The Ladder

I’m Stuck in a Dead-End Job

What to do when your job offers no pay and no prospects.

If teachers tailor their résumés to the jobs they’re applying for, and quantify their classroom accomplishments, they have a good chance of landing a job in a new field.


When Charles graduated from college in 2010, the national unemployment rate was peaking near 10 percent. “I delivered pizzas and did some other random stuff, but since I couldn’t find a job, I thought, ‘Well, my opportunity cost of going back to school is basically zero,’ ” he told me. Hoping to work at a museum or a historical site, he applied for graduate programs in history, and he eventually got a full scholarship at a lower-tier master’s program. Charles worked as a teaching assistant while working toward his degree, and after he graduated, he taught in the same program as an adjunct professor. But the university discontinued the curriculum he’d been teaching, and he accepted a job teaching history and literature at a private high school in a Southern state.

Now, Charles—who asked that I use his middle name to prevent his employer from recognizing him—supports his wife and daughter on $38,000 a year, without benefits. He emailed the Ladder for help. “I see no avenue for long-term career advancement with my current employer and no major raises on the horizon,” he wrote. “I love the subjects I teach and I also love making a difference in students’ lives as much as the next altruistic Millennial … but I also don’t want to be broke my whole life!”

Charles is not alone in wishing teaching paid more. The average starting salary for teachers is even less than what Charles makes: $30,377. Teachers’ salaries vary quite a bit by state, mostly in accordance with local cost of living, but in no part of the country is K-12 education a lucrative domain. 

That doesn’t mean Charles is doomed to a life of austerity and professional stagnation. He loves teaching and wants to keep doing it for several years, at least, and there are ways he can increase his income within his profession—both by looking for public-school jobs and by picking up higher-paying gigs on the side.

Teachers at private schools, surprisingly enough, earn far less than their colleagues at public schools. The latter are more likely to belong to a union, which translates into better pay, predictable raises, and the health and retirement benefits Charles lacks. Since his bachelor’s and master’s degrees aren’t in education, Charles doesn’t currently have the teaching certificate required by public schools in his state. But all 50 states offer other ways to get certified, often without a huge investment of time and money. As an experienced teacher with a master’s degree in his primary subject area, Charles is in an excellent position to obtain an alternative teaching certificate, which could open the door to a teaching job with more growth potential.

In the meantime—frustrating though it is that teaching professionals should have to take on extra work to make ends meet—Charles can maximize his earnings by working side gigs. He already does some freelance work in curriculum development, which he finds “challenging but rewarding and stimulating.” (Also, “It pays, but not a huge amount.”) He could also try parlaying his experience as an adjunct professor into a part-time position at a local university or community college.

But teachers’ tried-and-true side hustle is tutoring. Independent tutors can set their own hours and rates (depending on local demand); those who prefer to sacrifice a little freedom for more stability net anywhere from $25 to more than $100 per hour teaching for test-prep companies. Either way, it can add up to thousands of dollars in annual income for just a few hours a week of extra work. Tom Anderson, a public school teacher in New York City, says he’s doubled his income by teaching the GRE for Manhattan Prep, one of the best-paying test-prep companies. (Manhattan Prep is a subsidiary of Kaplan Inc., which, like Slate, is owned by the Graham Holdings Co.) Granted, test prep isn’t an area teachers tend to love the way Charles loves history. “I’m very happy that I found [test-prep work], because it allows me to keep doing what I love, but also make enough money to save,” Anderson told me.

Charles loves teaching, too—but he fears that he’ll burn out if he sticks with it for too long. He’d still like to work in public history eventually, and his background teaching and developing curricula certainly involves some of the skills required to work as a museum educator. But public history is a highly competitive field—and most jobs there pay even worse than teaching.

Briann Greenfield used to run the public history master’s program at Central Connecticut State University; she’s now the executive director of the New Jersey Council for the Humanities. I asked her how Charles could improve his chances of landing a public history job. She suggested that he attend conferences of the National Council on Public History, volunteer at a local museum or historical society, and take a course or two at a public-history program if there’s one near him. She advised him against getting a second master’s degree in public history—“it’s expensive to get another degree”—or pursuing a Ph.D., which “can take you down the wrong path if you are working in an institution where you have to be a real generalist.”

The good news is that if public history doesn’t pan out, the communication, interpersonal, and problem-solving skills Charles has developed as a high school teacher will serve him well in any number of jobs. School administration, which usually requires additional certification, is an obvious next step for teachers yearning for career growth. But Charles needn’t feel confined to education.

“Employers do like teachers,” says Terry Pile, a Washington-based career coach who is herself a former schoolteacher. “Teachers are very disciplined, they’re very good time managers, they’re generally pretty bright and get along well with people.” When Pile felt ready to get out of teaching, she took on a freelance writing gig for a local nonprofit, which turned into a job in public relations and marketing. Off the top of her head, she can name former teachers who went on to work in government, aviation, sales, psychometrics, and software development. Recruiters and HR departments are looking for “communication skills and adaptability, being a good fit in their culture,” Pile says. “The soft skills are still really important to employers, because they can teach some of the hard skills.” If teachers tailor their résumés and cover letters to the jobs they’re applying for, and quantify their classroom accomplishments (such as increasing test scores or reducing absenteeism), Pile says they have a good chance of landing a job in a new field.

Of course, none of this is easy. To change careers, you need to network, volunteer, freelance, attend professional conferences, and pursue special certifications. Charles’ advantage—apart from his master’s degree and teaching experience—is that he’s not desperate to leave teaching right away, which gives him time to plan his next steps. Knowing he doesn’t want to teach forever is just one more reason to look into tutoring, test prep, or another high-paying freelance gig now. The extra money will not only make life easier today; it’ll also give Charles the flexibility he’ll need to move into public history—or another career—in the future.

Need career advice? Got a problem at work? Email