Loyola University Chicago

Loyola Magazine


Leap, and your life will appear

Leap, and your life will appear

Despite a lack of sailing experience, Amy McCullough and her partner Jimmie left behind their lives ashore to set sail along the Pacific Coast. (Photos courtesy of Amy McCullough)


Taking risks can be daunting, but it can also open up a sea of opportunity

By Amy McCullough (BA ’02)

When I was an undergrad at Loyola, people often asked me what I planned on doing with a creative writing degree. Only half-jokingly, I said, “Probably wait tables.”

And, honestly, I did a lot of that. I worked a desk job for a year and waited tables for about two before figuring out that I might be able to mold my love and knowledge of music and knack for writing into a career as a music journalist. Shortly thereafter, I landed an internship (of the unpaid variety) at Willamette Week, a Pulitzer Prize–winning alternative newsweekly based in Portland, Oregon.

After a few months as a bartender/intern (followed by a few more as a bartender/freelancer), Willamette Week hired me on. Not only did I end up a full-time music writer, I was eventually in charge of the entire music section. I got what I wanted. I turned a degree I admittedly felt cynical about into a dream job. Then I ditched it all to go sailing.

That’s right: in 2008, I quit my illustrious music editor job, sold all my belongings, and moved onto a 27-foot sailboat with my boyfriend, now partner of 10 years, Jimmie. Oh, and there’s this important detail: neither of us knew how to sail.

So why on earth would I do such a thing? The short answer is love. I was head-over-heels for my main man, Jimmie, and we jointly decided that “regular” life—jobs, rent, bills, responsibilities—were eating up too much of our time—time we could be spending together. Togetherness became our ultimate goal. What started as a lovely afternoon of canoeing on Scappoose Bay ultimately led to our conclusion that living aboard a boat was the most realistic (read: cheap, immediate) means to this end.

So we set sail in the name of love. But there is another aspect we both found appealing about casting off: not danger or thrill-seeking, exactly, but the challenge—and deviance. Jimmie and I both loved the idea of doing something unusual and, perhaps most importantly, something no one else had the nerve to do.

It didn’t hurt that it also happened to be something so many fantasize about: sailing away. Part of the appeal was taking a leap, having faith that we’d be alright, that our self-sufficiency and resourcefulness and sheer wills would get us through. (You can read the full story of our adventure in The Box Wine Sailors, available now from Chicago Review Press).

Strangely enough, ending up at Loyola—and in Chicago, for that matter—was a similar leap for me. For reasons I won’t go into here, I dropped out of Illinois State University after five semesters and, on a whim, moved to Chicago. After a few months working at a record store, I considered going back to school. But for what? At this point, I was so dissatisfied, so disillusioned, so over it, to be frank, that I didn’t really know where to start—or how to finish.

I had been a communications major at ISU (with a focus on radio); now, all I really wanted to do was write. I figured if I was going to have any chance of completing my undergraduate education, I’d better pick something I felt like doing—forthcoming waitressing jobs notwithstanding.

I talked to a Loyola advisor, was given a scholarship (which certainly didn’t hurt), and, just like that, I was back in school. And this time, I did finish. My decision to leave ISU was personal (it was me, not them), but I did feel more myself in Loyola’s urban environment. The small class sizes and wonderful professors—David Michael Kaplan, J.D. Trout, and Barry Silesky, in particular—engaged me enough to pull me through. The rest (and the best) was yet to come: my career as a music journalist, crazy young love leading to my year as a happenstance adventurer, and becoming an author.

College students are very focused on “success,” no doubt, but perhaps they don’t often stop to examine what that actually means to them. I always wanted to write a book and see it published—though, believe it or not, I had no intention of writing about our sailing trip until it was over. Now I have held a copy of The Box Wine Sailors in my hands, I’ve read from it to friends, family, and complete strangers on a three-week book tour. I also always wanted to fall in love. I’ve been happily in love with Jimmie for a decade.

That said, I often don’t feel like a “successful” person; like most of us, I’m still figuring plenty of things out. Life is a process, one we only advance through by living. And for me, that living involves a degree of uncertainty, whether it’s going back to school for creative writing and having no idea where it will lead, jumping on a boat with the love of my life, or trying my hand at writing a book. Those chances have led to some of what I consider my greatest personal successes. Taking leaps—including my leap to go back to school at Loyola—played a huge part in that.

‌   ‌

About the author
Amy McCullough (BA ’02), an Illinois native, graduated magna cum laude with a major in English (Creative Writing Concentration). She is the former music editor of Willamette Week and has also written for SAIL Magazine, Eugene Weekly, and Finder, a magazine-style guide to Portland. Her first book, The Box Wine Sailors, was published by Chicago Review Press in November 2015 and spent over a month as Amazon’s #1 New Release in Sailing. She is currently a graduate teaching assistant and master’s student in the Department of Geography and the Environment at the University of Texas. She lives in Austin, Texas, with her partner (and former shipmate), Jimmie.