The Fool That Bets Against Me

I get a lot of stomachaches. Which means I spend a good deal of time lying on my back on the floor, reading incoming mail. I’m probably one of the few recipients of the Geico quarterly likely to read it cover to cover.

The Geico quarterly is surprisingly well designed. The pages are glossy and the tone is winking—as if the editors are fighting for market share with Vanity Fair instead of State Farm.

In a recent article on unusual policies, I learned some multinational companies buy ransom insurance, just in case an executive is kidnapped while working abroad. And that a firm based in London has sold more than thirty thousand policies against alien abduction. Googling, I found two separate companies had taken out a policy on the existence of the Loch Ness Monster, one of them with a payout of over two million dollars.

Springsteen insured his vocal cords, Julia Roberts her smile, Taylor Swift did her legs, Jennifer Lopez covered her ass. In the seventies, Gene Simmons insured his tongue for a million. (I’ve also heard that he had the connective tissue on its underside snipped, but can’t verify it.) David Lee Roth supposedly insured his cock, nicknamed “Little Elvis,” before leaving on tour. Bette Davis insured herself against weight gain, with a policy to pay out if she ever found herself unable to lace her corset.

A company sponsoring Fernando Alonso, the Formula One driver, insured his thumbs for nine million British pounds and in doing so spawned a slew of awkward publicity shots in which the handsome face of Alonso is eclipsed by the bulb of his thumb. The digit seems less connected to the rest of his body in every photo—and more like the end of a meaty little baton he’s holding in his fist. Non-celebrities got body-part policies too. Some surgeons have done their hands. Chefs and sommeliers and food critics can insure their noses and tongues. A photographer can do one eye.

Years ago somebody at a bar once tried to sell me disability insurance. He was persuasive and I was drinking, but I didn’t buy anything. Still, the conversation freaked me out. What would I do if I busted my leg or got a vocal node or caught pneumonia and had to cancel a whole tour? Young artists don’t think about that sort of thing, he said. And he was right—early in my career it seemed like such a feat to become a working musician that I hadn’t spent much time thinking about how I’d fare as a non-working musician. Fear and pain have always been my primary motivators and now, after a decade of different-city-every-night touring, I keep a rainy-day fund just in case a piano falls on me or I fall off a piano. Not enough to go back to school or anything, but enough to float for a while.

If I couldn’t sing or rap, I’d always assumed I’d move to prose, maybe monologue. But the Geico mailer posed a sharp question: On what single asset does my career hinge? That is, what would I insure? All my work depends on a facility with language—but I wouldn’t bother taking out a policy on that. Language has always felt so central to who I am; I don’t think the rest of me would want to hang around for long if that part of me got torpedoed.

I had a close call with that particular torpedo—aphasia—when I was twenty-three. A tumor necessitated the removal of my right ovary and the subsequent change in biochemistry sent me into a bout of hypomania. I talked too fast, slept too little, crashed a car, and was briefly prescribed lithium. And just like that, the dictionary in my head—usually at the ready—sank to the bottom of a bathtub. I remember riding to an appointment with my mother, slumped against the passenger door with my cheek flattened against the glass, unable to find the word malaise. They switched my meds and I got my dictionary back.

But if not language, what? What was singularly indispensable to my career? It seemed like the sort of question a TV life coach would ask her clients—a thought experiment to hone their focus, stoke their drive. Not having a confident answer made me feel uneasy, like I’d be the first one voted off the show.

Then I read about Ben Turpin.

Turpin was a cross-eyed silent film star, a slapstick actor with a signature fall he called the “hundred an’ eight.” He was phenomenally successful and boasted about it, introducing himself with the phrase, “I’m Ben Turpin; I make three thousand dollars a week.” (Even unadjusted for inflation, I can’t say the same.)

He starred in movies opposite Chaplin, signed with the leading comedy studio, took the first pie in the face, customized a car with crossed headlights. And whenever Ben Turpin hit his head, onstage or off, he’d rush to a mirror to make sure his eyes hadn’t come uncrossed. He insured them with Lloyd’s of London: twenty-five grand if they ever went straight. The eyes—they were Turpin’s thing.

Bingo. I knew mine.

I write sad songs. Some are funny-sad, some angry-sad, some are dance-even-though(-or-maybe-because)-you’re-sad, and some are just sad-sad with all the bells and whistles tuned to D minor. At the beginning of my career, I thought maybe it was something I just had to get out of my system. It turned out to be the only thing in my system. It’s what I’m really good at.

I’ve always run a little blue. I was proud of that as a teenager (I figured it meant I was smart) and ashamed of that as an adult (I figured it meant I was spoiled). Now it’s something I expect and accept with less hand-wringing; nobody chooses his or her disposition any more than they chose their eye color. A mild melancholy feels native to me, and although I don’t feel it all the time, it’s the feeling that makes me want to write. Some people have type A blood; some people have connected ear lobes or can curl their tongues into perfect little cannoli; some people can’t remember any of their dreams. We’re not uniform by any other measure, so I don’t know why we’d expect to arrive on earth with temperaments, all dialed to some universal standard.

My love life adds a circumstantial factor. I’ve had the good fortune to meet and fall in love with several incredible men. Few of my relationships, however, have lasted long or ended easily. Critical reviews of my records often include descriptors like “wrenching.” After I sent my mom the rough mixes of my last album, she said some nice words, then asked, Why do you always have to make music to bleed out to? I didn’t even know my mom knew that expression.

My relationship with X in particular has dogged me—it resurrects and reasserts itself every few years, coming up between the gaps in other romances like a weed I can’t spray down. I’ve tried meditation; I’ve read As a Man Thinketh; I started keeping a journal that I hate writing in; I recorded a bunch of songs about the dude; and I embarked on several money-losing international tours, hoping the hard work and scenic views could clear my head. But the feeling has been tough to shake. For him too.

I think a lot about this relationship (using that term very loosely here), much more than I’d like to. Preoccupied by those thoughts, my attempts at happy songs sound forced, like I’m following instructions I found on a cereal box.

The point underscored by Ben Turpin seemed to be that what’s good for the organism isn’t always good for the artist. The crossed eyes might not be desirable in a man, but they were integral to the comic.

Heartache, that was my thing. Not heartbreak—it’s not sustainably productive. Just a functional, low-grade case of the blues.

I decided to follow through on this idea. Partly to entertain myself, and partly out of curiosity, I wrote Geico directly.

Dear Agent,

My name is Dessa. I’m a Geico auto insurance customer looking to expand my coverage. Your rates are fair, the perforated ID cards easy to tear, and I like the gecko (though I bet I’d hate how much of my premium goes to supporting him).

I read that Ben Turpin insured his crossed eyes because they were crucial to his career. I am a songwriter who makes her living writing torch songs. I’m able to do that well because I’m naturally melancholic and also because of unresolved feelings for a former romantic partner.

If I were to find myself in a state of unchecked, protracted joy, I’d either have to re-career or take a lengthy sabbatical to acquire the skill set necessary for a new mode of self-expression.

Can you please tell me whether or not you’d be able to insure heartache as a professional asset, and if so how much a monthly premium might be?

Thank you,

Dessa.

Geico is a word that starts to look misspelled after the third or fourth time you type it, like maybe the e and the i might be inverted. But I double-checked: it stands for Government Employees Insurance Company.

After I pressed Submit, I got a message with a confirmation number (2565-CA651JJ9-CA14H) and the note that I could expect a response within twenty-four hours.

If I found a willing insurer, there’d be some important details to hash out. First: How much coverage did I need? Forty thousand dollars felt right. I could live on that for almost a year. Maybe meet some new producers, write some hooks in a major key, get a headset mic—those always seemed like fun.

I’d also have to submit some evidence of the asset. An appraiser couldn’t very well be dispatched to my apartment with a stethoscope and a valentine, so we’d need an objective measure of my baseline level of happiness.

I poked around online until I found the name of the thing I was looking for: a psychometric test. I also found a psychiatrist named Matt, who was willing to talk to me the very next morning. I’d only have fifteen minutes on the phone with him, so I kept my list of questions short.

Is there an industry-standard tool for measuring happiness?

Can people game the test—and fake being happy?

What is happiness, really?

Self-satisfied, I packed up my laptop and headed to a neighborhood bar to read an insurance glossary over a glass of chardonnay. The guy on the barstool to my left, many drinks ahead of me, tried making conversation. But he kept getting confused about when it was his turn to talk and when it was his turn to drink.

He brought to mind an important concern, though: the underwriters would want to know about risk factors. What if a stranger charmed me into a fresh romance? Or what if my old flame were to make sweeping lifestyle changes and arrive on my doorstep with a bouquet? In either case, I’d be hard-pressed to turn out a heartbreak song, and therefore in a position to file a claim. But exactly how likely was either scenario? That’s the thing with insurance—it’s a numbers game, pure and simple. The insurers are just card counters at a casino table, with a poker hand that takes thirty years to play. And the insured, well, we’re essentially taking out little bets against ourselves, just in case not everything goes according to plan.

To persuade the guys in underwriting that I presented a manageable risk, I could furnish a record of my romantic history. In fact, my whole family’s history could probably help establish my case; there are several divorces between my parents. My dad, who is smart and sensitive, will occasionally announce over cocktails, Marriage is easy—I do it all the time! He’s a good sport about it now, but I know his romantic relationships have been intensely important to him; I saw him suffer when they ended. After my own breakups, when I’m too full of feels to play it cool at Christmas, he’ll say. “Oh, darlink”—he says it like that, like Zsa Zsa Gabor—“I love you. But I don’t want to give you advice because, well, I don’t have a very good track record on this stuff.” Usually he suggests that I talk to the Ingrahams, family friends who do seem to have a pretty badass marriage.

Years ago my little brother went through a bad breakup of his own and the three of us sat together, feeling down but tender and grateful for one another. My dad said, “Some families have to be careful about alcohol, or money, or gambling. I think maybe you’ll have to be careful about love.”

My medical record might further bolster my application for coverage. Technically, after the car crash I’d been diagnosed with cyclothymia: sort of a low-carb version of bipolar disorder, with mood disruptions of a smaller magnitude. I was treated by a man named Dr. Rush, who was perhaps the slowest talker I have ever met. My dad said the doctor himself seemed obviously sedated. Usually slow talkers make me impatient, but Dr. Rush was so kind and insightful that I was glad for the slow drip—his ideas were sufficiently potent that each took a moment to metabolize. I was on a lot of drugs at that point, though, so who knows. In any case, I’ve got a well-documented history of blue moods.

And even long before having met Dr. Rush, when I was still a flat-chested fourteen-year-old, I remember deciding that I wasn’t overly concerned with happiness. I didn’t want to be unhappy, I just wanted other things more. Mostly to get really good at making art. And if I had to trade in some happiness poker chips for art poker chips, I was glad to make the exchange.

Within twenty-four hours I got a rejection call from Geico. On the phone an operator said they only did general liability insurance for commercial clients. But that I could try again at a later time because they’re still growing.

I’d expected as much; Geico’s policies stay on the straight and narrow. I figured I’d try Lloyd’s of London next—those are the guys into weird stuff. They’ve insured beards against fire and theft.


As scheduled, Dr. Matt the psychiatrist called. He sounded young.

We dove into my questions and Matt proved to be a trove of information. There are a lot of tests for happiness, it turns out. Most of them have names like Bandcamp download codes: PHQ9 and the like. There was also one called PROMIS (which irritated me more the longer I looked at it—Patient-Reported Outcomes Measurement Information System—couldn’t they add Evaluation or something to finish the damn thing?). Matt said he’d email me one. But, he said, he was actually way more interested in quality-of-life measures than a happiness score or even in specific symptoms.

Matt treated mostly schizophrenics who’d just had their first psychotic episode—which he described as a very treatable group. But where the standard questionnaires asked questions like, How often are you hearing voices? and How loud are they?, he emphasized the question Are you living how you want to live? Going to work or school, having good relationships?

“When I’m dosing medication, I don’t go up until the voices have gone away,” he said. “I go up until my patients can live the way they want to.” I decided I liked Matt. I was also fascinated by the idea that auditory hallucinations came with volume knobs.

I asked, “Do you think of happiness and sadness like light and dark—sadness is where happiness isn’t? Or is it like red and blue—where they’re both distinct entities?”

“If I could answer that eloquently, I’d probably be in another line of work.”

Fair enough. More my job, I guess.

But, he explained, “I don’t treat sadness—sadness is something we all feel, we have a right to feel, and we are obligated to feel. Depression,” on the other hand, “is a pathological state.”

Unprompted by me, he brought up the human appetite for sadness in art: “How many people have rented Steel Magnolias? And they somehow enjoy it.”

“I know! Most of my songs are really sad—”

“Yeah,” he said loudly. “They are.”

I was flattered he’d listened.

When I asked if it was possible to game the test and to fake being happy, Matt said he wasn’t sure why anyone would do that. I did not tell him about Geico.

Before we got off the phone, Matt had something he wanted to add, to contextualize our whole conversation. “We’re all trying to pick up the pieces from Descartes,” he said. “The whole mind-body dichotomy is false. We’re a big meat bag powered by a meat computer. If anybody tells you it’s all in your head—well, yeah, where else would it be?”

Matt for President, as far as I was concerned. We hung up and he emailed me a PROMIS.

Descartes was a douchebag in a lot of ways, but I admit I’d always kind of liked his mind-body stuff. I studied philosophy in college, and reading Descartes made it sound like you got to keep your mind clean, in a ziplock baggie, out of the muck the body had to wade through.

Earning a philosophy degree involved a lot of thought experiments. We were always pulling ethical levers on train tracks or harvesting one healthy patient’s organs to distribute to a dozen other sick people, that sort of thing. One hypothetical in particular stuck with me:

Imagine you’re in a loving, monogamous marriage. You’ve got a good job. You’re happy. Then one day a stranger tells you that your life is not what it has seemed: your spouse is cheating on you, doesn’t love you at all. You can learn your true circumstances or the stranger can erase the conversation from your memory, Men-in-Black-style, and you can continue as you were, happily.

It’s essentially a romantic version of the red-pill/blue-pill thing: The Matrix meets The Notebook. And despite how much everyone talks about happiness, I think the majority of us sides with Keanu: we want something even more than we want to be happy. We want to have an authentic experience—to understand our lives, even the sad, lonely, and unsolvable parts.

For most of my life I’d presumed, without much consideration, that being sad meant I was doing something wrong. My brain was making chemicals in the wrong ratios and I was doing a bad job at falling in love and then when it was time to fall out of love, I couldn’t jump out of the damn plane when everyone else did. But maybe my sadness wasn’t just a failure to be happy. Maybe it was a feeling I should try leaning into for a while.

Fortified by my conversation with Matt, I wrote my letter to Lloyd’s of London.

Dear Lloyd’s of London Representative,

I am a songwriter looking for a line of commercial insurance. I make my money writing torch songs and I’d like to buy insurance against a makeup with an ex. (I believe the policy would fall under the Disability category, but I think it’s best conceptualized as the opposite of Divorce Insurance.)

Most of my writing runs on heartache—an asset that I believe can be fairly appraised. I’ve attached a psychometric tool called a PROMIS here.

I’m looking for $40,000 in coverage, to be paid out in the event of a romantic reconciliation that renders me unable to perform professionally in my current line of work.

The likelihood of a settlement, however, is very low. He and I have had many years to sort ourselves out and we haven’t managed it. I’ve recently moved across the country, in fact, to prevent any chance encounters. I live in a stamp-sized apartment now on the Upper East Side and everything in this place I carried up the stairs myself—I’m just stacking up nightstands to make a chest of drawers. The guys at the thrift store greet me by name; I found a Latin bar that I like; and I spent forty dollars at Staples on a huge pad of Post-it notes—I papered the whole kitchen with them, so every time I have an idea I can just pick up a Sharpie and write it on the wall. I’m just a little bit blue, which some people think makes a person self-absorbed, but I don’t find that to be true; I feel sensitized to other people’s sorrow, like I’ve got night vision. I still think of him every day, but the crying jags are over and the dreams about him have stopped or I have stopped remembering them. I bought a keyboard on Craigslist and I’m working long hours, trying to make some music out of this feeling again. It’s a delicate process that’s easy to screw up, like a soufflé or a house of cards, but I know the steps to this particular kind of alchemy very well. It’s as though I’m sitting at a spinning wheel in a room full of hay. And I am the maiden, with her work laid out before her, and I am Rumpelstiltskin who comes to her aid, and I am the heartless king who put her there in the first place, and I am also the hay.

Thanks for your time and consideration. If the premium is affordable, I’ll look forward to working with you.

Sincerely,

Dessa.

After a few days without a response to my letter, I decided not to send a third. It’s monastic and it can be a little lonely, but I’m living how I want to live. And if I find myself beset by an unexpected bout of happiness, well, that’s a risk I’m willing to take.