Once upon a time, Bob Reilly was riding high in the saddle. As part of the top brass at big companies, he racked up a ton of rewards miles flying to and from Japan and other world capitals, closing deals, feasting on sushi and sake while helping provide a comfortable life for his wife and their three children, who the couple adopted from China, Korea, and the Philippines.

In every life, someone wrote, “a little rain must fall.” Indeed. In Reilly’s case, the heavenly droplets were accompanied by gale-force winds. At 52, he was diagnosed with Guillian-Barre Syndrome, an autoimmune disease that affects part of the peripheral nervous system. In a country where the fickle corporate culture writes the rules of the game, Reilly was out.

His next adventure, he said over coffee at Panera, was driving for Uber. “My first day felt a little bit strange,” he said, “because I was using my own car. It was more like the first day of high school.” At the same time, he was multi-tasking, trying to figure out how to use the company ride app.

It didn’t take long before Reilly was riding high in the saddle again – higher than ever, in fact. Here’s how high: Reilly, 68, recently clocked his 21,000^th ride, amassed during his five years behind the wheel. “It’s had a profound effect on me,” says the affable, garrulous native Washingtonian. “I didn’t realize how transformative it is.”

True to form, Reilly, who also writes, plays, and records music professionally, is busy cobbling together a book based on his adventures culled rockin’ down the highway. He’s even got a working title: Every Ride’s a Short Story.

An inveterate news consumer, Reilly said he feels most comfortable moving in this casual, unscripted world squeezed in a tiny motorized box on wheels, an intimate performance venue of sorts. If all the world’s a stage, as Shakespeare noted, you can find signs of that inside the car. “It’s like I’m on steroids,” exclaims the avuncular, garrulous Riley. I’m wired that way. It’s like going out and throwing myself in the pool.”

Here is a sampling of the (mostly) bouquets that drift across the polluted air as passengers hop in and out of Reilly’s reliable Honda Civic:

From a “tearful,” 82-year-old woman: “Please pray for my country. I’m from Afghanistan.”

From a Chicago divorcee poised to start a new life in DC: “I feel like I just spent an hour with my favorite uncle, bartender, priest, and therapist.”  

Another: “This may be my final conversation with a stranger. I have Stage 4 cancer.”

This from Cletus: “Robert, such a nice ride! I pray we meet again!”

Request from a Drag Queen headed to a parade:

“Don’t judge me!”

One more: “Best ride ever”!

An evocative and provocative, parting offer from a young Asian woman, while rubbing Reilly’s hands: “Is there anything else I can give you?”

It’s happened before, he said. When it does, Reilly has a warning. “Look,” he said crisply, laced with an air of finality, “that won’t help the rating that I give you. Let’s call it a day.” Apparently Uber drivers also rate the passengers.

If the ride is particularly memorable, that’s all the inspiration Reilly needs to come up with the lyrics to his next song. Before he sets out for his next ride, he has the draft jotted down. This ditty came to him after a ride where the customer was obviously stoned:

“I knew you were wasted when I picked you up.

I mean, you could barely stand.

My thoughts were confirmed when you leaned up and asked me

`When will this plane land?’”

You have to know who Reilly in order to grasp the contents of the clean-burning, psychosocial fuel he uses.  He grew up in a large, close-knit, Irish-Catholic family, where learned the importance of sharing.  

His profoundly meaningful connection with people, he enthused, underscores the daily drumbeat of “the diversity and range” that nestles in the backseat, origins sometimes unknown, bound for anywhere and everywhere. “This is what keeps me going,” he assured me, buttering a blueberry bagel. I’m just an old man in a richly diverse sea of humanity.”