You Are What/How/Where You Work
By Teddy Dondanville
There are some folks who would argue that having a complicated employment history is a bad thing, a sign of weakness, or a sign that you are unpredictable and have commitment issues. However, I think the more jobs you can cram into the employment history on a resume, the better.
If you examine my employment history, you will see that it’s varied. Like the scars welded into my skin, my jobs tell a story. It's a story, not just about odd jobs I’ve had, or legitimate forays into industries where I tried to build a career. It’s a two-fold story about exploring employment opportunities as a way to explore myself, and as a means to support myself after a delayed severance from Mom and Dad’s pocketbook.
A general disregard for high-paying salaries is a motif in my employment history, especially early on. Up until my adult life, I was never motivated by money. Rather, I’ve never needed to be. My parents raised me without ever allowing the pressure of financial stress to corrupt my development as a child. It was there, I’m sure, but it was hidden. So, when it came to work, craving money and chasing it wasn’t a behavior I developed.
Instead, I lived with the privilege of doing what sounded the best.
The author and his mother, climbing in the Shawangunk Mountains of New York.
One summer during high school, one of the older, “cooler” kids at my school, Brendan, told me that his boss was hiring. He assured me that I could join his pool-cleaning crew and learn the ways of the pool man (or pool boy, in this case). It seemed like an easy gig. Better than being bored at home. Plus, the raunchy teenager in me lusted for the hot homeowner and pool boy scenario. So I accepted.
I quickly found out I was there less as a second hand and more as friendly company. We drove around with the windows down, hot summer air wafting all around us, busting missions, and feeling filled with purpose. Between jobs, we ate fast food and smoked cigarettes. Then, after a hard day of labor, we drank a couple of beers like true blue-collar men.
Then, the summer ended, and Brendan never paid me. Eventually, many months later, I received an envelope in the mail with a couple hundred bucks in it. It was probably nowhere near what I should have earned, but then again, I’d have no idea. There was never talk of my salary rate in the first place.
At college in Boulder, Colorado, what sounded the best was skiing. For five winters, I skied incessantly. In between ski season, I lived an idyllic, dream-like existence where I got straight A’s and partied. I also worked so I could afford the lifestyle I was living.
By work, I mean soccer-themed babysitting. My first job in college was as a soccer trainer for the local soccer club. Twice a week, moms and dads dropped off their kids and scampered off to enjoy a two-hour, child-free existence. Meanwhile, I attempted to teach their kids, who were practically baby deer, how to kick a soccer ball.
My second job in college was working for the YMCA. I tutored and coached sports for after-school programs. During winter, I skied from the first chair at 9:00 a.m. to a hard stop at 12:00 p.m. Then, I’d blast back to the city just in time for the school bell to ring. During this time of my life, my diet mainly consisted of free YMCA food during snack time and bagel bites for dinner. I even got paid to direct LEGO-themed school-day-off programs, which was both nostalgic and aligned nicely with my construction history as a child.
A hot, sunny day on the farm in central Illinois.
My college jobs were real. But the financial need for having them was not. In reality, my parents were financially coddling me thousands of miles away from home. I wasn’t pretending to work, but I was pretending to be independent. So long as I got good grades, there was no reason to believe there was a problem. For each year in college, my GPA skyrocketed alongside my social life, alcohol, and drug consumption. Researchers are still trying to figure out this mathematical anomaly to this day.
In graduate school in Bloomington-Normal, Illinois, all forms of extracurricular employment ceased. So did a lot of the partying. The university had me on a full ride, and they were paying me for my labor as a teaching assistant. I was finally untethered to the ACH umbilical cord that stretched from my parent's bank account to mine.
My independence from my parents continued for a couple more years during my Peace Corps service. During that time, I received a monthly stipend from the US government. But after graduate school and the Peace Corps, things got real again. To support myself, I lined up a temporary job in a restaurant kitchen until I secured something better. Eventually, I transitioned to a career-worthy leadership position in the local parks and recreation department.
Then, COVID came and evaporated any semblance of work altogether. COVID also stressed my living situation. My roommate at the time, who was also my landlord, was panic-stricken by the pandemic. He no longer became comfortable with me living in his home, and gave me a month to move out.
Unemployed and evicted, I fell back onto the bank of Mom and Dad. Like a recidivist criminal who swears they’re out of the game and going straight, I couldn’t say no to the money. The financial pressure was too real. So, they co-signed and paid my lease. Meanwhile, I took work on a local organic vegetable farm. It was outside, and people needed to eat. It seemed noble. Plus, being young and able-bodied meant I could have the job. And my Spanish fluency sure helped a lot.
In the beginning, I knew nothing about farming, but I could follow directions. By the end of the summer, I was driving farm trucks and running crews. I was on the dirt and in the dirt. I was the dirt.
My employers even trusted me to operate the brush washing machine. The brush washer is a monstrous machine with a conveyor belt on the inside, a fan, brushes, and jets that spray water. It’s a drive-through car wash, except for vegetables. One day, as my luck would have it, my hair got too close to the external fan component of the machine. It swallowed my hair in seconds.
“Fuck…fuck… FUCK!” I screamed.
The dreaded brush washing machine…
Almost just as quickly, another farmhand hit the emergency stop on the machine. After I cut myself loose, I had a bleeding bald spot on my head the size of a Post-It note. Fortunately, I could keep the spot covered between the hair I had left and my daily hat-wearing habit. Even more fortunately, my hair grew back.
The brushing washer incident signaled the end of my role-playing as a farmer. My partner Whitney and I were leaving Illinois anyway. She finished her Ph.D. and wanted to hit the road. And I, now experimenting with the prospect of becoming a rock climbing guide and a self-employed writer, could relocate anywhere.
The destination was Estes Park, Colorado. Unsure if my job as a climbing guide would pay the bills, I looked for a second job (third, actually, if you count the writing I was doing on the side). I had a fantasy where I was the cool guy, rock guiding during the day and working nights at the local brewery. Plus, I was a damn good beer drinker, and any beer drinker will tell you that they can bartend.
After an introduction from a friend and a quick interview, I was hired on the spot. Between my beer-drinking background in a fraternity and above-average social skills, I was a shoo-in for the job. The only thing between me and being an expert beer pourer was learning about the product. So, I got straight to product testing before, during, and after my shifts.
Before long, I could talk to anyone about our beer selection. Lubricated by the same product I was pouring into pint glasses, I spoke to customers about anything.
When the blue-collar tradesmen came in during lunch to get drunk, I was a hyper-masculine, semi-problematic bartender. “Hell yeah, brother,” I’d say when serving yet another IPA. And when the tourists dropped in, I was a salesman, always upselling to get them to come climbing. I was like a tipsy chameleon, camouflaging with my surroundings, saying and doing anything to fatten the tip my customers left on the bar top.
Fortunately, when my climbing friends and co-guides visited the bar, my true people, I could be myself. I was their countertop confidant with overflowing advice. But perhaps more importantly, I was the cool guy with his hand on the handle to infinite liquid freedom.
When everyone left each night, when my cool guy fantasy crumbled, I was a crotchety janitor. I mopped floors and made the nightly migration to and from the dumpster like a two-legged raccoon. Behind the brewery, in the darkness, yearning for it all to be over, I frequently wondered how in the world I was scrubbing toilets at midnight with a Master’s degree.
That summer, I made the most money I had ever made in my life, but like all things, it eventually came to an end. I was moving to New York to pursue my guiding and writing careers further, and to support my wife in starting her career. We ended up in Albany, New York.
After a successful guiding season on the Shawangunk Ridge, aka the Gunks, my winter writing was not lucrative. As a result, the insidious nature of financial pressure came creeping back through the recesses of my life. I felt insecure and incapable. Being married and strapped with a mortgage added to the intensity of the financial insecurity. As a partnership, we made it through the year.
Overlooking the Estes Park valley, with Rocky Mountain National Park in the background
So, this winter, still holding onto the baggage from the previous year, I sought a temporary, seasonal gig to pad the bank account. I submitted two emails to local Christmas lighting businesses. I sold myself based on my familiarity with physical labor, bilingualism, and availability. I was ready now, take me or leave me.
That same day, I heard back from one of the companies. Later that day, I was schmoozing in an interview. But before the interview, I flopped my impressively sized resume on the table to display my readiness. Besides the size, they were most impressed by my climbing background and Spanish-speaking ability.
The following day, I was hired as a boom lift operator. As a boom lift operator, I am in charge of hanging lights on objects that cannot be reached from ladders or with painter’s poles, like forty-foot evergreen trees and mansion rooflines.
The work is hard, and the days are long. Besides the long hours, I struggle with the organized chaos of the company's operations. I also dislike the cognitive dissonance I feel about what I do and how wasteful and consumeristic it is. Sometimes, it feels like little parts of my soul evaporate for each plastic bag I cut open and throw away or for each minute my foreman leaves his diesel truck idling so he can snuggle inside like an adult-sized child.
The problem is, the money is too good. And there’s too much at stake. Out east, forty feet up, in the sleet and snow, I sometimes yearn for the umbilical cord I grew accustomed to. Instead, I’m cut off and forced into an employment situation I’ve dreaded and been able to avoid my whole life—a job that only alleviates financial pressure without elevating my higher purpose.
Fortunately, it’s only temporary. Soon, when the snow melts and the sunlight creaks its way through the dense northeast overcast, I’ll return to what I love. I’ll be back on the cliff, tied into a climbing rope. Or at my computer, organizing words into a sequence that helps my reader feel something.
My work as a climbing guide is physical, real, and risky. I crave the opportunity to handle that risk, to hold my life and my clients in my hands, cradling us and keeping us safe so we can grow. On the other hand, my work as a writer satisfies both the academic and the artistic aspects of me. When I get in my groove, I feel oddly robotic. My eyes operate like laser beams, scanning colossal amounts of content. My head floats on my shoulders, and my two arms and tens fingers operate autonomously, reaching, clicking, and tapping.
But I didn’t just apparate here. I had to evolve from a spoiled pool boy to a self-sufficient adult. Resiliency came with every letdown and subsequent transition. “Versatile” became one of my most prized attributes. And financial planning became the sharpest tool on my tool belt. None of which could have been possible without the support of my family.
It’d be naive to say I’m done. I am still evolving. And while I feel rightfully on my path as a guide and writer, I know from past experiences that the life and career I’ve created for myself are insecure. But that’s okay. I enjoy the hustle that comes with guiding when the weather is good and the autonomy I feel working anytime, anywhere, as a writer.
But let’s be real—if I don’t land some writing jobs, the next few months may include another employment detour. Maybe steelwork. In which case, “boom lift operator” is going to look pretty sweet on my updated resume.
Teddy Dondanville is a freelance writer focused on the outdoor industry and adventure sports. When not enjoying the cerebral and caffeine-fueled pursuits of writing, he works as a rock climbing guide in upstate New York. You can learn more about Teddy on his website.
