How I Became Addicted to Driving for Uber

It was a Sunday afternoon in late May, I was sitting inside a dark restaurant, utterly exhausted. The fatigue wasn’t a result of a wild night out filled with drinks. Rather it stemmed from a long Saturday night spent driving rideshare. It was only my second weekend behind the wheel for Uber, but I was already hooked—addicted, even.

As I sat there, I tried to mask the shakes that coursed through my tired body. Were they from sheer exhaustion, caffeine withdraws, or the thrill of rideshare addiction? Maybe all three—but I couldn’t quite tell. All I knew was that I kept glancing at my phone, checking the Uber app for surges, unable to shake the nagging thought that making money was more important than celebrating my grandmother’s birthday. Guilt washed over me, but the urge for quick cash was that intoxicating.

I received a trip request as soon as I turned on the Uber app that prior night. And little did I know that chime would be forever etched into my soul. First pickup was at a dark, rundown motel that echoed disarray and neglect. As I pulled up, my passenger waved, visibly grateful yet slightly embarrassed. “Thanks for picking me up from such a shady place,” he said, his voice laced with an apology. “I’m not from around here and had no idea it was this bad.”

With that, my journey into the night began. It was just the start of a wild ride! Before I could even drop him off at his destination, another trip request popped up on the Uber app. Notifications kept coming, and it never stopped. Just one ping after the next. I found myself chasing surge after surge from college town to college town—darting between Newark, Delaware, and West Chester, PA. The thrill of the hunt was intoxicating, each ping a reminder of the money I could earn.

The night ended with a heavy dose of reality when my last pick up was a rowdy group of college kids. They were the epitome of late-night revelry, and they quickly turned my car into a mobile party. Their requests for music quickly transformed into abusing the Uber platform as they insisted on making extra stops that weren’t in the app. Stopping at Wawa for some drunk snacks, followed by a chaotic series of drop-offs at different locations.

Never questioning anything that night, I acceptied whatever trip requests Uber threw my way. I didn’t think twice about what I was doing. Going wherever they wanted to send me. I was brand new to the gig, naïve in my excitement, and thought these trips were a godsend of quick cash that I so desperately needed because of my then current financial situation. It felt liberating, like I was in control of my destiny, even if that destiny included navigating the antics of intoxicated passengers.

During my grandmother’s birthday dinner, I shared my newly rideshare driving experiences with my family. To some, stories of picking up strangers—from college students to business travelers—were fascinating. Rideshare was still a novel concept in my market, and the intrigue of inviting a random person into my car was both thrilling and unsettling.

I remember encouraging my dad, who had recently retired, to consider driving for Uber as a part-time gig for some extra income. However, his interest was mostly skeptical. Struggling to grasp the concept of both gig work and rideshare, he raised only concerns:

“Is this safe?”

“Who books these trips for you?”

“Does your insurance company know about this?”

“And how does insurance cover you in case of an accident?”

Sure, these are valid apprehensions coming from a concerned parent. But I didn’t care—I was too enamored with the idea of almost earning $200 on a whim. No boss, no interviews, no rigid schedules, just me and my car, making money on my own terms. This felt revolutionary at that time (May 2017).

And I was right. This was the dawn of a new era in the workforce. Gig-work was changing the way people sought side hustles or part-time jobs, for better or worse. I had become a minion, pulled into the world of quick cash and flexible hours, and I couldn’t get enough—I needed my fix!

Chuck Driver | Gig-Worker | YouTuber | Blogger

I quit my corporate job to work full-time in the gig economy and start a YouTube channel. Follow me on my journey as I share rideshare and delivery experiences with you.

https://youtube.com/@thechuckdriver
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