I'm Retired! Now what?

July 14, 2026

I’ve always heard that the older a person is the harder they are to adapt to a changing world.  Now this isn’t the reason I had never used an Uber before, but I was still a bit apprehensive about trying something new.  I had always had good luck using the old school taxies.  Okay, maybe some of my taxi experiences haven’t been the best in the world. The first time I took a seat in a taxi was in Edinburgh, Scottland back in the 1990’s.  I scooted into the back seat and asked the cab driver to take me to my hotel.  This of course led to him asking me, in a most distinguished Scottish accent, “What hotel?”  With that question I was quickly stunned to silence, thinking, “Yea, that’s a good one.”  I’m not sure why I thought a city of half a million residents would have only one hotel, but I guess that was my belief for the moment.  Thankfully, the guy that I was hanging around with, who was also on my tour, had the good sense to remember the name of the hotel where our tour was staying.  Yes, that was my first taxi experience.

When staying in Las Vegas I never needed to think of Ubers because taxis are lined up outside the hotels five to ten deep.  I’ve usually had decent experiences with Vegas taxis, and I’ve always been willing to chat it up with any driver regardless the subject.  One night I let it slip that I was a college graduate, and this led to the driver drilling with questions pertaining to English grammar.  Apparently, he was a college student, and even more apparently, English was not his first language.  This led to me basically proof reading his term paper during the drive between Ceasar’s Palace and the MGM Grand.  Perhaps my worst experience came when Margaret and I scooted into a cab around two or three in the morning.   In a hush, but serious voice the cab driver went on a wild rant concerning how he thought that the movie Natural Born Killers was the coolest movie he had ever seen.  Yes, that was a little creepy.

My last several vacations have all been driving vacations, and the closest I’ve come to a cab ride in over ten years has been watching Cash Cab.  However, when I decided to fly to Chicago, I figured I had better step into the modern times and figure out how this Uber thing worked.  While planning my trip I downloaded the Uber app and was immediately bombarded with emails.  Everything was Uber this and Uber that.  To be truthful, I was all excited, and I couldn’t wait to try this new Uber thing that the rest of the world had been using for decades!

After grabbing my luggage at Chicago’s O’Hare Airport, I was ready to do whatever you’re supposed to do to get an Uber, but as I made my way out of the airport there was a line of taxis parked at the curb.  It was Vegas all over again.  Convenience outweighed my Uber curiosity for the moment, and I jumped into a waiting minivan taxi driven by some guy whose English skills were iffy at best.  Traveling tends to make me nervous which tends to make me talk fast.  Sometimes really fast!  So through my machine gun fire English, along with a bad attempt at sign language I informed the driver that I was staying at the River Hotel in Chicago and away we went!  After we were cruising down the freeway, he informed me that he had never heard of the hotel so I immediately dove into my luggage (which was shoved behind the backseat) trying to find the address.  I was so involved in trying to find the address I hadn’t buckled up for the ride, which turned into a bit of a hazard.   I quickly came to the realization that Chicago traffic is just as crazy as Dallas traffic, and I was sliding around the backseat like a bowling ball while trying to find the hotel’s address.  Finally I had a chance to click myself in, but after watching my driver zoom in out of Chicago traffic, I suddenly felt the need to ask for some bubble pack to wrap myself up in.

Staying at the River Hotel in downtown Chicago, I was pretty much within walking distance from everywhere I needed to go, but for my bar hopping, Boos and Booze Haunted Tour, I was going to need a ride.  To be honest, I might have actually enjoyed the five-mile walk, but Margaret was already freaking out because I was traveling to the dangerous city of Chicago in the first place.  Although, I’m pretty sure I could have handled the hour or two walk, I decide the time had come to use my new Uber app!  So in my hotel room I diligently put in my address where I needed to go.   Having completely no idea what I was doing, I expected a little wait time, but when my app told me that my ride would pick me up in two minutes, I threw myself into panic mode!  Just waiting for my elevator would take longer than two minutes!  Oh my gosh!  I was going to screw up my first Uber ride!

I thought about bounding down the twelve flights of stairs of my hotel because back in my college days I could fly down eight flights of my dorm in 30 seconds.  Yes, I timed myself one day.   To be honest though, I figured it would take me longer than two minutes just to find the freaking staircase, but I did manage to get to the street curb within the two minutes.  Now my question was, “Am I in the right spot?”  The Uber app told me that my ride would meet me in front of somewhere that was NOT the River Hotel!  Okay, time to program into panic mode again!  For a frantic minute or so I was hustling up and down the block pleading with anyone who looked like they were wearing a hotel or restaurant uniform, asking if they were familiar with my Uber hook up address.  Unfortunately, English was not the preferred language for most, and I got a lot of confused looks and shoulder shrugs.  As I was about to give up, one helpful soul mercifully pointed at the sign above his head.  Indeed, my pickup point was right next to my hotel.  There was no need for the two thousand steps I had put onto my Fitbit during my two-minute frantic search.

My app told to look for a black Kia, which I finally spotted.  However, the app didn’t inform me of the super cute brunet who would be my driver.  I wasn’t sure what the correct protocol for the meeting was.  I didn’t want to just run up to a car driven by a single woman in downtown Chicago and blurt out, “Are you for me?”  I’m not sure how acceptable such a greeting would be in any circumstance.  However, whatever I said must have worked, and the next thing I knew I was sliding into the backseat of this young lady’s Kia.

I’ve heard that Uber drivers are of the chatty nature, so I decided to indulge her a bit.  Besides, when I get nervous, I tend to be a regular vocal fountain of anything and everything, and while on vacation I’m always nervous. The young lady answered all my questions with a thick accent which of course led me to ask, “Where are you from?”  She was from Ukraine and told me that she had fled the homeland with her husband in order to escape the war.  For a few minutes there we had quite the conversation.  She didn’t smile much and seemed a bit nervous herself.  When I asked about her future, she simply told me that she had no plan, and for the moment was driving an Uber in Chicago.  Actually, that sounded like more of a plan than most of the people I know have.  I even told her that this was my first Uber ride, and basically had no clue what to expect.  I have to say that my first Uber experience might have been one of the highlights of my trip to Chicago.  Once we hit the meetup bar for my booze and boos haunted tour, I wished the young woman well and maxed out her tip.  I could only hope that all my future Uber drivers have such an appealing profile.

Well, this was not to happen for my return journey.  To be honest, I actually considered hoofing it back to my hotel after the fourth bar of my bar hopping ghost jaunt.  I’ve always liked walking, but the way that I was feeling after that potent tour I feared that I might just walk right into Lake Michigan.  Indeed, this was one of the more intoxicating boos and booze tours I’ve stumbled through.   Chicago is just loaded with quaint little bars with not so quaint little drinks.  My my!  I could nearly hear Margaret screaming at me all the way from Texas, “You’d better not walk!”  So with my trusty Uber app I found another ride.  Unfortunately, no stunning brunet with a cool, sexy accent this time.  Just some dude from another foreign land that I don’t remember.  I was just happy to get back to the hotel while avoiding a wade through Lake Michigan.