Now imagine if you went through the exercise, but instead of exchanging stories, you and your partner exchanged only memes. I can’t imagine that the experiment would hold. “The 36 Questions That Lead to Brain Rot,” maybe.

Of course, the young generations are not the first to communicate in these removed ways. The Gen-Z’s “It be like that sometimes” is the Baby Boomer’s “Life’s tough, and then you die”—one of those vaguely tautological phrases like “it is what it is” that fails to rise to a meaningful response.

The difference, however, is that the Baby Boomer’s platitude comes in response to someone’s story, whereas the Gen-Z’s meme comes in response to…another meme. Maybe we throw in a “LOL, been there dude.” We empathize obliquely—along with the hundred thousand other people who received the same meme in their DMs—but what’s true exactly for our friend we don’t know unless we ask.

In her book Technology and the Virtues: A Philosophical Guide to a Future Worth Wanting, the philosopher Shannon Vallor distinguishes between sympathy (abstract) and empathy (concrete). She writes: “Even a stranger with whom I empathize will appear in my experience not as an abstraction, but as a concrete, nonfungible individual with specific emotional experiences.” For all of its value, then—as comic relief, as a token of friendship, as a reminder that we are not alone—meme-speak cannot be a conduit for true empathy, and resorting to it may circumscribe, rather than expand, our worlds. As Ludwig Wittgenstein, an older philosopher, asserted: “The limits of my language mean the limits of my world.”

So the next time someone asks you how you are, instead of throwing up your hands (the text version would be “¯\_(ツ)_/¯”) and deputizing a meme in your feelings’ stead, dare to allow yourself to be known—in your own words. Send the novella-length text—the kind that takes multiple scrolls before you get to the end. Leave the podcast-length voice-note—I want it to be so garrulous and multitudinous that I have to take notes. Or, as I have attempted to do here, write the long-form piece, and hope that, despite infinite distraction, or perhaps to spite it, your reader follows you to the end. As Robert Lowell wrote, “Yet why not say what happened?” I already know that it be like that sometimes. I want to know how it be for you.

These are fragments of my own memory watching Anne Kauffman’s revival of Marjorie Prime, a play about memory, grief, and technology. The sci-fi drama (written surprisingly more than a decade ago) imagines a now-familiar future where the bereaved live alongside “Primes,” hyperrealistic recreations of their dead loved ones, programmed to learn and speak as though they were still alive.

Marjorie is at the center. She is a lovably loud, sharply stubborn woman slipping into dementia, attended to by the Prime of her late husband, Walter. She prefers to remember Walter as endlessly patient and eternally youthful, and so, Walter’s Prime appears as a 30-something-year-old version of himself who absorbs everything and corrects nothing. As Marjorie’s daughter Tess shoulders the care of a mother who can no longer accumulate new memories, she admits,

“I don’t know why we have to keep each other alive for so long.”

The line doesn’t land cruelly. It is worn, heavy with the incomplete loss of watching your mother succumb to dementia—there in body, but increasingly elusive in mind. It’s a cruel trick. We understand, then, the impulse to remember our loved ones as they were in their prime as opposed to their decline. Ultimately, the Primes are not there to keep the dead alive; they are there to make death gentler for the living. Can grief ever be eluded?

I sat there, listening, pressed against the carpeted wall of the Hayes Theater in New York, while my own grandmother lay in a hospital bed an ocean away.

A spicier plate of Kung Pao Chicken had comically sent her to the hospital four nights earlier, until her symptoms compounded, and, very uncomically, my father booked a flight to China the day after Christmas. There was a rush to understand her situation—the financiers in my family put on their metaphorical stethoscopes, fed their anxieties into search engines, and frantically searched for a version of the story that ended in recovery. My mother sat my sister and me down in the kitchen and explained, three times over, the cascade of complications: the stomach issue, or was it the blood thinner, or how could the doctor not have checked her brain monitor—but don’t worry, she said, she’s in the best hospital in the area (thank god). This is how my family confronts the possibility of loss: we rush to understand, hoping we can outpace the arrival of bad news.

We had laughed about the chicken. My grandmother had texted her friend at the senior home that she would be returning the next day.

She passed away on January 3, 2026.

I didn’t know where in my body to take the grief. I heard the news while on vacation with friends and tucked the ache away, thought I would let it pass through me. I hugged my partner, then went on with my day. I wanted to grieve productively, gracefully even, without burden. But the absence of immediate devastation felt, in its own way, like a kind of betrayal.

When I feel the familiar salt rush to the corners of my eyes, I see my mother sitting across from me, immovable, holding together my father’s world and ours. She carries our sadness, alongside our guilt—I think she knows the “best” version of my grandmother had faded in her final years, replaced by someone crankier, meaner, harder to love, and that she, like the rest of us, had subconsciously chosen distance. I feel the weight of not having tried to know more of my grandmother’s life, of shutting the door, of forgetting to say thank you. The best of her, perhaps also the best of myself, lives most vividly in my childhood memories—when there was no responsibility to do better, to love more deeply.

I find myself wanting to preserve the version of my grandmother that is easiest to carry, her prime. To remember selectively feels instinctual, protective even. Indeed, when my father asked which memorial photo to use at her funeral, my instinct was to choose a young, beautiful image—the one pulled up at family reunions to joke that she had been a catch.

But my father chose a photograph from last year—chose to remember her not in her youth but as she was (it seems) just yesterday. His decision struck me as an act of love that resisted perfection, one that insisted upon carrying the fullness of a person and not the compressed copy more efficient to store.

In the play, Tess reflects on her own life and says, “There’s the half where you live, and the half where you live through other people. And your memory of when you were young.” By the end of the play, three of a four-person show are Primes, sitting neatly at a dinner table and rotating slowly towards the audience.

The scene is at once poignant and perturbing. The Primes are not only evasions of grief, but also vessels for longing. They offer what real life so often withholds: second chances at conversation, courage to ask questions we were too busy or too afraid to ask the first (the only) time around. “What I wouldn’t give for one more languorous, pointless, revelatory stroll through a church with you, Nai-Nai,” to quote an earlier piece.

And yet it’s not real life. As pauses stretch, and intonations inflect improperly, you, the audience member, feel viscerally the ickiness of what you are witnessing. The preservation, possibly without consent, of humans when they were—to you, the preserver—most palatable, is a refusal to allow them the dignity of a proper ending. If freedom is letting people live, then it is also letting them die.

Our current moment in technological history is obsessed with two things, among others: 1) bypassing discomfort and 2) bypassing death. VCs are funding “griefbots” (I’m not even kidding) and chatbots trained on people both alive and dead—sometimes with consent, sometimes not. So-called transhumanists and figures like Bryan Johnson are spending their lives trying to extend them—optimizing, rather than living. In popular culture, echoes of Marjorie Prime abound in shows like Black Mirror and Pantheon, where the cloud preserves people’s brains. To echo Marjorie’s daughter Tess, “I don’t know why we have to keep each other alive for so long.”

In Marjorie Prime, the Primes offer a way to forestall loss. But postponing loss also defers the inward reckoning that needs to follow it. We don’t need a perfect replay of someone’s voice, or an algorithmically likely stream of words they might say in response to our current queries. Our lost loved ones have already given us everything that we need; the least we can do is recognize what we have been given, rather than look outward for answers, shortcuts through our grief.

In the immediate wake of my grandmother’s death, I found myself reaching for the breadcrumbs of wisdom she dropped over the years, searching for the grand meaning that her death was supposed to reveal (recall my need for even grief to be productive). I forgot that loaves are formed of breadcrumbs—that the grand meaning of her death is the fact that she lived, learned, and passed down.

In our obsession with keeping people alive, we forget that they are still alive: not only in our memories and in our values, but also in our unconscious gestures, in our dimples. Genetic inheritance is evolution’s design for immortality.

Grief, too, is a kind of immortality. Every time I feel it—when I see the pale stain where my grandmother’s teacup scorched the bedroom dresser at my house, or when I eat a steamed mushroom pork bun and think, reflexively, that she could have made it better, even when I remember her as she was in her later years—she is revived.

The cliché is that grief comes in waves. And I anticipate that it will, just when I need it to: when I get married, and I remember the profound, consistent way my grandmother loved my grandfather; when I have a family of my own, and I remember the feasts she cooked, and the rare gift of her smothering care.

There is no preservation of the dead, no stopping time for the living. There is nothing to do but to love, grieve, and live—which in the end are all the same thing.

We had thought, initially (and not very originally), to write a series of predictions for 2026 as a way of reflecting on, and making sense of, the events of this past year. But as we disagreed with our own arguments at every turn, we concluded that predictions were too rigid, too wrong a constraint for a world that feels increasingly like, to quote Joan Didion, “a hologram that dematerializes as [we] drive through it.”

Indeed, in the closing segment of Jimmy Fallon’s recent interview with Sam Altman, when asked for his prediction for “the biggest thing [he sees] happening out of ChatGPT in the next five years,” Altman says, apparently caught off guard by what seems like a reasonable question to ask the CEO of one of the fastest growing AI companies: “Five years is a long time.”

He settled on offering not his expectations, necessarily, but rather his hopes: that next year, the models will make small, but important, new scientific discoveries, and that in five years, the models will cure diseases.

This humanitarian hope—this original hope—is the platonic ideal of OpenAI, subject (as all “well-intentioned” billionaires’ hopes are) to the currents of the world—drifting, drifting, drifting, until finally arriving at a for-profit corporate conversion and the announcement of adult content all within the same week. Hardly anything these days seems able to escape the undertow of enshittification.1

It is easy to feel caught in the riptide, unmoored from today, with no purchase on tomorrow. In the span of a single year, so much seems to have come undone. Justice is increasingly militarized, whether in the descent of the National Guard on cities or in political violence framed as vigilantism. The threats of dehumanization and derealization are a constant, deafening din: diversity is out, xenophobia is in; people are being replaced by bots, falling in love with bots, descending into madness from bots, funding bots, shorting bots, giving bots all that data, all that water.

Reality, once rendered into memes, has become one: the Louvre was robbed in broad daylight, its password for the server controlling its CCTV systems simply “LOUVRE.” Absurdism is just another form of extremism.

While it is critical to confront these undoings—to bear witness to them, to refuse to look away, to take action in response—it is also important to keep hold of joy, of whimsy. Whimsy is the available imagination to think up new worlds. It is our reminder that the inevitable is a self-fulfilling prophecy only if we play along.

Heraclitus reminds us that “it is not possible to step into the same river twice.” Πάντα ῥεῖ: everything flows—the river, yes, but also you. We have agency against the currents acting upon us. So as we thrash about in this choppy, often unforgiving river that will take us into 2026, we invite you to join us in swimming—against some current, with another, towards something.

Here are the currents, and countercurrents, we’re tracking going into 2026. Swim on!

Currents

• The Indie Industrial Complex. A24 is not an indie production company. We repeat: A24 is not an indie production company. It is an independent production company, but it is also valued at $3.5 billion dollars, backed by the same VC firm invested in Anduril (defense tech), Affirm (buy now, pay later aka predatory lending tech), Fanatics (sports gambling tech), and OpenAI. It has merch for Christ’s sake—zines and tote bags. A24 is the production company equivalent to the performative male.

• Even faster fast fashion. TikTok shop launched in late 2023. By 2024, it was the fastest growing online retailer. It’s fast fashion live, we fear, set to the pace of China’s live-commerce machine.

• The body as lean, mean machine, emphasis on lean. So, Wicked: For Good came out, along with a deluge of articles about the cast’s collective weight loss as Ariana Grande and Cynthia Erivo in particular (but also Michelle Yeoh) appeared truly emaciated. Meanwhile, there has been an explosion of marketing around GLP-1s (and microdosing GLP-1s), including a controversial Ro ad featuring Serena Williams, one of the greatest female athletes of all time. We have no desire to litigate women’s bodies—that’s done quite enough. But we are troubled by self-optimization culture—including wearables, comprehensive health testing, and the gospel of Bryan Johnson—and its demands.

• The homogeneity of taste. An article in The Cut this year, titled “It Must Be Nice to Be a West Village Girl,” displays a group of girls, evidently of the West Village variety, crossing the street. They are the image of “cool girls”: none of them is looking at you, and they are all wearing the same uniform—simple white (or, if you really want to get crazy, black) top, medium-to-low-rise blue denim, Adidas Sambas, or black loafers. The uniform is cute. But we are suspect of letting the algorithm be the arbiter of cute rather than letting our own tastes be our guides.

• Sippy and sippier water bottles. We get the allure: sippy cups are easier to drink from, and we’re too dehydrated to make hydration any harder. But they’re kind of difficult to keep clean and…gross? And part of the great infantilization of brands?

• Self-soothing culture. A cute little $8 latte here, a $100 manicure there, the suddenly not-so-small habitual indulgence that doubles as a coping mechanism.

• Temporary possession. Renting everything—dresses, houses—and owning nothing. (On this note, we are intrigued by Real Estate Investment Trusts—REITs—as an alternative to the fantasy of home ownership for our generation.)

• Retrofuturism. Forward-looking design dressed in vintage aesthetics (see Fallout or this Claude ad).

• Nonsense. The unspooling of language to word-jumbles that lack semantic meaning, like 6-7; the reliance on meme-speak to capture what is a pretty complex human experience.

• “Non-toxic” and other weird value propositions. Ceramic-coated pans are not an “innovation” (Le Creuset celebrated its 100th year this year), and there’s something unnerving about “non-toxic” as a selling point. For example: the other week, Céline did a double take of a package for Vital Proteins collagen powder that read, ambiguously: “Now with 90% less plastic.” The packaging or…the protein powder? De-influence yourself and keep it simple: stainless steel, cast iron, olive oil, whole foods.

• The cult of celebrity. Biopics, memoirs, famous-people-give-advice books. Take it from one of our boyfriends: reading Shoe Dog: A Memoir by the Creator of Nike 1) is an aesthetically unpleasant experience and 2) won’t make you Phil Knight. There are much more interesting, much more transformative things to read and watch out there.

• The big education short. There have been about one billion articles published about how AI is devaluing traditional degree programs, including ours (which we wrote about here). Certainly, AI has been a shock to schools, one not yet fully absorbed. But we’re bullish on the resilience of schools to figure it out.

• Polarization. Still at record highs and likely to climb further. But a reckoning may be near. Marjorie Taylor Greene’s decisive break from Trump, covered here by the New York Times, may be a harbinger of a greater disillusionment to come.

Countercurrents

• Ceremony. Going to the movies, seeing a play. Going by the continuously plummeting box office numbers, we’ve lost all sense of it! Maybe we’re being hyperbolic, but there is something to getting up, getting dressed, going out, indulging in aesthetic pleasure, and being a real person, with other real people, that is good for you. The same logic applies to dining out vs. ordering delivery. Let us not ensnare ourselves in the sarcophagus of frictionless comforts!

• Third places. We need more third places outside of home and work, which, for remote workers, are the same place, creating all the more need for other places. And no, the Metaverse does not count, as much as the Zuck would like you to believe. And if you’re in SF, a city in desperate need of third places, check out SŌHN; one of our friends runs workshops there :)

• Buying fewer, nicer things. Trends, gadgets, new things. With the 24/7 worldwide bazaar at our fingertips, every day is Christmas, and Santa’s sleigh is an Amazon delivery truck. Internalize the mantra of “buy it nice or buy it twice.” Or Keats: “A thing of beauty is a joy for ever.” A piece of junk is a false joy for a minute that’s already passed.

• Medicine as medicine, and not a fashion statement. GLP-1s are life-changing, potentially life-saving drugs and should be treated, and marketed, as such.

• Taking a friend out on a date. You pay, and, no, you don’t send a calendar hold.

• Eating a carb for breakfast. Also, just eating breakfast.

• Taste as a reflection of our actual tastes?? Liking something because it sparks joy, and we say that unironically!!! Céline’s dad recently bought a painting by a Thai artist called BYBAMBAM. Though a significant departure from his usual tastes, the painting’s representation of dyslexia resonated with him, moved him, compelled him to hang it prominently in his home. That’s taste.

• Feeling our feelings, using our words. Watch a movie with a friend where you both cry. Then talk—at length—about why it made you cry. Resist the shorthand of something like “I’m dead.” Rediscover the language for your interiority.

• Slowing down, thinking through major life choices on longer time horizons, perhaps over a cup of coffee in an aforementioned third place. We get it, the present feels urgent and the future abstract. But inaction is action, and, day by day, we write our futures. The story need not be neat; the most interesting ones never are. But rather than follow a linear career, follow a truthful one.

• Not taking out the phone. What if we didn’t respond to the email immediately, or look up which animal has the highest blood pressure ASAP, just because we can? What if we let our curiosities play out just a few minutes longer?

• Hot water dispensers like this one. Ask our Chinese grandmothers—it’s good for you!!

• Majoring in the humanities. The CS major bubble has popped. Meanwhile, Ilya Strebulaev, a Stanford GSB professor known for his research on unicorn founders, posted an infographic of some of his research on LinkedIn, showing how Philosophy and Performing Arts majors have a greater probability of founding a unicorn than their Engineering and Economics counterparts. If the post-grad job market is going to be what it is (bad) no matter what, one might as well study what one actually loves. These days, being able to think about technology—rather than being able to create it—is the scarce resource. Reid Hoffman has a master’s in Philosophy. Just saying.

• Turning towards conflict. We both took a course at Stanford called “Interpersonal Dynamics,” more commonly known as “Touchy Feely,” which is essentially a crash-course in building intimacy. Relationship health is defined not by how much people fight, but rather by how well people fight: how they turn towards each other when they most want to turn away, how they face the difficult moment together.

2025 was a challenging year, full of rancorous, corrosive conflict. But we can always make a different choice. And grace, empathy, and love are always there for you to choose.

If you have room for one more New Year’s resolution for 2026, let it be to, as Seamus Heaney wrote, “walk on air against your better judgment.”

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My therapist stares back at me, understanding but unconvinced. I have just finished rattling off all of the reasons I feel confused and unhappy here, at the GSB. Before she died, my grandmother said that business school would not be a waste because it would expand my consciousness—and learning, no matter what sort, was always worthwhile. But I worry about the direction in which my consciousness has expanded. I catch myself buying into “frameworks,” obsessing about optimization, noticing less and less the beauty around me, feeling less and less the wonder in any given moment. I feel so foreign to myself. Who was she who wanted so badly to know how to describe butterfly wings, who cherished the word “gossamer” that her grandmother gave to her? Who was she who loved more than anything a good sentence, and knew one when she wrote it?

“Okay, so what do you want?” my therapist asks.

The question arrests me, stops me straight in my tracks, leaving me dumbfounded and defenseless. It taunts me with its simplicity, dares me to come up with a reply: okay, little miss smartypants, why don’t you riddle me this? My heart quickens, and my face flushes. I rack my brain, but it’s blank. All I can hear is the tinnitus in my ears from all of the clenching of my jaw. I have no idea what I want. More than that, I’m not even sure I know what wanting feels like. I have no idea where to begin answering my therapist; I don’t think I even understand the question.

“I don’t know,” I whimper. And then come the tears—the wet, hot, angry, mournful tears.

For as long as I can remember, I have wanted to be perfect. But that’s the same as saying I wanted to survive, which isn’t saying much. I cannot remember what would have scared me into silence in the first two years of my life, which I spent sulking and sucking my thumb until it turned black and bled. In any case, I never did the cute “goo goo ga ga” thing. I just sucked my thumb and bided my time. I wouldn’t speak until I could do it perfectly. I held my silence for two years and broke it only with full sentences. By that point, I had already been dressed in a Harvard onesie.

The fear only intensified. I peed my pants in the second grade because I couldn’t bear to fall behind in a typing game. I collapsed on the floor in the third grade because I received a 19/20 on an auto-dictée and thought for sure that I would never get into Harvard. This was me in elementary school; I’ll spare you middle and high school. But when I finally did get into Harvard—when I had achieved what had been, seemingly from the day I was born, my life’s purpose—I had never been more depressed in my life. I had lived my entire life in terrified service of someone else’s dream, locking my own desire (a dangerous thing) so far away in my psyche and so early that I am still looking for the key.

It was easy enough to numb myself with more pursuits of perfection: a trove of academic accolades, an acceptance to the GSB. But now that I’m here, feeling so ludicrously out of place that even I—typically so blind, deaf, and mute to myself—can’t help but notice it, I cannot run from the austere truth of my life: I have seldom known desire—not the real kind, anyway, the kind germinated by love rather than shame, spurred by joy rather than terror. I have seldom dreamed beyond the perimeter of fear.

“I don’t know,” I repeat, desperately.

“Do you want to try figuring it out?” my therapist probes, gently. She knows that “figuring it out” means letting go of everything that once made me feel safe and now makes me feel miserable; that it means mustering up the courage to step off the tightrope of my life, trusting that the safety net is there even if it was never there before, and I can’t see it; that it means healing my relationship with happiness, and not feeling repulsed by myself when I indulge in it.

“I don’t know,” I say again, crying harder this time so that I’m almost coughing, realizing that, although I can’t seem to bring myself to do it, the only life goal that matters right now is allowing the little voice of my desire to be heard and followed.

Whenever I have not known what to do, I have gone to my grandmother. I would bring a personal problem, and in return, she would bring a poem—she spoke in tongues, that way. The conversation would flow organically from there, and we would often wander to other topics. It could be frustrating—just tell me what I should do! my nervous heart would cry—but she knew not to. Her wisdom was never an answer—a detailed map, with directions to X marking the spot. Rather, it was a deepening of inquiry—a compass I was meant to use to chart my own course, even after (especially after) she was gone. She is gone. Literature is the guide she left me.

So I turn first to Saul Bellow’s Seize the Day, because it is the story of a loser, and I’m not feeling too hot about myself. Wilhelm—the main character who embodies anything but “main character energy”—doesn’t know what to do either. The title of the book—Seize the Day—is an injunction to a character who has for too long yielded his days instead.

Throughout the novel, Wilhelm lacks any agency: he figures himself as “a ball in the surf, washed beyond reach, his self-control…going out.” While he has made decisions throughout his life, they are marked less by conviction than by confusion, each one the result of much hand-wringing, culminating not in the expression of his will, but rather in the collapse of it: “He had decided that it would be a bad mistake to go to Hollywood, and then he went. He had made up his mind not to marry his wife, but ran off and got married. He had resolved not to invest money with Tamkin, and then had given him a check.” Neither his mind nor his body can access his true desires, which, unarticulated, build up a congested, choking pressure. He desperately wishes to regain control of his life, but he looks to Tamkin to “transform his life” and to his father to “carry [him] this month,” unable to stand on his own.

Occasionally, flashes of lucidity strike him. At one point, he is suddenly overcome with love for “all these imperfect and lurid-looking people,” realizing the insignificance of his own imperfections to being loveable, and loved. At another, he remembers a passage from Keats’s Endymion that the woman who nursed him used to read:

Come then, Sorrow!
. . . .
I thought to leave thee,
And deceive thee,
But now of all the world I love thee best.

In plain English, the passage is an embrace of sadness after an initial rejection of it. I think of a line my grandmother often quoted to me, the last line of Coleridge’s “This Lime-tree Bower My Prison” (a poem, basically, about turning FOMO into JOMO): “No sound is dissonant which tells of Life.” Joy is great. But sorrow, to borrow again from Keats, has its music too.

In the end, it is humanity in all of its mundane, ugly, divine forms—“I labor, I spend, I strive, I design, I love, I cling, I uphold, I give way, I envy, I long, I scorn, I die, I hide,” and, finally, “I want”—that leads Wilhelm to his ultimate salvation. I want. That definite expression of desire, that sentence I don’t know how to finish, clears the blockage in his system. At a stranger’s funeral, Wilhelm sobs uncontrollably, finally moving “toward the consummation of his heart’s ultimate need”: not to escape suffering, but rather to grieve it and love it, too. For, in God’s eyes, pity is no less worthy of love than glory.

Re-reading Endymion, the lines immediately preceding the passage that Wilhelm remembers strike me as true to my feelings: “Bewitch’d I sure must be, / To lose in grieving all my maiden prime.” But I can’t stop there: I must then invite Sorrow in. Learning from Wilhelm, who got it wrong until middle age, the first step I must take in order to recover the voice of my own desire is to grieve, accept, and learn to love its loss in the first place.

So that’s how a loser did it; what about a winner? It turns out that the answer is the same, that it lies in loving humanity, necessarily including oneself. Siddhartha, of Herman Hesse’s novel by the same name—after a lifetime of searching in vain for his true happiness in various teachings (of the ascetic Samanas, of Gotama the Buddhist) and direct experiences (physical love with Kamala, working in business)—finally finds it not in self-denial, devout following, radical independence, or over-indulgence, but rather, like Wilhelm, in “belonging to the unity of all things.” Just as Wilhelm encounters “the inexhaustible current of millions of every race and kind,” so too does Siddhartha encounter the current of the river, containing “all the voices, all the goals, all the yearnings, all the pleasures, all the good and evil.”

In contrast to Wilhelm—middle-aged and unemployed, estranged from his family, directionless, and next-to-broke—Siddhartha is young, with every privilege imaginable: he is a Brahmin’s son; he spends his days bathing in the sun and resting in the shade; and he is loved by everyone. Nevertheless, Siddhartha, too, is unhappy. Yet while Wilhelm is too paralyzed by insecurity to allow his true self to emerge, Siddhartha—even though he has no idea where it dwells—is determined to find it. He has no certainty that he will find inner peace, yet he knows very well that his pursuit of spiritual truth will require him to let go of everything he has ever known and loved—first his father and the security of childhood, then Kamala and the privilege of riches, and finally his own son and the illusory feeling of control, completing the circle of life. His quest is thus the ultimate expression of conviction.

If Wilhelm’s grief and acceptance is the requisite first step, then Siddartha’s courage is what must follow. Yet, for all my admiration of Siddhartha, his story represents a Platonic leap of faith: I cannot realistically see myself leaving my family behind to wander into the woods and starve myself to begin my journey to self-discovery. But parables were never meant to be prescriptions, words to follow by the letter. Siddhartha himself rejected dogma in pursuit of his own values. The lesson is only this: you must go your own way; trust that you will find it. And know that, in the end, no matter how circuitous the journey, it will have been good.

“I don’t know,” I stammer again. I am grieving now. And I (almost) feel proud.

Maybe you mistake other people’s dreams for your own, maybe your self-worth feels inextricably entangled with external validation, maybe you believe that you can achieve your way to happiness, maybe you’re exhausted playing pretend all of the time, maybe you want to imagine something different for yourself, maybe you have a tiny, almost imperceptible voice inside you crying out to be heard. Maybe, in other words, you’re like me.

In that case, I’m here with you. From the trenches, here are a few pieces of advice for how to tune in to that little voice, and to listen to what it has to say:

1. Go to therapy if you can access it. A good therapist will coax out who you are denying yourself to be. Let the sorrow in. Grieve. And give yourself lots and lots and lots of grace—you’ll need it to keep going.

2. Start a support group. It’s much more fun than it sounds. Danielle and I, along with another friend at the GSB, started meeting every other week. We called it “Designing Our Lives.” We whiteboarded, we cried, we yapped, we did it all. Most importantly, we held each other accountable to staying true.

3. Set aside time to reflect. Like, more time than you want. No reflecting gets done in the rat race. Think about who you are, who you’ve always been. When have you felt most alive—not when you’ve been most amped up on stress, but rather when all of your best energies were activated? What stories are you telling yourself about why you can’t make certain choices in your life—and are they really true? These are not fun questions (I know), but deferring them is a recipe for a crisis later in life.

4. Use people you trust, people who have known you a long time and have your best interests at heart, as a sounding board. This one’s a bit tricky because your self-definition needs to come from you. But trusted outside perspectives can help, especially as you’re getting your feet under you. My uncle, for example, has been calling me out for years for not living authentically. I leaned on him a lot to remind me of who I am.

5. Get creative, and be expansive. Leave no stone unturned. There are more jobs than consulting, finance, and tech, and as we wrote about in our last issue, you probably don’t need as much money as you think you do. Go through the Financial Visioning activity we laid out there, and then get cracking on your research!

6. Trust your intuition. If you feel like you should be happy, but you’re not—you have the “right” job, the “right” salary, but you’re tired all of the time and something doesn’t feel right—listen to that voice. If your excitement about something scares you shitless—like you’re finally doing what you want, and it feels against the rules—listen to that voice, too. You know more than you think you know about what you really want. Your body will tell you.

7. Then go for it.

If you’ve made it this far, I’m so so proud of you!!! Go get ‘em!!! And by ‘em I mean your dreams!!!

“How much do we actually need to make to live the lives we want?”

“It depends on what you want. Where do you want to live—California or New York?”

“And do you want to send your kids to public school or private school?”

Numbers—all in the millions—were thrown on the table. They seemed at once completely made up and totally plausible—it’s true: the American Dream of homeownership, for example, feels increasingly like a relic of the past, but do we really need as much wealth as we think we do to live the lives we want? Wanting to lasso the fantasy, I pulled out my iPad as a makeshift whiteboard and did the math.

We modeled our ideal lives: two incomes, a house in a high-cost coastal city, occasional international travel, childcare, college savings, money for parents who might need help. We discussed property taxes and 529 plans. Someone insisted on a line-item for out-of-pocket healthcare costs.

The marker squeaked to a halt at $450,000 in annual household income—assuming public schooling for two kids and some cushion for taxes and savings.

In the midst of peak “broligarchy”—on Collins Dictionary’s shortlist for word of the year, describing the plutocratic oligarchy of mostly male, often libertarian tech billionaires whose influence now shapes everything from AI regulation to the cultural zeitgeist. On any given week at Stanford, chatter might include Elon Musk’s negotiating a pay package that could be worth $1 trillion, Jony Ive’s accepting a reported $1 billion deal to advise OpenAI, or a Stanford computer science PhD’s walking away with a $100 million compensation package from Meta.

Against that backdrop, our very bougie dream life penciled out not to the frequently thrown around and completely arbitrary benchmark of $10 million in ten years, but rather to $450,000, across two individuals, per year. Point-blank, this is a lot of money—eye-watering for most of the country and multiple lifetimes of income for many families I grew up around. But, it is nowhere close to the eight-figure entry fee to adulthood many of us had subconsciously presumed we needed to pay.

The question is how we drifted so far from a realistic number in the first place.

I didn’t grow up anywhere near this world. I was born into a cramped house in Flushing, Queens, where my grandparents, aunt, uncle, and parents all lived on the same rented floor. As a kid, “enough” meant parents who got through school by day and work by night so that we could eat a good steamed fish together at dinner. Money was aspirational, as phantasmagorical as the taste of freedom, and painfully concrete, as physical as clipping coupons and counting pennies.

When my parents moved us to suburban New Jersey, I watched how quickly “enough” shifted—how proximity to larger houses and nicer cars rearranged our sense of what a happy life required. I carried into adulthood a hunger for upward mobility: first as a mortgage trader in New York, then as a venture capitalist in Los Angeles, where status was often something you could purchase if you knew where to look.

I came to Stanford hoping for some perspective, a two-year window to rethink the version of ambition I’d absorbed in New York and LA. Instead, I landed in the eye of the storm: the epicenter of tech-driven wealth, just as artificial intelligence turned Silicon Valley into a gold rush running at 2x speed, hiring “10x engineers,” whatever that means.

A classmate once shared a five-year “mission” slide, a personal plan with bullet points like “Make $3M+ with medium-high probability” and “Develop a track record as a CEO.” The “Why” column was noble: buy a home near family, have the flexibility to be present with future children, build something meaningful in her home country, avoid ever taking a job out of financial fear. I frequently hear classmates, many in their twenties, casually say things like, “I need to make $10 million in the next decade,” as if they are talking about a Whoop goal. When I ask where that number comes from, the answers are almost always the same: a shrug, a pause, and then, “I don’t know. Feels right.”

The impulse to aim high is earnest, and here, it feels completely relatable. I’m not criticizing my friend; I could have written the same slide. I’ve put financial pressure on my own partner without ever calculating what “enough” meant for me.

My older friends in venture capital have also talked about a lifestyle maintenance benchmark, somewhere on the order of the double-digit millions–enough to pay for Nueva School (which sits at a comfy $62,560/year before extracurriculars) and Tahoe homes inside gated communities where nothing lists for under $4 million. At one point, my partner asked me, “We’re going to make all this money so our kids can inherit $20 million by 21 and turn into spoiled brats?” Hearing it said aloud made the whole thing feel even more unhinged.

It would be easy to dismiss all of this as a song performed on the world’s tiniest violin, but there is a universal story beneath it: when you’re sitting inside a wealth maximization spiral, the problem’s constraint is not in money but in imagination. If you decide, consciously or not, that your floor is $10 million by 40, the universe of acceptable careers collapses to a sliver. Your menu of reasonable jobs becomes: big tech, hypergrowth start-up, late-stage private equity, quantitative hedge fund, and a ruthlessly optimized search fund—maybe.

I’ve watched classmates reverse-engineer their lives from a hypothetical payout instead of from the kind of work they actually want to do. People who once talked about teaching, climate policy, or starting a scrappy, non-venture backable business now say, “I can’t afford that path,” not because their current rent bill is out of reach (though here in Palo Alto, it often is), but rather because the path will never deliver on the arbitrary benchmark on the arbitrary timeline they’ve internalized as immutable, ineluctable fact.

The psychological effects are just as corrosive. If you step onto the treadmill, it’s hard to jump off—and meanwhile the treadmill keeps accelerating. Your home in San Mateo isn’t good enough—you move to Hillsdale. Then Atherton. Your Tahoe condo becomes a house in Martis Camp. Then again—skiing in Aspen is much more desirable than anywhere in California. Fractional jet ownership? Soon you realize it’s better to own it outright.

The Lakeport whiteboard session felt vaguely illicit because naming what a life actually costs breaks an unspoken code. Our number was messy—smudged by debates about state and property taxes, and by the private-school dilemma: is it as simple as a preference, or is it an uncomfortable confession that American public education feels broken, and a guilt that opting out perpetuates a system not everyone can escape? It forced us to see how much of our own childhood biases we were sneaking into the math.

People here don’t talk about money directly because it’s “tacky.” But that’s not quite the truth, is it? Ambient fear gets repackaged as ambition. I know people earning more than my parents ever dreamed of who privately panic because someone else landed an equity package that looks like a misprint. It’s easier to pretend you’re immune than to admit you feel behind.

So I left that weekend—in Lakeport, ironically a mildly polluted lake and an hour’s drive but a far cry from Sonoma, where our peers have second, third homes—feeling oddly relieved, and a little embarrassed that my relief required a whiteboard. In a valley obsessed with 10x-this, trillion-that, landing on a number that is high by any nominal measure, yet modest by the broligarchy’s, made the world feel, briefly, back in proportion.

Split between a couple, $450,000 comes out to $225,000 each. I figured: I’d earned around that in my last two roles—the first when I was barely 3 years out of college—and, like most MBAs, I expected my income to rise, not to fall. So the number didn’t feel like fantasy math.

But this number is only my number, a result of my honest assessment of my needs, and, yes, my wants. If you want to try your own version of the Lakeport exercise, try what we call a Financial Visioning activity. This exercise is the prologue that most of us skip in favor of optimizing our Roth IRAs and 401ks right away.

• Step 1: Write down everything you want in the life you imagine. Everything—bicoastal beach homes, every B2B SaaS subscription, healthy knees, love, a year’s supply of pasta, children, annual Christmas trips home, Aesop soap—don’t censor yourself.

• Step 2: Sort every item into 3 buckets: HAVE, WANT, and NEED. NEEDs are non-negotiables, WANTS are self-explanatory, and HAVEs are meant to remind you of what’s already here.

• Step 3: Build your MVL – your Minimum Viable Life. From the NEED bucket, calculate the current cost of the simplest version of your life. Then dip into your desires from there, and know that, wherever you stop, you will already have everything that you need.

Write these down before reading another headline about another person’s windfall. You don’t need to chase somebody else’s dream, you need to know only what’s enough for you.

You wake gently to the sound of cooing doves as Somnium wakes you at the perfect moment in your sleep cycle. Vesta has already picked out an outfit for you to wear based on your agenda, and as you enjoy your breakfast, Culina replenishes your supply of your favorite bread and coffee beans. Ordo runs through your day, seamlessly …

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Her eyes linger on you for one second before darting down to focus on her taste buds. She twirls a forkful of pasta into her mouth, the fork gently clinking against her teeth before her lips close and form a smile full of pleasure. The little director in your mind punches the air in triumph.

“Good?” you ask.
“Mm…”…

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For many, business school is an opportunity to pause and to re-take stock, of one’s career, of one’s life. School, alas, does not actually slow time; but it is a privilege to savor time in this way: in classes dedicated to interrogating one’s values, in circles of friends dedicated to designing one’s life to align with those values, in meditative (and sometimes silly) conversations that wind around Stanford’s many sculpture gardens (and even result in the formation of a certain newsletter).

In these moments, in the cradle of magical thinking that, for better or for worse, is Stanford and the Silicon Valley, our many possible futures spread out before us, each beckoning us with its own particular sheen, each, at least in that instant, apparently limitless.

In the Cantor Rodin Sculpture Garden on Stanford’s campus, there is one work in particular that we love: The Three Shades. The three figures are identical casts; their difference is purely one of orientation. So we rotate ourselves into different positions: who we might be if we looked towards building a media company, or raising a VC fund, or founding a startup, or getting a PhD in English, or maybe Psychology, or doing something else entirely.

But the days still pass. Dust gathers on the possible futures not chosen. Rodin’s Three Shades are not alive as we are, but ghosts, perched above his Gates of Hell. Suddenly, we are reminded of the facts: that we can never live out our counterfactual lives, that instead of any of them we have chosen to spend two years in business school, that business school may or may not be preparing us for the actual futures that lie ahead of us, that at some point we will need to begin to answer our questions turned over and over and over and deferred.

The Critique

We think that unease is part of why a recent Poets & Quants article went viral in our LinkedIn circles. Sensationally headlined “WE’RE NOT LEARNING ANYTHING” and cherry-stitched together from student interviews, it punctured the glamour of the GSB, the business school with the lowest admissions rate in the world. With business school ringing in at a cool $170K+, it’s tempting to see the headline as confirmation that the time isn’t worth the cost, perhaps validation for those who abstain. Appetite salivates at the spectacle.

But while Poets & Quants isn’t exactly the paragon of journalistic integrity, the frustrations expressed in the article are familiar and credible: required courses that are frozen in the 2010s, with little connection to an economy transformed by AI despite being set at the source of the sea-change; “Room Temp” cold-call lists that train students to prepare only selectively, when it is their turn; and a lottery system that can leave students unable to take the very classes for which they came to the GSB in the first place. And the anecdotes are reinforced by data: survey scores on classroom engagement have slipped to historic lows.

As much as we might wish to dismiss the click-baity article as just that, the central question it raises is non-trivial: what is the point of business school, if not to learn about how to manage the businesses of today and tomorrow?

After all, professional schools are meant to transmit professional knowledge: lawyers go to law school to learn to practice law; doctors go to medical school to learn to practice medicine. If business students go to business school and…don’t learn to manage the businesses they intend to run or create, then are all of the stereotypes true—that business school is nothing more than a glorified two-year-long break for burned-out white-collar professionals, where all of the hard work takes place before you get in, and from which point you leave with a network-and-brand-inked stamp of approval that grants you undue access to people, capital, and leverage?

For some, there might be truth in that ROI assessment. Over a 40-year-long career, the network and the brand will more than pay back the cost of two years and $170K. Plenty of things have been written about how no recruiter was ever fired for hiring a Stanford MBA graduate. But these answers are tired.

What’s harder to articulate, and maybe more valuable, is the subtler education an MBA can offer: learning how to evaluate and bet on people, including yourself, and how to wrestle with questions that begin with “why.” These are the skills that grow scarcer as everything else gets automated. (Here we must caveat: these arguments are not limited to the MBA, as higher education as a whole is under fire on this front, but that’s another whole can of worms best saved for dinner and a glass of wine.)

A Brief History of the Higher Aims (and their abandonment)

It might surprise you, and then not surprise you at all, that the MBA was born as a reputational project. At the turn of the 20th century, “big business” faced public mistrust after a string of corporate scandals. In an effort to recast managers as rational stewards of capitalism rather than mercenary opportunists, the first schools, starting with Wharton in 1881, set out to rebrand management as an academic discipline on par with law or medicine. From the outset, however, the reality was far less noble: schools struggled with overcrowded classrooms and uninspired teaching, and many students prioritized the promise of lucrative corporate careers over “changing lives, organizations, and the world” (so goes Stanford GSB’s motto)—a familiar tension between higher aims and market logic.

Higher education more broadly had already absorbed the logic of industrialization. Reformers in the early 20th century described schools as factory assembly lines, organized around standardization and efficiency. Similarly, government and foundation money poured into business schools after WWII, pushing schools to mass-produce managers through a mechanized, quantitative curriculum-–the birth of “management science.” With the Cold War and the Space Race, this mandate gained further legitimacy: Sputnik in 1957 spurred a national obsession with math, science, and measurable, repeatable outcomes.

Ironically, the very models meant to legitimize management also made it easier to undermine and control it. Agency theory, in particular, reframed managers not as custodians but rather as self-interested agents to be monitored. And business schools fed consulting and finance pipelines with the very tools that eroded managerial autonomy. In other words, the snake eats its own head in an infinite loop of distrust, self-interest, and distrust again.

All of this history then begs the question: if the higher aims collapsed long ago, what, if anything, does business school still teach that justifies it?

On Judgment

In undergrad, the Core at UChicago required one full year of Humanities and one full year of Social Sciences. I’d sit in the library, jittery on late-night caffeine, staring unseeingly through a glass-domed ceiling as I considered Durkheim. His work embodies the “higher aim” of education: to train our judgment to see the invisible architecture of society. His texts taught me to see how norms and institutions might shape behavior as much as individual choice, and that many “facts” are merely social constructions—it is trust in these “facts,” rather than the “facts” themselves, that stabilizes a system.

Later, on the trading floor, the systems I studied were mathematical rather than social. My work demanded judgment, too, though filtered through “universe rules” of mortgage pricing models. The Job-To-Be-Done was to apply them—under pressure and with incomplete information—to determine where the world might move next.

In hindsight, my path feels like a microcosm of business education’s own drift. Durkheim embodied the early higher aim: cultivating judgment by training students to interrogate systems with no single “right” answer. Trading mirrored the mid-century pivot to “management science,” where judgment was still needed but increasingly mediated by models. As I write, I’m seeing a lesson that was portable across stages: how to make decisions when certainty, or completeness, is impossible. Though the form of education may change, the “why” remains the same: the burden of education was always on me, the student, not only to learn the tools, but also to learn the discernment they require.

The “how-to” skills are the easiest to measure and the fastest to package into a curriculum—which is exactly why professional and vocational schools market the hell out of them. My own Achilles’ heel, according to the job market, was not knowing how to “walk me through a DCF [discounted cash flow].” I never did banking, nor sat through Training the Street, so it was the simplest gap to point at and blame school for not filling. But the more I think about it, the sillier the complaint sounds: a DCF is exactly the kind of thing you can learn on Youtube, or outsource to a model, and it’s relevant to most business jobs only obliquely. The fate of codified skills is replication at scale, until their scarcity premium collapses, and they become commodities.

The real work of business school, then, is not to hand you another “how,” but rather to train the muscle of “why,” the sensitivity to the problems worth solving, and the people worth betting on.

Feynman’s line—“If you think you understand quantum mechanics, you don’t understand quantum mechanics”—is a reminder that at the frontier of knowledge, certainty is an illusion. The hardest questions will always demand judgment in the face of incomplete information.

The Sandbox

We start the MBA with a class called Lead Labs, designed around a deceptively simple question: Why would anyone follow you? The format is role-play—think fast…a volcanic eruption has stranded your company’s only airport, or: negotiate a term sheet, except—surprise!—the VC hates your co-founder. To anyone with a real job, these exercises probably sound comical. MBAs cosplay crisis management. Even within the class, people split 50/50 between love/hate of the contrivance. When locked in a room to figure out how 6 people survive a fictional plane crash in the Sonoran Desert with 15 random items, the loud athlete might insist on salt tablets being essential, while the quiet engineer might say nothing about the fact that they will absolutely dehydrate you. The group ranks salt tablets first and moves on.

Try it yourself:

Sure, it’s an artificial exercise, but it strips away polish and forces you to notice the rules of power, and how classmates show up under pressure. The MBA is a sandbox where people reveal themselves: in group projects, on trains to Busan, in moments of stress and triumph and pride and existential dread. You learn who follows who, and who follows through. And in learning others, you, still amoeba-shaped and bleary-eyed, begin to learn yourself.

You get to decide what kind of leader you want to be when you grow up.

The point is not necessarily that your future co-founder is sitting next to you in Accounting. It’s that two years of high-frequency exposure whets your senses so that when the right person comes along, potentially five or ten years later, you’ll know. Take dating: most relationships don’t end in marriage, but the full-time DJ you met at Nowadays sharpens your intuition for the kind of person you actually want to spend forever with (I now spend it with only a part-time DJ).

My part-time DJ below:

Statisticians call this kind of search the optimal stopping problem. When faced with a series of unknown options, the math says to spend the first 37% calibrating (reject them all) and then to commit to the next one that beats the best of the first batch. In a parking lot, it means driving past the first third of spaces to set your baseline, then pulling into the next spot that is ideal. Of course life is messier (please don’t run regressions to find the co-founder of your future child). As we’ve said, the model isn’t king; it simply captures something we already do intuitively as we live, make mistakes, and try again. Business school is nothing more, and nothing less, than a dedicated laboratory where one tunes one’s own proprietary judgment model—otherwise known as: wisdom.

Forking paths

I am reminded of Borges’s The Garden of Forking Paths. Every choice to spend time here clears a new field of possibilities. Put more pessimistically, every choice to spend time there closes off countless others. For six years after college, the skeptic in me dismissed business school as wasted narrowing, when the real world is full of paths that at least lead somewhere. That is, until I pulled the trigger three months before the application deadline.

But the narrowing is intentional. You enter the labyrinthine garden now so that later, in the wild, you’ll have an inner compass to guide you. The paradox of business school is that the most valuable thing it teaches is never explicitly taught. What resists direct instruction, and thus what resists automation, is judgment—the “why” behind our insights, our words, and our choices. Why work? Why follow this person? Why this problem, and not that one? Why now? Why me? There is a reason why this is the question that children always ask. Asking “Why?” is how we make it in this world.

Maybe that’s why, despite its credential-factory trappings, the MBA endures. You return again and again to the same question—why did I go to business school?—and discover that the value lies not in its answer, but rather in asking it better the next time. Two years in the sandbox compresses a decade’s worth of natural experimentation, so that when the forking paths appear again, five or ten years later, you recognize the path worth traveling.

That, to us, is the circular book of business school: the end loops back into the beginning, we return to the same questions but as different people, each time with greater sensitivity and attunement. “I could not imagine any other than a cyclic volume, circular. A volume whose last page would be the same as the first and so have the possibility of continuing indefinitely,” says Albert in Borges’ story. Our last First Day of School is no last at all. At least, that’s the idea, if we learn well what business school has to teach us.

Things I started to notice at home after everything would turn grey for six months in Boston.

The second boy I ever said “I love you” to had broken up with me for the first time that winter break (he would do so two more times before finally letting me go), so in the spring I was never closer to my girl friends, who didn’t like him. We dressed up, we went out, we danced, we got hurt, we ate too much, and then too little, we were, mostly, indestructible.

More importantly, I had fallen in love with poetry—not writing it, but rather analyzing it—and in the last two years of college I did all that I could to take poetry courses and not much else and still graduate. There was too much to say about words and lines!

In my junior year, in a tutorial meant to prepare English majors to write their senior theses, I wrote a 28-page paper on Elizabeth Bishop’s animal poems. It was called “Elizabeth and Friends” and began:

“I am so eager to go to the circus,” wrote Elizabeth Bishop to her friend Donald Stanford on April 5, 1934, right after drawing him a picture of how birds warm themselves in chimney pots at Vassar College: three black birds perched on one merry-go-round-shaped chimney pot, two “with their tails inside” on either side of one “switch[ed] around” with his head poking in. Vertical squiggly lines rise from the chimney pot and the birds to the sky—perhaps they are heat waves from the pot, or chirps from the birds.

And in my senior year—after many nights that crept into mornings spent clandestinely camping out in the law school library past closing until I would finally half-skip, half-dance back to my dorm at 5AM, high off of a new discovery, or a damned good sentence—I completed my thesis, a 65-page review of Seamus Heaney’s entire poetic career. It was called “How Airy and How Earthed: Seamus Heaney’s Dig to the Sky at the Bottom of It All,” and it is stored in the university’s archives.

It, too, began whimsically, with an epigraph of a nursery rhyme that Heaney kept with him through adulthood and that encapsulates his dual airiness and earthliness as a poet, concerned with the cosmos of the universe as much as the bogs of Ireland:

One fine October’s morning September last July / The moon lay thick upon the ground, the mud shone in the sky.

I turned in my thesis on March 9, 2020.

The next morning, the university announced that all students needed to vacate their dorms and return home within the next five days.

That’s when time started to slide.

A couple of quarantined months later, I graduated from college from bed via YouTube live-stream. I was newly boyfriendless (yes, this was the third and final time that that same boy broke up with me), and soon to be jobless. The job I had lined up—a position in the mailroom of Creative Artists Agency, where I hoped to read things and get paid (albeit for just north of minimum wage)—was indefinitely postponed because of the pandemic, and in time would be eliminated. George Floyd had been murdered a few days earlier. The COVID-19 death tolls continued to climb. The world seemed to be emptying itself, opening like a monstrous sink hole in the place of everything we ever knew.

Like everyone else, I did my best to carry on. And since no one back then could see two weeks in front of them, I leapt without looking. At the advice of an older friend—a data scientist in tech and fellow humanist in college, a musician—I researched what product managers did. It was a job I had never heard of in college, happily sequestered in my stacks of poetry books, but after many cold emails and coffee chats, it seemed like one that might actually suit me, requiring a mind that is at once analytical and creative, the ability to communicate with and guide people, and, perhaps most of all, empathy. (Yes, empathy is actually a quality for which PMs are explicitly valued—it shows up in many rubrics for career progression! Communication, too—in my first year of work I was nominated for a company-wide storytelling award.) And so I began a new and unanticipated career as a PM in tech and was fortunate to work at companies that valued my unique way of breaking down systems and whose missions I supported: financial inclusion, renewable energy.

I also fell in love, in a big way, with a boy I met on the internet and drove six hours to meet for the first time and have been with ever since. I worked remotely and spent a lot of time driving through the Sierras with my dog as my boyfriend briefly settled in Reno, Nevada, a city for which I developed an unexpected fondness. It was cold, but it was desert-cold. The Sierras turn purple just like the San Gabriel Mountains do. I was a poetry critic turned product manager; he was a ballet dancer turned software engineer. Together, we drifted across the west like tumbleweed, our stems displaced but our branches entangled, a rootless home that was nevertheless still home.

I marked the passage of time with the mile markers. Still, the highway hypnosis set in. Before I knew it, my early twenties had flowed imperceptibly into my late ones.

It was desire that finally sharpened my perception of time—ultimately my awareness of being alive. Many days of the week, many weeks of the year, my work offered me morsels of purpose: I got a thrill out of poring over customer research with a critical lens, identifying themes across disparate threads and reading between the lines for the needs behind the problems; I took pleasure in learning the new languages, of the engineers, of the designers, of the lawyers; I relished collaborating on designs in Figma until they looked just right to my aesthetically obsessed eye; I found gratification in building features that made even the slightest difference in the world—tools to help people living paycheck to paycheck get into a better financial position, tools to help solar businesses sell and install more systems. Work-life balance still existed in tech, and I made time to read and try new things and be in nature outside of work.

But, having watched my mother, who dreamed of becoming a poet and became a lawyer instead, never fully recover from her own pragmatism, I was keenly aware of how malnourishment of the soul manifested. Over the years, my hunger for more humanism and creativity in my work had intensified from a subtle pang to an intolerable vacancy. My body had begun to consume itself as I ground my teeth at night, gnawing at nothing but my own enamel. I knew that the moment I stopped hungering would be the moment I started to die.

So, logically, I went to business school. (This is a joke.)

But in truth the decision was earnest: as I entered my late twenties, after nearly two decades spent sprinting towards finish lines, I wanted to afford myself two years dedicated to being unfinished; and many mentors of mine, including ones in the arts, believed that business was the widest keyboard one could play on and felt sure that I could find my tune.

It turns out, business school is a very revelatory and very strange place to be if you’re a humanist at large trying to navigate your 20s in the AI era.

Very revelatory, because even if you go to business school only to return to art and start a newsletter with your trader-by-day-poet-by-night best friend you meet there, maybe that was the whole point. Birds’ homing instincts evolved from the necessity of departure: birds know where home is because they’ve always had to leave it. It might be similar for humans. As T.S. Eliot wrote,

We shall not cease from exploration
And the end of all our exploring
Will be to arrive where we started
And know the place for the first time.

And very strange, because all sorts of other forces can interfere with your magnetic field. Like the current pulling you towards the conventional post-business-school paths. Or the draw of funding, and the idea of founding a venture-backable business. Or the all-consuming noise about AI, and posts like “YC on how to spend your 20s in the AI era.”

So, in honor of our waning twenties in the AI era, we’ve redlined the compilation of YC’s advice that’s been floating around with some notes of our own (bolded = our thoughts).

YC’s guide on how to spend your 20s in the AI era, edited by us

Core takeaways

• Best time in history to start a company due to AI

  • It’s also one of the most competitive times in history to start a company, and it’s tempting to build for the wrong reasons. Never before has it been easier to get from nothing to a working prototype, which means that the barrier to entry is lower, but the bar for quality is higher. Your 20s are also the best time for reflecting on why you would found a company and what you would want to spend the next 10 years building. If you’re not starting a company out of deep personal conviction—a clarion call that will eat up your nights and weekends—you’re feeding someone else’s ambition.

• Real outcomes over credentials - $10M revenue beats press coverage

  • Empirical learning is valuable. That doesn’t mean theoretical learning is not. Don’t earn credentials for credentials’ sake. But don’t underestimate the cultivation of critical thinking skills that happens when you set aside time for education. Learning to think is important in learning to do.

• Technical skills are newly valuable in AI-first world

  • Yes and no. Even the moguls seem to disagree on this point. Jensen Huang said, “Over the course of the last 10 years, 15 years, almost everybody who sits on the stage like this would tell you it is vital that your children learn computer science. And in fact it’s almost exactly the opposite. The technology divide has been completely closed.” Reid Hoffman, who by the way earned a master’s degree in philosophy, tweeted just a couple of months ago, “This is why I'm so outspoken about the importance of the liberal arts. They’re the training ground for understanding human complexity and having the right tools to build generational companies.” Yet the going rate for AI technical talent is, I don’t know, a bajillion dollars. So who knows.

• Agency and independence are the differentiators humans retain over AI

  • Given that agentic AI has both of these things, we’d like to believe that humans retain many other differentiators over AI. In our last issue, we wrote about one in particular: “But our bots do not write, or speak, or mean. They mimic symbolic patterns, convert those patterns into phonemic ones, and produce something that ‘means’ something only in the sense that it has semantic meaning.” Meaning-making remains ours to do.

Speed of success has accelerated

• Previous milestone was series A funding 1-2 years out of college

• Current reality are [sic] $10B companies within years of graduation

• New metric is 0 to $10-12M revenue in 12 months

  • Sure, you might be able to get to $10-12M in revenue in 12 months. But can you perfect organizational design? Talent retention? Leadership voice? Compounding brand identity? These are vital to the building and scaling of durable businesses, and they take time.

• B2B SaaS now shows hypergrowth previously reserved for consumer social

The technical expertise renaissance

• Pre-AI: domain expertise was king, technical skills commoditized

• Post-AI: technical expertise is now the differentiator

  • Again, we maintain that critical thinking remains a differentiator. But we also disagree that domain expertise has been dethroned (and that it can be developed in a timeline of 1-2 months, lol). It remains important not only to have a distribution advantage, but also to build the right products. In the same talk we cited earlier, Jensen Huang continues, “The people that understand how to solve a domain problem—those people who understand domain expertise—now can utilize technology that is readily available to you.” The power of AI lies in the augmentation of domain experts who can apply it usefully and responsibly in their fields.

• College students leading AI implementation over experienced professionals

• Opportunity here to become a “forward deployed engineer” in any industry

  • If you don’t know what a “forward deployed engineer” is, you’re not alone. All it means is an engineer who works directly with customers to solve their problems. Its roots lie in the military, where forward deployment is the practice of establishing a military presence in a foreign country. We don’t know why business people are always appropriating terms of warfare. You’re a B2B SaaS engineer—not a combat soldier.

  • Still, the value of closing the customer empathy gap is meaningful. As technical capabilities accelerate faster than human understanding, the most valuable builders are often the translators, the ones who can transform advanced technology into practical utility. And we’re not talking only about engineers—designers, marketers, and beyond benefit from “forward-deploying” (gag, read: embedding) themselves into the environments they hope to change.

Advice for students & new grads

• Go “undercover” in industries you want to disrupt

  • Skip the “go undercover” bit (see below for why that’s weird) and instead ask your classmates, friends, neighbors the big question: “How can I help you?” If you ask 50 people how you can help, you will surface patterns that highlight your unique insight. From there, you might find a problem worth solving that actually aligns with your expertise.

• Timeline of 1-2 months to become expert in new domain

  • We’re sorry, but who can become an “expert” in a new domain in 1-2 months? Even considering the efficiency gains with AI, this statement is hyperbolic to the point of being irresponsible, a reflection of ego more than expertise.

• Industries are receptive to “AI magic” from college students

• Avoid credential maximization, focus on real outcomes, not external validation

  • Are market outcomes—like the $10B valuation mentioned above, let’s say, or even “YC25” on your LinkedIn—not external validation? Whether the piece of paper is a diploma or a term sheet, it’s still external validation, and you can’t achieve your way to happiness. You don’t need academic or market validation to be worthy. None of your friends love you for your “real outcomes.”

  • Separately, this statement coming from YC feels pretty hypocritical. YC runs four batches per year. The reality is that it relies increasingly on quick signals over deep diligence. Under this model, credential maximization is one of the most streamlined paths to success.

• Beware of entrepreneurship programs that teach you to “lie” or fake progress

• Learn through side projects, not just coursework

  • God knows we’re in the era of the side hustle. Of making sure that every second of every minute of every hour of every day of our lives is optimized, even while we’re asleep. While side projects are great, you don’t need to be productive all the time. You don’t need permission from your Oura ring to take a nap, and you don’t need your Apple watch to take a meandering bike ride through the neighborhood with a friend. You can read a book that’s not self-help or self-advancing. You can paint a bad picture. You can fall on your ass. You can drink fruit smoothies and lie out in the sun, not because you’re recovering from a tonsillectomy, but just because it makes everything better. You can do what you want to. You will be loved for it.

Should you drop out?

• Do you trust the company/founder?

• Is it actually a good startup?

• Are you genuinely done with college?

• Additional considerations

  • Have you explored alternative career paths?

  • Are you making a fear-based or excitement-based decision?

    • We actually love this one. No notes except that we might not have relegated it to a sub-bullet under “Additional considerations.”

Starting a company

• Make sure you have financial runway, 6-9 months minimum living expenses

• Try not to do it alone, find a co-founder to work with

  • Yes, completely agree, AND we actually wouldn’t overthink the whole skill complementarity thing as much as the internet overhypes. Startups are emotionally destabilizing; having someone to share the weight is often the reason a company survives. So choose your partner wisely—not necessarily for how their skill-set supplements yours, but rather for how they see the world and how you treat each other.

• Being niche at the start has always been the recipe to succeed

  • All good, but most importantly think about your why.

It is easy to feel unmoored amidst all this talk about AI. To re-ground ourselves, then, here’s our small guide on how to spend your 20s, and your 30s, not necessarily “in the AI era,” but just in the world.

1. Make room for exploration: Make like a bird and get lost! Then find your way back home. Trust your instincts, follow what draws you, learn to read your inner compass.

2. Make room for cognitive dissonance: You won’t always be consistent. Welcome disagreement, and changing your mind. As Walt Whitman wrote in “Song of Myself,” “Do I contradict myself? / Very well then I contradict myself, / (I am large, I contain multitudes.)”

3. Be kind to yourself (and others): Don’t beat yourself up when you encounter dead ends! It’s all information. As my grandmother always said, “Work is never lost.” And give the same grace to others—the smallest interactions (with waiters, with friends) define our character.

4. A good hour and a bad hour: If you’re like us and your line to your inner voice has been disconnected for…too long, try an exercise we like to call “a good hour and a bad hour.” It is what it says it is: throughout the day, or at the end of each day, keep a log of what you did, and if those hours you spent filled you with energy or drained you of it. Notice the patterns. They’re messages from you. The goal is simple: to have more good hours and fewer bad ones. Over time, hopefully, you’ll have a life that you won’t want AI to automate.

5. Don’t hurry so much: The meme puts it best:

   

   YC might tell you that you need to reach a $10B valuation before you’re 25, Forbes might show you 30 people who have achieved more than you before they’ve turned 30, and internalized pressure might convince you, especially as a woman, that you need to achieve everything you want to achieve in your career before you have children. But try not to race your way out of your 20s. Live slow and die old. Things move too fast in this world as it is.

6. Surround yourself with people you admire and want to learn from: People often talk about wanting to reform systems from the inside, and while we deeply admire people who dedicate their lives to changing corrupt and destructive systems, we also caution them not to let those systems change them in turn. We are mimetic creatures by nature. We learn by watching and repeating whether we like it or not. So watch what you want to model. Because as one of Nietzsche’s apothegms goes, “He who fights with monsters should be careful lest he thereby become a monster. And if thou gaze long into an abyss, the abyss will also gaze into thee.”

7. Surround yourself with love, including from yourself: A top school doesn’t make you lovable. A prestigious career doesn’t make you lovable. Botox doesn’t make you lovable. A curated Instagram doesn’t make you lovable. Ask your friends why they love you—I guarantee you none of them will cite any of the things you’ve chased to outrun your own insecurities (and if they do, they’re bad friends). You were born imperfect and lovable. Both God and human evolution agree on that fact.

So we’ll leave you with this prompt: how would you change your life if you really believed that you didn’t need to maximize anything—be it prestige, productivity, wealth, or beauty—in order to be loved? And how can you work on giving yourself permission to make those changes?

We’re in this together. We love you.

Then our answer is this:

When you are a writer you are effectively a translator of sense—of vision, of experience, of the visceral, of the sublime—and so I write to listen closely to life so that I may capture what it is saying faithfully, and make it legible to others: its immediacy, its force, its unflinching horror, its insistent beauty.

Also this:

To understand who we are. I write to make sense of the nature we’ve inherited and the nurture we’ve learned—to surface the stories we have carried within us all along.

What we’re saying, in many words, is this: anyone alive with words has the capacity to be a writer. She who perceives, he who feels—both are writers.

In past posts, we’ve described a disorientation of sense at the hands of large language models. Our helper bots can rearrange words, giving you a menu of ways to express the same thing; speak in metaphor decently well, though often too cloyingly; and drop bars that have all of the trappings of beauty, and yet are not beautiful.

But our bots do not write, or speak, or mean. They mimic symbolic patterns, convert those patterns into phonemic ones, and produce something that “means” something only in the sense that it has semantic meaning. Now, we’re not linguistic philosophers (though one of us is descended from one), but we posit that semiotics—or the study of meaning-making—has to do not only with the arrangement of symbols and their dissemination in context, but also with the consciousness (or lack thereof) of the messenger. To convey meaning is at once a practical act and a metaphysical one. The uncanny valley is boundless. No matter how advanced the models become, they will always remain just that: models. Representations. Replicas. Forgeries. Frauds.

When we reach for an LLM to anesthetize our fear of the blank page, we bypass the disquieting uncertainty that makes writing truly meaningful. As Flannery O’Connor wrote: “I write because I don’t know what I think until I read what I say.” Joan Didion came to a similar conclusion: “I write entirely to find out what I'm thinking, what I'm looking at, what I see and what it means.” This process of discovery and distillation requires the writer to metabolize the world slowly: to release heuristics and falsehoods and clichés and half-truths; to regard the order of things with receptive curiosity and reverent attention; to arrive, finally, at something true. Writing is a form of thinking as well as self-making: in the pits of ambiguity, and in the misfires of off-kilter sentences, we discover what we want to say, and in turn who we are.

But it’s not an entirely solitary activity: to communicate is a social act, driven by our instinctive drive to be heard and known by others. Good writing will offer, “Here is how I see the world…does it speak that way to you, too?” And it will offer this communion across time and space, as writers are always speaking to their invisible friends, to you, and to me, and to someone yet to come.

If we let machines speak for us as proxies before we’ve found our own voice, we risk not only truth, but also love.

AI creep

You’ve likely noticed an insidious style of writing begin to creep over the internet like an invasive species. It’s benign enough to ignore, you think—easy to read, good enough considering the efficiency gain. We at Whimsy HQ are no strangers to a good LinkedIn hate-scroll (doom-scrolling = endlessly scrolling through vacuous or negative information, symptoms: dissociation, despair; hate-scrolling = endlessly scrolling through garbage or provocative information, symptoms: anger, also despair). The posts on our feeds come from profiles that represent real humans—maybe even real humans pasting their GPT’s output into the text-box—but there is no mind, only machine.

We often send each other marked-up screenshots of AI language slop—not to mock the humans posting it but to mourn the graveyard of fully fledged ideas: post after post of voiceless, viral content, provocative theses neatly outlined with emoji bullet points that garner an endless stream of likes and comments in unspoken praise of the LLMs that wrote them. People share the post, but no sharing actually happens. It’s a holographic feast that leaves you nauseated and starving.

It’s only towards the end of the hate-scroll that we notice the sadder thing, the loosening grip—the surrender. We’d rather hide behind LLMs than reveal our true thoughts, take cover under words that fit the formula for viral growth than risk having our own words fall flat on engagement metrics. After all, if AI represents the promise of super-intelligence, do we then represent the embarrassment of sub-intelligence? Every time we scroll, we imagine ourselves hacking through the invasive plant’s thick and gnarled branches trying to clear the way back to reality.

In honor of our journey through the thicket, we’re here to map the perils. (Note: this doubles as a drinking game.)

Our 9 Circles of Written Hell™

1. Buzzword Bingo (this one’s a layup).

   To quote Mama Virginia Woolf: “Words do not live in dictionaries, they live in the mind.” And I promise you—“paradigm shifts” do not live in my mind. Is your startup idea really “unprecedented”? “Future-proof”? And while we’re on the subject, when you ask us to differentiate between a 10x founder and a 100x founder, are we still on a linear scale? Perhaps the next decade begs for the i⁵x founder, since the whole thing's imagined anyhow.

2. The Overwrought Antithesis.

   “It’s not X, it’s Y.”

   “The real question isn’t if ___, but how ___.”

   “This isn’t just about ___, it’s about ___.”

   Or, bonus example including the ubiquitous question-answer structure: “The risk? Minimal. The reward? Massive.” (Show! Don’t tell us the answers!)

   Look for them—once you see them, you can’t unsee them.

3. The Alliterative 3s!

   “Speed, scale, stability.” “Code, context, capability.”
   Growth, grit, guacamole. Leverage, liquidity, linguini.
   This is your brain on ChatGPT.

4. Anaphora Inferno

   Repetition is powerful.

   Repetition is persuasive.

   Repetition is predictable.

5. “The Adverb Is Not Your Friend.” (Stephen King)

   An example is best:

   She gently touched his arm and softly whispered, “It’s going to be okay,” while he nervously glanced around the room. The wind howled eerily outside as the candle flickered weakly on the desk. He slowly touched his keyboard, tepidly erasing the adverbial letters “L,” “Y.”

   versus

   She touched his arm. “It’s going to be okay,” she said. He glanced around the room. The candle flickered on the table. Outside, the wind howled. He touched his keyboard and erased the adverbial letters “L,” “Y.”

6. Binary Bait

   You’re either building AI—or getting replaced by it.
   Ship fast or die trying.
   You’re either part of the solution or part of the problem.

   I wonder, if we introduced an “and” to sentences like these, how much more interesting the internet might be…

   You’re building AI and getting replaced by it.

   Ship fast and die trying.

   You’re part of the solution and part of the problem (relatable).

7. The Hollow Hedge

   Even as they confidently assert brazen hallucinations as well-researched facts, our large language models are apparently also not too sure of themselves and just want us to like them! Somewhere along the way, they picked up a manufactured politeness—probably from junior women asking for raises (we, too, were trained), perhaps in an attempt to pass the Turing Test.
   Common examples: “Just something to think about….” or “It’s kind of amazing how we do this…” I particularly like “A bit of a shift is happening” and am curious how one distinguishes the shift from the bit of the shift.

8. The Prophetic Catchphrase

   “The future is here.”

   “That’s the thing about X—it’s Y.” For example: “That’s the thing about time—it always runs out.”

   If it belongs on Home Goods wall art, it doesn’t belong in your prose.

9. The Em-Dash Witch Hunt!

   Before you come for my precious, beloved, unassailable em dash—that wonderful embodiment of the stream of consciousness—as the telltale signature of ChatGPT, consider all of the above. How the em-dash—which, speaking of semiotics, is a legitimate symbolic representation of a break in a thought like this one—became the single scapegoat, we do not know, and we are here to come to its defense.

   
   Take Emily Dickinson’s “Crumbling is not an instant’s Act” (not only for its lovely use of the em-dash, a punctuation mark she loved and used liberally, but also for its warning to us in our time…). Here is the last stanza:

   Ruin is formal — Devil's work
   Consecutive and slow —
   Fail in an instant, no man did
   Slipping — is Crashe's law —

   The em-dash after “slipping” enacts the slip — one slip — and then another. The poem ends at this last slip—crashes as promised by the penultimate word. It seems abrupt until you realize that the em-dashes carried you there. Crumbling is not an instant’s act. It is the result of one too many slips.

TLDR: it’s not the em-dash’s fault!!! God, even our accusations of what makes writing unoriginal aren’t original. Think bigger, people. Leave the em-dash alone.

New Rules on the Block

We’ve returned from hell and brought the em-dash back with us. To restore the ground beneath our feet, let’s come back to what good writing should feel like. Because LLMs are trained on all of the good writing rules, you’ll notice that a few of these rules are now worth breaking. We’re also not saying we’re experts, so we’ve borrowed a few principles from the greats. And before you say “this is only applicable to fiction, why would I use this for work?”—just pause, take a breath, think about it…

• Play with structure. Try flipping the narrative arc, or starting in the middle. Let form follow feeling. “All style is, is the awkwardness of a writer in stating a fact,” Hemingway once said, so if the sentence feels awkward, instead of criticizing it, let it be a signal that you’re on your way to saying something. Then edit it. Then edit it again. Then leave it when it feels like it’s awkward in just the same way that you so delightfully are.

• Let the rhythm stutter, as one might in conversation. Try overlapping thoughts, or interrupting yourself. Pull a Virginia Woolf and just write long sentences given relief only by semicolons—or take em-dashes for a spin.

• Give resolution a rest! Leave the question unanswered, let your readers bask in the tension of silence…

• Write badly, for yourself. Then edit. Then remember your reader. Hemingway again, “The first draft of anything is shit.”
  But also: “When you first start to write you get all the kick and the reader gets none, but after you learn to work it’s your object to convey everything to the reader so that he remembers it not as a story he had read but something that happened to himself.”

• Don’t wait to be inspired. As a callback to the beginning of our piece, “She who perceives, he who feels—both are writers.” So, hate to break it to you, but you are indeed a writer. And writers don’t get to wait until they are decidedly “in the mood” to put thought to paper. From Octavia Butler: “The second [rule] is to write, every day, whether you like it or not. Screw inspiration.”

• Use whatever medium gets the words out. Moleskin, Notes app, your favorite Speech-to-Text provider—we’re not so stodgy as to say that writing must start with a pen and paper (even if it hurts). The form can evolve as long as the thinking persists.

• LLMs are (sometimes—mostly not—but sometimes) okay. AI editors can be helpful for proofreading or editing grammar after the fact—that is if you’re not intentionally trying to break away from grammatical convention. For the process of writing itself, we think it’s best used as negative space against which to define yourself. Maybe you have a couple of stray thoughts you want to stitch together, and you ask ChatGPT to help out. Resist the temptation to accept what it feeds you. Respond to it, resist it, wrestle with it: is that really what you mean—really, really? Listen closely for your own voice—we bet it’s telling you what you really want to say.

• “Keep human!” wrote Henry Miller, “See people, go places, drink if you feel like it.” Stories are alive in the world around us—look up and breathe in. Even your LinkedIn post will be better for it.

• Pay close attention. Tell us about what your protagonist is holding—not “fruit,” but the dusty skin of a peach, thumb-split and half-bloomed in the Southern heat. Not “depression,” but “the way the eye of a tornado must feel, moving dully along in the middle of the surrounding hullabaloo” (Plath). Not “anxiety,” but “the cousin visiting from out-of-town depression felt obligated to bring to the party” (Benaim).

• Conceal strategically. The details that matter, matter. The details that don’t, don’t. “Description begins in the writer’s imagination,” Stephen King reminds us, “but should finish in the reader’s.”

• Be patient. Good writing takes time. Just as knowing yourself takes time. Take your thoughts out on a date, and let your drafts teach you. They will reveal, gradually, the truth. Writing is not an instant’s act, either.

For more pointers, see the Marginalian’s summary of Zadie Smith’s 10 rules of writing, Kurt Vonnegut’s 8 guidelines for a great story, David Ogilvy’s 10 no-bullshit tips, Henry Miller’s 11 commandments, Jack Kerouac’s 30 beliefs and techniques, John Steinbeck’s 6 pointers, Neil Gaiman’s 8 rules, Margaret Atwood’s 10 practical tips, and Susan Sontag’s synthesized learnings.

Here’s to blank pages, and happy endings.

P.S. If you ever feel like you can never quite capture the truth of what you see, or how you feel, know that you’re not alone. Here’s a poem, and a prayer, for those moments. To remind you that yes, it’s impossible, and yes, it’s urgent to try anyway.

Epilogue

By Robert Lowell

Those blessèd structures, plot and rhyme—
why are they no help to me now
I want to make
something imagined, not recalled?
I hear the noise of my own voice:
The painter’s vision is not a lens,
it trembles to caress the light.
But sometimes everything I write
with the threadbare art of my eye
seems a snapshot,
lurid, rapid, garish, grouped,
heightened from life,
yet paralyzed by fact.
All’s misalliance.
Yet why not say what happened?
Pray for the grace of accuracy
Vermeer gave to the sun’s illumination
stealing like the tide across a map
to his girl solid with yearning.
We are poor passing facts,
warned by that to give
each figure in the photograph
his living name.

Read more

Read more

We begin in medias res, not knowing yet if what we are witnessing…

Read more

We all know the adage: two’s company; three’s a crowd. The three-body problem is famously unstable. Vogue recently published a piece titled “If The White Lotus Teaches Us Anything, Let It Be This: Never Take a Three-Person Girls’ Trip.” In other words, triadic tension tends to wobble, and someone always ends up orbiting. Four is more stable, but can split into predictable pairs. Five is tricky with a “swing vote” dynamic. But what about six? No laws of nature are compelling you into any one configuration: you can be three couples, or two triplets, or, in poetic terms, a quatrain and a couplet (the closing 6 lines of a Shakespearean sonnet), or a complete sestet (the closing 6 lines of a Petrarchan sonnet). Like a jazz sextet, to borrow this time from musical terms, there is harmony with responsibility in every note.

Still, numbers alone don’t guarantee intimacy. I’ve been in groups of three that felt expansive, and in groups of eight where no one said anything real. Anthropologist Robin Dunbar might explain that it’s a question of cognitive load. His research suggests our brains are wired for layered social circles (interestingly in multiples of five): five intimate ties, fifteen close friends, and fifty meaningful connections. But intimacy isn’t just about who fits in which layer—it’s about how fluidly people can move among them. Some of the most electrifying moments happen in the liminal space, when someone who was once a plus-one becomes a confidant, or when two people make an unexpected connection that shifts the group’s center of gravity.

The fabric of intimacy. There’s a specific kind of intimacy that lives in the pause before someone speaks. Silence can be deeply meaningful when met with attention—when we bask in the safety it invites. I think these brief moments compound, like a symphony of micro-calibrations that move a group from coordinated to connected. Human glue made of shared time, and maybe a second glass of wine.

Intimacy also scales through narrative. The Science of Storytelling explains that humans bond through the stories they share. Every group has an implicit script: heroes vs. villains, what the good guys are fighting for, and how gravity works in their world. To belong, you internalize the story. To matter, you become the protagonist. In his writings, Yuval Noah Harari uses the term "imagined orders" to describe shared beliefs and stories that humans create to organize society and assign meaning to things. These imagined orders (e.g., myths, religions, laws, and ideologies) enable large-scale human cooperation by shaping trust and understanding. They are based not necessarily on objective truth, but rather on collective belief. It’s how Theranos was able to raise $9 billion—not because the tech worked, but rather because people wanted to believe in the myth of a “female Steve Jobs.” More than just backing a diagnostics company, they were buying into a modern reimagining of an old origin story.

For all the ways in which technology has abstracted our connections, there has been a growing hunger to feel something real again. You can see it in the resurgence of supper clubs, the way we romanticized analog hobbies in 2020, the therapy-speak that’s crept into Hinge profiles (@beam_me_up_softboi for a belly laugh). In a post-(acute)-pandemic, post-remote, post-“hustle culture”, post-hypergrowth moment, people are finally asking: what if intimacy is the point?

In one of TikTok’s/Instagram’s many viral trends, one reel format that has emerged is the collation of the small moments in life—the moments of intimacy we share with our friends, with our partners, with our children, with our animals, with nature—bearing the caption, typically in all lowercase letters: “almost forgot that this is the whole point.” The reels are set to the first few notes, played on the piano, of “Take My Hand” by Matt Berry. The trend is a collective invitation to intimacy—to take each other’s hands, to whisper in lowercase voices, to remember why life is worth living.

After decades of designing for efficiency and scale, of getting more done with fewer people, maybe we're starting to remember—and to protect fiercely—the quiet joy of building deliberately, with people we trust. Move fast and break things met with move slow and nurture things.

And yet, as our personal lives bend toward reconnection, the workplace drifts the other way. The age of the deployment of AI agents means that more and more, white-collar workers find themselves leading tools rather than teams. Or the “team” becomes a silent stack of models, plug-ins, and prompts. Ted Chiang writes that AI is a form of lossy compression—it preserves what we can measure and discards the rest. Like a JPEG that blurs subtle gradients in service of saved storage, AI smoothes the interpersonal mess that comes with collaboration in favor of saved costs.

In Singapore, nearly 1 in 5 full-time workers are projected to be displaced by automation in 2028—the highest rate in Asia. It’s perhaps unsurprising for a country that’s long stood as a global emblem of efficiency and innovation. But this projection points to a deeper reckoning that most advanced societies will have to confront. As tools become more capable, it's no longer a fantasy to imagine a one-person, multi-agent, billion-dollar company. What once took 100 people to build now takes just 1. So if AI renders 99% of knowledge-work obsolete, what is left for our knowledge to do?

The Marxian prediction feels more prescient than ever: alienation as the inevitable consequence of labor, divorced from its social and creative roots. In this new paradigm, human-to-human interaction will matter more, not less. And the companies that build for this end, where people feel seen and needed, will be the ones that endure. So the fundamental question to ask is: how do we design for this new world? Do we focus our recruiting efforts on joining companies that preserve human connection, through product or through culture? Create them ourselves through distributed leadership and community-first design? Or fund the next generation of institutions that don’t just run on output, but on culture?

Maybe what I meant to talk about here isn’t optimal group size, but rather the optimal conditions for intimacy—how we create it, how we lose it—and the absolute necessity of it. The future of work may be an automated, asynchronous place, but the ancient circuitry of belonging will always endure in our brains. In the end, whether it’s a startup or a six-person congregation on Memorial Day, maybe it’s the means that gives the whole end meaning. To feel seen, and connected, to be part of something with a beating heart.

There’s a poem by James Wright called “Lying in a Hammock at William Duffy’s Farm in Pine Island, Minnesota.” The long, particular title summarizes the project of the poem: he describes everything that he sees lying in this hammock in great, loving detail. This attention is a kind of intimacy, a communion with the present moment, and all of its inhabitants. After this extended exercise in devotion—almost prayer—he concludes: “I have wasted my life.” In other words: he has spent his life in a forgetful haze, failing to remember that this attunement with our very world—noticing the peculiar way the butterfly sleeps, noticing the fading sound of the cowbells as they “follow one another / Into the distances of the afternoon”—is the whole point.