Cobbling together a living gives many an opportunity to follow their passions

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J. Brian McCrory has been an Uber driver and runs a personal taxi service, but he says driving the Bella’s Ice Cream truck is more fun because of the kids’ excitement when they spot him. Photo by Amy Jackson J. Brian McCrory has been an Uber driver and runs a personal taxi service, but he says driving the Bella’s Ice Cream truck is more fun because of the kids’ excitement when they spot him. Photo by Amy Jackson

Ethan Lipscomb tore the shirt from his thin frame and tossed it through the artificial fog and colored lights off the stage in the basement of the Jefferson Theater. The crowd erupted and the drummer punctuated the landing of the shirt with the hit of a cymbal. Lipscomb launched into the next song with his band, Just Sex.

The next morning, with ID-check bracelets still fastened around the wrists of many sleeping concert-goers, Lipscomb reported to work as a barista at Shenandoah Joe Coffee Roasters. Next week he could be doing construction again. Welcome to Charlottesville’s gig economy, where unsalaried millennials and Gen-Xers patch together a living from whatever work they can find, often while making art or music.

“My job is I work at a coffee shop and I pick up side jobs,” says Lipscomb, who has also acted at Live Arts. “Whether that be construction or music or event planning. …I’ve been a pool and spa technician. That paid a ton of money, actually. Roofing.”

Ethan Lipscomb works as a barista at Shenandoah Joe during the day, and fronts the synthesizer-led band Just Sex at gigs around town. Photo by Jackson Smith
Ethan Lipscomb works as a barista at Shenandoah Joe during the day, and fronts the synthesizer-led band Just Sex at gigs around town. Photo by Jackson Smith

Coffee shops in Charlottesville have changed in tone and layout during the last 20 years. In 1997, Mudhouse on the Downtown Mall featured a living room-like layout with black leather couches. Large scrapbooks sat on the coffee tables and regulars would fill them with doodles, poems and stories. Evenings featured poetry readings and acoustic music performances. It was a place where people came to talk to strangers.

Today, the couches and scrapbooks are gone. In their place are rows of open laptops and coffee-sipping freelancers with earbuds guarding them against the overtures of their fellow workers.

A generation ago, cobbling together a living was almost unthinkable. Since the end of World War II, the trend had veered toward higher standards of living and more stable lives for most Americans. But for many people born during the 1970s onward, the white-picket-fence lifestyle has only been something they’ve seen on television. They pass from college through their 20s and 30s and beyond, waiting to start families and buy houses. Waiting for salaried jobs with benefits that are harder to come by.

The music business—both locally and nationally—is particularly tough. Music sales have dropped to almost nothing as services like Spotify and YouTube distribute artists’ intellectual property while paying them literally pennies for tens of thousands of streams. And local owners of live venues have different ways of paying bands.

“Some venues will say to you, ‘We’re going to take [all of the money] up until 100 people,’” Lipscomb says. “After you have 100 people who came in the door and paid $10 a ticket, then you can start making money. And then you have some venues that will say, ‘We’ll just cut you a percentage at the door.’”

Even if the bands get to keep all of the cover charge, the math still doesn’t work out very well. Lipscomb says that a common scenario might be that three bands play a show together, with 70 people paying the $10 cover charge; $150 would pay for promotion, fliers and the sound guy. That leaves $550 to split between the three bands. The two opening acts each get 30 percent and the headliner keeps 40 percent. If that headlining band has three members, they are only paid about $73 each. And managers of music venues often require that a band not play anywhere else in Charlottesville up to a month ahead of the booked date.

This is why so many musical acts in Charlottesville are now one- or two-piece bands, according to Lipscomb. Adequately paying two guitarists, a bassist, drummer and singer has become close to impossible. Just Sex includes Lipscomb singing and playing a synthesizer, plus a live drummer. Occasionally they are joined by a bass player.

“If I could have a full band, I definitely would,” Lipscomb says. “I would have a four- or five-piece. I’m in two bands…it comes down to a financial thing. We would love to scrape by and make money to survive—none of us are trying to get rich. We’re trying to do what we love. We’re gonna do that, but that requires us to eat and have a room to practice in.”

The drive to succeed

J. Brian McCrory also dabbles in art and music. He is one of many locals who have driven for Uber but is now skeptical about the company.

McCrory started driving for Uber about a year ago. “That was my first foray into gigging,” he says. “First it made a lot of sense to make cash quickly. But as I went on it was clear that Uber drivers really don’t make very much at all. Keeping the costs of the car and keeping it drivable and on the road, the AC working, it’s a tough gig for sure. The whole dichotomy of Uber probably needs a second look from its higher-ups.

“When I started out I could make between $80 and a $100 in a regular 10-hour day or $150 if I worked on weekends, but I’d be working till 3 in the morning,” McCrory says.

Because of changes in Uber’s rates, that income dropped to about $50 a day. The drop in income came on top of McCrory’s realization that neither Uber nor his personal auto insurance policy covers the liability of driving his car for hire. He has scaled back his time driving for Uber, doing so only when other gigs have fallen through or failed to pay.

“I do everything,” McCrory says. “People are always asking, ‘What are you doing now?’ At the moment I am driving an ice cream truck. I [also] drive a personal taxi service, I am helping to record an album for a budding artist, and I teach classes in batik and drawing. There’s plenty of other little things thrown in from time to time as well.”

The ice cream truck gig is fun, at least. McCrory drives for Bella’s Ice Cream, a local company with two trucks. He says he likes it better than Uber, although there still isn’t a lot of money in it.

“What makes [driving the ice cream truck] a good day is that you’re out making people feel nostalgic—the kids love it and do dances to the songs,” McCrory says. “The kids all help each other out. They’re always pooling their money to help a kid who doesn’t have anything. It gives you faith in humanity.”

Working as a personal taxi service (he’ll take people to Washington, D.C., or Baltimore, for instance) outside of Uber, McCrory finds customers occasionally by word of mouth. It pays better without Uber taking a cut.

Like many people in the gig economy, McCrory does not have health insurance.

“I haven’t had [health insurance] for a really long time,” McCrory says. “Even with a decent job it was a difficult thing to secure. It’s been rough, I have a lot of back problems…my partner does have insurance, very good insurance, but spousal benefits are almost impossible. They’re like half of his paycheck every pay period.”

McCrory has a bachelor’s of fine arts in illustration and design from the University of the Arts in Philadelphia. He says that if he could find a full-time, salaried job as an art teacher then he would like to make the transition, but he hasn’t had any luck. Meanwhile, he says there’s an upside to staying in the gig economy.

“I have done a lot of soul searching and figured out that I am more of an ambivert than an introvert or an extrovert so I love mixing up my job from day to day so that I don’t have to talk to people some days and get to talk to people other days,” McCrory says. “It keeps it fresh. It keeps it flowing and happy for me. I definitely have less money but it’s better for my soul, I think.”

McCrory and his partner would like to adopt children, but the lack of financial stability has been a factor in holding off.

“We talked about kids. I absolutely love kids,” McCrory says. “I think it’s completely impractical [to have kids in the gig economy]. I think you have to be in a pretty good situation to consider having children in this day and age. There are so many issues with just keeping a regular 9-5 job. …I definitely don’t think I would consider it unless I had something that I knew was going to support me for a long time.”

Settling in

Jay Taylor’s elderly mother and a son in high school keep him tied to Charlottesville in spite of a résumé that would land him a good job in many other places.

“I had a full-time gig here where I managed the [Martin Luther King Jr.] Performing Arts Center,” Taylor says while sitting on a bench in McGuffey Park on a Saturday afternoon. “It was more than 40 hours a week. It was like 60, sometimes 80 hours a week. I lived, ate, drank, breathed, slept that job and I had no time left for myself or my family and I kind of regret that actually.”

When Taylor’s mother was diagnosed with Alzheimer’s disease, he needed to spend more time with her than his job allowed. So he quit the Performing Arts Center and moved into the gig economy. Now he makes stuff, fixes stuff and moves stuff.

“I own a box truck so I move things and I make things,” Taylor says. “But I mostly fix things. I also work in the film and theater world and do lighting and sound and sets.”

Jay Taylor quit his 60-hour-a-week job to spend more time with his family, and has since become a member of the gig economy by working as a carpenter, handyman, set designer and mover. Photo by Ron Paris
Jay Taylor quit his 60-hour-a-week job to spend more time with his family, and has since become a member of the gig economy by working as a carpenter, handyman, set designer and mover. Photo by Ron Paris

Skilled in carpentry, wiring, mechanics, plumbing and decorative arts, Taylor’s jobs come via word of mouth, and he can do anything from trimming out a bathroom to building a film set. Taylor, who’s married and is decades older than the average gig economy worker, would like to focus on work in the film industry but film jobs are sparse in Charlottesville.

“I work for a local promoter doing music videos from time to time,” Taylor says. “I do props and sets and design, making their vision of what the thing should be come to life. Art meaning set, background, the visualization of whatever the mood is that they are trying to go for.”

Hiring a mover with experience in the arts and set design appeals to some of Charlottesville’s affluent residents, which is what keeps Taylor in business, he says. Most professional moving companies won’t show up to move just one or two pieces of furniture.

“I guarantee you that you’ll be able to get it cheaper,” says Taylor. “But that’s not why you’re hiring me. It’s more than just moving the sofa. I’m gonna do it with a smile, I’m gonna do it carefully, I’m going to do it intelligently.”

Taylor had health insurance but recently lost it due to a sudden premium increase.

Taylor and Thomas both grew up in Charlottesville. Thomas attended Tandem Friends School and went on to study film at the New York Film Academy.

“I’m trying to put back into production my documentary on local jazz music,” Thomas says. “It’s about when it is appropriate to clap at a jazz performance. And I do all the things I have to do to keep the rent money moving.”

Thomas has also done construction work and general handyman duties. “I’ve done mechanical work, car repair for friends, I can do brake jobs and whatnot,” he says. “My other main gig is I do draft system installations. Install beer systems. We redid the taps here at Miller’s, I did the taps at Smoked [Kitchen and Tap] in Crozet. We’re getting ready to do a full brewery install…so that should be fun, installing all the big tanks and pipes.”

But Thomas has had just about enough of the rising rent and lack of opportunity in Charlottesville. Also, he has not had health insurance since 1998 and has not visited a doctor in six years.

“I am trying to go somewhere else,” he says. “Just trying to figure out the right place. I have to move out of my current abode in the fall. I don’t want to get stuck into a lease here in Charlottesville again. The rent is so high and the pay is so marginal that it makes it difficult. I’d like to be somewhere bigger with better public transportation. Thinking of like Seattle, Portland, maybe Charleston if I want to stay closer. They have more opportunity, bigger markets. I’m much more likely to find better pay.”

Sean Thomas has done construction work and general handyman duties. “I’ve done mechanical work, car repair for friends, I can do brake jobs and whatnot,” he says. Photo by Ron Paris
Sean Thomas has done restaurant work, in addition to construction work and general handyman duties. “I’ve done mechanical work, car repair for friends, I can do brake jobs and whatnot,” he says. Photo by Ron Paris

Meanwhile, Thomas isn’t bitter about being in the gig economy. Several weeks after being interviewed in person, he reached out by email to clarify that he’s okay with his career choice.

“I have come to enjoy gig work,” Thomas says. “It allows me to take on as much work as I want, or to take off time for family or travel. It does mean I have to pack in more work when the season is good then schedule other activities in the down times. I would like to make an official career out of gigging.”

The right balance

Jessica Glendinning seems to have found a smoother spot in the gig economy than anyone else interviewed for this article. She is a yoga teacher and a freelance editor and writer specializing in corporate communications. Sitting around her dining table beside a wall of books, with the sound of unseen dogs behind a closed bedroom door, she seems content and comfortable.

“Anyone who is a full-time yoga teacher in Charlottesville can tell you that it is almost impossible to make a living teaching yoga,” Glendinning says. “If you were to teach for three or four different studios and teach five classes a day, you could possibly make it happen. Right now it’s a form of supplemental income.”

Yoga studios have popped up around town even faster than breweries. Competition for students is fierce. And alternatives like Pure Barre, Zumba and Pilates add to the squeeze on local yoga teachers.

“I’ve had this conversation with folks in Charlottesville that we’re at a point of maximum saturation with yoga,” Glendinning says.

 Jessica Glendinning works as a part-time yoga teacher while most of her income comes from freelance writing and editing. She says she’s seen a shift in the economy since she started gigging, in that new companies are bringing in more people on a contract basis. Photo by Amy Jackson
Jessica Glendinning works as a part-time yoga teacher while most of her income comes from freelance writing and editing. She says she’s seen a shift in the economy since she started gigging, in that new companies are bringing in more people on a contract basis. Photo by Amy Jackson

Writing and editing is Glendinning’s main gig, while the yoga classes wax and wane as freelance writing contracts come and go.

“I’ve been writing since I was old enough to hold a pencil. It was always just fun. Back in 2007 I started doing the National Novel Writing Month…that was the first time I started taking it seriously,” Glendinning says.

She started writing professionally when a company that she was working for full-time needed an employee to ghost write for its CEO. Later she moved on to writing corporate blogs and newsletters as an independent contractor.

“As of two weeks ago I had an ongoing contract that was supposed to be 15 to 20 hours a week that turned into two to five hours a month. So it’s a period of transition now.”

Glendinning’s niche in corporate communications gives her periods of greater stability than most freelance writers enjoy [full disclosure: The writer of this article is a freelance journalist living in the gig economy]. Instead of trying to sell one article at a time, she secures contracts that include a planned schedule of blog entries, newsletters and other materials.

In spite of the yo-yoing income, Glendinning is happy with her situation.

“I’m not built for a cubicle,” she says. “For a long time when I first started freelancing I was also supporting myself with part-time work. I look at it now and think about it…oh man, having a paying job with a steady paycheck and health insurance. And then you’re like, ‘I realize how much that sucks.’ I almost feel like I’m unemployable. As a freelancer, what does your résumé look like? I’ve gone back and forth. Do I want to give this up? No…I am so much more productive here with dogs on my feet.”

Glendinning has health insurance through her partner. “It would be really difficult” to make this work if she were single, Glendinning says. “I squeezed by for a few years, but it’s a lot nicer now knowing that if a contract dried up that feast or famine is balanced out by having someone else in the household with an income.

“Since I started doing this, the general economy has changed,” she says. “Not as many people were doing this. But it has shifted and now a lot of newer companies are just bringing people in on a contract basis and not having to pay for things like health insurance.”

A 2016 survey commissioned by Freelancers Union indicated that 35 percent of the total American workforce are freelancers. That’s 55 million freelancers, up from 53 million in 2014.

“If you interact with someone within the gig economy, even if it’s just an Uber driver, I know that Uber doesn’t require people to tip, but Uber drivers make less than any other ride service by far. They definitely would appreciate a tip,” says McCrory, the former Uber driver. “Also know that if someone’s working a job that you think is a little job a lot of time it’s to support a dream of theirs. So just being extra nice and kicking in a little extra if you think they did a good job is really helpful.”

*This article was updated at 12:07pm May 12 to reflect the correct spelling of J. Brian McCrory’s name.

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