Dan Kennedy, former McSweeney’s advice columnist on all things paper and paper-related, is working hard at crafting his follow-up to his first book, Loser Goes First: My Thirty-Something Years of Dumb Luck and Minor Humiliation. Using the miracle of the Internet, we’re giving our readers a special inside look at Dan’s creative process.

This is my gay little morning-pages exercise. You can write about anything as long as you write something. So I am writing that this is stupid and that I am sitting in my living room like a jackass. Yay. Woo hoo, I am a writer now since I am writing “anything no matter what it is” on my morning pages, even though I haven’t written a thing in months. Yay, everything is working just like it’s supposed to. Ass ass ass ass ass ass ass ass. Japanese. Balled-up clouds! Whatever. Nothing is going to happen just because I wake up early and Matthew’s brain raced in fits and starts. It raced like this all the time, spitting forward strings of numbers and tripped and triggered memories of largely anonymous sexual encounters that his retired winter-coat-catalog-model wife knew nothing of. Little trysts that never managed to get him back to age 19, usually scored at a country club his father belonged to, as did his father, as did his father, as did his father, and his mind is racing again. It’s ticking these numbers and shooting him into little squints and spasms of regret, even though any client or colleague or neighbor would tell you he’s a sane, upstanding member of the community. He knows he is not insane and he’s basing this mostly on the fact that he is liked in Old Greenwich. And then it’s right back to the numbers never stopping.

31, 784, 5, more than 24, 40

31, the number of people at work that by now, Monday at 11:21 a.m., knew Matthew was fired from the firm he worked at up until Friday. They maybe even knew the circumstances by now—which, because Matthew passed out, is more than even Matthew knows.

784, the number of dollars it costs monthly to drive a leased BMW 700 Series sedan around Connecticut trying to find something to do until 6 or 7:30 p.m. That’s when he returns home to aforementioned heavy-outerwear-model wife who is still under the impression that Matthew has a job. And a career, and a heart, and a head, and that all of these are still intact.

5, the number of years he has been married.

More than 24, the number of what Matthew describes as “mostly minor parking-lot hand-job situations at the club that I drink myself into liking the idea of.” These have all occurred in maybe the last two years of his marriage.

40, the age he used to be nowhere near.

Let’s say Matthew was a man in one of those jokes in which three men of varying ethnicity are granted the opportunity to ask only one question to some sort of master of the universe. And of course the master of the universe would reveal a truth that might help the man asking, or maybe all of mankind, if it were the right question. You’ve heard of this type of joke, right? So, one of the men might ask how to cure cancer, for instance. The punch line comes usually in the form of one of the men asking, “So, I can only ask one question?” Matthew would be smarter and more savvy and more strategic in this situation. He would know he was granted the opportunity to ask only one thing, and he would be smart enough to know that the one question would have to be one of those questions so broad and reaching that it would actually be a crafty way of having many questions answered.

He would, however today, simply ask:

“Am I living in a Steely Dan song?”

He remembers all of their songs from the radio. Not because he likes Steely Dan, but because he was always afraid he would end up one of the marginalized loser characters in their lyrics, like the one dating a 19-year-old in “Hey Nineteen,” or the one in “Deacon Blue” who complains that they have a name for the winners in the world, and who says he wants a name when he loses, and whose dream it is to “drink Scotch whiskey all night long and die behind the wheel.” Matthew is not a fan of this band; he has simply spent the better part of 40 years remembering every detail of every character in every song in case he should start to notice any of these traits in himself. As a result, he has an encyclopedic knowledge of every lyric and every title of every song the band has written and recorded. He knows what year each song was released, how much it was played on the radio, and by which stations in Connecticut. He actually doesn’t even like the way the songs sound—the way they’re sung or the way the instruments are played. It’s not like he enjoys having to listen to every one of them. And he is not the kind of man to have ever considered whether his fate is starting to mirror the fates of these lyrical characters simply because he has held the words in his head for far too long. And on this particular morning, now at around 11:40 a.m., he seems to start speaking to himself quietly in a way that suggests he may be having some sort of revelation.

“No, no, no, no, no, no.”

And then, still in a whisper, he asks himself the question out loud.

“Which one of you fuckers am I becoming?”

He then spits casually out the driver’s-side window. The majority of the spit lands inside and runs down the Corinthian-leather interior onto his forearm and elbow on the armrest. At first he is upset, and then deflated. And then he starts spitting, and spitting, and spitting, and spitting, making so goddamned sure it all lands on the inside of the door. He even spits and spits and spits at the passenger-side door and onto the inside of the windshield in front of his face. And then his mouth is as dry as a Brooks Brothers shirt (15, 34/35, $69.95, 3 for $185.00). It tastes like fear, regret, self-hatred, and stale ambition. And it tastes like the convenience-store coffee he bought so as to not tip off the clerk at the corner gas station where he has bought one every morning on his way to work for the last 11 years. He starts to curse.

At first a sensible assortment of three- and five-syllable profanities, and then as his speech and car accelerate, the same one-syllable profane word repeated over and over in a short and fast staccato rhythm. Maybe six or eight times and then he looks like he is going to either cry or punch something. He never cries. He never punches a thing. And that’s when he stops.

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Whoa. OK, we should all actually get in the habit of the morning-pages exercise. I kind of started out by making fun of it, but I think this one might actually work.