Navigating the High-Wire Act of Self-Employment

A trip to camp mirrors the trepidation and exhilaration of life without a day job
Photo submitted by Mo Perry

I couldn’t have predicted that quitting my day job would land me 25 feet off the ground on the shore of Lake Superior, but as I held on for dear life to a couple of wobbly ropes, I suddenly understood that self-employment takes leaps of faith both literal and otherwise. And it took a trip to camp to prove it.

Summer camp as a kid (varieties: horse, Baptist) left me a mixed bag of memories: that first delicious taste of independence; an unfathomably wise 16-year-old counselor explaining to me that the anaconda in “Baby Got Back” was a euphemism; sneaking back to my bunk bed to eat peanut butter from the jar in protest of the soggy green beans being served up in the mess hall.

These memories returned to me when I heard about Camp COCO, an October weekend retreat on the North Shore hosted by the Twin Cities coworking company. COCO provides freelancers and entrepreneurs with shared office space and a community of fellow risk-takers without guaranteed paychecks. (I work out of the northeast Minneapolis location, and my partner loves to point out the irony that after spending years aching to escape the drudgery of a day job, I now gladly pay for the privilege of going to an office.)

The agenda for the weekend included four keynote speakers (including Arctic explorer Will Steger), an array of workshops and presentations by various Twin Cities entrepreneurs, and physical adventures. It was billed as “a multi-sensory mashup of adventure, exploration, and edutainment,” the idea being that all the elements that make camp valuable for kids—the chance to unplug, forge new relationships, discover new reserves of resilience and horizons of possibility—are equally worthwhile for adults, particularly the unique brand of adult drawn to the self-employment life. And there was a promise of unlimited craft beer on tap all weekend. Which helped.

The weekend at its best offered the excitement of being surrounded by people looking for inspiration and transformation. Being out in the woods fostered the kind of radical openness that’s hard to achieve when everyone feels safe and comfortable in the trappings of daily life. The weekend was bursting with conversations among people living unorthodox and inspiring lives—with all of the anxiety that sometimes entails.

And that’s how I found myself on the adventure ropes course, traversing those high-slung wires (whose usual participants are mostly fourth graders). As it turns out, there’s a surprising amount of overlap in the skills needed to navigate a ropes course, grade school, and self-employment or life as a freelancer (courage, balance, resisting the instinct to freeze up and topple over, remembering to look up and take in the scenery now and then).

At the changing of the year, in the season of resolutions, that moment atop the wire—level with the yellow and red treetops, Lake Superior joining the sky at the horizon in a shining seam of blue—encapsulates a lesson we can all take to heart: Even in the shakiest of circumstances, when we remember to be unafraid, that’s when we can see the beauty.