You know how all those fashion, foodie mavens are telling you your life will only be better if you embrace a philosophy of having the best of everything? They may be wrong.

Essay by Frank Bures, Illus­tra­tion by Will Din­ski

In the late 1990s, my wife and I got in a U-Haul, hit I-90 and headed west for a few days until we came to Port­land, Ore­gon. We had no jobs, no apart­ment, and no notion other than get­ting out of Minnesota.

We chose Port­land mainly because it was cheaper than the other places we’d liked on a month-long road trip through the West (San Fran­cisco, Seat­tle, Mis­soula), because it had a great book store we both fell in love with, and because I had a cousin who lived there in the north­east part of the city, which was some­what less trendy back then. (Our first night, police found a body in the park across the street.) The plan was to stay a year, then try the other coast, then who knows? We were young! But we loved it and stayed for nearly five years. Then, when we started think­ing of breed­ing, like salmon, we decided to swim back to the pool in which we were bred.

For a vari­ety of not-very-well-thought-out rea­sons, this brought us to Madi­son, Wis­con­sin. It wasn’t too far from our fam­i­lies. It had a stel­lar rep­u­ta­tion. And for the Mid­west, it pos­sessed what might pass for cachet. It was lib­eral and open minded. It was a col­lege town. It had cof­fee shops and bike shops. Besides, it had been deemed a “Cre­ative Class” strong­hold by Richard Florida, the prophet of pros­per­ous cool. We had no way of know­ing how wrong he was about Madison…and about everything.

Florida’s idea was a nice one: Young, inno­v­a­tive peo­ple move to places that are open and hip and tol­er­ant. They, in turn, gen­er­ate eco­nomic inno­va­tion. I loved this idea because, as a free­lance writer, it made me impor­tant. I was poor, but some­how I made every­one else rich! It seemed to make per­fect sense. Madi­son, by that rea­son­ing, should have been clam­or­ing to have me, since I was one of the mys­ti­cal bear­ers of prosperity.

Soon after we arrived, how­ever, I was sit­ting at my desk won­der­ing where all these cre­ative, self-employed bohemi­ans might be, when I watched an unset­tlingly large woman lum­ber out of the apart­ment next door. She stood in the sun and blinked like she hadn’t seen it in years. It took her an ago­niz­ingly long time to shuf­fle across the park­ing lot to the dump­ster, where she deposited her trash. Then she began the trek back. After the door slammed behind her, I never saw her again. In most parts of Amer­ica circa 2003, this scene would have been unre­mark­able. But I couldn’t get it out of my mind. It stayed with me and filled me with dread, as if there was some hid­den mean­ing in it; as if the woman was an omen, and her trash bag was filled with my dreams.

Nonethe­less, we tried set­tling in. I began writ­ing for the local mag­a­zine. My first story was based on Richard Florida’s “Gay Index,” one of sev­eral mea­sures that was sup­posed to indi­cate how wealthy your city can be. The more gays there are, he rea­soned, the more tol­er­ant your city is, and the more cre­ative class work­ers would flock there. My story was called, “How Gay is Madi­son?” The answer, of course, was “very gay.”

We tried to meet our neigh­bors. Across the hall was a guy our age who worked in the UW-Madison’s phar­ma­col­ogy depart­ment, but who seemed to strug­gle for any­thing worth say­ing. Over din­ner he asked us what our hob­bies were. Like stamp col­lect­ing? I won­dered. Like macramé? He never returned the invitation.

The guy upstairs seemed more promis­ing. He had some brain dam­age from a bar fight, in which his head was bashed into the side­walk. But he still read books and kept pet par­rots. He even slept with them, until he acci­den­tally rolled over and killed one of his favorites. In the end, we drifted apart as well.

For some rea­son, these and most other rela­tion­ships never quite blos­somed the way we’d hoped, the way they had in all the other place we’d lived. For a time, my wife had a soul­less job with a boss who sat behind her, star­ing at the back of her head. I found work in a dusty tomb of a book­store, doing data entry with cowork­ers who com­plained about their neu­ro­log­i­cal dis­or­ders, or who told me about the mag­i­cal crea­tures they saw on their way home, and who kept web­sites depict­ing them­selves as minotaurs.

I’m not sure what exactly I expected, but within a year or two it was clear that some­thing wasn’t right. If Madi­son was such a Cre­ative Class hotbed over­flow­ing with inde­pen­dent, post-industrial work­ers like myself, we should have fit in. Yet our pres­ence didn’t seem to mat­ter to any­one, cre­atively or oth­er­wise. And any­way, Madison’s econ­omy was hum­ming along with unem­ploy­ment around four per­cent, while back in fun, cre­ative Port­land, it was more than twice that, at eight and a half per­cent. This was not how the world accord­ing to Florida was sup­posed to work. I started to won­der if I’d mis­read him. Around town I encoun­tered a few other trans­plants who also found them­selves scratch­ing their heads over what the fuss had been about. Within a cou­ple years, most of them would be gone.

“And I asked, ‘Hey, aren’t you upset the schools suck?’ and peo­ple said, ‘Oh, no, i really love my school. I make sure for my kid it’s all about values.’”

One of these peo­ple was a woman named Pene­lope Trunk, a brand­ing expert, a Gen Y prog­nos­ti­ca­tor, and a ruth­less, relent­less self-promoter. Her arrival in Madi­son could not have been more dif­fer­ent than ours. She announced on her blog that she’d done exhaus­tive research and con­cluded that the best place in the coun­try for her to live was Madi­son, Wis­con­sin. Trunk’s name was splashed across the papers, and seemed to con­firm every Florid­ian sus­pi­cion. Local cap­i­tal­ists bankrolled her new com­pany, Brazen Careerist. She blogged and blogged and blogged about how best to choose the place to work and live. She was an apos­tle of Florid­ian doc­trine and flew around giv­ing speeches about how places could attract the shock troops of the cre­ative econ­omy the way Madi­son had attracted her.

One day I met Trunk for cof­fee. She was loud and brash and talked over the din of the other peo­ple. She seemed to be under the impres­sion that I’d come to her for career advice, which she gave and to which I politely lis­tened. And while I liked her energy, I could tell by the way peo­ple shot her dirty looks that Madi­son was going to be a tough fit.

Four years later, Trunk left town, which seemed odd, given her much-ballyhooed arrival. By then, we had fallen out of touch, and I was never quite clear on her rea­son for leav­ing. So I called her to find out what had gone wrong. Trunk now lives on a farm in south­west Wis­con­sin, (she divorced her hus­band and mar­ried a farmer). On the phone, she was still brash and bom­bas­tic and as she told it, her hon­ey­moon with the city started to end almost as soon as she got there. One day her ex-husband was googling, “sex offend­ers,” and he dis­cov­ered there were four reg­is­tered on their block. Next, she dis­cov­ered that the pub­lic schools were ter­ri­ble. “I started talk­ing to every­one,” Trunk said. “And I said, ‘Hey, aren’t you upset the schools suck? How is every­one send­ing their kid here?’ And peo­ple said, ‘Oh, no, I really love my school. I make sure for my kid it’s all about val­ues.’ I mean the bull­shit that peo­ple were telling me was utterly incred­i­ble. Then it just became like an onslaught. Tons of lies. Madi­son is a city full of peo­ple in denial. Peo­ple don’t leave Madi­son, so they don’t real­ize what’s good and not good.” I asked her if she had any regrets, or if the move was a wrong one, or if she had any advice for other peo­ple look­ing to relo­cate. Or maybe, I sug­gested, life was just messier than research?..."