Vermont Freelancers Share the Ups and Downs of Being Their Own Boss | Seven Days

They set their own hours. They’re not on anyone else’s payroll. Their time is their own, but generally so is the responsibility for their health and unemployment coverage, vacation time, and Social Security contributions. They are gig workers, freelancers, temps or independent contractors, and their ranks are swelling.

In the 2022 American Opportunity Survey conducted by consulting firm McKinsey, 36 percent of employed respondents described themselves as “independent workers,” up from 27 percent in 2016. Although that category included full-timers who also do “side hustles,” 72 percent of the respondents said they had only one job.

A quarter of the respondents cited “autonomy and flexibility” as their reasons for taking independent work. Digital platforms and startup culture benefit from that flexibility, using workers as needed for a particular season or project rather than keeping them on staff.

But adaptability can become an opportunity for exploitation. “Has ‘Gig Work’ Become a Dirty Word?” a New York Times headline asked in May 2023. While acknowledging that the artistic professions have a long history of freelancing, the story noted that these days, “for some, gig work has become shorthand for instability and low wages.”

In a Times guest essay on January 28, labor expert Terri Gerstein described how the “exploitative gig business model” has spread to hospitality, retail, janitorial and other sectors, touching off lawsuits and legislation in some states. Labor advocates argue that many workers are misclassified as independent contractors even though they do the primary work of a company rather than supplying a temporary need. A new rule from the U.S. Department of Labor went into effect this month; it aims to separate those who are truly “in business for themselves” from those who depend on a particular employer for work.

As deputy executive vice president of the Associated General Contractors of Vermont, Matt Musgrave has worked with the Vermont Senate on recent legislation governing the adjudication of cases of alleged labor misclassification. Some workers want to “run their own show, make their own hours,” Musgrave said, and “the market would like to go do that. But then you have some of the labor organizations come in [and object], and I think they’re not wrong.”

Such disputes might arise in Musgrave’s field when, for instance, a member of a home-building crew is injured on the job and learns that their independent status makes them ineligible for workers’ compensation. In Vermont, however, there “haven’t been a legion of cases,” he said.

The vast diversity of self-employment — from technology to the trades to the service sector to education to the arts — makes it difficult to generalize about these workers’ needs. For this issue, we profiled six independent workers who knowingly chose the freelance path over other options. All but one fit the more restrictive definition of gig workers as being “in business for themselves”— and the one exception has since become a full-time employee. A seventh independent worker, cartoonist Kristen Shull, depicts the conflicts of her artistic self-employment in graphic form.

— M.H.

Walk the Walk

Kylee Harvey doesn’t count her daily steps. But if she did, it would likely be an impressive number.

That’s because Harvey, the sole employee of Leash & Love, typically goes on six to eight dog walks every day. Built-in exercise is just one of the things the 33-year-old Burlington resident likes about running the pet care business that she founded in 2023.

Before launching Leash & Love, Harvey worked for 12 years as a dental assistant. During the pandemic, the job became extra tough, she said, because she was required to wear an N95 respirator and multiple layers of protective gear for 10 hours a day.

“I was starting to feel like I wasn’t quite happy and fulfilled,” she said.

Then, in 2022, Harvey’s partner suffered a traumatic brain injury and she quit her job to care for him. As he began improving, she decided to try walking dogs to make some income.

Within a matter of weeks, her name had spread through word of mouth, and her calendar was booked with appointments, both walking dogs and taking them to and from doggie daycare. A lifelong animal lover, Harvey realized she might actually be able to make a living caring for others’ pets.

Registering a limited liability company, or LLC, was easier than Harvey imagined. She filed an online application, paid a fee of $125 and got a formal certificate from the Vermont Secretary of State’s Office a few weeks later.

A year into being self-employed, Harvey is making around $1,000 a week, charging $30 for a 30-minute walk and $50 for an hourlong one. She gets her health insurance through Vermont Health Connect, as she did when she was a dental assistant.

In the hopes of bringing in more money, Harvey has expanded her services. She transports dogs to their owners’ weddings and cares for cats and the occasional guinea pig or rabbit. She also boards dogs in her Burlington home. Luckily, she said, her pit bull mix, Naje, is happy to share his space — though Harvey sometimes finds herself sitting on the floor while the dogs take over the couch.

As she grows her client base, Harvey said, she finds it hard to take a full day off every week, and work is constantly on her mind.

But she also finds excitement in the constant learning and hustling that come with running a fledgling business. Not even the dreary weather this winter has dampened her enthusiasm.

“I love being with the dogs so much that I haven’t yet felt like Man, I really don’t want to do this today,” Harvey said. Even on cold and rainy days, “I’m pretty happy.”

— A.N.

Following Through

Ten years ago, Jess Kirby quit her job as a corporate diversity and inclusion consultant in New York City to work on her lifestyle and fashion blog full time.

The move was a gamble: Kirby had started posting online as a fun hobby, not as an intended career pivot. But she also saw potential for her blog to fill a vacant niche. Having just moved back to her native Rhode Island, Kirby had a distinctive New England aesthetic that set her apart from big-city content creators in her posts about fashion, travel and interior design.

Big-name brands took interest, including Hyundai, Anthropologie, Sézane, Athleta and Sephora. Within six years of starting the blog, Kirby had quadrupled her previous salary at the consulting firm. Fulfilling a longtime dream to move to Vermont, she and her partner bought a home in Woodstock in 2020.

Today, the 39-year-old has 130,000 followers on Instagram, almost 100,000 followers on Pinterest and about 6,000 Substack newsletter subscribers. She posts interior design tips, such as a video showing her garage-turned-bathroom transformation in 30 seconds; fashion hauls, often featuring cozy knit sweaters; and local travel advice, such as “A Fall Getaway Guide to Mad River Valley.” While Kirby declined to share specific earnings, she noted that creators with similar followings typically earn several thousand dollars per post.

“Once I got a manager, that was when it really felt like Oh, wow, this is official; this is a career,” Kirby said. “I was partnering with brands … that I never even dreamed of when I started.”

Kirby has an LLC with two employees on the payroll: herself and her partner, who works on the business full time as Kirby’s photographer. She contributes to an IRA and buys health insurance on the private market, which she described as one downside of working for herself.

But overall, she said, the freedom that comes with the job exceeds the lack of benefits. She works anywhere from 30 to 60 hours per week, which includes shooting photos, writing content, corresponding with companies and reading other blogs for inspiration.

“If you’re a creative person, it’s hard not to work for yourself,” Kirby said. “Other structures can feel so restrictive.”

Now, Kirby is looking to make a second career pivot, moving away from fashion and beauty content and into the travel industry. With a 4-year-old daughter, she’s found herself desiring more online privacy and hopes to make her content less about herself and more about things to do in New England.

As part of that transition, Kirby stopped using a manager and significantly reduced her number of brand partnerships. She makes less money as a result, she said, but the change is worth it for her mental health. Through her Substack newsletter, she’s also started writing about topics such as overconsumption and the ethics of influencing — a self-awareness that seems to resonate with her audience.

Having a personal website and email newsletter helps Kirby avoid relying too much on any one platform for income. She doesn’t have a presence on TikTok and thus isn’t worried about a potential ban of the social media app that U.S. lawmakers are considering.

Empowered by her financial autonomy, Kirby said she can’t imagine getting a job offer that she would take.

“Technically, no matter where you work, there’s no guaranteed paycheck, because your employer has no loyalty to you,” Kirby said. “To me, the freedom and the ability to create the life and career that I want far outweighs any of the cons.”

— H.F.

On the Go

Vanessa Defayette of Ticonderoga, N.Y., didn’t become a traveling nurse for the typical reasons. Many registered nurses sign up for these short-term contract jobs to explore the country and try out different cities and hospitals before deciding which ones suit them.

Defayette did it to avoid a two-and-a-half-hour commute. After she’d worked 17 years as a registered nurse in a neonatal intensive care unit in Albany, N.Y., the nursing staff there unionized, and the hospital eliminated the rooms where nurses like her slept between shifts.

So Defayette accepted her first three-month contract as a traveling nurse, or “traveler,” in the neonatal ICU at the University of Vermont Medical Center in Burlington, just 75 minutes from her home.

“I’ve been a New Englander my whole life, so it wasn’t like I was there to check out New England,” the 39-year-old Massachusetts native said.

Defayette’s six-month stint as a traveling nurse occurred in 2022, a time of considerable discontent and burnout in nursing generally. With the pandemic still raging and nurses leaving the profession in droves, hospitals relied on travelers to fill their ranks and meet their mandatory nurse-to-patient staffing ratios.

“There was a huge demand,” Defayette recalled. “So, to get a good person, the hospitals would pay more.”

Often, much more. According to Vivian health data, the average salary of traveling nurses in the U.S. still exceeds that of their counterparts on staff. Most traveling nurse agencies offer medical, dental and vision insurance for the traveling nurse and their families; 401k plans with company matches; travel and housing reimbursements; and assistance with state licensing and certification.

“When I was a traveler, you could easily make $200,000 a year,” Defayette said. Her compensation package even took into account Burlington’s high housing costs.

There were other perks to the temp job. Because she wasn’t on staff, Defayette didn’t have to serve on hospital committees, which meant she didn’t have to drive back to Burlington on her days off.

On the downside, Defayette had to “float,” or move from one unit to another depending on the staffing needs of the day. That could mean working in a unit she wasn’t thrilled about. And, in general, traveling nurses get much less orientation than permanent staff when they’re hired and must hit the ground running.

“But it’s fun. It’s exciting,” she added. “And, if you like to step outside of your comfort zone … it’s a way to challenge yourself.”

Ultimately, Defayette liked UVM Medical Center so much that she joined the staff as a permanent employee, choosing job security over the benefits of being a traveler. Why did she decide to stay put instead of checking out other cities?

“If I didn’t have four kids, I would have loved to do that,” she said. “But I paid off my husband’s student loans. I’m a very nice wife, and I remind him of that often,” she added with a laugh.

— K.P.

Bagel Whiz

In Marshfield and its environs, Anne LaBrusciano is known as “the bagel lady.” And that moniker is well earned.

For more than a decade, LaBrusciano, 59, has been making New York-style bagels in her home and selling them at local markets and co-ops.

Before the pandemic, she ran the baking biz part time and also designed apparel for Salaam Clothing in Berlin. But when COVID-19 hit, the design work dried up and people started buying her bagels “like crazy,” she said. “That’s when I was like, All right, I guess I’m doing this full time.”

As the sole proprietor of Whizzo Bagels (the name is a nod to a popular Monty Python sketch), LaBrusciano makes 55 dozen bagels a day, five days a week. Her Marshfield kitchen is certified as a home bakery and inspected annually by the Vermont Department of Health. Last year, she said, she sold $64,000 worth of bagels and netted around $49,000. She gets medical coverage through the state’s Vermont Health Connect marketplace.

LaBrusciano’s workday begins at 5 a.m. She spends about four hours baking bagels that she’s shaped the day before. As they bake, she churns dough for the next day’s order in her 30-quart Hobart mixer and bags bagels in packages of four. She delivers the goods herself two days a week and pays someone to do it the other three days. Typically, she’s done with work by noon.

“Even though you’re up early, you have a nice afternoon and evening where you’re not working,” said LaBrusciano, a self-described introvert. She spends those hours taking walks with her two dogs and gardening. Though she laments the lack of a paid vacation, she likes having the flexibility of deciding when to take time off.

Bagel making isn’t LaBrusciano’s first foray into self-employment. In the 1980s and ’90s, she designed velvet and linen vintage-inspired hats, which she sold at craft fairs in Boston and New York City to the likes of actors Glenn Close and Ally Sheedy. It was on her trips to the Big Apple that she discovered the chewy, shiny-crusted H&H Bagels — a New York institution — that inspired her to try making her own similar ones.

Making bagels is a less risky business than sewing hats because there’s a dependable customer base, LaBrusciano said.

“I know how much I’m going to make every week, and I know people are going buy them,” she said. In addition to her seven retail accounts, she occasionally makes bagels for Jewish community groups and recently provided batches to Darn Tough Vermont and Cabot Creamery employees.

Several years ago, LaBrusciano contemplated expanding her business and met with staff from the Vermont Community Loan Fund for an analysis. The process made her feel vulnerable, akin to standing naked in front of a crowd, she said. But it also made her realize that she wanted to remain small.

“Everybody’s like, ‘Grow! Grow!'” she said. “But I feel like I’d probably make the same amount of money and it would just be more stressful.”

As for her retirement plan, LaBrusciano, who is divorced and has three grown kids, said she plans to have her house paid off in five years and will rely on income from a rental apartment and Airbnb on her property.

“Some people might think it’s crazy,” LaBrusciano said, “but I feel OK about it.”

— A.N.

Mix and Match

Sitting down at a Burlington breakfast spot, Luke Jonathan took a moment to laud one of the benefits of not working for other people.

“It’s really hard to beat having the freedom to meet someone for coffee when you feel like it,” he said with a grin. “We’re not on this planet for too long, so I don’t think there’s a more valuable currency than time.”

Jonathan, 42, is a self-employed graphic designer who moonlights as DJ CRWD CTRL, a member of Burlington collective the Aquatic Underground. After a bad experience working for a large local company, he decided to bet on himself.

“I learned at a very young age that finding an occupation you can actually enjoy is pretty integral to happiness in life,” he said. “So that has always been my goal … as opposed to pushing paper for other people and wasting away as a cog in a wheel.”

Jonathan has been self-employed for five years. “The extra paperwork and tax stuff is … well, it’s terrible. There’s no sugarcoating that,” he admitted. But every year he finds it a little more manageable. “Pulling gigs together is like trying to get a plane off the tarmac; once you’re actually in the air, things get much easier.”

To bring in more work, Jonathan broadened his services from graphic design to web design and serving as what he calls a “digital architect.”

“Financially, I’m really just scraping by right now,” he said. “My rent and my bills are paid; I have a roof and food. But I’m not banking anything. There’s no savings or anything like that.”

He lacks health insurance coverage. “I’ve been exploring options,” he said, “but they are slim to none as far as affordability.”

To supplement his income — but mainly for the love of it — Jonathan still regularly DJs. He’s quick to point out that he doesn’t believe it’s possible to make a living solely as a DJ in Vermont.

“There’s just not enough gigs,” he said. “You’d really have to have a stranglehold on the city and venues to generate enough money. Plus, DJ work is pretty exhausting; you’re hauling yourself and all this gear in and out of nightclubs at 2 a.m.”

Would Jonathan ever work for a company again? “If it offered an actual, viable work-life balance and I didn’t feel exploited … yeah,” he said. “But I haven’t seen too many companies out there that fit that description.”

He wishes the older members of his family better understood his generation’s economic situation, recalling a recent argument with his uncle in which “he was telling me all this stuff, like ‘Get out of the clubs and stop drawing pictures. Get a job stocking shelves and work your way up.'”

“I had to tell him … how different things are these days compared to when he was growing up and you got a job and worked it until you retired, which is what he did,” Jonathan said. He sees the prejudice against gig work as akin to “all that ‘Stop eating avocado toast’ bullshit that boomers kept throwing at us.”

Jonathan is at peace with his decision to freelance.

“For me, it’s all about being present and living in the moment,” he said. “And that concept is what being in the gig economy is all about.”

— C.F.

Shoot Your Shot

In 2017, Arielle Thomas was fired from her job as a sales associate at Green Mountain Camera. With just $200 in her bank account, she had no idea how she would afford rent or make payments on the MacBook laptop she had recently purchased.

Fear of financial ruin lit a fire under her, she recalled. The same day she lost her job, Thomas resolved to start her own freelance photography business. With an associate’s degree from the now-defunct Ohio Institute of Photography and Technology, she was determined to put her education to work and make it as a full-time photographer.

“God kicked me in the ass and got me moving,” Thomas said. “I had all of this free time now to hustle.”

At first, she took any job available, even photographing a wedding for just $500. She scoured Craigslist for side hustles to make ends meet. But as she expanded her portfolio — shooting everything from boudoir portraits to a protest in Albany, N.Y., to merchandise at a bike shop — her business took off.

Today, the 34-year-old charges $5,200 for an eight-hour wedding shoot and engagement session. Her gross annual revenue has steadily increased over the years, from about $50,000 when she started in 2017 to almost $90,000 today. Most clients come to her through word of mouth and a Vermont wedding referral network, so she doesn’t have to hustle for bookings.

Even with that growth, Thomas finds her finances “still terrifying and scary,” she said. “It’s probably always going to be that way, because the ebbs and flows of working for yourself are so up in the air.”

Thomas uses Medicaid for health insurance, and she puts $50 into a retirement account every week. One of the tougher financial aspects of the job is its seasonality: While she’s usually booked with weddings almost every weekend of the summer, she said her income from March to May is “nonexistent.” Such fluctuations necessitate careful financial planning so she can maintain the same standard of living throughout the year.

But ultimately, Thomas said she wouldn’t trade the ability to make art for a living for the stability of a more traditional role. She has the freedom to set her own schedule and almost never feels the need to use a morning alarm. Her long-term goal is to open her own wedding venue.

“Follow your dreams. It’s going to be hard, and it’s scary, and it’s going to suck sometimes,” Thomas said. “But it’s totally worth it in the end.”

— H.F.

Let Them Eat Comics

By Kristen Shull

Kristen Shull is a comic artist residing in Burlington. You can read more of her comics on her Instagram (@ego_gala) or every other week in the comics section of Seven Days.