Four years ago, I sat, a fresh-faced prospective intern, across from WW’s notoriously cantankerous assistant Arts & Culture editor, Steffen Silvis, and told him I wanted to write about music. He said, “You and everyone else in this town.” So, you can imagine my surprise at eventually landing the music editor job in the fall of ’06 (after serving time as a WW freelancer, assistant Finder editor, calendar editor and assistant music editor)—quite an honor in a town bursting with musicians overwhelmingly talented and a scene uniquely synergistic. I knew if I ever moved on, it’d have to be for something truly awesome.

Now, I’m about to embark on an honest-to-God adventure. In a week, I am moving onto a 27-foot sailboat headed for Mexico’s Sea of Cortez with my boyfriend (see “High Seas, Low Wages,” WW, June 25, 2008). Perhaps not surprisingly, my introductory column as music editor was all about how I have a tendency to skip out on jobs and towns, how I’ve always rather vainly been in search of the right fit. Being a music writer, especially one in the ever-growing musical mecca that is Portland—a scene small enough to be manageable, fresh enough to stay interesting and friendly and communal enough to be both weirdly inviting and endlessly captivating­—was by far the closest thing I’d found. It kept me here longer than I’ve lived anywhere (outside of my parents’ house) and at WW twice as long as any other job. It made my first and longest-standing love—music—my life. Then I met something that I loved even more (yes, a boy), and things got complicated.

It started with a trip to nearby Scappoose Bay to scout out a Chicago-style hot dog joint for WW. Afterward, my guy and I whimsically rented a canoe from Scappoose Bay Kayaking—turns out, we enjoyed being on the water so much that we bought a raft, then our own canoe, then…we conjured up this crazy scheme to buy and move onto a sailboat. At first, it seemed like a pipe dream; how could we give up good jobs (he works at Intel) and a great city for something completely unknown? It might have been a moment in Todd Haynes’ Dylan epic I’m Not There that gave me resolve enough to realistically consider the idea; Richard Gere’s Billy the Kid character says, “The more you live a certain way, the less it feels like freedom.” His words have stuck in my gut ever since.

Sure, it’s sappy, but it’s also true: The impetus for this trip was our desire, as a couple, to simplify our lives to the point that all we’d have to do is be together. As such, I’ve eliminated rent, bills and material things from my life, keeping only a box of clothes, some photo albums and my record collection (hey, I just said I love him more). I had, for so long, let work muscle out my life; for a little while, at least, I’m letting life, and love, take precedence. I’ve realized that it’s OK to do something different, even if what’s left behind—a music section that will now be ably led by longtime WWer, fellow music fanatic and all-around swell guy Casey Jarman—doesn’t suck. Oddly enough, when the thing you do every day is your dream job, it still rings true: “The more you live a certain way, the less it feels like freedom.” Freedom, here I come.

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MORE: Amy’s going-away show, featuring Aqueduct, BOAT and Graves, takes place Wednesday, July 30, at the Towne Lounge (also see Clublist Spotlight). 9:30 pm. $8. 21+. Check out her farewell muxtapeon LocalCut.