I first said goodbye to all that—though I don’t hold New York to be all that, a monolith precluding the all thatness of other places—a long time ago, in 1985, at seventeen. Prior to my departure I had been the sort of native Manhattanite to whom that famous New Yorker cartoon, the one I’m sure is mentioned elsewhere in these pages, the one that shows everything west of the Hudson River as a perspectival plain of diminishing signification, didn’t seem funny at all. What’s funny about that? It’s totally true, and everybody knows it.

Yeah, arrogance. New York is full of it, I was full of it, the kind of arrogance that’s extra numbing, mind-stuffing, because it’s backed up by what I’ve come to know as “seeming inevitability,” ie, yeah, anyone who’s anyone will at some point move to New York. Or die in obscurity with failed dreams. Yeah, all the brilliant people are here. Yeah, here’s where it’s really at, and you know it’s true, and anyone who says anything else is just not up to the challenge, the snuff, the shit.

In the diffused sparkle of refraction of Joan Didion’s adorable and probably accurate portrayal of what it’s like to be from somewhere else and move to New York and get what you can from it and stay a little bit too long and then leave, I proudly and grouchily represent the bright lights of the native. For visitors—you can stay a lifetime and be a visitor—what is at stake, according to Didion, is the dream of New York, the abstracted coordinates of its glamour and legendariness. You want to be there because it is like living on a Monopoly board. It is like living in Oz. Natives get that, are fed it along with their mother’s milk, plus they get the extra-added glamour of secret knowledge and self-exile and hard-wired urbanity. Didions bring a knowingness to their efforts at urbanity: Rubanity, I’ll call it. Natives just bring it.

In high school I went out a lot, to nightclubs and bars. Danceteria, the Mud Club, Limelight, Save the Robots, Pyramid, Area, Beirut, bars in the East Village, which at that time ended at Avenue A. I snorted lots of cocaine, and made out with bouncers in exchange for free entry to clubs. Bouncers—Nigerian bouncers, bouncers from Berlin, underage bouncers I had known in grade school—waved my friends and I out of the crowd, to the front of the line, ushered us inside where we would shed our coats and get free drinks and dance dance dance till five in the morning. That’s what I did in high school. By the time I left for college I had renounced a bunch of things, including the highlife, and was leading with latent bookishness and vegetarianism and a closet full of attitudinal old clothes I had amassed at the Salvation Army on my corner next to the gay bar, long before old clothes were called “vintage.”

Goodbye to all that, hello end-of-the-world rural pinhead Vermont, for college, dropping out to live in Boston “You-Call-This-a-City” Massachusetts for a couple years, then back for more college in the Happy Valley of Western Mass, where I had my first sweet taste of real small-town, albeit college-town.

I moved to a very small city, really a town, in Iowa, for graduate school. There at the outskirts where farmland abruptly swelled I witnessed organic vegetable farming, cooperative living, and the fulsomeness of rubes and radicals and serious artists doing their business in generative ease, relative privacy, and cheap comfort. Lots of bands and visuals and ideas. I did not miss the compression of the city; I did not miss my parents, who I felt in their high-mannerist urbanity had taught me nothing of worth. I spent summers on screened-in porches, went back to visit the city about once a year, and when I walked the streets, late eighties-early nineties, I was made to cry. This is before the homeless people were stored wherever they are currently being stored; they were living, eating, shitting, sleeping all over the streets and one had to step over them at every corner, doorway, subway grate, and step over them everyone did, seemingly as though this was an acceptable situation. Seemingly inevitable: Oh, it’s just so fabulous in New York, you can really just learn to step over people’s suffering bodies. Cities are so cool, and this is the coolest, so hardcore, and you can learn to live with this. No one spoke of it. On visits I would come home and ask my parents how they could live like this. They honestly had no idea what I was talking about: This was their fabulous city. I was inured to the fabulousness by the dirty, hungry people lying around on the street; they were inured to the dirty, hungry people lying around on the street by their imprinting of fabulousness, the fabulousness impressed upon them when they arrived in the West Village in the 50’s from their respective outposts.

At the age of thirty I came back to New York to be literary, and it worked. Return of the native in the clothing of the naïf. Wolf in clothing of sheep. I had abruptly tired of outposts, of decentralized living—the city still an epicenter—and I had something very specific I wanted to do, within the specific culture of the literary. And I had noticed that every time I came back to visit I had a marvelous time, suddenly, in that specific culture.

So I came back, and said hello again to all that, and it genuflected back at me. I sucked up the transitional, transactional energy like a newborn mosquito. That’s where language is. I get my total buzz on when the buzz is there to beget. I am supremely familiar, you could say “comfortable,” with cityscape—noise, bustle, crowds, action, stimuli such as the very poor, the very rich, the very beautiful and the degraded, lights and smells of food on the street, shouts of people selling things for lots of money or begging for money or scamming with infants in their laps. Bumping into people I know in parks and bookstores and arthouses. For six or seven inexhaustible years I was one of those culture-workers who expends themselves beautifully, for whom the city is working, and what I did there I probably could not have done anywhere else.* Once I had accomplished that, I was just as abruptly done with New York, and I left. New York is a place for being public, for wanting to be famous. I achieved a degree of recognition in my field and became a public figure and found I didn’t like it. It served me well in launching my Literary Project, but did not serve my soul well.

I didn’t move far away, but I will never move back and I don’t visit often, or as often as you might think, and when I do I am happy to leave again, often on the same day. “SOHO GIVES ME HIVES”: that’s a t-shirt meme I brainstormed in the late 90’s, as the transformation of that deathly quiet neighborhood from artists’ cheap housing and site of freewheeling conceptualism to Mall of Outrageous Crap was completed. There are lots of neighborhoods and enclaves and scenes and nodes of NYC behavior that give me hives—too many to give shout-outs to. There are wonderful people I see only in the city, who refuse to get on the Amtrak to come visit upstate—train of diminishing signification—and who I sadly bid farewell after each lovely brief encounter.

I go down to the city, about once a month, two hours on the train with the other suckers, usually to attend or present or facilitate a potentially dazzling literary event. In New York City, in the dusk-filled streets or in the cold wintry streets, in streets when the light is pretty or streets when everything looks crappy and grimy, I see a tremendous amount of samey-ness, the kind that didn’t used to be there. Posers and wannabees and money-hounds EVERYWHERE, when in my youth they were restricted to the bridge-and-tunnel funnels of Eighth Street and midtown, Lexington Avenue and Central Park and, eventually, Soho. You could spot these chumps a mile away, and they were different from tourists, who came to gawk and then went back home; they were tourists who overstayed, put down roots for no good reason, who could lay no legitimate claim to the greatness of the city’s historic convergent energies, who had simply made money here and could therefore make it anywhere. New York City manifests itself now shamefacedly as a chump-factory, a chumphouse. It’s Chumptown. Artists who live there are living dangerously, close to extinction, dangerously close to the source of their art’s diminishment, an ouroboros of economic exigency. It’s well documented: Chumps need artists and artists need chumps, but they’re supposed to stay out of one another’s sight in order to maintain the necessary illusions! There have always been chumps in New York, but they used to be bashful chumps who bought the brilliant ones their drinks.

There’s this thing that happens, where I speak to a 20-something or 30-something sweetheart, a Joan Didion who’s moved to New York recently, and I realize at a certain point that their expectations of it are actually very low, compared to my own, because they cannot possibly imagine what it used to be like, the New York of the recent past, of the late 70s, 80s, 90s. They have no idea how far any of it has fallen, how sterile Chelsea, how horrorshow Soho, how lame-ass the LES. All by comparison. I’m not even going to mention Brooklyn, because Brooklyn is nothing but a brand name. Forget Queens.** Visual culture does not often represent what’s past; I’m sure a slew of movies soon will, but right now with the exception of Chico and the Man and early, secret, legendary Madonna as incarnated in Lady Gaga I don’t know what is widely culturally understood of what was cool in those times. Whit Stillman? The 80s art world via Basquiat? Graffiti? Michael Douglas in Wall Street? I’m afraid this latter giant face has eclipsed the faces I knew, the faces of the brazen, the bold, the class- and culture- and gender-vultures, non-rich aspirants to splendor, gamy artist-class fast-talkers, children of choreographers, children of sculptors, excitable children of alcoholic Midwesterners, those for whom there was no money changing hands.

There is the fallacy of nostalgia, and there is the fallacy of the fallacy of nostalgia. You’re not supposed to ever say that something used to be better, because then you are vainly trying to hold that something in stasis, cold in the frame of reference in which you knew it, and this is narcissistic and regressive and cranky and blinder-ed. It is ungenerous to those whose references are framed more recently, to those who we must make way for and learn from: to the young. Those who are making their way in the world, and making the world. Those who could, at this point, be our children, if we had given birth to the children we aborted in high school and college and graduate school.

But we have already said goodbye to all that dualistic relativism, in this new world. It’s a “both/and” world we live in: Every cranky, aging generation feels that things used to be cooler, or more imaginative, or riskier, or etc.; many things actually did use to be cooler, riskier, etc., and this argument against the insistence that something could actually have been qualitatively so, probably quantifiably if you had the time, serves most those for whom the status quo is best maintained: Chumps. For if it’s never true that things have degraded, deteriorated, absolutely—and of course the same is true of improvement—then there’s never any impetus to halt the degradation. Or to look for something better elsewhere. You’ll keep paying rent until you can’t.

So yes, it’s true. New York City used to be cool, and now it’s not. It’s not at all. It is boring and dismaying and stymied; everything potentially cool in it is overwhelmed and inflated and parodied and sold. You can’t even love the absurdity of it because it’s too painful and we cannot be allowed anymore to callously love, for their absurdity, systems that oppress and impoverish. New York is a giant sinking pile of crap compared to what it used to be. Literally sinking, now that the waters rise so much quicker, the winds blow so much harder than even scientists predicted. Lately I like to imagine that I will have the privilege of seeing in my lifetime real estate values in the city plunge wildly, freefall, as Climate Events force visitors to admit that they pay top-dollar to perch on coastal landfill.

In New York City these days I see loads and loads of formerly brilliant people—gender champions, visual whizzes, start-up ho’s, crackerjack dancers, actors, journalists, and chefs—who have stayed too long at the Fair, to use Joan’s wistful archaic turn of phrase, are baffled and internally conflicted as to why they can’t admit that New York sucks so hard. Why they can’t draw the proper conclusion: That if they are to work all the time in order to pay super-high rents that make it impossible for them to do their art, if they never have a chance to see the people they came here to see, who are also less brilliant now that they are muffled by the smog of wrongness that hangs over New York (thicker than the smog of smog that hangs over Los Angeles, another city that’s not even half as cool as everyone who’s moving there says it is), if they are living somewhere that is giving them less than they are giving to it, then they should leave. They should find somewhere to live, perhaps collectively, perhaps not individually, perhaps they should try to make sense of this whole living-somewhere thing in a way that doesn’t pretend, as New York City does, that we are all ruthless rock stars with amnesia and aphasia and lifetime amniotic sacs.

The brilliance of Didion’s essay: She makes no claims for New York City but that it is what it is to those who regard it. She claims only that for various ineffable reasons having mostly to do with aspirations and the qualities of light at different times of day, people come to New York bringing with them their youth and they apply their youth, and they ought to leave before their youth is exhausted and it no longer applies to New York. This seems to happen just as their prime breeding years clock in. As a native of New York I grapple herein with a different set of coordinates for departure: I must leave behind my love, my home, my turf, my territory, my breeding ground. I must punish New York for its lameness by my desertion. Punish and improve. How can you help New York City to return to some of its former coolness? Leave it before you yourself are a chump, and perhaps by attrition it will rise again.

*I founded a literary magazine and press. I hosted many large literary parties and readings. I established myself as a public print-culture figure on the final cusp of the pre-internet age.

**What goes on in Queens is hysterical. Why do you need to displace natives of Queens from their apartments in order to be a member of a community of artists who do not want to go to Manhattan, ever? Or who never get to be at home because they can’t afford to waste the time going back there. Why not populate Detroit? Or Albany? Or Pittsburgh? Or some other charming small city with a low profile and vacant properties you can buy from the city for a dollar? From there you can FTP your PDFs for a fraction of the cost of living and when it’s time to have babies you can stay where you are because your apartment is big enough! Or you live in a house. You live in a house with a door that opens onto a yard. Maybe you share the house with friends.

Excerpted from Goodbye to All That: Writers on Loving and Leaving New York, edited by Sari Botton. Available from Seal Press, a member of the Perseus Books Group. Copyright 2013.