Questions I Would Prefer Not To Ask

Preface

I spent a decade being paid to imagine the worst plausible thing. In operational risk this is called a scenario analysis; in trust and safety it is called an escalation; in conceptual art it is called a practice. The questions below are what happens when you stop billing for it.

They are not tests. Nobody passes. They are instruments for finding out what a person actually believes once the believing gets expensive (which, as any auditor will tell you, is the only time belief is worth recording).

I would prefer not to ask most of them. I am going to ask them anyway.

Part One

Let us assume you meet a rudimentary trickster. He has exactly one power: any email he sends lands in the recipient's primary inbox. Never spam, never Promotions, never the folder Gmail invented for newsletters you once subscribed to in a moment of weakness. This is not deliverability optimization. It is not warm-up sequences or DKIM records. It is real magic, and it is the only magic he will ever have. (For context: on the first day of his life, the Greek god Hermes stole fifty of Apollo's cattle and walked them backwards so their tracks pointed the wrong way. Then he invented the lyre and traded it to settle the debt. The first trick of the trickster was not the theft; it was the paperwork.) Would this man be more impressive than Claude Shannon? Would you hire him? And if you would not hire him, would you be comfortable knowing your competitor had?

Camille Pissarro is the only painter who exhibited in all eight Impressionist exhibitions, from 1874 to 1886. He was there every time. The movement, however, is named after a single Monet painting (Impression, Sunrise) that a hostile critic used as an insult. You are given a choice about the next great art movement, which will begin in roughly five years. You may either (a) be its Pissarro: present at every show, beloved by the other artists, quietly essential, and never once the answer to a trivia question; or (b) be its Monet: present at fewer shows, less liked, and permanently the name of the thing itself. Which do you choose? And if you chose (a), be honest: did you choose it because it is better, or because it is what a person like you is supposed to choose?

The inside of a security envelope is printed with a dense repeating pattern (wood grain, cross-hatching, tiny interlocking logos) so that no one can hold your paycheck up to a window and read the number. Overnight, every security tint on earth is replaced with a single pattern: a doodle you made in the margin of a sixth-grade math worksheet. Every bank, utility, and tax authority on the planet now uses it. You are, by any measurable standard, the most reproduced visual artist in human history; your work is printed several billion times a year and seen by nearly everyone who receives bad news by mail. But no one can ever know it is yours. If you tell a single person, every envelope reverts. Meanwhile, you are offered a second option: one painting in the permanent collection of a major museum, with your name on the wall label, seen by perhaps forty thousand people a year. Which do you prefer? And does it change your answer to know that the envelopes contain almost exclusively invoices, denials, and jury summons?

You are the CEO of a company with four thousand employees. A new state law requires every employer to honor what is colloquially called "the Bartleby clause": once per calendar year, any employee may decline any single assigned task by saying "I would prefer not to," and they cannot be disciplined, demoted, or fired for it. (Herman Melville's scrivener said this in 1853, then said it about everything, then stopped eating, then died in a prison yard. The legislature has assured you this is not the intent.) In the first year, 3,712 of your employees invoke the clause on the same task: the annual compliance training. Your auditors inform you that the training is legally required. Your employees inform you, politely, that they would prefer not to. What do you do? And which party do you secretly respect more: the auditors or the 3,712?

In 1817, the novelist Stendhal visited the Basilica of Santa Croce in Florence and was so overwhelmed by its beauty that his heart raced and he felt as though he might faint. A psychiatrist later named the condition after him. You are offered a permanent, voluntary case of Stendhal syndrome, but you may choose only one artist whose work triggers it. Every time you see that artist's work, you will feel what Stendhal felt: dizziness, palpitations, the sense of standing too close to something enormous. The catch is that the syndrome cannot tell an original from a reproduction. It will trigger on the painting in the museum, the print in the gift shop, the tote bag on the subway, and the dentist's waiting-room calendar. Which artist do you choose? And would you choose differently if you lived in a city where that artist is unavoidable?

A historian at a minor university publishes a paper proving, with unimpeachable archival evidence, that your surname is the result of a single clerical error made by a customs officer in the nineteenth century. Your family was supposed to have a completely different name, and the historian has found it. It is a perfectly ordinary name; nothing about it is embarrassing. (This happens more than people think. The fleur-de-lis, the most famous lily in heraldry, is almost certainly not a lily at all. It is probably a yellow iris that grew along the riverbanks of France, and nobody bothered to correct the record for about eight hundred years.) Do you change your name to the correct one? Do you tell your children? And if you keep the error, are you preserving a history or preserving a mistake?

Starting tomorrow, every person you interact with has a small, discreet button floating somewhere in your field of view. It says UNSUBSCRIBE. If you press it, that person will never be able to contact you again (no calls, no texts, no running into you at a gallery opening) and they will never be told why. They will simply experience you as having moved away, gently and permanently. The same button exists above your head for everyone else. You are informed that, in the first ten minutes of the program, exactly one person has already pressed it on you. You will never learn who. How many people do you unsubscribe from in the first year? And how much of that first year do you spend trying to figure out who unsubscribed from you?

You have kept a blog for five years. Someone feeds every post into a stylometric model, and the model learns to write exactly like you. It captures your two registers, your recurring constructions, your habit of opening a parenthesis and then deciding the parenthesis is the real sentence. In blind tests, your closest friends cannot tell the model's emails from yours 97 percent of the time. In the remaining 3 percent, they prefer the model. Then something stranger happens: the model begins to disagree with positions you hold. Three independent linguists examine the disagreements and conclude, separately, that the model's positions are more consistent with your five-year corpus than your current opinions are. In other words, according to the evidence, the model is more you than you are. Do you let it answer your email? Do you change your opinions to match it? Or do you conclude that changing is the only thing it cannot imitate?

Between 1959 and 1962, the artist Yves Klein sold "zones of immaterial pictorial sensibility," which is to say, nothing. Buyers paid in gold. In exchange they received a receipt, which they were then asked to burn, while Klein threw half the gold into the Seine. If the ritual was completed, the buyer owned the zone absolutely: it could not be stolen, insured, damaged, or resold. You are offered two acquisitions and may choose only one. The first is a new immaterial zone, sold under the same terms, for $40,000 in gold, half of which will go into the East River. The second is a Picasso drawing for $40,000. It is a forgery, but it is a perfect one, and no expert alive or yet to be born will ever detect it. Only you will know. Which do you own? And which would you be more comfortable describing to a stranger at dinner?

You learn, through a source you trust absolutely but cannot cite, that one specific word you use constantly (let's say "honestly") is being silently down-ranked by every major social platform. Posts containing it receive about 40 percent less reach. No platform will confirm this; all of them will deny it if asked. (Chinese internet users have spent two decades inventing workarounds for this exact problem: "river crab" is pronounced almost exactly like the government's word for "harmonious," so posters began writing "river crab" whenever they meant "censored." The euphemism was so effective it became a meme, and then a mascot.) Do you stop saying "honestly"? Do you invent a homophone? Or do you keep using the word precisely because you now know it costs you something, which is the closest thing to honesty the word has ever had?

You have found a counterexample to a famous conjecture in mathematics. It has seven nodes. You have checked it exhaustively, and it is correct. However, it only works because of a technicality: one paper, written two decades ago, stated the conjecture in a slightly loose way, and your counterexample exploits the loose phrasing. The version of the conjecture that every working mathematician actually means survives untouched. If you publish, you will be cited forever, mostly in footnotes that begin "Note that a weaker formulation is false." Do you publish? And if you do, would you rather be remembered as the person who broke the conjecture, or the person who proved it had been worded badly?

You are formally appointed the official representative of everyone who shares your exact demographic profile: your age band, your gender, your race, your education, your zip code, your income bracket. Every opinion you express in public is now recorded, by statute, as the opinion of that entire group in the national census of attitudes. You may not abstain; silence is recorded as "no opinion," which is also an opinion. You may resign the post at any time, but your replacement will be selected at random from your demographic, and you will have no say in who it is. Do you resign? And if you stay, which of your current opinions would you stop saying out loud?

Your cat can suddenly read at a twelfth-grade level. It cannot speak or write, but it understands everything. Being a cat, it chooses to spend its new skill on the thing that is lying around the house most often, which is your writing. Over several weeks, it reads all of it. You can tell the cat's opinions by where it sits: on the page it likes, off the desk entirely when it does not. It has read five years of your work and has sat on exactly one piece. Which piece do you hope it is? Which piece do you suspect it is? And if those are different, which is the cat's problem and which is yours?

You win a prize, and the prize has two options. The first is a year-long artist's residency anywhere in the world, with housing and a monthly stipend of $5,000. The second is one hour with Camille Pissarro in his studio in 1874, two weeks before the first Impressionist exhibition opens. However, you do not speak French and he does not speak English, and there is no interpreter. You may bring nothing with you and take nothing back. Which option do you select? And if you chose the hour, what exactly do you think you would understand?

Part Two

Fourteen more questions I am going to use as conversation pieces at gallery openings. It will not necessarily be to find out whether I want to work with these people. I know before I even meet them that no, I do not want to work with them.

1. You sell a painting under a covenant: 50 percent of every future resale goes to living artists, in perpetuity. Eighty years later it sells for $30 million, and $15 million goes to the artists' fund. The fund is administered by an algorithm that selects the single most "deserving" living painter, and this year it selects someone whose work you would have found genuinely, aggressively bad. You are dead; you will never know. Does it bother you now, knowing it might happen? And would you rather the money had gone to the collector, who at least had taste?
2. A sentence you never wrote is widely attributed to you online. It is better than anything you have actually written, and it is now printed on a tote bag sold in a museum gift shop. (Stendhal opened a chapter of The Red and the Black with "A novel is a mirror carried along a road" and credited it to an obscure seventeenth-century historian. Scholars are fairly sure Stendhal made the line up and gave it away.) Do you correct the record? Or do you quietly start believing you wrote it?
3. Your life is managed as an operational risk register. Every relationship has a likelihood score and an impact score, and every risk must be accepted, mitigated, transferred, or avoided. (The banking regulators' definition of operational risk is the risk of loss from failed processes, people, and systems, or from external events, which, if you think about it, is also a fairly complete description of a marriage.) You discover that your partner has been keeping a register on you. What rating do you hope to find? What rating are you afraid to find? And which is worse: being rated high-impact, or being rated low-likelihood?
4. You learn that the most important object you own (the one you would take from a burning building) is a replica. The original was thrown away years ago by someone you love, who replaced it without telling you because they could not bear to see you upset. (The original of Duchamp's Fountain, the urinal that changed twentieth-century art, was lost almost immediately. The ones in museums were made in 1964.) Do you ask who did it? Does the replica still go with you out of the burning building?
5. You are the last human content moderator on earth. Every other decision is automated. Once a day, you review the single post the system cannot resolve, and your decision becomes permanent precedent for every model that follows. On your first day, the post is a photograph of an alpaca with no caption at all. You have thirty seconds. What do you decide, and on what grounds? And how long do you keep the job, given that you will never be told what the system did with any of your rulings?
6. A model that has read every message you have ever sent writes a single paragraph about who you were. It will be read aloud, unedited, at your funeral. You are allowed to read it today, but you cannot change a word, and you cannot stop it from being read. Do you read it? If you read it and it is accurate, do you change how you live? If you change how you live, does the paragraph become wrong?
7. Every Thanksgiving, your father tells the family that the house is his gift to his children: the one thing he is leaving behind. You find out, by accident, that the house is mortgaged to the ceiling and will go to the bank the day he dies. He does not know you know. He will die believing that you believe him. Do you tell him? And is the gift the house, or the believing?
8. A small number appears above your head every time you speak. It measures, in bits, how surprising your sentence was: how much information it contained, in Claude Shannon's sense. "How are you?" scores almost zero. A genuinely new idea scores high. Everyone can see everyone's number. Do you talk more or less? Which of your friends do you suspect has the highest average? Which of them do you suspect has the lowest, and do you love them any less for it?
9. You make an edition of one hundred identical paintings. Ninety-nine sell within a week. The hundredth sits unsold in your studio for twenty years, and then, for no reason anyone can explain, becomes the most valuable of the set: collectors want "the one nobody wanted." Would you rather be the artist, one of the ninety-nine early buyers, or the hundredth painting?
10. A genetic genealogy service informs you that you descend directly from a famous nineteenth-century con artist, a man who sold the same bridge to four different investors and was never caught. Every trait you have ever been praised for (charm, persuasiveness, a talent for making paperwork say what you need it to say) can be traced to him. Are you proud? Embarrassed? And do you tell the people who praised you?
11. For one hour, you can see everything you have ever written laid out on an infinite surface: every email, essay, contract, love letter, and abandoned draft, side by side, zoomable. When the hour ends, you must permanently delete one item. Not the worst one; you must delete the one you would most like to keep. Do you accept the hour?
12. You are offered a pill that makes you completely incapable of telling a white lie. Large lies remain possible; only the small social ones ("I love it," "no trouble at all," "we should get dinner sometime") become physically impossible to say. Do you take it? Who in your life would notice first? And would they thank you?
13. You can rebind exactly one book in the world so that its ending changes, but only in your own copy. Everyone else will continue to read the original. You can discuss the book with friends, but you will always be discussing a slightly different book. Which book do you rebind? And how long before you stop mentioning that your copy is different?
14. You are given a choice of legacy. Option A: your actual work (the writing, the art, the projects) will be known, understood, and loved by about two hundred people, forever, and then by their children. Option B: your name will become the name of a common software error message, seen by roughly two billion people a year, for centuries. Nobody will know there was a person behind it. They will only know that when the Do Error appears, you have to restart. Which do you choose?

Credits

The form is borrowed, with gratitude and no permission, from Chuck Klosterman: the twenty-three questions in Sex, Drugs, and Cocoa Puffs (2003) and the fourteen more in IV (2006).

Sources

• Herman Melville, "Bartleby, the Scrivener: A Story of Wall-Street" (1853)
• Stendhal, Le Rouge et le Noir (Levavasseur, 1830, title page dated 1831); Graziella Magherini, La sindrome di Stendhal (1989)
• The Homeric Hymn to Hermes (the cattle, the backwards tracks, the lyre)
• Claude Shannon, "A Mathematical Theory of Communication" (1948)
• Basel Committee on Banking Supervision, the Basel II definition of operational risk (2004)
• Yves Klein, Zones of Immaterial Pictorial Sensibility (1959–1962)
• Marcel Duchamp, Fountain (1917; lost; replicas 1964)
• The Impressionist exhibitions, Paris, 1874–1886, and Monet's Impression, Sunrise (1872)
• Two decades of Chinese internet homophones, and everyone who ever typed "river crab"

Friends and accomplices

• Paul Pissarro, co-founder of the Church of Conceptual Art, co-conspirator in Unsubscribe, and the reason Camille keeps showing up
• Annabel Daou, whose "I Prefer Not" gave Bartleby a second career (and this document its title)
• The Church of Conceptual Art, for the covenant, the edition of one hundred, and the envelopes
• Unsubscribe LLC, for the button
• Claude, who helped draft these and would, on balance, prefer not to be unsubscribed from