Rideshare by Robert – Anxiety, Paranoia & A Heart-Pounding Ride

Almost eight years ago, I embarked on a journey that profoundly and unexpectedly changed my life forever. Some journeys in life are carefully planned and skillfully charted out.

Others, like the one I’m sharing in this blog, land in your lap like a hot cup of coffee, and you must deal with the mess. Or, what appears to be a mess. You see, our capability to see clearly and respond with balance is often adversely impacted by the unexpected and what we perceive to be a crisis, an unwelcome event, or simply a lemon in disguise.

In my case, I opted to identify the season I was experiencing as both a crisis and an unwelcome event, when in fact, it was a lemon ripe and ready to become a tall glass of refreshing lemonade. I just couldn’t see it at the time.


A perfect storm was unfolding. I sensed the clouds gathering over several years in my industry as many companies were going through downsizing, which eventually was renamed rightsizing.

An attempt to make it more palatable to the people tasked with the firings and layoffs, and to make it more palatable to the recipients. Advancing age, and decreased spending in the government sector, eventually cost me my job. At the time, I figured I would easily reinvent myself and find a home with another logistics company.

I felt my 35 years of experience as an executive and my many contacts should make things relatively simple to land a job. Well, my confidence and optimism didn’t match the reality of the marketplace. In short, I had “aged out” and was experiencing this reality in real-time through a series of second and third interviews that yielded zip.

In two cases, people I had mentored along the way got the job. I was delighted for them, and simultaneously thinking, “Congratulations, you got MY job!”

After six months of this all-consuming exercise of finding full-time employment, a friend suggested I get away from my phone and laptop and drive for a rideshare company. I was already feeling down about my situation and was struggling with my identity when this person suggested I put my executive role on hold and reconnect with people for a while. His timing could not have been more ridiculously perfect.

He knew my high-relational self and how I was losing touch with this critical element in my life. So, I took his advice and began driving part-time to break up the draining experience of seeking job opportunities.

I would love to tell you it was the ultimate cure, well, it wasn’t.

In fact, I was somewhat miserable as I questioned why I was put in this little box shuttling strange people around in my car risking my life, or at least the fresh scent of my car interior after some drunk creature releases a load of vomit into the air.

After about four months of this self-pity, I responded to a pick-up request by another rideshare driver. I rushed to the scene off a major highway. When I arrived, I found a family of Nigerians outside the driver’s car with pieces of luggage everywhere. The other driver ran out of gas while taking this family to the airport. They were getting dangerously close to missing their flight, so we quickly loaded up my car. Five riders, and luggage to the ceiling. I was hoping and praying I didn’t get pulled over in my frantic race to the airport.

From the moment I arrived to transfer them into my vehicle, until the time moment we arrived at the airport and unloaded, this family was singing and celebrating being rescued. It was then that I realized my purpose in rideshare.

It’s not all about rideshare, it’s about rescue. Rescue and encouragement. How can this time together be of benefit to each rider aside from providing a safe and on-time drive?  It was then that the creative energy filled the hours of driving. Learning, growing, sharing, encouraging, and sharing life during each ride. New connections and friendships emerged, and new opportunities unfolded.

The brand, “Rideshare by Robert” was created to umbrella several projects including a book by the same name which journals my first seven years driving and over 25,000 rides. The book is a collection of short stories and observations on the rideshare experience.

I’m excited and thankful to launch this blog with you today. The blog will be a collection of new stories and experiences, and hopefully content for a new book somewhere down the road.

I hope you enjoy this new journey and the first story. Looking forward to hearing from you.

Anxiety, Paranoia, and A Heart-Pounding Ride

Another Wednesday morning on the road. Mid-week and Wednesdays are typically a bit slower than the other workdays in the region. I had been driving since 6 a.m. and completed a few rides to the airport, a healthcare provider heading to work at a local senior center, and I just accepted a ride on the edge of the city.

I’ve come to appreciate both the mundane and the monstrous rides over my years as a rideshare driver. All real and all very human. I’ve witnessed a very broad range of people at their best and worst in my little field lab on four wheels. Regardless of what unfolds during each ride, one thing has become extremely evident. All the people who enter my vehicle and all the circumstances that take place during the ride are stories. Some are captured and shared like the one I’m writing about, but most simply happen. Living stories moving through space and time. A slice of life in humanity and with humanity.

I pulled up to the rider’s dwelling place, noted my arrival on the rideshare app, and waited for the person to appear. And what an appearance indeed. Half dressed, in shorts, pumps, no shirt and profusely sweating, he ran across the street and quickly jumped into my car.

“Go, go, go, oh shit, go! They’re coming, hurry, go, go,” he immediately started yelling from my back seat.

He was hopping around my back seat from left to right while peeking out the rear window.

I calmly told him I would move as quickly as I could and try to relax. My words were lost in his angst.

“Drive faster, don’t stop at the light. They are right behind you. They will shoot us. Keep driving, oh fuck, keep driving!”

I realized he was beyond the point of calming down, The ride was only 15 minutes. We were heading to the hospital emergency room. No surprise, and frankly, he helped me to stay calm and focused. He was pounding on the back of my seat, and screaming every time I was forced to slow down due to city traffic.

“Turn here, turn up this alley, now, we need to lose them. They have guns, turn now, we’re dead, oh shit, we’re dead!”

I complied,

I turned up the alley, wheels burning rubber, dodging trash cans, people, and property. After running several traffic lights, I tried to reassure him.

“Hey, look. I think we lost them. They aren’t behind us anymore.” He yelled,

“Really? Are you sure?” I feigned excitement and yelled back, “Yeah, yeah, we lost them. We lost them. They’re gone! They’re gone!”

He started sobbing and mumbling to himself. During the last four minutes of the ride, I continued to yell as loud as I could, “They’re gone! They’re gone! We lost them. We’re safe!”

I had a conflicted mix of feelings as I pulled up in what I surmised to be a familiar stop in the life of this troubled soul. Another traumatic experience, another day, another emergency room. I continued yelling my mantra as he quickly exited my car and ran into the building. “They’re gone! We’re safe! We’re okay!”

I just finished one more ride, with one more human. One more story.

No time for deep reflection on what just happened as the all-too-familiar audible alert from the rideshare app that another life needed a ride. I accepted the ride request and moved toward another story.



I have made every attempt to provide anonymity to all individuals portrayed in this book. The names have been changed to protect the innocent, and in some cases, the not-so-innocent. I have substituted the characteristics of individuals in the stories to further my attempt to maintain anonymity. Conversations are based on my best recollection and notes. Although I have spent time with celebrities and public figures in the last seven years, I have intentionally omitted their names. Locales, and other details of when and where the rides occurred, have been modified to maintain my objective of rider protection and anonymity.