The Truth About Moving to America’s Hippest City


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I recently moved to Portland. It’s almost a cliché with all the buzz about Portland being a hip, environmentally conscious, artistic haven, best-place-for-any-lifestyle place. The city breeds the best bands you’ve never heard of, over 300 miles of bike lanes, Bernie Sanders fans, breweries, juice shops, and coffee bistros on every corner that serve local ingredients. It’s less expensive than San Francisco and Seattle, and home to many clean, green parks. There’s also no sales tax, legal marijuana, and a person to pump your gas for you.

“Yeah, Portland sounds pretty great.”

And it is a great city, but when everyone knows about it and decides to move there, especially young twenty-somethings like me, the transition into the hippest city in America is not so stress-free.  My roommate’s friend, a single mom, made me aware of Portland’s crisis when she told me about her friends, also moms, leaving their homes because they could no longer afford the ever-increasing rent. Word around the block is Portland will be the next San Francisco. Have you been to San Fran lately? The place is a mess. Rent is through the roof, there’s no place to park, and homelessness is pervasive.

“Maintaining it’s cool vibe will become increasingly difficult as the city faces a housing crisis.”

Three weeks ago, when we first arrived in Portland, Taylor and I worked on an organic farm in Banks, OR, fifty minutes outside the city. Almost every day, we drove into the city to apply for jobs and scope out neighborhoods. We quickly learned that landlords wouldn’t accept us until we found jobs (understandable), however, more distressing was the fact that signing a lease would drain almost our entire bank accounts. A temporary sublet was our best option, allowing us to split the rent of a room and earn more time to look for jobs. After a week, a couple women seeking a third roommate graciously accepted us (most sub-lessees turned down a couple).

Portland has a competitive job market. Even snagging a server job is, what I feel, harder than it would be in other cities. The applicant pool is overflowing with young people attempting to live in the city of their dreams. Many are like me, recent college grads looking for restaurant work while they hope to find something more meaningful, as promised by their college degree.

In the hippest city, the promise of a liberal arts degree is as fake as factory farm chicken.

At least until experience comes with it, hence, the catch-22 of every twenty-two year old’s life (Parents, I know it will pay off in the long run, etc.) In my college town bubble – now realizing the full bubbleness of the bubble – I was invincible, ready to take on the world.

“Low and behold The Big Pop, life has hit me with a road block that I should have expected, but under the surface, hoped to bypass. The Impossible Job Search.”

In the kitchen, my roommate’s friend asked us how we planned on making a living in Portland. I told her we might rent a two bedroom apartment and turn the second bedroom

tony app

micro apts in Portland are $1000/mo

into an Airbnb. That way we could live in a nicer place and still earn enough to pay for rent. We even considered renting a whole house to run an Airbnb hotel.

Little did I know, a lot of people have had this idea and are successfully pulling it off. Landlords find it lucrative because they aren’t dealing with several permanent residents. However, the practice of Airbnb houses has become a problem in cities like San Francisco, where it’s become so widespread, opponents argue it’s preventing permanent residents from finding a home. Portland has a tinge of the “Airbhb effect”, but with their eye on San Francisco, the city will probably crack down sooner, before it gets out of control.

As for now, we are still looking for jobs. Sometimes at night I feel dejected and unsure, but I wake up the next morning with renewed strength. The fact that every living person gets through this time in their life is both amazing and reassuring. I know I will end up on my feet, and when I do, the challenge of getting there will have taught me valuable life lessons that taking a safer route wouldn’t have. After all, I chose this path of moving across the country to a city where I don’t know anyone. I chose not to go home to my parents after college and should be proud of how far I’ve come. It’s about time I put up a fight, and even now, I have back-up boxing gloves.

“For my entire life, the dial has hovered somewhere between “Great” and “Doing Fine.” Even now, I am Doing Fine.”

One thought on “The Truth About Moving to America’s Hippest City

  1. Pingback: 5 Reminders for a Recent College Grad in a New City – Write Outside

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