Seasons Magazines

Seasons Magazines

On the Road with Uber

Online ads for ride-sharing jobs are tempting: Be your own boss! Make extra money on the side! Earn up to $1,500 a week! It’s a growth industry fueled by the ubiquity of smartphones. The marketing is a siren song, luring potential drivers to “Get your side hustle on,” and “Cash in on the action.”

Ride-sharing job opportunities are at our fingertips, Uber being the most prominent. It’s the only service of its kind to continuously operate in Connecticut since launching in 2014. And nearly 10,000 drivers in the state choose Uber, with the company maintaining a full-time driver resource center in Stamford.

“The beauty of Uber is there are no typical drivers,” says Danielle Filson, company spokesperson and a University of Connecticut graduate.  “It’s for everyone and we see every type of driver. Drivers continue to choose Uber because it offers a unique, flexible work opportunity that fits around their own lives, not the other way around.” She adds, “Our goal is to make transportation as reliable as running water, for everyone, everywhere.”

Part of Uber’s appeal for passengers is that when you enter your destination into the app, the company shows you an upfront fare, so you always know what you’ll pay before you ride. No math skills are necessary, and there should be no surprise charges.

To figure out what the hype is all about, we decided to ride along for one evening in the greater Hartford area — a journey complete with a few bumps in the road, and the occasional sharp left turn.

Shifting Gears

Ken Green, 65, recently moved to Avon after living in West Hartford for the past 20 years, having lived in Hartford before that. As we climb into his black 2017 Volkswagen Jetta, he points out that he’s one of very few Uber drivers to use a manual transmission.

“I grew up on a farm in Ohio; my first car was an MGB with a stick shift,” he says. His current car is brand new. Up until this spring, he drove another Jetta that had been recalled under the so-called “Dieselgate” emissions scandal. Green says that Uber prefers its drivers have late-model cars and one requirement is that his car must have been made within the last 13 years.

He opens the Uber driver app on his iPhone. The app will “ping” the closest driver when a passenger requests a pickup. He says the job is convenient because he can turn on the app at any time he’s ready, day or night.

Sitting in the parking lot of a Chick-fil-A in Enfield does not exactly yield a flurry of “pings.” In fact, our current location seems to be a dead zone for Uber fares. He explains that hubs like airports and train or bus terminals are prime Uber grounds, but these locations also add to driver competition, and the customer’s destination can be quite distant.

“You can get a $2 fare or a $50 fare,” he says of the airport in Windsor Locks. “I picked up a guy on Friday from the airport who I thought wanted to get to Hartford. He said, ‘No, Great Barrington.’  So I was happy to take the drive. It was a beautiful day in the Berkshires, no traffic. Sometimes you just get lucky like that.” He notes that a Connecticut driver can take passengers to Massachusetts, but company policy requires additional certification for Green to pick up passengers across state lines.

Looking to become an Uber driver? Green’s tenets for taking the job are simple. He says you must like to drive, be patient, and be flexible. “If you have a good passenger, it’s fun,” he says. “I had opportunities to get back into the old corporate scene, but I wanted to do something different. This is different.”

Taxi Driver

As we hit the smooth tarmac of I-91 south in search of a fare, Ken explains a bit more about how the gig works. He mostly drives for Uber during the daytime, but not for fear of his safety. “I’ve pulled up to mansions, and to some bad areas in the North End of Hartford,” the driver says. “But everybody has been very nice to me, whether they seem penniless or a millionaire.”

A few exits down the highway, we get “pinged” with our first customer. A patron at a local watering hole has enjoyed a few too many drinks during happy hour, and needs a ride home from Windsor Locks to Simsbury. It’s not the driver’s usual scenario, but Ken obliges.

We pull up behind the restaurant to find that some good Samaritans called Uber on behalf of the rider: a large, blond man with dark sunglasses and a thick Rolex watch. He’s wearing mesh basketball shorts and a light blue polo shirt, and seems to be sweating profusely. The concerned onlookers usher him into Green’s backseat.

We’ve barely traveled a half-mile down the road when it becomes apparent that our passenger — let’s call him “Shades” — isn’t belligerent, just a bit disinterested in his surroundings. By the time we hit the highway, he’s already changed his mind. Not content to head home in his condition, he tells Ken to take him to his closed office instead, where he’ll presumably sleep off his intoxication before going home.

So we re-route to Farmington, with Ken taking the change in stride. He simply plugs the new data into Waze without missing a beat.

“Shades” says he’s got some late-night work to do at the office and his work involves “investing a lot of money.” Say no more.

“Both of my kids use Uber,” Ken says as “Shades” drifts off into a slumber in the back seat. We both breathe a sigh of relief that the man has kept from repeating his appetizers all over the pristine Jetta.

“I’ve driven some people who have medical issues before,” says Ken. “A lot of my regular passengers who I take to the airport can’t drive anymore because of their health. I’ve become someone they can trust. I’ll often meet people in baggage claim to help; I try to make it easy for people.” As we cruise past the new Hartford Yard Goats stadium, just off I-91, “Shades” begins to gently snore.

Ken is not only a smooth driver with a flexible approach, but he soon begins to show a vast knowledge of local landmarks. As we pass the headquarters of Aetna, he points out that the building is the largest example of colonial style architecture east of the Mississippi.

“It’s an adventure,” he says of driving for Uber. “I think it’s fun. But you have to be up for it.”

“Shades” groggily wakes up. He’s never used Uber before; He probably won’t remember this trip anyway. His fare comes to a grand total of $20.47, paid for by his good Samaritans, which is a small price to pay for avoiding a DUI. After he stumbles up to the door of his office, and we ensure he’s safely inside, Ken heads back to I-84 and gets on going east, with the expectation that our next rider will hail from Hartford.

Eastbound and Down

We pass under the “the stack” of three highway overpasses, and the driver notes that one of them is a road to nowhere. “It was a mistake,” he chuckles under the triptych of blue-covered roads. We’re soon near the Capitol building in Hartford, and Ken points out the tallest building in Connecticut, CityPlace I. There’s little time for sightseeing, however, as his phone lights up with our next fare.

We pull up to the Harford Courant building, expecting to find a journalist or a weary press operator in need of a lift. Jose is instead a worker for one of the companies that shares office space with the Courant — a busy call center offering customer service for a florist. He’s just coming off his first day of work there, and needs a short ride home.

“I started using Uber a couple months ago. It’s definitely been helpful, and it’s a lot cheaper than always using cabs,” Jose says. “With my health condition, I can’t drive. I was diagnosed with multiple sclerosis four years ago.” He continues, “Going from the Hartford Courant building to my home, it would be about a $5 savings each trip using Uber instead of a cab ride.”

Jose, who’s 26, ends up with a very small $3 fee for the ride home, which is automatically rounded up to $5 by the Uber app, since there’s a $5 minimum charge per ride (which varies depending on the location and size of the driver’s vehicle). Ken makes sure Jose gets safely inside before setting the Jetta back in motion.

As we maneuver through a construction area near the UConn campus, Ken points out the Wadsworth Atheneum and its big red “Stegosaurus” sculpture. We turn down Main Street and the city seems to be emptying out for the night.

We’re not getting any “pings,” despite our central location. It’s all part of the unpredictability of the job, according to Ken. “You never know where you’ll be going, or who’s going to get into the car next,” he says. We swing past Bushnell Park, and he notes that it was designed by the same person who designed New York’s Central Park.

He says Uber is also expanding a service locally called Uber Eats: a food delivery service in Stamford, New Haven, and Hartford. He’s done some of those drop-offs too. Suddenly, we’re “pinged” for our next pickup, at Union Station.

Ken says a lot of his riders come from the train station and bus station downtown. Our next passenger, Paul, is waiting for us alongside a Greyhound bus. His duffel bag and backpack seem to be weighing him down; he moves with the dogged determination of a weary traveler. As he gets in the car, he tells us he’s coming in from New York where he went to see a doctor. His destination is his apartment, nearby.

“I always use Uber. It’s just more money if you don’t,” says Paul. “It’s not perfect but the vast majority of drivers I’ve had are respectful, reliable, and know what they’re doing.”

He says his little brother, who lives in the San Francisco area, has also worked as an Uber driver part time. “He just found it’s really easy to make a little extra money on the side.” Our passenger is a graduate of Hall High School and grew up in West Hartford. He returned to Hartford about four months ago after graduating from New York University.

Paul’s ride is brief and his fare only comes to $3, also rounded up to the $5 minimum. It’s a typical short trip, the kind of around-town shuttle ride one would expect from an urban taxi service.

Highway Star

We exit the city and hit the HOV lane on the way back to Enfield. It’s getting late in the evening, past the time Ken would normally be wrapping up his work for the day. The open road and empty backseat allow him to open up a little bit about himself.

The driver is semi-retired from the camera business. “I was selling high-speed cameras for the last 12 years,” he says. “I got downsized, and started driving Uber this March.”

His wife, Kim, who is overcoming her own personal challenges, “decided she wanted to open a meditation studio, and I wanted to be flexible enough [with work] to help her. She’s a Stage IV breast cancer survivor. After she opened the studio, she went in for a hernia surgery. She’s used meditation to cope with pain over the years.” The couple has two college-aged children.

He says there are some limitations to driving for Uber. The company doesn’t compensate him for wear and tear on his personal vehicle, and he also pays for gas. Ken says Uber takes 20 percent off the top of every ride per trip. In addition, riders pay a $1 booking fee, which also goes to the company.

Ken’s current job, while social, is also fairly solitary when it comes to meeting other Uber drivers. He says he rarely meets up with other drivers to talk shop, but there is a weekly meeting on Park Road where drivers can receive new training from the company. For Ken, and thousands of other Uber driver across the state, the “gig economy” has become both lucrative and a personally rewarding job.

Passengers are able to rate Uber drivers on a five-star scale, and drivers in turn also rate passengers. It’s no surprise that Ken boasts a 4.8-star rating. Passengers are also able to provide brief written reviews, and Ken’s are glowing. Comment after comment reads, “Thank you for welcoming us to Hartford!” and simply, “Thank you for getting me home safely.”

Mike Briotta is a freelance writer and admittedly mediocre driver. Despite numerous moving violations throughout the years, and a few crashed vehicles, he’s somehow managed to retain a valid driver’s license. Look for him appearing soon in an Uber car — as a passenger.

Photography by Todd Fairchild, of West Hartford, is a longtime contributor to Seasons. Find him online at