Double Shift: 6 Stories of Teachers With Side Hustles

Bartender. Nanny. Waitress. Retail worker. Painter. Housekeeper. Graphic designer. One of the realities of classroom teachers in the United States is that many do not make enough money to rely solely on their salary. So they seek out second jobs and side hustles, sometimes juggling several at once, to supplement their income.

Over the last several months, EdSurge has interviewed dozens of K-12 teachers who work at least one other job outside of the classroom. In March, we published an in-depth story that examined how and why such a dynamic exists in the field—and detailed what it’s like for teachers who are seemingly always on the clock.

Below are profiles of six such teachers, each of whom has at least one additional job during the school year. They hold those jobs for different reasons—to pay off student debt, to afford an apartment without roommates, to set themselves up to leave teaching for good, to online shop guilt-free, to afford the occasional take-out order—and with varying degrees of necessity. But whether they live in Illinois, New Hampshire, Missouri or elsewhere, they each concede that despite their education and certifications, their teacher salary alone is not enough to afford them the lifestyle they had hoped to one day attain.

Stacey Robinson

In her 22 years as a teacher, Stacey Robinson has almost always worked at least one other job outside the classroom. Most of the time, including now, she has juggled multiple extra jobs, scraping together enough money to pay the bills, feed her voracious teenagers, pay for their extracurriculars and save enough to give them a nice Christmas.

It’s a wonder one person is able to keep track of it all, let alone actually do the work. On top of teaching third and fourth graders full time, Robinson also works 10 hours per week as a school custodian, which brings in about $600 extra per month. She earns $25 for every school sporting event she manages, too, taking money at the door and operating the concession stand during three or four ball games a week. She cares for elderly patients, including her father, at an independent living company that pays her about $650 per month. She also paints houses for around $20 an hour.

She’s also cleaned houses for other families over the years, including her now-retired superintendent. Robinson cleaned his house every two weeks for $50 because, as she recalls it, he probably thought she could use the money. He wasn’t wrong. “I didn’t know the meaning of a savings account,” she says.

She started her career making $32,000. After more than two decades, she only recently broke $40,000 in her teacher salary.

“It doesn’t go far at all. At all,” she says. “If it did, I wouldn’t work myself silly the way I do.”

Yet Robinson still loves the job and finds joy in it, despite having to hustle to make ends meet.

“I amaze myself,” she says, sounding truly amazed. “I don’t know how I do it.”

Most of the other teachers in her school have outside jobs as well. One is a travel agent on the side. Another sells cosmetics. Another tutors. Others sell clothes for a boutique. But it’s not really something people fuss about. “Everybody has just understood. We all know we’re going to have to do more [than teach]. We don’t make a whole lot.”

Megan Hines

Megan Hines and her husband Brett are both high school teachers in Delaware, in a district just over the state line from the town where they live in Maryland. They also co-own and operate Buzz Meadery, a business they started in 2020 that produces, serves and sells mead, or honey wine.

The meadery takes up much of their free time on evenings and weekends these days, as they try to build it up to be a community staple and a profitable business. But even before they had that, both Hines and her husband were working second jobs and side hustles on top of teaching. Over the years, Hines has worked as a babysitter, housesitter, bartender and more. For a few years, she ran a baby sleep consulting business where she worked with clients who had infants and brought in as much as $2,500 a month before eventually selling the company. She cared about the topic—at the time, she had an infant of her own—but says, “I definitely wouldn’t have started it if I didn’t need the money. It was a lot of extra work that I would have preferred not to do.” Her husband has held a number of outside positions, too, including as an employee at a tractor supply store.

The meadery, though, is different, Hines says. It’s not just something they drummed up to earn extra money. It’s an outlet for them, a place where they can direct their passions for environmental sustainability, community and science.

“The only reason we have a good outlook on life is because we have this balance. If we were just teaching, we would probably be a lot more frustrated,” Hines explains. “We’re making a product that tastes good. People enjoy drinking it. We enjoy serving it.”

Most people who come to the meadery know that Hines and her husband are teachers. They include it in their story about starting the business and mention it on social media. “In our community, almost every teacher has another job. I don’t think people question it,” Hines says.

She doesn’t think her teaching salary is particularly bad—in fact, relative to how teachers in other states are paid, it’s quite good, she notes. But for someone with a master’s degree plus 60 credits, on her way to earning a doctorate, her earning potential elsewhere could be a lot higher.

That may not matter for much longer, though. Hines has already informed her district that she is leaving her position at the end of the school year to focus full-time on the mead business. Later this month, she and her husband are opening a juice bar, too. They want to move into a bigger space that can accommodate more customers, stay open more days of the week (it’s currently open Friday to Sunday) and bring in more sales.

Teaching, in a lot of ways, was perhaps getting in the way of that growth.

Reaghan Murphy

It was a stranger walking his dog who happened across Reaghan Murphy, unconscious in her car, following a severe panic attack that left her hospitalized more than a year ago.

That she arrived at this point was not altogether surprising to Murphy, or to any of the people who know her best. Her workload—and the mental, psychological and financial burden they carried—had become untenable.

Murphy teaches life skills to 35 students with a wide range of developmental and intellectual disabilities. Each student has an IEP and needs individualized academic, physical and emotional support. She may be teaching one of them to recognize the number 2, another to multiply and a third how to recognize shapes—all in the same day. It is not easy work.

And when she leaves that job, which pays her $45,000, she heads to another. She bartends near Wrigley Field, where the Chicago Cubs play, when baseball season is in full swing—so, around this time of year—on weekends and occasionally weeknights. And twice a week, she nannies for a family with three elementary-aged kids, shuttling them to extracurriculars and helping them with homework “just so I can pay a freaking water bill.”

She actually likes both of her outside jobs—the bartending is mindless, social and fun, and she loves the children she nannies. But she resents the fact that she has to do both, on top of her teaching job, to pay the bills. And they wear her down. As a bartender, she has to work late nights. If those nights are followed by early mornings for school, she’s typically running on only a few hours of sleep.

“I have no savings. I live paycheck to paycheck,” she said in an interview earlier this year. “I’m getting paid next Friday, and right now I have $60 in my bank account, after gas, groceries, student loans, rent. There are times I go in the negative. … I’m not a Starbucks person. I bring my lunch to work. I probably haven’t shopped for new clothes since I became a teacher. I don’t have money for that.”

She also really loves her classroom teaching position, but not at her current salary, which forces her to take on other jobs just to afford to stay in the classroom. It is so far from sustainable that she can’t imagine keeping at it for much longer.

“I love what I do, but why do I deserve to stress out this much every single day, every single week, wondering how to pay for things?” she asks. “I don’t think I should be paid lavishly. That’s not what I’m asking for. I just want to be able to cover the bills.”

Brad Dal Bon

Brad Dal Bon doesn't like to sit still. The high school physical education teacher can get a bit restless if he’s just watching television or finds himself with too much free time on his hands. So he works.

Outside of teaching, he’s had a graphic design business for more than 20 years. And last year, feeling like he had still more time to spare—particularly as he and his wife became empty nesters—he went to a job fair angling to become a mailman. Instead, he wound up taking a job at a brewery. “I pour beer,” he says of his job function.

Dal Bon typically works one weeknight, one weekend night, and then picks up shifts whenever one of his coworkers needs someone to cover for them. On weeknights, he might get out of school at 3:30 p.m. and start at the brewery by 4:30 p.m., getting home between 9:30 and 10:15 p.m. “I’m tired but not exhausted. I go in and am fired up to work at the brewery. It’s fun talking to people,” he says.

Money used to be tighter for Dal Bon and his family, he says—back when his kids’ expenses were high, on top of groceries, the mortgage and all the other bills that adulthood brings.

Now, though, on top of his nearly six-figure teacher salary and two side hustles, plus the two jobs his wife works, he sees the extra income as going toward a “slush fund,” allowing him to cover repairs and make discretionary purchases guilt-free. It could be fixing up the car, or buying concert tickets, or “jumping on Amazon to buy little things” that 10 years ago he wouldn’t have done.

The brewery serves a lot of locals, and Dal Bon has seen many familiar faces come through since starting the job there—former students, colleagues, parents of his current students. He says he probably runs into a former student—now of legal drinking age—almost every shift. And when coworkers see him behind the bar, that’s usually how they learn about his second job.

Dal Bon doesn’t mind it one bit. He has no shame around his extra jobs.

“It’s just how it is,” he says. “I wouldn’t care if I’m working at McDonald’s, where I’d probably be working with my students. It’s all the same to me.”

Lindsey Spencer

Lindsey Spencer lives closer to Canada than she does to Boston, in a small, rural part of northern New Hampshire where her teacher salary is enough to get by, but only just.

Spencer makes $45,000 as a special education teacher at an elementary school. She can cover her rent, utilities and groceries with that. She also puts it toward her cell phone bill, credit card debt and student loan payments. But those are just the things she does to survive. To live? Well, her teacher salary doesn’t quite cover discretionary expenses. Her budget is too tight.

So Spencer waitresses. She picks up shifts on weekends, ramping up during her town’s busy seasons (it is very tourist-driven, she says) and scaling back when business is slow. She can walk away from a four- or five-hour shift on a good night with $300.

“It’s quick money, it’s easy. You show up, you put in effort, and when you go home, it’s done, and you’re walking out with cash in your hands,” Spencer says.

That’s quite unlike her experience with teaching, especially in the last couple of years. “We have more and more to do with less and less time and resources. … It’s not as enjoyable as it used to be.”

With her extra income from waiting tables at a local brewery, Spencer likes to indulge in the occasional bar trivia night with friends—an experience that typically costs her around $40. Another splurge is takeout sushi. Her favorite roll costs $15, she admits sheepishly, and she often orders two of them so she can have lunch the next day. “I have to really budget to go out and get sushi. It costs a lot.”

She wishes she made enough money to take an annual vacation without too much sweat. She’s gone on one trip in the last two years, and it was to New York City for her first-ever Broadway show, “Ain’t Too Proud.” She picked up extra shifts during the two months leading up to the trip, and a friend even covered the tickets to the show. But Spencer was responsible for the hotel stay and her bus fare.

“The only way I could afford to do that was because of the waitressing,” she says. “But I was still in a state of panic over it. The hotel was, like, $500 for the two nights—an exorbitant amount of money. Having that taken out of my account at one time—I was anxious. I had the money, I had some backup cash, but I was in a state of panic the whole time. If my job paid me even $10,000 to $15,000 more, I don’t think I would have been as panicked as I was.”

Spencer says that, after that experience, she probably won’t be taking any trips for a while.

Nicole Gray

Nicole Gray gave herself a few years to get adjusted as a special education teacher before she sought out a second job. She felt she owed it to her students to get the hang of things, to learn to manage a classroom, before she filled up more of her days with other responsibilities, even if she and her husband were barely “squeaking by” in those early days.

But since 2015, Gray has been juggling multiple jobs at once. She does seasonal work at Kohl’s, a department store retail chain, from August to January. Until recently, she also worked at a winery on weekends, though she admits, “I don’t know anything about wine.”

Between those two positions, she would regularly work 24 hours on weekends, picking up a morning shift at Kohl’s and an evening shift at the winery. And sometimes, on her way home from school during the week, a child care program near her house will text her and ask her to come in for a couple of hours, so she also earns money there, though it’s inconsistent.

“All of the extra jobs are because I wanted to do this job,” Gray says of teaching. “My four-year bachelor degree wasn’t free. My student loans are $1,200 a month. It’s like having a beach house we don’t get to go visit.”

The winery was the most reliable supplemental income Gray had, since the child care program only calls when they need her and the job at Kohl’s is seasonal. But that closed permanently in April.

“So I’m like, ‘Great, where do I want to go next? Target? Food Lion?’” she asks sardonically.

Gray is tired. She is tired of hustling on the side to subsidize her teacher salary. She’s tired of the mistreatment from parents, administrators and—increasingly—students.

“I struggle with a lot of animosity,” she says, noting that teachers these days are viewed as “whiners and complainers” by much of the public. “I have been punched. I have been stabbed with a pencil. I have been put in a headlock. I have been called a b—h more times than I care to think about. They have no idea what we face when we go in to school every day.”