A recent episode of the AMC series “Mad Men” showed its female characters navigating a husband’s departure for Vietnam and the land mines awaiting career women in 1964.

“I realized, watching it, these women were all 26,” says Paige Prather, who moved to Portland in August and who is also 26 years old. Unlike her TV sisterhood, Prather, who has a bachelor’s degree in anthropology, has not picked a profession. Unmarried, living rent-free in her sister’s attic, she is looking for part-time work in customer service, or a full-time position in the arts. Graduate school also looms as a possibility. The crazy-making multiplicity of her situation is not lost on her. 

“I sometimes think we’re the scatterbrained generation,” says Prather. “You have so many choices, and you know what you end up doing? Nothing. You become the DJ-fashion-designing-knitting-coffee-maker.” 

In August, 23-year-old Kate Williams, whose jobs have included barista, bartender and coffee roaster, ditched Portland for the third time. “I’m going to California — going, not moving,” she emphasizes. “I want an opportunity to miss my home instead of resent it, and I’m starting to resent it.” 

I’ve left Portland twice for brief stints because I couldn’t take it. The weather, the teenage angst. But Portland is a really strong vortex. Once you get here, you can’t leave. I would say eight out of 10 people I know are not from Oregon. The (media) exposure the city has had in the past few years has just exploded: Portland is green! It’s so great! And it can be, so the people keep coming. 

You can live out the broke kid’s dream. People have these adorable illusions: I’ll come to Portland and sell my paintings! For lots of people, this is an excuse to not have ambition. I used to curate at (the cafe) the Rocking Frog, and people would come in with their art, and I’d be like, “You want people to pay money for this?” 

I’m moving to Huntington Beach. No, I don’t have a job, and I will be living with my aunt. I might go to massage school and do it down there, or go to Austin, or come back to Portland. But I don’t want to come back to the same routine, to a customer service job. I need to work toward goals, and I need to leave to make that happen. 

I think Portland is in a way in danger of being a sort of incubator. People absorb its resources but don’t recycle them. They’re taking their careers elsewhere, and Portland earns a reputation of being a steppingstone rather than a destination. 

Working in vest and tie, Abraham Sutfin looks like a 19th-century tradesman as he fixes bicycles in his 6-month-old shop. Sutfin’s business model, too, is of another era, costing less than $500 to launch in a storeroom behind a minimarket on North Williams Avenue. What brought the 27-year-old Pittsburgh native to Portland two years ago? “The Pacific Northwest is what I’m after,” he says. “It’s one of the only places left that has old-growth forests. I love the ocean; I love snowcapped mountains.” 

I came (to Portland) with that black box of tools and worked out of my garage. I have a customer who knew the owner of the market. This space was empty; she told him about me. (The response) has been pretty amazing. I work on $100 Fred Meyer bikes, and I’ve had $4,000 road bikes. I don’t have a huge inventory, and I don’t have fancy bling, shall we say. I like the feel. I think it’s less intimidating to come into a place like this. 

Natalie Poulton, 28, moved to Portland last year, and immediately sold her car. “It was a financial burden, and I want to ride a bike everywhere,” says the Ohio native. A college graduate and certified yoga instructor, Poulton dreams of opening a community yoga center-slash-teahouse. She currently works as a manager at Grand Central Bakery. 

I visited (Portland) in 2008. The first place I ever walked into was a little shop, and the woman came over and said, “You need to wear red.” She brought me over a shirt. She just was really genuine. And then I found out she didn’t even work at the store! That’s what it was about Portland; people were really making connections. 

I found getting work ridiculously easy; I had a job within a week. But a lot of people here really struggle. I work with 28-year-old people who make $8.50 an hour and smoke pot all the time and come to work and they’re lazy. You could not go to Wooster, Ohio, and do what people do here, or Columbus or Cleveland. I don’t understand the structure of it, or why people would want to do it. In five years, what are you going to have, if you’re not building real relationships, if you’re just doing what you feel like doing? I hired (a guy) at Grand Central. He’s one of the nicest people, but he’s 42 without any roots. He has no savings; he’s living on his sister’s couch. He’s the quintessential Portland person. If Portland is Neverland, he’s Peter Pan. 

Journalist Matt Davis arrived in Portland from London four years ago at age 26. Rising to the title of news editor at the Portland Mercury, Davis decamped earlier this year for New Orleans. 

I’d heard that Portland was a “livable” place and had a sense from reading about it that it was energetic, on the cusp of some kind of breakthrough, especially where green job creation was concerned. When I arrived I found that “livability” was generally reserved for the majority of white people who score sweet government jobs and that most everyone else is either funding their existence with family money, working for Wieden+Kennedy or barely surviving. 

People leave Portland for all sorts of reasons. Mainly they realize it’s a waste of time and they’d probably be happier somewhere else. I saw plenty of bright people buckle. Pour all their energy into drawing comics or the local bike scene instead of doing something constructive with it, something that might be relevant on a national or international scale. They lose confidence. The waste of potential is a tragedy. I hate to think of it 10 years from now, all those twentysomethings depressed because their lives (are) stuck. 

It’s not necessarily all their fault. The economy has left twentysomethings with a harder path to navigate than the previous generation. Plus most of them grew up being told they were special little flowers, with unique “creative talents,” and it’s a rude shock to land somewhere that tells you, simply, “We’ll pay you minimum wage for waiting tables, and you’ll be pooling tips.” The creative class will eat itself, eventually, or tattoo itself to death. And so will Portland. 

Raised in Austin, Paige Prather left a job at the University of Texas in research and collections to come to Portland. Though she immediately found volunteer work at two arts organizations, paid employment has proved elusive. 

I can’t get anything. It’s been five weeks and I haven’t even had an interview. Including Craigslist and walking into places and talking to people my sister knows, I would say (I’ve tried) between 75 to 100 places. The young people I’ve met have been, “Good luck! It took me two years.” I made a friend who has her master’s in library science; she’s been applying for three years and is working part time as a page. She admitted to me she has a trust fund. 

Portland is a lot like Austin — it’s a small city, it’s progressive. It didn’t feel like it was too scary a transition. And Portland has a lot of young people. (But) if I can’t get a job, I can’t live here. I don’t have a special income that can support this never-ending quest. 

My parents were divorced, and from both households I was always told you can be whatever you want to be. My mom was always supportive of whatever decision I made; I never felt in any danger of disappointing them. I think there’s some idealism there, because they each worked 70 hours a week to support their families, but I was not expected to take a job I didn’t like just to make money. It was my aunt who sat me down and said, “Be realistic and do one thing.”