They were giving away money. That was the reason I took the long subway ride from Brooklyn to Harlem one Sunday morning in August. Once I arrived, though, it was all too clear that I wasn’t the only one who had heard about the opportunity. The open audition for “Who Wants to Be a Millionaire?” was supposed to run from noon to five, but already, a little after eleven, a line of would-be millionaires snaked out of the lobby of the Apollo Theatre and down the sidewalk. We were a diverse bunch of dreamers. I waited in line behind an effete Jewish guy and an older African-American man who was discussing the pros and cons of Obamacare, and just in front of a petite young Korean woman, who did her best to respond politely to a lady who seemed unable to keep herself from sharing the strange, likely fictitious, details of her own life, most notably the masters degree in reverse psychology that she claimed to have earned from Nassau Community College. Before we were admitted, en masse, to the theatre, the reverse psychologist wandered off, drawn away by another, even more powerful dream.

To have a shot at winning any money, I needed to intuit the qualities that the producers were looking for from the thousand or so people who would audition in the course of the day. The producers wanted to make entertaining television, and I had to assume this meant they wanted us to be voluble and emotional and wacky. While we waited to take the multiple-choice test that started the process of winnowing our numbers down, we were blasted with overloud pop music, and occasionally instructed to stand up and dance so that they could film us for a promo about the audition process. I thought, Couldn’t this somehow be a secret part of our evaluation? Couldn’t they simply be watching a direct feed from this camera and picking out the lively ones? I leapt up and gamely waved my arms back and forth. All the single ladies. All the single ladies. All the single ladies. Uh-uh-oh-oh-oh-oh-oh.

I passed the trivia test, which earned me the right to stay behind as hundreds of less savvy applicants were shown the door. Next came two more hours of waiting, then an in-person interview in which we discussed our answers to their questionnaire—“What is an embarrassing story about you?” “Do you have any hidden talents?” “What would you do if you won a million dollars?” The game had already begun. To secure an appearance on the show, you had to spin an interesting narrative about yourself or put on display your charismatic quirks. You had to prove that you were willing to sacrifice the last shreds of your dignity. It was at this stage of the process that I overheard one of the friendly twentysomething (white) producers coaching a heavy-set African-American woman before her on-camera interview to “just go in there and be a crazy mama. Just be a crazy mama.”

Did I mention on my questionnaire that I could perform a serviceable impression of Chewbacca? Did I offer that up to them as proof of my willingness to give them whatever they wanted in exchange for a chance at their money? Yes. Yes, I did. The rest of my interview in the cramped bowels of the Apollo Theatre was merely a formality. I would be good on the show because of X, Y, and Z. When I was twelve, I was an actor in a sex-ed video starring Bill Nye the Science Guy. I would spend a million dollars on the world’s greatest first-anniversary present for my wife. Can I do the Chewbacca now? Of course I can. It is a great and unholy sound, and for several seconds all talk in that room came to an end. A guy who recognized the noise for what it was clapped from somewhere back in the line. I boarded the train back to Brooklyn, uncertain that I had succeeded, though I needn’t have doubted the Wookiee’s allure. Two weeks later, I received a postcard informing me that I was part of the “contestant pool,” and a week after that a producer called to tell me that my episode would shoot in seven days’ time.

There are plenty of ways to explain my psychological problems with money, but let’s begin with autobiography. My father was a physicist who, upon relocating to the Pacific Northwest, taught himself to be a mechanical engineer and who, until the final decade of his career, insisted on running his own small firm. Practically, this meant that he paid several engineers regular salaries while he took home whatever was left, a sum that was sometimes considerably less than what he could have made if he had been willing to let someone else be his boss. It wasn’t that my father was irresponsible about money, only that it didn’t rank especially high on his list of priorities, and, anyway, he was sure he could get enough of it if he ever really needed to.

As a young man, I made similar assumptions about my own life. I graduated from college, spent a year in Africa on a fellowship, then came back to New York City to make my life in writing, which is to say that I did other, entirely unrelated things to make ends meet while I waited for my literary stardom to take hold. First, I was a bartender, and then later I was a tutor to wealthy high-school students. In my early twenties, I took up poker, and while there were some months where I scratched out my rent in home games and underground clubs, I wouldn’t want to calculate what tiny sum I might have been making as an hourly wage from playing cards. Somewhere down the line, my thinking went, there would be a huge book advance or a MacArthur “genius” grant to make up for all those years of paltry income. “Irrational optimism,” I believe, is economists’ term for this approach to financial matters.

My trouble with money goes deeper than simply being unrealistic about how I will get it. I suffer from an extreme version of the ubiquitous middle-class problem of not being able to believe completely in its reality. Each time I earn it or spend it, I am struck with the vertiginous sense that somehow I’ve been badly tricked. Weirder still to me is the choice not to spend the money I make and instead to save it, so that my wealth transforms into a mere number on a page. I understand that I should want the number to be large so that one day maybe I can own my own apartment, I can travel to Berlin if I want to, or I can retire and stop working altogether; I should want the number to be large because then I’ll know I’m winning; I should want the number to be large because, all things being equal, my life will be easier than if it is small. But, still, the absurd abstraction of money constantly tempts me to do things like empty my savings and throw it all down on black at the roulette table, because I don’t entirely believe that, win or lose, it will really change anything.