“That ain’t workin’, that’s the way you do it
Get your money for nothing, get your chicks for free”
– Dire Straits, 1985
We’ve all done things for money. Some noble. Some necessary. And some that still wake us up at night in a cold sweat, with the faint echo of elevator music and the itch of polyester uniforms. From the moment we’re tall enough to reach a cash register and can fake a smile that says, “Yes, I’d love to help you find your size in a shoe we haven’t carried since 1983,” we’re ushered into a world of occupational roulette. Sometimes you land on “Valuable Life Experience.” Sometimes “Please never speak of this again.” Each new job is a spin of the wheel—and the average American spins that wheel about a dozen times in their life¹.
Work has a way of throwing us headfirst into humanity’s most curious corners. You find yourself serving the public, navigating team meetings that feel more like hostage negotiations, and learning the exact temperature at which your soul starts to leave your body during a summer shift in the middle of a parking lot. Some jobs are strangely magical: they give you purpose, teach you patience, or let you watch a grown man cry because his coupon expired yesterday. Others are a unique form of punishment, dreamt up by someone who once said, “Let’s pay people to do this, but not too much.”
Still, every job leaves a mark—emotional, psychological, or in some cases, permanent back pain. Some gigs provide you with stories that become the centerpiece of dinner parties. Others give you stories you only share with your therapist, or when you’re trying to get out of jury duty. But they all count. They all add up. And if you’re lucky, you walk away with enough money for rent, a little new material for cocktail parties, and just enough dignity left to do it all again next week. Welcome to the world of work. The good, the bad and the ugly.
Work That Didn’t Feel Like Work
Driving an Ice Cream Cart
Van Nuys, California
My very first job was about as wholesome and sticky as it gets: cruising the neighborhood on a little ice cream cart at 13 years old. The cart had a tiny puttering motor, but the only real noise was that incessant tune blaring from the speakers—“Brahms’ Lullaby,” over, and over, again. To this day, I have no clue why nearly every ice cream truck in in the world gravitates to that lullaby², but it drilled itself into my brain all summer long.
I had no assigned route. After all, I was only 13 and the world was my popsicle-eating oyster. I’d wander familiar streets, including my own, ringing the bell for anyone with a sweet tooth and a bit of spare change. In this line of work, anyone with a dime could be my best customer or my worst. Rich or poor, polite or bratty—it didn’t matter as long as they had the coin. Transaction first, personality second. That was my motto.
Even at this ridiculously entry-level position, I encountered some challenges. One was a “gang” of kids (picture the Little Rascals, but meaner) who made it their mission to regularly relieve me of all my ice cream and cash. Yeah, robbing the ice cream kid. I’d end my day with an empty freezer and empty pockets, then sheepishly return the cart to the owner. Fortunately, he was a kind older man who took it in stride. He’d just shrug and say, “Better luck next time,” as if getting mugged by third-graders was all part of the learning experience. And, in a way, it was.
I learned that not all customers are good customers, and sometimes the house or the street gang wins. But despite the occasional heist, I loved that job for the simple independence it gave me. Just a boy, a cart full of Fudgsicles, and the open road.
Making Big Donuts and Small Tacos
Van Nuys, California
A few years later, in my early teens, I landed a gig at a pair of local drive-through eateries where I pulled double duty: mornings at The Big Donut, slinging sugary confections, and evenings at the Pup ’N Taco, dishing out fast-food tacos and hot dogs. For the uninitiated, Pup ’N Taco was a Southern California fast-food chain known for exactly what its name implies—think hot dogs and tacos under one roof³. They both sat on a busy corner across the street from a huge Baptist church, which meant Sunday mornings brought a deluge of hungry parishioners and charity events.
One day, the church placed an order so large it could have fed the entire choir: 100 dozen donuts for a special event. Their only request? “Do not include ANY powdered sugar donuts.” Apparently, these treats were destined for a group of blind seniors, where powdered sugar tended to end up everywhere except their mouths. So what did our mischievous little team do? Naturally, we made 100 dozen powdered sugar donuts. Every single one coated in the very substance they explicitly forbade. We figured, what’s the worst that could happen? Our answer came in the form of an irate phone call later, but hey, we couldn’t see that coming… and apparently, neither could their guests.
Our bakery antics didn’t stop there. We became famous for what we dubbed our “Exploding Jelly Donuts.” Here’s how it worked: whenever a particularly grouchy customer tried to get one of us in trouble with the manager, I’d quietly serve them a special jelly donut just for them.
Normally, you give a donut one generous squirt of jelly with a big syringe-like injector. For our “exploders,” we’d pump in twenty or thirty shots of jelly—so much that the donut was practically at critical mass. We had to plug the injection hole with a bit of dough just to keep it from oozing out. The unsuspecting victim would get their donut, take a big bite and… KA-BOOM! Jelly would erupt like Mt. Vesuvius, all over their nice clothes.
One time, a group of giggling grade-school girls came by after church, dressed in their Sunday best. The first girl innocently asked for a jelly donut. I served up an extra-extra-jelly donut with a smile.
The poor kid took one bite and got a crimson eruption of filling all down the front of her pretty dress, splattering onto her shoes. Her shocked gasp was followed by the kind of laughter that only 10-year-olds and devious donut makers can appreciate. Miraculously, we never got complaints about these messy pranks. And even if we had, it wouldn’t have mattered. Our manager was even more laid back and absent-minded than we were. He just chuckled and said, “Oh, those kids!”
Our cheekiness even extended to the written word. On particularly slow days, I took to doodling inside the take-out boxes. Once, just for grins, I sketched a little “artwork” to vent my frustration with the perpetually cranky customers. The drawing depicted a hand raising a “middle-finger salute”, accompanied by the friendly suggestion: “Next time, go to Winchell’s.” Winchell’s was our rival donut shop down the road. Immature? Absolutely. Effective at making us laugh? You bet. For the record, that customer never complained either. Maybe they actually did go to Winchell’s. Who knows?
It was greasy, it was sugary, and it was completely inappropriate at times. And it was a blast. Working at the Big Donut and Pup ’N Taco taught me the fine arts of fryer oil alchemy and customer relations, or rather, how not to handle them. More importantly, it was my first taste of real workplace camaraderie: a bunch of teenaged troublemakers united by donuts, tacos, and the shared goal of making it to closing time with our sanity intact.
Serving in the United States Navy
Oahu, Hawaii
After high school, I traded in my donut apron for a Navy uniform. At 18, craving adventure, I enlisted in the United States Navy and soon found myself in boot camp in San Diego. Navy boot camp was an experience unto itself. The adjutants (sometimes called drill instructors) had a charming wake-up routine: at 4:00 a.m. sharp, one would barrel into the barracks, run a nightstick around the inside of an empty metal trash can, and bellow, “Rise and shine, maggots! You got ten minutes to shit, shower, and shave!” My parents never said that to me at home, so it was an eye-opening introduction to mornings in the military service.
Boot camp also taught me the importance of a skill I hadn’t anticipated: smoking. Yes, smoking cigarettes. You see, during field exercises, our adjutant would periodically yell, “Smoke break! Smoke ’em if ya got ’em.” If you didn’t smoke or didn’t got ’em, you’d be “volunteered” for some lovely alternative activity like scrubbing out the inside of putrid garbage cans. After observing a few poor non-smokers get saddled with extra chores, I quickly decided that lung cancer might be the lesser of two evils. So, I became a smoker purely for professional reasons. It was either light up or clean up, and I knew which one I preferred. Thus, I made sure I always “got ’em” when the call came. The Navy may have improved my discipline, but it definitely ruined my lungs.
Eventually, I survived boot camp and was fortunate enough to land a plum assignment as The Assistant to the Chief of Staff for Commander, Fleet Air, Hawaii. In plain English, that meant I got to live and work on a Naval air station on Oahu—about as sweet a duty station as one could possibly dream up. Ironically, I volunteered for duty in Vietnam. That’s how I learned how to get what you want in the military: ask for the exact opposite.
During boot camp, one of my fellow recruits dreamed of “seeing the world” from the deck of a large naval vessel, so he opted to become a Boatswain’s Mate. Boatswain’s Mates are responsible for a wide range of tasks related to seamanship, including ship maintenance and deck operations, supervising working parties and damage control teams, and operating equipment for loading and unloading cargo. So, where did they send him? To a Swift Boat, patrolling the Mekong Delta in Vietnam, getting shot at from both sides of the river.
After six months of sharing a crowded barracks, an even better opportunity popped up: my older brother, who was also in the Navy, arrived in Hawaii and invited me to split a two-bedroom beach house with him on the tip of Waimea Bay on the North Shore. Suddenly I was spending virtually all of my off-duty hours surfing legendary breaks like Waimea Bay, Banzai Pipeline, and Sunset Beach.
I’d get off work, swap my uniform for board shorts, and stay in the water until sunset with his friends. For a surfer barely out of his teens, it felt like winning the lottery. I absolutely loved those 18 months in paradise. I mean, how many people get to live with family, do a meaningful job, and ride world-class waves every day?
But, the job wasn’t all sunshine and surf. As part of the Fleet Air staff, I occasionally had to embark on aircraft carriers for a few days while our staff conducted Vietnam War game exercises. If you’ve never been on an aircraft carrier, imagine a floating city the length of three football fields, with 5,000 sailors and officers aboard⁴. Aircraft carriers are over 1,000 feet long, with up to 25 decks stacked high—basically a giant maze of floating steel. On my first carrier voyage, I was completely awestruck and thoroughly disoriented.
One morning, while I was standing on the bridge, the commanding officer casually asked me, “Sailor, why don’t you run down to the mess hall and bring me back a cup of coffee?” Being eager to please, I snapped to attention: “Aye aye, sir!” and trotted off, only to realize I had no idea where I was in that gargantuan vessel.
I figured the mess hall had to be somewhere below decks, and since I was already at the top, I went down. And then further down. I roamed one corridor after another for what felt like an eternity. After a lengthy odyssey involving dozens of wrong turns and at least one accidental visit to the engine room, I finally stumbled upon the mess hall. I grabbed a cup of coffee and then attempted to retrace my steps to the bridge. Easier said than done. I was hopelessly lost in a labyrinth of identical hallways and hatches.
Two hours later, I eventually found my way back to the bridge. I sheepishly presented the stone-cold coffee to the officer of the deck, and said, “I have a cup of coffee for the commander. Do you know where he is?” He just smirked and replied, “Oh, he left over an hour ago. He’s having lunch.” So much for making a good impression. If there’s a record for the longest coffee run in Naval history, I’m pretty sure I set it that day.
Despite such misadventures, my Navy stint was overall a rewarding chapter in my life. I learned about teamwork, responsibility, and how to navigate both massive ships and military bureaucracy, even though I never did fully conquer the layout of that carrier. And when my enlistment was up, I left the Navy with entertaining memories, and perhaps more importantly, an addiction to nicotine that would take years to shake. Not a bad trade-off, all things considered.
Ski Patrolling at Snow Summit
Big Bear Lake, California
Shortly after returning to civilian life in the late 1960s, I traded ocean waves for snowy slopes. I landed a plum job as a ski patroller at Snow Summit, a ski resort in Big Bear Lake, California. If the Navy had been regimented and strict, ski patrol was its free-spirited cousin. Our mission was to rescue injured skiers and keep the mountain safe, but how we did that left room for a lot of interesting experiences.
Ask any ski patroller and they’ll have a catalog of crazy injury stories. The craziest call I ever responded to involved a young man, fresh from two grueling combat tours as an Army infantryman in the jungles of Vietnam. You’d think after facing that, a little recreational skiing would pose no threat. Fate had other ideas. On his first “civilian” day skiing, his friends brought him to Snow Summit. Late that morning, we got an alert: an injured skier up on the mountain, needed assistance.
I raced over and found this poor guy moaning in pain with a crowd gathered around. It turns out he had taken a tumble and somehow landed on his metal ski pole… hard. The pole had snapped in two, and one jagged half impaled him straight through his upper thigh, missing, some vital “male parts” by millimeters. It was like a scene out of a war movie. After surviving two tours in literal war zones without a scratch, this unlucky fellow gets impaled by a ski pole on a ski slope in California.
We carefully stabilized the injury—trying not to think about what could have happened if that pole had gone a smidge to the left—and carried him into an ambulance and off to the local hospital. In the end, he made a full recovery and, from what I heard, even kept skiing—albeit with a healthy respect for his ski poles from then on.
Probably the worst injury I encountered was a woman who completely lost control on an intermediate run and zoomed all the way to the bottom, crashing through a snow fence at high speed. By the time she came to a stop, she had broken her back in three places. It was a terrifying sight, but there was a silver lining. Because her uncontrolled descent ended right at the base area, ski patrol, and an ambulance were on-site almost immediately. She received urgent care and eventually recovered. However, I suspect her appetite for alpine skiing diminished considerably.
Of course, in between the dramatic rescues, there were moments of absurdity. One morning around 10 a.m., I was dispatched to what sounded like a very serious situation: “Possible unconscious skier on an intermediate run, not moving.” I hustled over, expecting the worst—a heart attack or head injury perhaps. Instead, I found a woman sprawled out on the snow, eyes closed.
I gently shook her shoulder: “Ma’am? Are you alright? Are you hurt?” She opened her eyes, looked up at me, and burst out laughing. No injury at all—she was drunk as a skunk, napping mid-slope. It turned out her ski poles were the special type that were hollow inside, essentially giant flasks designed to be filled with schnapps or whatever liquid courage one prefers.
By mid-morning she had emptied both poles and was absolutely snockered, hence the impromptu on piste nap. I told her I’d take her down in a rescue sled so she could sober up at the first aid station, but she stubbornly refused to be strapped in. Instead, we struck a deal: if she held on tight to the back of the sled, I’d ski her down slowly. Seemed simple enough.
Well, it turns out “slowly” is relative when you’re three sheets to the wind. Every gentle turn I made, she just let go and barrel-rolled off into the snow, laughing hysterically. I’d stop, help her back on, and we’d continue, only for her to tumble off again at the next bend, cackling with delight. What should have been a five-minute sled ride to the bottom became an hour-long comedy routine. By the time we reached the base, we were both in tears—from laughter, thankfully, not pain. Eventually, she sobered up, I got one heck of a story, and to this day I can’t see a bottle of Peppermint Schnapps without laughing.
Ski patrolling was an incredible job. It combined the adrenaline of emergency response with the laid-back vibe of ski culture. One minute you’re rushing to splint a broken leg, the next you’re cracking jokes on a chairlift. I loved the camaraderie with my fellow patrollers, the satisfaction of helping people, and the simple joy of spending every day on the mountain, even if much of it was dealing with the results of others’ bad decisions. It set the stage for my next chapter in the snow world. One that would prove even more pivotal in my life.
Cutting and Styling Hair
San Fernando Valley, California
At the end of the ski season, I went directly from the slopes to the salons. In the 1970s, following my ski patrol days and some wandering, I decided to become a hairstylist. I enrolled in the Charles Ross Hair Academy, which was reputedly the top cosmetology school in Los Angeles at the time. The Academy was just a stone’s throw from Hollywood and the hubs of the music industry, so our training had to be cutting-edge.
It was an exciting scene: picture a busy salon floor with ’70s disco music blaring from the overhead sound system, giant mirrors reflecting people’s wild new hairdos, and gossip flying faster than scissors snipping. I learned to cut, color, perm, and style alongside a motley crew of aspiring hairdressers, many of whom dreamed of styling celebrities one day.
I encountered plenty of quirky situations in school, but one stands out as an inadvertent science experiment. During my training at the Academy, a customer came in requesting a permanent wave—a “perm.” For those lucky enough not to know, a perm involves soaking the hair in a rather pungent, caustic chemical solution—usually ammonium thioglycolate. It’s a delicate process. Applied correctly, the perm solution reforms the hair’s structure to create lovely curls. Leave it on too long and you risk frying the hair. I rolled this client’s hair meticulously on dozens of perm rods and applied the solution. After maybe 15 minutes, I decided to test a strand to see if the curl had set.
I gave one roller a little jiggle and—plunk—it fell right off her head and onto the floor. I froze. The hair had essentially disintegrated at the root. Apparently, she had very fragile, damaged hair to begin with, and the solution was too much for it. My instructor, suppressing a smile, swiftly kicked the fallen perm rod under a cabinet and whispered,
“Congratulations. You’ve just given your first ‘kick perm.’”
Fortunately, the client never noticed anything amiss, and I breathed a deep sigh of relief. I also learned a valuable lesson: sometimes, you can’t see what’s happening right under your nose. But most of the time, caution is your best friend.
Working in an L.A. salon in the late ’70s provided a front-row seat to cultural trends—and nothing was more of-the-moment than Farrah Fawcett’s hairstyle. Fawcett, the breakout star of Charlie’s Angels, had this iconic feathered, big-hair look that basically defined an era. Suddenly every young woman who walked through our salon doors would plop down in my chair and declare, “I want a Farrah Fawcett.” It became the most common (and in some ways, the worst) request, but not because the style was flawed.
Fawcett’s feathered flip was gorgeous on her, but it didn’t suit everyone. Try explaining to a client that her bone-straight, fine hair might not magically transform into Farrah’s luscious mane. Some understood, but many were determined.
So I’d dutifully attempt to give them voluminous layers and wings, spray on two cans of hairspray, and send them off feeling like a star. Farrah’s influence was that massive: millions of women worldwide were copying her look⁴, whether it flattered them or not. Who was I to deny the trend? But, I have to admit, for every botched Fawcett wannabe, there were a few clients who walked out looking like they just stepped off a TV set. Those moments were golden.
When the disco era waned and the 1980s came knocking, I eventually moved on from professional hair styling. But those years in the salon taught me more than how to feather bangs or execute a perfect blowout. I learned how to talk to anyone. When you’re giving someone a perm, you have about two hours of idle chit-chat, so you better make it good. I learned how to stay calm when a client is freaking out about a bad cut (pro tip: never say “Oh my God!” out loud). And I developed an enduring respect for the transformative power of a good hairstyle, as well as the havoc of a bad one. To this day, I still have nightmares of perm rods popping off in my hands. Go figure.
Teaching Skiing at Vail Ski School
Vail, Colorado
After hanging up my shears, I eventually found my way back to the mountains, but this time, as a ski instructor. I headed to Colorado and became a PSIA-certified instructor at the Vail Ski and Snowboard School. This was in the early 2000s, and by then I had over 50 years of skiing experience under my belt. Next to ski patrolling, teaching skiing might just be the job I cherished most of all. There’s something magical about sharing a sport you love with people from all over the world. And I do mean all over. Vail’s slopes are an international melting pot⁸.
The ski school’s range of students was immense. From bright-eyed first-timers who—except for movies on television—had never even seen snow, to seasoned experts looking to refine their technique. The variety kept me on my toes. On any given day I could be assigned a family from Mexico that didn’t speak a lick of English or a gaggle of teenagers from Texas who thought skiing just meant point your feet down and go. I quickly learned there are two types of students that test an instructor’s patience: those who don’t understand you, and those who just don’t care. Sometimes they even overlapped.
I learned the importance of being able to say, “¡Desacelera, o te vas a estrellar contra la letrina y te vas a golpear el coco! Translated: “Slow down, or you’ll crash into the outhouse and injure your noodle!”
My most challenging student ever was a middle-aged man who absolutely could not grasp the fundamental concept of skiing: stand up on your skis. He fell every thirty seconds, then just lay there like the chalk outline at a crime scene. Over and over. Crash, splat, “Help!” It was the longest morning of my life.
By contrast, I was also assigned dream students. One Presidents’ Day weekend, the ski school assigned me a three-day private lesson with a gorgeous, athletic divorcee from Florida who already knew how to ski quite well. Essentially, she just wanted a personal mountain guide to show her the best runs and maybe offer companionship for lunches and chairlift rides along the way. Twist my arm, why don’t you!
We spent three glorious bluebird days cruising all over Vail’s expansive back bowls and freshly-manicured groomers, laughing and swapping life stories. I’d give her pointers occasionally, but truth be told she didn’t need many. On the last day, she handed me a tip that was almost as breathtaking as the views from the summit. I won’t lie, I felt a bit like I’d hit the jackpot: getting generously paid to do what I love, under perfect conditions, with delightful company. Best. Ski. Days. Ever.
Of course, being an instructor isn’t all glamorous powder runs. There were times I had to bluff my way through answers. Every so often, you get that know-it-all boyfriend who wants to show off in front of his girlfriend by probing the physics of skiing: “Can you explain to me exactly how the shape of the ski affects the turn radius in relation to centripetal force?” When faced with such a question, I learned to flash a confident smile and launch into something like:
The ski’s sidecut geometry—a curved shape defined by its radius—controls turn radius through edge engagement. As the ski angles, the edge curvature tightens, reducing the turn radius approximately by r ≈ Rs × cos(θ), with Rs as the sidecut radius and θ the edge angle. Centripetal force Fc = mv² / r increases as r decreases, requiring sharper edge control and more skier strength. Factoring in torsional rigidity, camber flex, and energy loss through dampening, the ski acts as a dynamic control surface, converting speed into directional changes through snow friction.
He nodded, and never ask me a question again. Sometimes faking it is a skill unto itself.
I loved every minute of teaching skiing. In fact, I loved it so much that it inspired me to achieve another life goal: writing a book. After years of swapping wild instructor stories over après-ski beers, I compiled the best of them into a collection. In 2005, I published my very first book, Ski Instructors Confidential: The Stories Ski Instructors Swap Back at the Lodge.
I hadn’t a clue how to write or publish a book, but I felt compelled to preserve those hilarious and poignant tales of life on the slopes before someone else beat me to it. To my astonishment, the book struck a chord with readers and went viral. Not only did I enjoy meeting people from all over the world, but I also walked away with the confidence that I could tell a darn good story.
Driving Off-Road Jeep Tours
Vail, Colorado
Even Paradise can have an off-season. Summers in Vail were slow for ski instructors, and one particularly cash-strapped summer I picked up a job with Timberline Tours, one of the biggest river rafting and off-road Jeep touring companies in the valley. I’d never driven off-road professionally, and Timberline preferred it that way. The ad said “No experience necessary.” I guess they wanted to train guides in their own style rather than break any bad habits. I soon found myself piloting an open-top Jeep full of tourists over rocky mountain roads and remote trails, showing off Colorado’s backcountry.
One sunny morning, the dispatcher sent me to pick up a group of four guests at a posh five-star hotel in Vail. I pulled up in my pristine Jeep, and out came four women in their 40s, already radiating vacation energy. They were all married, successful, and on a girls’ getaway weekend—three days free from husbands, kids, and responsibilities. In short, they were ready to cut loose. As we headed toward the trailhead, I gave them my usual spiel:
“Alright ladies, today we have two options on the menu. We can take the nice easy route—stay clean, and enjoy the scenery. Or, we can take the rough and dirty route and really have some fun. What’ll it be?”
It was unanimous and instantaneous: “Rough and dirty!”
From the moment our tires left the pavement, those women were transformed. Every bump, every mud puddle, every steep climb up a boulder was met with hoots of delight and high-fives all around. They were constantly egging me on: “Go faster! Hit that mud over there!” So I obliged. We plowed through mud holes that splattered the Jeep from hood to taillights.
We crawled up craggy paths at angles that had them screaming with delight. Half out of fear, half out of joy. By the midpoint of the tour, these ladies had gone from chic and composed to looking like a pack of university spring breakers on an off-road bender—hair wild, clothes drenched in mud, faces flushed with excitement. And they loved it.
At one point I stopped atop a scenic overlook where you could see the entire valley below. They stumbled out of the Jeep, laughing, and posing for selfies—muddy clothes and all—proclaiming it was the best day of their trip. On the way back down, I might have taken one or two “bonus” detours through especially mucky bogs, just to hear them roar with laughter again. By the time I dropped them off at their hotel, the Jeep was caked in filth and so were they.
They looked like they’d been through a war—albeit a very fun one. As they wiped mud off each other’s cheeks, they thanked me profusely and pressed a hefty tip into my hand before strutting through the front doors, turning heads as they slogged through the lobby. I imagine the concierge nearly had a heart attack at that sight. I drove away grinning from ear to ear. I had mud in my teeth, a fat tip in my pocket, and a great story to tell. Who knew that playing in the dirt could be so much fun?
That summer with Timberline Tours taught me that adventure comes in many forms. Sometimes it’s high-altitude skiing. Sometimes it’s low-gear rock crawling. I discovered a different kind of satisfaction in guiding people, giving them an experience that lets them unleash their wild side. I also learned that a group of cooped-up moms can party harder than anyone when given a Jeep and a little freedom.
Those off-road escapades rounded out the list of jobs I truly loved. Each one, from ice cream vendor to Jeep driver, had fed my soul in some unique way. But life isn’t all dream jobs and happy customers. Inevitably, one also stumbles into employment that’s less… enjoyable. Thus, with a mix of dread and hindsight humor, I present the flip side of this story.
Jobs That Made Me Question My Life Choices
Shoveling Sand
Van Nuys, California
Right after I got out of the Navy, I found myself a broke college student in need of a part-time job. The early 1970s economy wasn’t exactly kind to job hunters, and most gigs I came across paid a measly $5 an hour. Then one day I spotted a notice on the a bulletin board: “Help Wanted – Part-time, physically challenging job, $8.50/hour.” My eyes nearly popped out of my head. $8.50 was a king’s ransom for unskilled work back then—over $60 an hour in today’s money⁵. Physically challenging? I was 21 and fit as a stallion. No problem! I grabbed the tab with the phone number and called immediately.
The next day, I showed up at the Wagnild Cement Mixing Plant, a large concrete supplier in the Valley. The owner walked out to greet me—a wiry, no-nonsense guy with forearms like Popeye. He didn’t bother with any form of interview beyond, “You willing to work hard?” I nodded. “Good. Follow me, I’ll show you what you’ll be doing.” He led me to the edge of a humongous pit on the property, maybe 50 feet deep at the lowest end. Running up from the shallow side of the pit was an enormous conveyor belt, stretching into the sky, which presumably transported sand up to the mixing facility.
As I peered down, I saw that the entire bottom of the pit was covered in sand. The owner explained the situation: they used this belt to move sand, but inevitably a lot of it spilled off the sides of the conveyor and accumulated in the pit below. It didn’t magically remove itself, and that’s why I was here. My job was simple in description if not execution: jump down into the pit, shovel all the spilled sand onto the belt or out of the pit.
Thus began the most back-breaking labor I’ve ever experienced. Four hours a day, I basically engaged in hand-to-hand combat with sand. It was me, and my shovel against gravity. I’d scoop up a heaping shovelful from the pile at my feet, then pitch it over my head to onto the conveyor belt. Repeat ad nauseam. The sand had its way of sifting back down, so you often had to shovel the same sand multiple times as it slipped away. The pit had sections so deep I’d be standing in sand up to my thighs, trying to dig my way out. Every muscle in my body burned: arms, back, legs—muscles I didn’t even know I had. I was basically executing extreme CrossFit before CrossFit was even a thing. And getting paid for it.
Each day, I’d emerge after my self-imposed four-hour shift, looking like a sugar cookie—coated head to toe in sand, sweat soaking through my shirt, utterly spent. I’d collapse into my car, drive home, and fall asleep immediately after coughing up what felt like a sandbox from my lungs. The next morning it was back into the pit. After two weeks of this, something funny happened: I caught a glimpse of myself shirtless in the mirror and realized I was absolutely ripped! Apparently shoveling tons of sand is as good as any Schwarzenegger workout. So at least I got a “beach bod” out of the ordeal, including authentic beach sand in every crevice of my body.
Despite the grueling nature of the job, I never considered quitting. I was young, needed the money, and knew it was only temporary. There was a strange pride in it too—like surviving a boot camp of one’s own making. When I finally shoveled the last grain and the pit was clean, I climbed out and heaved a sigh of relief the size of California. The owner handed me my pay and, I think, a respectful nod. I had done it. I defeated the sand monster. And I earned every damn penny of that $8.50 an hour.
Baskin & Robbins 31 Flavors
Van Nuys, California
In my ongoing quest for “easy” jobs that wouldn’t fry my brain while I focused on my studies, I thought I’d found the holy grail: scooping ice cream. I mean, how hard could it be? I pictured a sweet little shop, free ice cream, happy customers, and a blissfully simple work experience. So I answered the ad and got hired at a local Baskin-Robbins 31 Flavors store. I was about to discover that even the most innocent-sounding jobs can have serious attitudes.
The shop owner was a very kind-hearted, wonderful man, who had a full-time career in a technical field. He ran the ice cream store as a side-gig. But boy, was he detail-oriented. He ran that Baskin-Robbins with the precision of a tech firm. For instance, before each shift, every employee had to practice scooping ice cream to ensure each scoop weighed exactly 4 ounces (113 grams). Not 4.1, not 3.9. Four on the dot. We would literally measure our practice scoops on a scale.
He had calculated exactly how many scoops could be sold per tub and cross-checked that against the daily receipts. If the numbers didn’t add up, it meant someone was “heavy-handing” their scooping and robbing the store of its profits! He could pinpoint exactly which employee was the culprit based on who was working which shift and how much off the inventory was. Then they’d get a friendly “coaching session” on proper scooping technique (read: keep wasting my ice cream, and you won’t be scooping here much longer). So much for carefree.
The irony of all this portion-control madness was that we, the employees, were allowed and even encouraged to eat as much free ice cream as we wanted while on duty. The logic was that you should know the product in order to sell it well. Well, OK. Twist my arm. In my first month, I devoured a mountain of Pralines ’n Cream and Jamoca Almond Fudge. I rationalized it as research—how can I possibly extol the nuances of Chocolate Ribbon if I haven’t explored its depths personally? Let’s ignore the fact that my jeans were getting tighter. That’s just the cost of education.
It turns out scooping ice cream at Baskin-Robbins isn’t so simple after all because—news flash—they offer way more than just 31 flavors. Sure, at any given time there are 31 flavors in the case (the “31” originally stood for one flavor for each day of the month), but the company has a library of over 1,400 flavors they rotate through⁶.
And then there are seasonal specials, sundaes, banana splits, milkshakes, ice cream cakes, and novelty items. I had to quickly learn an extensive menu: not just the difference between Mint Chocolate Chip and Chocolate Mint (a real thing), but how to assemble a Brownie à la Mode, how to write “Happy Birthday” in icing on the top of a cake, and the exact geometry required to balance three scoops on a single sugar cone without it toppling. It was a lot to take in.
The customers, for the most part, were great—kids giggling with excitement, families on outings, and the occasional heartbroken teenager seeking solace from a double-scoop. But scooping presented its own physical challenge: some of those ice cream tubs felt like they were frozen solid to the core of the earth. Have you ever tried gouging out rock-hard Rocky Road while a line of customers stands horrified, watching the veins on your face explode? I’d often have one arm submerged in the freezer, wrestling with a scoop through the tub, praying it wouldn’t slip and send a chunk of ice cream flying across the room—which actually happened once or twice. Eventually, I developed a technique and some muscles I hadn’t used since my job at the sand pit.
One memorable night, a mother came in with her young son who was maybe 4 years old. The kid had been very brave at his dentist appointment earlier that day. The irony wasn’t lost on me: celebrating a successful trip to the dentist with a mountain of sweets. His Mom told him he could have anything he wanted. The boy’s eyes went wide as I rattled off flavors. All 31 of them. He paused, looked up at me, and said, “I want… all of them.” Mom gave me a resigned nod as if to say “We started this, so let’s finish it.” Challenge accepted.
I got a gigantic sundae bowl and proceeded to scoop a miniature ball of every single flavor we had—a true 31-flavor masterpiece, with syrup, sprinkles and whipped cream on top. This thing was a rainbow monstrosity, and the kid’s face lit up like a Christmas tree. He managed to eat maybe a third of it, making an absolute mess in the process with melted ice cream all over the table and floor. But it was clearly the highlight of his young life. Cleaning it up was a pain, sure, but sometimes you have to play the role of the Ice Cream Fairy to make the magic happen.
By the end of my stint at Baskin-Robbins, I had a new appreciation for the phrase “It’s not all sweetness and light.” Sure, I was surrounded by ice cream and generally happy vibes, but the job had its stresses—be it precision scooping or marathon rushes of customers on a hot summer day. Ultimately, the combination of brain freeze, an aching scoop arm, and the calculus-level portioning wore me down and I left to pursue other ventures. Still though, to this day, I can’t walk by a Baskin-Robbins without instinctively checking if the scoops in the display case are the right size.
Thom McAnn Shoes
Van Nuys, California
One of the more soul-crushing jobs I took in my college years was as a salesperson at a Thom McAnn shoe store at a local outdoor mall. Thom McAnn, for those who don’t recall, was once a huge shoe retail chain⁷, though, by the time I joined, it felt like its glory days were well behind it. I got the job through a friend, despite knowing absolutely zilch about selling shoes, even though I’ve worn them all my life. But once again, I thought, “How hard could it be?” People come in, they say “I need a size 9,” I fetch it, they try it on, and they’re done. Right? Oh, sweet naïve me.
The store manager was a fellow named Jim McAvoy. Jim ate, slept, and breathed shoes. He was a fastidious company man, climbing the Thom McAnn corporate ladder, with his sights set on becoming a regional manager one day. Under his watch, selling shoes became an art form, And we lowly sales associates were his apprentice artists, expected to follow the Grand Doctrine of Footwear Sales to the letter.
Jim taught us three core rules:
Rule #1: Never assume a customer is “just browsing.” In Jim’s eyes, everyone walking into the store was a guaranteed sale unless we screwed it up. If someone so much as glanced at a loafer, we were to be at their side: “Hi there, can I help you find your size in that?” Heaven forbid we let them leave without at least attempting to put something on them.
Rule #2: the Turn-Over Technique. This was our strategy for salvaging a sale when the original salesperson (say, me) wasn’t sealing the deal. Let’s say I was helping a customer and things were going south—they weren’t buying what I was selling. I had to swallow my pride, flag down a colleague, and effectively tag out: “Excuse me, Bert, can you assist me in finding something for this young lady?” Then I’d slink away, tail between my legs, while Bert swooped in with a fresh approach and made the sale. If he failed to close, he’d tag Salesman #3, and so on. The idea was that by the third pitch, surely someone would say something that resonated with the customer. In practice, it often felt like a desperate relay race of pleather pumps and egos.
Rule #3: Never come back from the stockroom empty-handed. This one was practically scripture. If a customer asked for a shoe we didn’t have in stock, you never admitted defeat. You returned with something—anything—that was vaguely similar. The logic was that maybe they’d like the alternative, or at least appreciate the effort and try it on. If Mrs. Jones asked for a black stiletto in size 7 and we were out, you might come back with a navy kitten heel in size 10 and say, “These are a similar style. Why not give them a try?” Utterly nonsensical? Often, yes. But occasionally the customer would shrug and say, “Well, I do need a roomy pair of navy shoes…” and bam, sale. It was all about refusing to let them leave without considering something else.
I remember one humbling encounter that put all these rules to the test. A well-dressed woman came in looking for a pair of elegant patent leather pumps to wear to a formal event that evening. Immediately, my internal alarm bells went off. I knew our stock was spotty because of a truckers’ strike that delayed shipments. The chances of having what she wanted in her size were slim to none. But I greeted her cheerily and sat her down.
I measured her foot with a classic metal Brannock Device (might as well do something right), and she said she needed a pair of black patent pumps, size 8. I knew for a fact our dress shoe section was decimated from holiday sales and we hadn’t received new inventory in over three months. But per Rule #3, I couldn’t just say “Sorry, we’re out of that.” So, off to the back room I went, dread slowly enveloping me.
Sure enough, no black patent pumps in 8, 9, or even 13. In fact, the closest thing we had in an 8 was a pair of Chuck Taylor All-Star high-top basketball shoes in black canvas. I stared at those Chuck Taylors and had a tiny devilish thought. No… I couldn’t. Or could I? A mischievous impulse took over. I emerged from the stockroom with the Converse sneakers in hand and approached the lady with a cheerful face.
“Well, ma’am,” I said, “unfortunately we’re out of black patent pumps in your size, but I do have this lovely pair of Chuck Taylor All-Star high-top basketball shoes. They’re black, lace-up, and certainly make a statement. Would you like to try them on?”
She looked up at me, stunned, as if I had lost my ever-loving mind—which, at that moment, I probably had. Her expression was somewhere between disbelief and offense. The same way you’d look at a visitor from the planet Voltar who just offered you a Zhilakai Crystal Orb. Before she could unload on me, I smoothly segued to Rule #2 and motioned over to Bert: “Excuse me, Bert, could you help this young lady? She’s looking for a patent leather pump in size 8, but the closest thing we have is this lovely pair of Chuck Taylor high-tops. Perhaps you can assist her further.”
Bert shot me a What in the hell are you doing to me? glance, but nevertheless, stepped in and politely restarted a conversation with her. I slithered away to the stockroom, where I doubled over in silent laughter with a few of the other guys. I had technically followed the rules: I didn’t come back empty-handed! Jim might not have approved of my choice of the substitute product, but hey, sometimes you need a little comic relief on a dull day of shoe selling.
As you might guess, that lady did not walk out with sneakers, or anything else, for that matter. Even Bert couldn’t salvage the sale. Jim later gave me a mild scolding: “Use common sense with Rule #3!”, but I think even he had to chuckle at the absurdity of it all.
Selling shoes taught me that sometimes a job can be both mindless and high-pressure at the same time—a truly unpleasant combo. You’re cleaning the display case for the tenth time that day, but also worrying about quotas and mystery shoppers. I lasted one season there, long enough to witness the full glory of the holiday rush and one too many instances of people trying on shoes without socks. When I left, I can’t say I was sad to hang up my shoe horn. I walked away with a newfound respect for retail workers and an abiding hatred of the phrase “I’m just browsing.”
Working For a Temp Agency
Van Nuys, California
Desperate times call for desperate measures. In my case, that meant signing up with a temp agency when I couldn’t find work anywhere else. If I can offer one piece of heartfelt advice to any job seeker: never, ever, go to a temp agency. It’s a grab bag of employment, and every assignment illustrates just how low some employers are willing to stoop when they need a disposable worker for a day. Through the agency, I had a series of unglamorous one-off gigs, but one stands out as the absolute nadir.
I was sent to a factory warehouse that manufactured commercial fire extinguishers—those big red metal canisters you see mounted on walls virtually everywhere. When I arrived, the supervisor explained my task with a straight face, as if it were perfectly reasonable: the company had produced a batch of 500,000 steel nozzles that screw onto the end of the extinguisher’s hose, but discovered that the internal diameter was too small.
None of these nozzles passed inspection. If they couldn’t be modified, they were essentially junk. Half a million pieces of junk. Throwing them all out would be too costly, and retooling a machine to fix them automatically was apparently not in the cards. So what did they do? Hire a temp, of course. My job was to manually enlarge the opening of each nozzle by drilling it out. One by one.
I sat on a stool next to a colossal wooden crate filled to the brim with tiny steel nozzles—literally hundreds of thousands of them. In front of me was a drill press fitted with a bit of just the right size to grind out the excess metal inside the nozzle. The supervisor demonstrated: pick a nozzle from the “bad” pile, insert it onto the bit, pull the lever to drill through, and then toss the corrected nozzle into the “good” pile. Repeat ad infinitum. Then he left me to it with a cheery, “Let me know if you need anything,” and probably thanked his stars he wasn’t the sucker doing this God-forsaken job.
I worked that drill press for hours on end. Bzzzt, thunk. Bzzzt, thunk. One nozzle at a time. After the first thousand or so, I started calculating in my head: at, say, 5 seconds a nozzle, how long will it take to do 500,000? I’ll save you the math: that’s about 2,500,000 seconds, or roughly 29 days of non-stop drilling—assuming no breaks.
The repetition was endless. My hands vibrated from the constant drilling, my eardrums were flattened from the sound. I became a nozzle-inserting automaton. Every time I dared glance at the crate, it looked just as full as it was when I started as if a malicious elf was refilling it when I wasn’t looking.
By the end of the day, I had churned through maybe 8,000 nozzles. A mere dent. I went home that night and dreamt of being chased by an unruly fire extinguishers. Somehow, I lasted a full month on that assignment, coming in day after day to grind away at that mountain of metal. When the contract mercifully ended, I’m proud to say I finished the last nozzle in the crate. I half expected a parade in my honor, or at least a certificate of completion for “500,000 Nozzles Drilled,” but nope, just a “Thanks, you’re done.”
It remains the most numbingly repetitive task I’ve ever performed. But, on the bright side, I developed a tremendous appreciation for any future job that didn’t involve doing the exact same thing 500,000 times.
Retail Sales at Vail Sports
Vail, Colorado
Fast forward many years. I’m living in Colorado, loving life as a ski instructor/writer, but instructing is seasonal, and writing eight books hasn’t exactly made me Stephen King-level rich. So in between, I still needed filler jobs. One autumn, I decided to stick with what I knew (skiing) but try a different angle: retail sales.
I took a job at the Vail Sports store, which is a ski gear and apparel shop at the base of Vail Mountain, part of the Vail Resorts family. I figured this should be easy. I know skiing inside-out, I’ve worked for Vail Resorts in other capacities for a decade, and I even wrote for a ski-oriented website. Selling a few jackets and goggles? Piece of cake, right?
Oh, how wrong I was. This job turned out to be a crash course in corporate absurdity and frustration. It started off promisingly enough: we had a formal multi-day orientation where various managers welcomed us, with the HR manager making a wonderful, heart-felt speech:
“I’m here to support you. If you have any questions or concerns, please come to me and I’ll address them immediately. We’re all part of a family here at Vail Sports.”
I was cautiously optimistic. We had a couple of weeks before the ski season started, so I expected thorough training on the cash registers, the point-of-sale system, product knowledge sessions, etc.
Instead, I encountered a masterclass in undertraining. The store’s cash register system was notoriously convoluted—there were dozens of different discounts (season pass holder? employee? flash sale?) and special promotions that required entering all sorts of codes. I kept asking, “When will I get trained on the registers?” Each day the answer was, “We’re busy now. We’ll get to it soon.”
Days passed. Weeks passed and suddenly it was Opening Day—the slopes were open, customers were pouring in, and I was scheduled on the register with zero training. It was trial by fire, with a line of customers a mile long and me fumbling through menus like it was the first time I’d ever seen a cash register. Which it was.
Needless to say, mistakes were made, the line moved at a glacial pace, and I got more than a few death stares from impatient skiers wanting to get on the mountain. I’d end each shift sweaty and frazzled, feeling more like I’d run a marathon than working a cash register.
Then there was the HR manager who had so warmly promised open communication. A few days into the job, I had a question—something minor about scheduling. I saw her in the back office and politely said, “Excuse me, do you have a moment? I need to clarify something about next week’s schedule.” I barely got the sentence out before she snapped,
“Are you serious? Can’t you see I’m busy? I have way too much going on to deal with your ridiculous, miniscule problems. Come back at the end of the week!”
It was as if someone flipped a Jekyll/Hyde switch. I walked out of the office wondering if I was crazy or if the orientation had been a shared hallucination.
The working conditions turned out to be pretty unfavorable too. For one, we discovered there was no employee break room. During our shifts, which could be 8-10 hours, we had nowhere to retreat for a few minutes of peace. I had to sit outside, next to the dumpster to eat my lunch—which, on snowy days was thoroughly enjoyable. Most days, I was scheduled to work alone in the store for long stretches at a time, meaning no bathroom breaks unless I begged a fellow store employee to watch the shop for a minute. There were days I literally ran to the restroom and back, praying a customer hadn’t walked off with half the merchandise in my 90-second absence. It was absurd.
The kicker came after about a month of this. Despite all the annoyances, I was trying to stick it out until ski season was in full swing and I could perhaps transition back to teaching skiing. But one slow afternoon, after rearranging the same display for the tenth time, I realized I dreaded coming to work. My usual upbeat self was getting crushed by the sheer pettiness and stress of a job that really shouldn’t have been stressful at all. I decided I’d had enough. And pfft, I was out of there.
Beaver Creek Information Center
Beaver Creek, Colorado
You’d think by this time I would have learned to avoid quasi-customer-service jobs at ski resorts, but a few years after the Vail Sports debacle, I was in another tight spot financially. It was the fall before the 2014–2015 ski season, and I was once again broke and on the hunt for another job. Any job. The only decent offer I had was a position at the Beaver Creek Resort Information Center.
I told myself, information desk? That sounds easy. Answer some questions, and give directions, great!
I imagined cozying up in a warm office, cheerfully telling guests where the nearest bathroom or the ski school was. After all, Beaver Creek is a fancy resort known for its hospitality. They even hand out free chocolate chip cookies every afternoon—truly the good life. What could go wrong?
The short answer? Basically everything. This job was a classic case of bait-and-switch. The title was “Information Specialist,” implying I’d be dispensing helpful information all day. In reality, I spent most of my time being a combination lost-and-found clerk and a personal punching bag for frustrated tourists.
My supervisor was a master of passive-aggressive management. On day one, she gave me a mind-numbing task like, “Please re-fill the brochures on the counter.” I’d do it, double-check it, and tell her it was done. Then she’d surreptitiously redo the entire thing herself while sighing dramatically. It was undermining, to say the least. Why ask me to do something if you’re just going to do it again, yourself? But any attempt to clarify or ask if she wanted it done differently was met with an exasperated, “That’s fine, I’ll handle it.”
Strangely enough, dispensing information was the smallest part of my duties. The bulk of my days revolved around managing the resort’s Lost and Found, and let me tell you, that was a window into the sheer chaos of human density. Ski resorts are where lost personal belongings go to disappear until the summer thaw. The amount of stuff people lost on the mountain was staggering: phones, wallets, keys, goggles, gloves, you name it. And they all seemed to end up under my care.
One of the first principles I learned as a kid learning to ski was, “Never carry anything important in your ski jacket or pants pockets, because if you drop it on the mountain, it’s likely gone forever.” Apparently, none of our guests got that memo. On a typical day, a skier would come slumping into the Center with a panicked look. They’d explain that they were riding the chairlift, decided it was a perfect time to pull out their new iPhone to take a selfie, and—whoops!—dropped it somewhere into the snow 40 feet below.
“Has anyone turned it in?” they’d ask hopefully as if a phone would magically find its way down the mountain into our lost and found within the past twenty minutes. I became practiced at giving sympathetic smiles and delivering bad news gently:
“No, I’m sorry, nothing’s been turned in yet. But here’s what you can do: fill out this lost item report in triplicate with your contact info. A lot of these phones surface when the snow melts in the summer. If someone finds it then, we’ll let you know sometime in July.”
They looked crestfallen at the prospect of waiting months, and I marveled at how they ever thought whipping out a phone while riding a chairlift in the middle of winter was a good idea.
And it wasn’t just phones. People would come in claiming they lost literally everything: wallets stuffed with all their credit cards, Social Security cards, wads of cash, expensive sunglasses, and even jewelry. One guest lost their wedding ring on the slopes—he pulled off his glove and the ring flew off with it into the powder. His wife was not pleased, to put it mildly, and I got to witness that awkward tension firsthand as they filed a report, along with their divorce papers. The resort did its best. Sometimes as far as going out with metal detectors in spring to find valuable stuff, but more often than not, lost items stayed lost, sometimes consumed by the Cookie Monster.
The “found” side of Lost and Found was often amusing. We’d accumulate a bizarre collection of single skis from people falling off lifts or dropping skis in the deep snow, random boots, and the most mismatched assortment of gloves and hats imaginable. By mid-season, we had enough orphaned gloves to outfit a small army of one-handed munchkins.
A few lucky items were reunited with their owners quickly, but many just lived for years in our back closet limbo. We donated what we could after sufficient time passed, but even the Salvation Army had no use for ONE glove, ONE ski pole, or a broken wristwatch from Target.
Amidst this, my supervisor would still give me other odd tasks, and then double-check everything I did as if I were a toddler. It was clear she didn’t trust any of us underlings to do things “right.” Meanwhile, she was quick to snap at me for interrupting her with “trivial questions” like what to do when a guest “misplaced” their young child.
The absolute breaking point came on a frigid January day. A well-heeled woman stormed into the Information Center, furious. She slammed a single ski boot down on the counter and hissed, “This place is unacceptable!” Startled, I asked how I could help. She proceeded to rant that someone had stolen one of her boots. Not a pair. Just one. I tried to clarify: only one boot? She had one with her. It turned out she had mistakenly left one boot outside the lodge—why one and not the other, I’ll never know—and now it was gone, presumably taken by a Russian double-agent on assignment from Moscow.
I attempted to take her information and file a lost item report, but she wasn’t having any of that. She wanted action, as in me magically producing her missing boot now. She yelled, threatened “to have my job,” and even accused me personally of running some kind of single boot theft ring. It was so absurd I would have laughed, but her intensity was too scary.
My supervisor heard the commotion and, instead of backing me up, whisked the woman away with saccharine apologies, as if I’d grievously failed. After the guest left—still sans boot, of course—I got a seething lecture about “customer service” and how I should have handled it. How exactly? Produce a boot from thin air? That incident, combined with my supervisor’s relentless nitpicking and the endless stream of lost iPhones I had to log, pushed me to my limit.
I quit that Information Center job not once, but twice in the span of four months. The first time, I gave notice and left mid-season to try to find something else. Unfortunately, that “something else” didn’t pan out, so a couple of weeks later, I asked if they’d take me back to finish out the season. They did. My second exit was a month before the season ended—when I walked out for good, vowing that no matter how desperate I was, I would never return to the purgatory of Lost and Found again.
Office Supplies & Office Depot
Avon, Colorado
Finally, we come to the last circle of my employment hell: big-box retail. In another between-the-seasons slump, I reluctantly accepted a job at the Office Depot in Avon, just down the road from Vail. The ad intrigued me because it mentioned a “busy technology center” where I could help customers pick out laptops and printers and solve their basic tech problems. They only wanted me four days a week, which left hope I could write or do other worthwhile things on the side.
Given I had over ten years of experience as a computer tech and network administrator—not to mention being the default IT fix-it guy for friends and family—I thought I’d be a perfect match. For once, my skill set aligned with a side job! But alas, corporate retail had other plans.
On day one I learned a crucial detail: I would not be allowed near the tech center or customer computers until I’d been employed for a full six months. Company policy. Why hire a tech-savvy employee and then bar them from using their expertise for half a year? Your guess is as good as mine. Instead, I was relegated to general floor duties. The store was cavernous, with aisle after aisle of everything from reams of paper to ergonomic chairs. It wasn’t exactly bustling in the off-season, so the managers needed to keep us busy doing who-knows-what.
They handed me a delightful daily assignment: each morning, I was given a list of 100 specific products somewhere in the store. My task was to find each one. It was essentially a scavenger hunt, designed to familiarize me with the store’s layout and inventory. The first few days, I approached it with a sense of dutiful learning. But, by day four, it felt more like they were just giving me busy work to justify hiring me. Which, of course, they were.
After the morning hunt, there was a lot of standing around trying to appear helpful. I’d straighten some shelves here and there, and ask wandering customers if they needed assistance finding anything. Often, they were just there to grab a specific item and go, not exactly needing a personal shopper for a package of ballpoint pens.
One of the most ridiculous tasks the management insisted on was what I’ll call The Alignment Game. Much like my Vail Sports experience, Office Depot wanted every shelf picture-perfect. But here it was even more regimented: employees were explicitly instructed to continuously walk the aisles and “face” items so that the front of every box and Scotch Tape dispenser was flush with the shelf edge.
I was told that if the regional manager stopped in and saw a single misaligned product, the wrath of God would descend on us.
If a customer picked up, say, a pack of Post-it notes to read the back and then return it to the shelf slightly askew, a little alarm bell went off in my manager’s head. He’d nudge me: “Go straighten that, quick!”
Evidently, the specter of a rogue regional manager inspecting our store loomed large in his mind. I often wondered if regional managers truly had time to inspect the alignment of printer paper? Didn’t Office Depot have bigger problems than wayward employees like me?
Needless to say, it was one of the most mind-numbing jobs I’ve ever had. For someone who likes to be productive, creative, or at least intellectually engaged, being a human Roomba tidying up pens and reams day after day was torture. The kicker: I could see the tech center from my station, with long lines of harried customers asking questions I knew the answers to, but wasn’t allowed to go help them. Instead, I was refolding a box of file folders for the tenth time that week.
By the end of the second week, the familiar feeling of anguish washed over me. I realized I dreaded going back after my three days off. That was a huge red flag. Still, I tried to tough it out for a little while—maybe the monotony would ease as I got to know the place better. It did not. The feelings grew faster than mold on a half-eaten sandwich.
After about a month, I decided life was too short to spend one more minute arranging printer cartridges by color. I walked into the manager’s office and gave her my immediate resignation. She started with the “customary two weeks’ notice” speech, to which I responded, “Trust me, you’ll manage.” And with that, I clocked out of Office Depot for the last time.
Dancing out to my car, I remember taking a deep breath of the cool mountain air and thinking, I was not put on this Earth to micro-adjust staplers on a shelf. I had tried to make ends meet with that job, but in the interest of sanity, sometimes quitting is the right thing to do.
If there’s one thing I’ve figured out after a lifetime of clocking in, clocking out, and occasionally running for the exits, it’s that every job teaches you something. Sometimes it’s a new skill. Sometimes it’s just knowing how much caffeine you need to get through the day. I’ve learned how to deal with people—the kindly grandmas, the furious boot-less ladies, and the kids who think “free samples” means 20 cups of fudge.
I’ve learned how to fake confidence when I have none. I’ve learned that sometimes you just have to laugh when you’re drilling nozzle number 47,329 and wondering where your life went wrong. And I’ve learned how satisfying it is to walk away from a bad gig with your head held high, even with your tail is figuratively between your legs.
Some of my jobs were genuinely enjoyable, others were downright absurd. More than a few felt like punishment for sins I’m not even aware I committed. But each one left behind a little nugget of wisdom. Or a story worth telling at a dinner party. Or writing an article like this. They taught me resilience, the importance of humor in the face of tedium, and that elusive balance between doing what you must and pursuing what you love.
In the end, maybe that’s the real paycheck from all these experiences: walking away a little funnier, a little tougher, and a whole lot wiser than when I started. The song lyrics, “Money for nothing, and your chicks for free” might be a rockstar’s life, but for the rest of us, it’s money for hours—sometimes hard, sometimes ridiculous— that truly shapes who we are.
About the Author
Allen R Smith has been writing humor since the Abraham Lincoln administration. A three-time America’s Funniest Humor award winner, he’s penned thousands of articles for print, the web, and any other medium that’ll tolerate his unique style of writing. His work has been quoted, reposted, forwarded, and ignored in 27 countries. Since 1805, he’s teamed up with ChatGPT, to produce a new breed of humor writing.
His first book, TPS Reports and Other Workplace Nightmares, is in its second printing and remains a cult classic among over-caffeinated middle managers. His second book, How to Fake Looking Busy While Getting Promoted, earned five-star reviews from The Bellwether Review, The National Discourse, The Zeitgeist Chronicle, and some guy who claims he read it during a Zoom call.
Smith resides at the Shady Holler Heights Retirement Community and Bait Shop in Oceanside, California, along with his loving wife, Maebelle-June, their three grown children, Cletus, Tawny Rae, and Ember-Lynne, and their devoted emotional support Emu, Chairman Meow.
Endnotes
¹ According to the U.S. Bureau of Labor Statistics, Americans born in the latter half of the 20th century held an average of about 12 jobs from age 18 to 56.
² The classic ice cream truck playlist typically includes tunes like “Turkey in the Straw,” “The Entertainer,” “Camptown Races,” and indeed Brahms’ “Lullaby,” all designed to be simple, catchy, and heartrendingly repetitive. (Fun fact: A Chicago Sun-Times article once listed “Brahms’ Lullaby” among the top ice cream truck songs.)
³ Pup ’N’ Taco was a Southern California fast-food chain founded in 1956, known for an eclectic menu of hot dogs (“pups”), tacos, and pastrami sandwiches. It expanded to about 100 locations before the owners sold the chain to Taco Bell in 1984, after which the brand ceased to exist.
⁴ Modern U.S. Navy aircraft carriers (like the Nimitz class) are over 1,000 feet long and carry around 5,000 personnel including the air wing. They indeed resemble floating cities, with dozens of decks and virtually everything from post offices to hospitals on board. It’s very easy for a newcomer to get lost in the labyrinth of corridors!
⁵ Adjusted for inflation, $8.50 in the early 1970s would be equivalent to well over $60 in today’s dollars. No wonder that job posting caught my eye—at the time it was offering about 30–40% higher pay than typical entry-level gigs, hence my eagerness despite the vague “physically challenging” warning.
⁶ “31 Flavors” has always been Baskin-Robbins’ tagline (one flavor for each day of the month), but over the decades the company has developed a catalog of more than 1,400 ice cream flavors in total. At any given store, the roster of 31 is rotated from this huge flavor library, alongside seasonal specials and limited-edition creations.
⁷ Thom McAnn was a major American shoe retailer founded in 1922. By the late 1960s, it operated over 1,400 stores across the U.S., making it one of the largest shoe chains in the country at the time. The chain declined in the following decades, and by 1996 all Thom McAnn standalone stores were closed (the brand lives on as a line of shoes sold in other outlets).
⁸ In 2015, TripAdvisor ranked Vail the #3 most popular U.S. ski destination for international travelers, with especially large numbers of visitors coming from countries like Argentina, Mexico, Australia, and Brazil. Vail and its sister resort Beaver Creek have long catered to an international clientele, which means a ski instructor there might teach guests from six different continents in the same season.
⁹ In retail lingo, “facing” means pulling products to the front of the shelf and aligning them to create the appearance of fully stocked, orderly shelves. Many chain stores enforce strict-facing routines to maintain an illusion of abundance and cleanliness. It’s a common practice (employees often do it multiple times a day), though the extreme emphasis some managers place on it—sometimes above customer service or sales—can seem absurd to the staff on the ground.
