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A Boomer's Journey Through Summer Jobs: Lessons in Reality

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Chapter 1: Nostalgia of the Summer Job

Having returned to my hometown, I occasionally visit a grocery store where I worked during my teenage years. The most vivid memories I have are of the parking lot, pushing grocery carts into neat rows, sometimes even until midnight. There was something oddly attractive about that nighttime solitude—perhaps it was the sense of isolation, or maybe the parking lot's abandoned feel that gave me a strange sense of freedom.

In truth, however, that was a far cry from freedom. I was earning minimum wage with set hours and responsibilities. If someone spilled something in the soup aisle, it was my job to clean it up. This experience mirrored school, serving as my parents' attempt to teach me the value of hard work and money. My older brother had gone through the same routine, so it was simply my turn.

Sadly, I absorbed this lesson too well. This was the "real world"—doing things you don’t particularly enjoy. I had to brace myself for that.

When it was time to apply for college, I chose to write about my grocery store experiences in my application essay. It clearly left a mark on me, shaping my perspective. I recall writing about the diverse characters I encountered there, such as a friend on probation and a pregnant coworker. What lessons did I learn? Perhaps to avoid their paths?

My English teacher suggested I discard the essay, which stung deeply. I had poured my heart into that piece, only to be told it was worthless. After some reflection, I decided to start anew, ultimately crafting an essay about a summer camp experience filled with invigorating hikes. It was a safe, pleasant story, and it worked.

The same teacher oversaw the yearbook, where every senior had a chance to share their thoughts. I wrote about how my school was populated by "privileged kids." Once again, my teacher tried to persuade me to reconsider. This time, however, I stood my ground, and it made it into the yearbook—a decision I still regret.

Chapter 2: Retail Realities

For the next few summers, I found myself in various retail roles, usually at Best Buy. Similar to my grocery job, only a few memorable individuals stood out during those stints.

At one point, Best Buy urged cashiers to sell magazine subscriptions at checkout. It felt disingenuous—selling a Sports Illustrated subscription to someone simply looking for affordable headphones. I rarely pushed the subscriptions, and although my bosses occasionally pressured me, they eventually stopped after realizing their tactics were ineffective.

One new employee excelled, selling thirty subscriptions in a single shift. Curiosity led me to observe her approach. When customers inquired about credit card charges after the trial, she confidently assured them there wouldn’t be any.

During this time, I also began smoking pot regularly. I remember old high school friends coming in while stoned to buy CDs. One friend purchased three albums: Gorillaz' "Demon Days," Nine Inch Nails' "With Teeth," and The White Stripes' "Get Behind Me Satan." We spent that summer driving around, immersed in those sounds.

The work ethic my parents had hoped to instill seemed to be taking root, albeit in a different form.

Chapter 3: Post-College Uncertainty

After completing college, I felt as lost as I had before. It turns out that years of substance abuse do little to clarify one's direction. I landed a temporary full-time role in the county’s elections division while also working as a delivery driver. My Fridays were a blur—working at the county from 9 AM to 5 PM and then driving from 5 PM to 4 AM to serve the late-night crowd at a restaurant.

In hindsight, none of it really makes sense. Part of me seemed to be punishing myself, while another part sought to distract myself from the emptiness of my life.

I remember driving through the quiet early hours, the calm of the night enveloping me, listening to music on the radio, and smoking with friends. I would even buy cigarettes for a customer in a hospital without legs for an extra twenty bucks.

These were the lessons imparted by my summer jobs. This was my comfort zone.

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