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Friday, September 23, 2022

My Two-Year Stint as an Uber Driver

    At the beginning of 2016, my entire life was in shambles―my marriage was on the rocks, I was a temp at the law firm that I work full-time now with a cloud of uncertainty hovering over my head, and I was on the brink of financial ruin.  I also had taken a long hiatus from writing as I tried to put the pieces of my life back together. The first step that I took in that direction was to earn some extra money as a part-time Uber driver in the Chicagoland and outlying areas. The money that I made from driving was okay―it helped me stay afloat until I figured out what I was going to do in the next period of my existence. Being an Uber driver was like taking a course in human psychology―I had to know when to be talkative and when to just be silent because the Uber experience was all about the customer feeling comfortable as well as feeling safe in my vehicle.

 My First Fare as an Uber Driver.

    Learning the terrain of driving for Uber wasn’t too difficult of a task to master, and I was both excited and nervous to get my first fare. I can remember it like yesterday―it was a typical weekday as I’d put in my eight at the law firm and took the Metra home. My car was parked at the station about a mile and a half from my house, and I had decided to get right to it once I got off the train. I then hopped on the expressway and headed toward the Loop once I activated the Uber app, and the app chimed as I approached 87th Street.

    I quickly exited Interstate 94 and headed in the direction of West 83rd Street as my first pickup was on 84th and Holland Road. I tried to let the app steer me in the right direction, but I was extremely nervous because I couldn’t remember where Holland Road was. Damn, I was going to mess up my first fare over a small technicality and get cussed out in the process. I went too far and wound up near Simeon High School on Vincennes Road, but I quickly found my bearings and remembered that Holland Road ran through the newly built mall area at the time and doubled back to the hair salon where my first customer was waiting patiently for me to arrive. It turned out that the woman I picked up was very sweet and understanding, and my entire experience with her was pleasant. She lived about a half-mile from the salon, and I dropped her off in no time and was onto the next fare. She gave me a five-star rating in spite of being a few minutes late, and I remember saying to myself, “Yeah, I can do this.”

Uber Driver

 The Pros and Cons of Being an Uber Driver in Chicago.

    There were several perks to being an Uber driver like having the ability to cash out the same day you drive, and that came in handy on several occasions. I also could write off certain expenses on my taxes like gas and auto maintenance, and the best thing about driving for Uber was that I could pick my own hours and was essentially my own boss. I preferred to work in the evening and had many profitable nights doing so. I live in the south suburbs, so my routine in the beginning was to work my way toward downtown Chicago because it’s where the money was. As I became more seasoned, I would work my way toward Midway Airport on the southwest side of town because I was guaranteed to collect a fare of twenty dollars or more by picking someone up from there.

    Just as there was an upside to driving for Uber, there was also several drawbacks to deal with as well. Customers weren’t always friendly, though my experience was easy-breezy 95% of the time. There were also many days where it wasn’t worth my time to be out there―I often remembered that my worst night moneywise was making only sixteen dollars for four hours of work. I quickly learned when the best time to drive was as well as when I should stay at home. The worst part of being an Uber driver was the fact that you could potentially get terminated for too many bad ratings. Your fate was totally in the hands of your customers, and if your rating fell below a 4.6 rating, Uber could exercise the option of suspending you and shutting off your app. Fortunately for me, my rating never dipped that low, and I retired from driving with a solid 4.89 rating.

 My Best and Worst Customer Experiences as an Uber Driver.

    The coolest thing about driving for Uber was that I got to meet some interesting people from different parts of the country and all walks of life. One of my best experiences was fraternizing with two young men from the Chicago underground music scene. They were underground artists who collaborated with the likes of Chance the Rapper, whose career was just beginning to rise at the time, and I picked them up at a recording studio near the Back of the Yards neighborhood and took them to a spot on the northside.

    I met some interesting people at the airport as well―one of my fares was a very nice young lady from San Diego who was a student at the University of Chicago and lived in the Hyde Park community. I also met a delightful couple from Kansas City who were avid fans of the Royals and hickory-smoked barbecue. I dropped them off on the northside from Midway Airport as it was the couple’s first time in Chicago, and I told them about some of the most common attractions in the area. Another cool fare that I had was a former minor league baseball player I dropped off at Midway Airport, and we had some thought-provoking conversation. He had played with some current major league baseball players and alleged that one of them was taking PEDs in order to stay competitive at the big-league level.

    Now there’s a flip side to every coin, and my interactions with Uber customers were no different. I’ve dealt with people with nasty attitudes, people with bad hygiene, and people who were sloppy drunk to name a few. I once picked up this couple from a club downtown, and I was very concerned that the young lady was going to die from alcohol poisoning. She was completely wasted, and her boyfriend did everything that he could to keep her awake in my backseat. Needless to say, I got them to their journey’s end as quickly as possible with no further complications.

Beautiful Young Woman

    I also picked up this guy one night who used a fake name on his Uber account, and he made me an offer to be his full-time driver because the previous driver quit. I politely and tactfully declined his offer―stating that I had a full-time job already. I could plainly see that he was into something shady over the course of our brief encounter, and my guess was that he and his crew trafficked young girls for prostitution because his phone was ringing off the hook nonstop to pick up some of those girls and bring them back to his house for a private party. He also alluded to the fact that the cops were constantly harassing him to the point that he had to use Uber drivers to conduct his business. I knew in that instant that I wasn’t going to get caught up in being a mule for his illegal enterprise on any level, so I quickly cutoff the conversation and took him, his crew and his girls to their round-trip destination as soon as humanly possible.

    The absolute worse fare that I ever had was a young lady who I picked up in the South Loop area. I was making my way back downtown from the western suburbs on Interstate 290 when my app chimed. I got off at the Canal Street exit and picked her up at an apartment complex on West Van Buren Street. She was an attractive young Black woman who happened to be an independent artist singing at various nightclubs throughout the country. She was very pleasant and personable at first―she even sat in the front seat of my car which was something customers rarely did unless there were multiple passengers or ride-share customers. She was slated to perform at a nightclub just to the north of the Loop off of Ogden Avenue.

    Everything was fine until we arrived, and as luck would have it, my app began to malfunction as soon as we got close to her destination. She pinged the address as opposed to entering the exact address in the app, making it extremely difficult to find the place. I realized later on that I passed by the nightclub a couple of times as the street was extremely dark and difficult to see, and in the midst of trying to find the spot, the young woman became belligerent and disrespectful. She went on and on about being late for her show and not being from Chicago was the reason why she pinged the address, and I finally got fed up with listening to her diatribe and demanded that she get the hell out of my car. She quickly changed her tune and began to plead with me―explaining that she was sorry for going off and begged me not to put her out of my car, and we finally found the club that was in a secluded area just to the north of the street we were on.

    Luckily for her, I had a change of heart because I was beyond ready to get her out of my hair and deal with the fallout from Uber afterward, and luckily for me, I eventually found the building without having to call the police in order to remove her from my car. She quickly opened the passenger side door and scurried toward the entrance of the club as there were still a crowd of people hanging around outside, and I promptly gave her a one-star rating without hesitation before I drove off. I needed time to blow off some steam because I was ready to call it the night after dealing with this crazy-ass young woman but sucked it up and pressed on instead.

 The Calamity that Ultimately Hastened My Decision to Quit Driving for Uber.

    It was toward the end of the summer in 2017, and I was having a good day in terms of racking up customers on a typical Saturday afternoon and early evening. I was almost ready to close up shop, but I hadn’t gotten that one big fare that I needed to put me over the top as I was hovering around the $200 mark for the entire day. So, I continued to hang around the Loop a little while longer. My next fare prove to be the jackpot, or so I thought. I scooped up these two young couples in the West Loop―it turned out that they were in town for the Cubs vs. Cardinals series, and they’d just wrapped up eating dinner and were heading home to Bloomington, Illinois, home of Illinois State University. This fare was going to put me over the top for the night―$115 plus a $50 tip for two additional hours of work.

    Both couples seemed nice enough as the four of them went to ISU together and were recent graduates. One of the young men sat in the front with me, and we had good conversation. He was a baseball fan like me, and I vaguely remember that we had other interest in common. To make a long story short, everything had gone smoothly until we were thirty or so miles outside of Bloomington. I could then feel my transmission beginning to go out, and I prayed that I was able to drop the two couples off and make it home without my car breaking down on me. Thankfully, I made it to Bloomington and dropped them off―but not without complications. My car did stop on me before I got them home, but I let my engine cool off somewhat and was able to start it up again with the two young men’s help. They were very considerate and helpful, and out of concern for my well-being, I exchanged numbers with the young man who sat in the front with me just in case something went wrong.

Interstate 55

    I said my goodbyes to the two couples and headed back toward the Interstate. One of the young women tipped me forty dollars in cash in addition to the $165 on the app, and I hoped that I made it home in one piece. I stopped at an Amoco a block from I-55 to get some Arizona tea and peanuts, and I let the car sit for a moment to cool off the engine a little longer because it started to give me trouble again. Once I finished my first bag of peanuts, I hit the road again. I didn’t get thirty miles out before my engine started smoking badly and ultimately blew out. I was stuck on I-55 in the middle of nowhere on an early Sunday morning, so I put my hazard lights on and walked to the nearest mile marker post about three quarters of a mile down the road. My hazard lights had stopped blinking once I got back, so now I had a dead battery and a blown engine. I got a text from the young man asking if I were alright, and I told him that I was fine because I didn’t want to burden them any further.

    And to add insult to injury, my insurance company couldn’t help me because it was Sunday morning, and I was stranded in an area that didn’t provide me service. Thank goodness that my wife had AAA, so a tow truck was going to pick me up sometime in the early morning. But the problem was that I had to wait almost eight hours before the guy showed up. Needless to say, I didn’t get any sleep that night because it was pitch black outside, and a different eighteen-wheeler would zoom by every five minutes, which made me nervous. I prayed to the Lord to bring me out of this situation as I put my complete trust in Him.

    The tow truck finally showed up at 6:45 am, and we were on our way back to Chicago once he fastened my car on the flatbed of his truck. We were about 130 miles from city limits, and the tow ended up costing me $700. The $205 that made on my last fare to Bloomington was officially up in smoke at that point. We then arrived in my driveway two hours later, and I thanked the guy and hit the bed after I conversed with my wife for a half hour.

 Reflections on My Tenure with Uber.

    My overall experience with Uber was good, and I’m grateful for the opportunity. Driving for them opened up my mind to parts of the city and surrounding suburbs that I was unfamiliar. The Uber experience also helped me better understand the nature of people, and I felt in my spirit that it was truly meant for me to go on this journey for almost two and a half years. However, I made up my mind after the Bloomington fiasco that my days of driving for Uber were numbered. I also had the misfortune of paying two car notes for eight months after my car broke down, but it turned out to be a blessing in disguise because my credit score had risen a hundred points once I paid off the old car that sat in my driveway for almost a year. I had quit driving shortly afterward, and quite honestly, I don’t remember my last fare as I couldn’t wait to start the next chapter of my life. In hindsight, I have no regrets whatsoever and would do it in a heartbeat if faced with a similar situation. All praise, honor, and glory to Yahawah Bahasham Yahawashi.

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The Three Most Difficult Facets of Writing for Me 

How My Spiritual Journey Affected How I Write 

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My Two-Year Stint as an Uber Driver

     At the beginning of 2016, my entire life was in shambles―my marriage was on the rocks, I was a temp at the law firm that I work full-ti...