July 2024
Around the same time that I began my writing career, I applied to be a walking tour guide in Portland, Oregon. It sounded like a fun way to help make ends meet while I was getting things off the ground. Turns out, that almost all of my colleagues were actors in some capacity, and this was a side hustle for them. And that’s how I viewed it as well - a side hustle. A gig to last until I got where I was going. It would become so much more than that though, and I would continue being a guide long after writing began paying the bills. Only ceasing once moving into the woods made it logistically unfeasible.
I was so nervous the first year of giving tours, that I was more or less going through the motions. Doing my best to provide quality infotainment without forgetting any of the larger bullet points. Reciting all of the time-tested dad jokes I was taught. Making sure I finished on time and hopefully with the same number of people I started with. But things began to change once I started giving culinary tours.
I was still disseminating plenty of informative nuggets about the city I loved, but now I was also providing history, background, and samples of the Willamette Valley’s bounty. Something I am very passionate about. I began to grow, and things started to click. For the first time in my adult life, my creative side finally had a safe place to flourish.
At the risk of making what some might consider a laughable claim, I believe that being a tour guide is a craft to be honed and at a certain level, an art form. I’m not saying that all the people doing it see it the same way or that all situations lend themselves to such lofty aspirations. The content of the tours and your relationship with them are factors that contribute mightily. I gave every tour with the intent of conjuring magic because these were magical tours.
Not only did I provide walking and driving culinary excursions of varying sorts, but I also got to lead hiking tours, waterfall & wine tours, day tours of the Columbia River Gorge, Mt. St. Helens, Mt. Hood, and a ton of specialized or multi-day private outings all over the PNW and for a number of stellar companies. Over the years, I discovered that being a guide provided personal growth and character-building opportunities as well.
It forced me to face my fears, fight through jitters, and somehow tame my manic butterflies back into calm caterpillars. It taught me how to read people, anticipate situations, and take the temperature of a room. Being a guide made me a better writer and public speaker, and transformed me into a historian and a performer. A circus ringleader. Massager of human egos and corraler of bodies. It is equal parts memorization and improvisation. It’s soft skills and hardline timing within a delicately choreographed ballet. When you love the tours you give, it’s heart and soul on repeat.
Just like any and everything else I’ve done for a living over the last 15 years, the paycheck was secondary. It’s primarily love of the game. Because when all cylinders are firing, it’s as good as it gets. Akin to the feeling a comic gets when they kill, a musician when they slay, or even a teacher when they have a breakthrough and the birth of new thought with a student. Like a chef in the groove or a quarterback calling audibles confidently and effortlessly the length of the field and into the endzone.
Of course, it’s not all cuddles and coffee cake. The spectrum of experiences is a broad one. I’ve been heckled and harassed. Called a liar and a hack. I’ve been hit on, swung on, spit at, accosted, kissed, hugged, and mugged. I’ve broken bread, broken up fights, and curated love affairs. I photographed wedding proposals, witnessed epiphanies, induced laughter, shared tears, and watched countless tourists get white girl wasted. Sometimes I helped. I also made more friends from strangers than I can count.
I knew the houseless, hustlers, bankers, and baristas that haunted almost every block in the city. I saw the best and the worst of Portland on any given day, during the course of any given tour, and occasionally, within the same breath. I gave private tours for couples that spanned days, and public tours for 25 that covered hours. I walked backward, forward, and sideways while espousing the virtues of walkability. And drove through rolling vineyards and National Scenic Areas, pointing out the importance of urban growth boundaries.
It is an intrinsic and proud part of my being, whether I am actively guiding or not. As much as I am anything else, I am a tour guide.
I was thinking you would make an excellent tour guide.