A Journey Of Self-Discovery Through Uber

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“What is my life right now?”

I found myself uttering this question as I sat in the parking lot of a well-established gentleman’s club in the Chicagoland area.  I asked myself these six words repeatedly throughout my five-month journey driving for Uber. Whether it was picking up drunk 20-somethings from an upper-class bar in Lakeview or dropping off an 18-year-old high school senior to a hookah lounge in the suburban town I currently reside in, I’ve encountered the gamut of the human experience while driving for this millennial taxi service. So why Uber? What would compel me, a male in his early 30’s, to drive strangers he had never previously met to all of these random locations across the city of Chicago and its surrounding suburbs? Oddly enough, this is the #1 question I received from passengers while driving for Uber. Perhaps, we should dive back to where everything started.

So why Uber? What would compel me, a male in his early 30’s, to drive strangers he had never previously met to all of these random locations across the city of Chicago and its surrounding suburbs? Oddly enough, this is the #1 question I received from passengers while driving for Uber. Perhaps, we should dive back to where everything started.

Before driving for Uber, I was dead set on becoming the world’s greatest school counselor.  Growing up, I was painfully awkward. I’m not talking about “Oh, he’s a little different” type of awkward. I’m referring to the type of awkward where you stick out like a sore thumb. This badge of awkwardness included being overweight, an uneven hairstyle, oversized glasses and odd outfits including this incredible purple sweat shirt/sweat pant combination that made me and Barney the Dinosaur have way too much in common. I carried this awkward sense of style through my freshman year of high school and like you’d imagine, I was the target of ridicule and teasing from classmates and peers alike. The bullying was especially bad from 7th-9th grades. There were nights during those three years I would sit in my room and wonder it got better or if the rest of my life would be this painful and sad. Needless to say, as I blossomed into adulthood and grew out of some of my awkward ways, I made a decision that I would do everything in my power to make sure the next generation of adolescents didn’t feel that same emptiness that I felt back then. I figured the best way to do that was to become this rock star school counselor that kids would look up to and respect.

The biggest deterrent to my dreams of becoming the Bon Jovi of school counselors was my lack of teaching and/or educator experience. Coming from a writing background, I knew jumping into an unknown career path would be filled with bumps and bruises but after two years of grad school coursework and a rewarding counseling internship experience at a south suburban high school, my rock star training was complete and I was ready to jump right into the world of education. Finding a school counseling job right away would be challenging so I decided to gain more experience by becoming a substitute teacher and building a network of contacts which in turn, would help me turn into Bon Jovi. Unfortunately, life doesn’t work out the way you planned sometimes and my dreams of becoming the Jon Bon Jovi of school counselors didn’t come to fruition.

What went wrong? Why wasn’t I able to become the life-changing Jon Bon Jovi school counselor that I had aspired to be? Maybe I should’ve set my sights lower and aimed to become the Richie Sambora of school counselors instead.

My first mistake in my new substitute teaching position was putting myself in a deficit right off the bat. I had this preconceived notion that substitute teaching would be a breeze and I would be able to focus more on networking with other educators to achieve my ultimate goal of becoming the next Bon Jovi. I mean how difficult would it be for a responsible and intelligent adult in his late 20’s (at the time) to enter a classroom and deliver pre-written lessons to a bunch of 14 to 18-year-olds?  My thinking was I would walk into each classroom that I was in, tell the students what the lesson was for the day and then read a book for the rest of class while I monitored the students to make sure they didn’t physically harm each other. How hard could that possibly be? I should have known the answer to that question when one of the first students I interacted with asked me one of life’s most important questions.

“Hey Bro, have you ever smoked weed?”

Anyone who has any experience as an educator knows that if a student asks you a question like this, then your response should be something along the lines of “That’s an inappropriate question. I can’t answer that” or “Please don’t ask me inappropriate questions like that again.” What was my response?

“Sure I have. I can’t mention much more than that, though.”

I should have known with that response that substitute teaching would be a big challenge for me. I had every intention of being a disciplinarian as a substitute teacher.  I really did. After all, this job was just supposed to be a temporary thing and I really wanted to do well in this role so I could impress the right people and ultimately attain that school counseling job I had been working so hard to achieve.  I did certainly impress people alright, but it was the wrong group of people. Students at all four high schools in the district I was employed in loved my quick wit, sense of humor and overall style.  My reputation spread among the school district as “the cool sub.” Soon, students constantly requested their teachers for me to sub their classes and for the first two and a half years, I would constantly get requests to fill in for teachers.  Teachers seemed to love having me come in to sub for their classes. I thought: “Oh hey, being ‘the cool sub’ actually works! Maybe I can keep this going for a year or two and then find a connection that will help me land that elusive school counseling job.” If you haven’t noticed by now, things haven’t worked out the way I intended and this was no different.

I ended up working exclusively at one high school in the district and things went great at first. Everything then went sour and rumors about me spread among the faculty and my reputation went from that of Mr. Holland (Mr. Holland’s Opus) to Ms. Halsey (Bad Teacher). Working at this school soon became a negative experience and I would come home from work most nights mentally exhausted not unlike what I felt when I was 13! The one incident that triggered my decision to abandon my rock star school counselor dreams and leaving education all together was when a teacher flat out told me: “If the office ever asks you to sub for me, please don’t do it.” I would’ve accepted a valid reason but this teacher just came up to me and said “don’t sub for me” without even a simple reason. That incident was the climax of a year and a half of stress, anxiety and mental anguish. Plus, it had been four and a half years since I had been substitute teaching and sometimes, no matter how hard you try to be successful at something, it’s just not going to work out. So with everything building up, I finally had enough and said goodbye forever to my dreams of being the Jon Bon Jovi of education and resigned from my substitute teaching job.

After closing that four-and-a-half-year chapter of my life, I soon found myself without a regular income and no idea what I wanted to do next. While brainstorming for possible ways to make money while I searched for my next full-time job, I had that eureka moment which was similar to when I decided I wanted to become a school counselor. I quickly remembered while I was in Florida for a music festival, several friends mentioned how much they enjoyed using a rideshare service called Uber. After doing a little more research regarding Uber I was so awestruck that this service existed. The whole concept itself seemed so incredibly amazing. You make money for driving people around to random locations and the only training and/or certification needed is a clean driving record to go along with a vehicle made within the last 10 years.

“This might be an easy way to make money while I figure out my next career path.”

With this thought in mind, you would think I would’ve signed up for Uber right away and been on the road making that dough. Remember, nothing in this story (and in my life up to this point) has worked out the way I planned. I was still terrified of entering the rideshare world.  It seemed so simple yet, one big thing kept me from driving random strangers around the Chicagoland area: my social anxiety. This is an issue that came up with substitute teaching, but I managed to beat that challenge. We’re talking about a whole different kind of social anxiety here. The very idea of driving strangers around and having to make small talk (something I absolutely loathe) with said-random strangers terrified me. It took me a month of convincing myself that I would actually enjoy driving strangers to random locations. I officially took the leap and signed up to drive for Uber five days before the Christmas holiday. Much to my surprise, I was approved to drive for Uber just three days later.

“Three days? That’s it? Well, that was easy!” I thought to myself.

I can’t believe it only took three days for me to sign up. With the easy sign-up process out of the way, I turned the app on for the first time and waited to brave into the Uber abyss.

Ding! Ding! Ding!

“Woah, someone is calling for me to pick them up!”

That first ding came on Christmas night after I exchanged gifts with my parents and I didn’t have any concrete plans that night.

“Well, I guess I have plans now.”

I got in my car and drove 10 minutes to the address given on my app. I nervously waited for this passenger, a female, to walk to my car. I had no clue what she looked like or if she would even be a female. For all I knew, a knife-wielding serial killer could’ve approached my car and attacked me with his knife. After a five-minute wait, a female in her early-30’s, entered my car and after confirming this was the person I was supposed to pick up, I loudly yelled: “YOU ARE MY FIRST UBER PASSENGER EVER!!!”

I probably shouldn’t have yelled at her like that because 1) I probably scared this poor woman and 2) She still could’ve been a knife-wielding serial killer and my unnecessary exciting shrieking could’ve provoked this woman to attack me with her knife.

My fears were put to rest, however, and this lady wasn’t terrified after I yelled at her. My first venture into Uber ended up being an enjoyable experience.

“Wow, that wasn’t so bad! I think I might enjoy this Uber thing!”

After a week of driving to both airports, various suburbs and in Chicago-proper, I started getting the hang of driving for Uber. Sure, I was having to pay for gas way more frequently than when I was aspiring to be the Jon Bon Jovi of school counselors but in this one week, I had met all kinds of unique people ranging from rich businessmen to Wicker Park “hipsters” to suburban teenagers. I loved the variety of all the people I was meeting in this one week. Maybe driving for Uber would be beneficial for me while I figured out my next full-time professional endeavor! Soon the biggest weekend of the year was fast approaching and I braced myself for what was sure to be a crazy adventure.

New Years’ Eve: A day meant to celebrate the previous year and ring in the coming year with all the people you love. New Years’ Eve is also a day for people to get extraordinarily intoxicated.

Combining the two meant a boatload of money for me in one night in my capacity as an Uber Driver. I had planned on driving until all hours of the night in an effort to make a boatload of money. There was only one problem with this proposition. I had been invited to a New Years’ Eve party by two friends that I had grown close with over the previous two months. This is a problem that would come up far too often during the five months I drove for Uber. Do I go out and have fun with my friends or sacrifice time with them in order to make money?

I drove around my hometown for three hours in the early evening which mainly involved dropping off passengers to restaurants and bars and most of these conversations with these passengers were very pleasant. Three hours passed faster than I could blink. Afterward, I drove to my friend’s apartment in the city, rung in 2016 with some of my closest friends and left two hours after midnight with lots of time to kill and even more money to make. This is where things took an interesting turn.

After hearing the familiar “Ding! Ding! Ding!” sound on my phone, I drove my vehicle to the destination listed on the app: A small dive bar in Avondale. As I pulled up to the bar, I anxiously waited for this male passenger to enter my vehicle. In preparation for driving on New Years’ Eve and New Years’ Day, I did copious amounts of research and found all these horror stories of passengers puking in their drivers’ cars, having confrontations with their drivers and generally unpleasant and downright scary incidents. With this knowledge, I was scared that my first passenger of 2016 would be some drunk lunatic. I was partly right on this one.

“I’M DRUNK! TAKE ME HOME NOW!!!”

These were the first words that came out of this man’s mouth.

“Okay. Sure,” I said calmly.

I may have sounded calm but inside I was an anxious mess. An intoxicated person yelling at me is not my idea of a great experience, so I wanted to drop this man home as soon as possible. During this 10 minute ride, I was told I needed to drive faster, I needed to talk louder and I needed to get him home before he puked in my car.

This man had said the magic words. I drove as fast as humanly possible because there was no way I was going to let my 2015 Toyota Corolla become soiled with an angry drunk man’s vomit. Fortunately, Mr. Angry Drunk Man was an exception to an otherwise great late night/early morning of driving people home safely from their new years’ events. One lady even gave me champagne from the party she attended. Free champagne? Sign me up! All in all, I’m glad I was able to successfully manage my time with my friends and make money driving on one of the busiest nights of the Uber experience.

Throughout the next five months, I was able to successfully set aside time to drive Uber, apply for jobs and make time for friends and social activities although it wasn’t easy. There were times I wanted to hang out with certain friends or I was invited to a party, but I didn’t do these things because I knew I needed to make enough money to get by. There were also times that I felt so hopelessly stuck. I couldn’t believe I went from being a substitute teacher working for a great position as a school counselor to becoming a taxi driver. There were nights, especially during the week, where I would sit in my room and wonder if I would be able to find a traditional full-time job or would I be resigned to driving Uber for the foreseeable future. Little did I know it at the time, but Uber was secretly a blessing in disguise.

As I’ve mentioned before, I always struggled with social anxiety growing up. Being terrified of meeting new people and putting myself out there in order to make friends defined most of my 20’s. My social anxiety steadily improved by the time I reached 30 but I still felt so far behind compared to most of my peers and friends. I didn’t realize how much I would be going out of my comfort zone driving for Uber because I would be forced to make small talk with all types of strangers. The more I drove for Uber, however, I found myself being able to easily talk to most of these passengers without any fear or hesitation. Whether it was the 18-year-old from a western suburb who hit on me and called me “the cutest and best Uber driver ever” or the Pixies fan that commented on me listening to Bandit’s cover of “Where Is My Mind,” during our ride, I found myself feeling so calm and relaxed the longer I drove these random strangers around. I even picked up someone so frequently that we ended up becoming friends and now we drink together a few times a month. My social anxiety was not the only thing that greatly improved because of my Uber experience.

Due to my social anxiety, my interviewing skills were incredibly poor. At various job interviews over the years, I would often find myself a nervous mess which would involve me fumbling over my words far too often and end up with me leaving a bad impression with whoever I was interviewing with. Trying to find a traditional full-time job was a scary experience because of my poor interviewing skills. Knowing that I had to go through this process when I had the interview skills of a scared monkey was something I wasn’t too excited about. Over time and after several phone and in-person interviews with various companies and organizations, I found that my interviewing skills vastly improved over a five-month period. At first, I had no idea how or why my interviewing skills could improve so rapidly after struggling with this skill most of my adult life. Then, it hit me: Constantly meeting new people through Uber allowed me to work on my social anxiety skills which in turn, helped me not feel so nervous during these job interviews.  Eventually, this improvement in my interviewing skills paid off big-time as I nailed an interview for a great position at a card production and manufacturing company.  The interview went so well that this company offered me the position within two weeks after doing one last Uber extravaganza Memorial day weekend, I started a new chapter in my professional life.

Looking back on the last few months, driving for Uber was one of the best things to happen to me. I started this five-month journey utterly and completely lost about where my life was headed. Through the medium of Uber, I not only got to meet all sorts of fascinating people, I also strengthened personality traits I’ve struggled with for most of my life. Even the negative things I didn’t like about Uber-like the app not telling the driver where the passenger is going until the trip starts, the drunk passengers and sacrificing so many of my Friday and Saturday nights in order to make money seem insignificant compared to the personal growth I achieved during the last five months. I don’t regret a single thing about driving for Uber because I’m a better person for that entire experience and now, I have story after to story to share with friends, family and anyone new I meet.

From the bottom of my heart: Thank you Uber for changing my life in every humanly way possible.