For Gen X Women, Changing Careers Is Complicated

What happens when our careers hit the wall—do we stay or should we go? These three women took steps to make a radical change in their 40s and 50s.

When Jill Auckenthaler walked into her first class of nursing school, she stared out into an auditorium of 18-, 19-, 20-year-old faces. At 40, she had decades on most of her classmates. She had worked as a painter up until then, and had already experienced job changes, cross-country moves, getting married, and other transitional moments that come with age.

Auckenthaler had earned a master’s degree, she’d taught, she had a studio space of her own, and had worked her way up into a position as an administration manager of an art non-profit. But with a newborn son at home, she had reached a point where it all wasn’t enough.

“As an artist, you’re doing everything,” says Auckenthaler, now 47. “You’re promoting, you’re networking, you’re working at a gallery, you’re making the art. I usually had five or six jobs. But even doing all this, I couldn’t make enough money to support myself or my family.” During her unpaid maternity leave, she realized her job wouldn’t allow her the flexibility she needed to parent. She quit the nonprofit, which meant leaving a lifetime of career-building behind to restart in a new field.

Women 55 and over are the fastest-growing segment of the U.S. workforce, according to Bureau of Labor Statistics projections. Yet career complacency and immobility can be the norm for middle-aged women. Job security—whether it’s the pay, a set schedule, work-from-home flexibility—becomes increasingly valuable as the reasons why women’s work shifts as they get older. Familial responsibilities, such as rearing children and caring for aging parents, traditionally fall on women more than men, meaning career prioritization comes second at best. If women who leave work to focus on family attempt to rejoin the workforce, a 2018 study from the Harvard Business Review found that stay-at-home parents are half as likely to land an interview as unemployed parents and only one-third as likely as employed parents.

Employer respondents in the study saw stay-at-home moms and dads as “less reliable, less deserving of a job, and, the biggest penalty, less committed to work, compared with unemployed applicants.” This “mommy gap bias” stems from the expectation that parents who prioritize their families do not meet ubiquitous ideal worker norms, most of which require absolute commitment to a job and are arguably impossible to attain for women responsible for caregiving. While new-to-the-workforce 20-somethings might frequently job-hop (employers expect, and often applaud it), it’s assumed middle-aged workers know what they want and should stay longer, remaining career stagnant. This can lead to unhappy employees sticking it out until retirement. For women, it exacerbates the emotional labor they shoulder and reinforces age discrimination and the fear that older women aren’t as “hireable” as men of the same age. Above all, it only increases the wage gap, which is at its widest for women in their 50s.

A midlife career change is therefore risky for an age-gender group defined as caregivers, breadwinners, and matriarchs. Those in their 40s, 50s, and 60s have potentially more to lose if their decision to change careers doesn’t pan out. Funda Duval, an actress turned software engineer, said while the end of her marriage at 45 made her feel like she was “being dangled over a pit of alligators,” it was 100 percent of the reason why she changed careers. While married, Duval freelanced in the art world, and like Auckenthaler, moved from job to job, acting gig to acting gig as opportunities arose. When she divorced, the safety net of her ex’s financial stability disappeared. Being a stay-at-home mom and taking roles and odd jobs as they came wasn’t a viable way of life anymore. Yet as someone who hadn’t previously held a desk job and therefore felt unskilled for the traditional 9-5, surrendering to “the man” was unnerving.

“As a middle-aged woman, I feel invisible,” Duval, now 52, says. “But what can I do with the feelings of sadness? I can apply them. I can learn something new that will benefit my standing in the world. I can scale up, and become someone who I like.”

Duval began with asking herself what were the “good,” flexible, well-paying jobs, and quickly got over mourning her former life out of necessity. Duval had previously picked up work—translating, recording and producing audiobooks, sound engineering—that often left her tinkering on the computer. While learning different proprietary software, Duval found joy in the code’s puzzles and language. She taught herself to code over the course of a year, followed by a six-month boot camp. Not long after, Duval landed a job as a full-time, mid-level software engineer. She’s never looked back. “I started to not care about acting because I had to survive, but also because I really fell in love with coding.”

Even when they work out for the best, drastic career pivots are packed with emotion. “It was definitely a hard decision that involved a lot of sadness and anger and frustration and loss,” Auckenthaler says of her career change. It’s not a choice that happens in a vacuum. Middle-aged women are reckoning with an endless stream of responsibilities and commitments that factor into their decision-making: marriage, school tuitions, mortgages or rent, playdates, scraped knees, groceries, friendships, aging parent is ill, holiday travel, car repair, self-care. If work financially powers all of life’s obligations and resources, prioritizing a job change, let alone restart in a new field, is anything but simple.

“It’s almost impossible to juggle career and family,” Duval says. “It’s like designed to make sure that we have trouble with it.” Despite outpacing men in college enrollment and degrees, women make 79 cents for every man’s dollar. For women of color, the pay gap actually widens if you’ve earned a bachelor’s or advanced degrees. But it’s also the non-work obligations that stretch the wage gap: 54 percent of women take leave from work when becoming a parent as opposed to 42 percent of men. Without a national paid leave policy, this usually means that women are taking home less or no money during their time off. Additionally, women are eight times more likely than men to look after sick children or manage their children’s schedules, which will take time out of their work day or other daily responsibilities, and are more likely to leave a job entirely to care for elderly family members. When a woman reaches retirement age, she may have earned a cumulative $1,055,000 less than her male counterparts when accounting for the lifelong pay gap and common workforce interruptions.

Middle-aged women more than anyone are aware of the need to balance these obligations, Duval explains. “In our 20s and 30s, we have the illusion that we have unlimited freedom, unlimited wealth, unlimited power, and unlimited personal satisfaction,” Duval says. “But the unsexy reality is that those illusions hold people back from making practical decisions. If you can’t make the X amount of dollars you need to feed your kids, anything else you’re doing is stressful. The wolf is going to come to the door, and no one is going to save you.”

Statistically, if women like Duval and Auckenthaler attempt to make a career change to better their family’s standing financially, they’re still behind men. And the opportunity to make a career leap significant enough is a privilege many people simply can’t afford. For people who rely on public benefits such as Medicaid and the Supplemental Nutrition Assistance Program (SNAP), taking a slightly higher paying job could result in losing critical resources they bring home through these programs in what’s described as the “cliff effect.” Exorbitant housing prices in cities keep qualified people from moving for work, and a full-time worker earning the federal minimum wage cannot rent an affordable two-bedroom apartment anywhere in the country without paying more than 30 percent of their income, according to the National Low Income Housing Coalition’s annual Out of Reach report. Forty percent of Americans would struggle to come up with just $400 in an emergency, and 69 percent have less than $1,000 in savings. We work to make money, and enough of it to live as comfortably and securely as possible. How Americans can achieve that security, in addition to the familial responsibilities, weighs heavily on women.

It’s also what leads many middle-aged women to feel stuck in “golden handcuffs.” The security of a salary or solid health care benefits their family so much so that they end up staying in a job they hate to their own detriment. Jana Welch, a former COO at a boutique advertising agency, explains that after spending just over 25 successful, established years in the field, she started to question why the work wasn’t fulfilling anymore. “I was seeing young people come in with lights in their eyes and such promise, but three to four months in, the lights were going out,” Welch says. “I started asking myself, ‘Am I making the lights go out of their eyes? What’s the problem here?’”

At 55, Welch left her executive-level advertising job to start her own real-estate business, blending her skill of matching people to solutions and “DIY, fixer-upper” taste into a new career. “It felt like a natural transition for me. I have been through the process of buying a home and it was not very pleasant. I remember thinking when we went through that, that if the broker we worked with had actually listened, kept us informed, managed our expectations, and attempted to demystify the process, I would have felt more empowered and certain about the decisions made,” says Welch. “That’s when I realized the things I needed from the broker were actually things I enjoyed doing and did very well in my advertising roles.” Welch says that so much of her reputation was built on her communication and organizational skills, and, just as importantly, being attentive, caring, and responsible. “Having a career that allows me the opportunity to help someone find a place to call home, a home that could potentially stay in a family for generations, brings me joy. It felt like the right move for someone who is essentially trying to make this world a happier place to live.”

And it proved to be the right choice for Welch. Now, she says, “I’m COO, CEO, CFO: I’m everything.” But, she says, the risks and unknowns of being in control of her profession are scary. All three women credit their well-established support networks for helping them navigate the daunting transitions. “It was a little like jumping out of a plane with a parachute, but not knowing where you’re going to land,” Welch explains. “I was hoping it would be in a soft, beautiful, peaceful pastoral scene, but you never know. I don’t think I could have pulled it off when I was younger because I didn’t have the community I needed to rely on.”

After graduating from nursing school, Auckenthaler’s first job was on a medical surgery floor where she struggled to keep pace, struggled to connect with her co-workers and patients, struggled to be passionate about her work. “After eight weeks, I was fired from that job,” she says. “I was like, holy fuck, what now!? I wasn’t someone to get fired from a job. I was devastated. My self-esteem just plummeted.” Luckily, she says, a friend of a friend already was helping her make other job connections, and not long after, Auckenthaler started as a palliative care nurse, a field that better suits her personality and skills. “I’m really drawn to this type of care and think it’s an honor and privilege to be in the space where people are taking care of sick loved ones. I love the personal interactions that are meaningful and profound, but I also really love the clinical part of it.”

Auckenthaler, Duval, and Welch have all found success and happiness in their new careers, and attribute it to planning and practicality, supportive networks, as well as the privilege and opportunity to do so. Yet, the financial motivations behind their midlife changes remain in focus; the job, in many ways, is still a job. “I gained 30 pounds since I started coding,” Duval says. “I thought I was going to be a sexy Mr. Robot–type, but it turns out that’s not real life.” Even in sought-after tech jobs, “You can’t fooseball away the fact that you’re squinting at a screen nine hours a day. I didn’t come out unscathed,” she says.

Auckenthaler says she certainly misses being an artist, and “the dreamer side” of her doesn’t get as much time as it used to. Still, she’s more financially stable and professionally rewarded than before, and that has made the trade-off worthwhile. “I would encourage people to make the change to get unstuck,” she says. “If I hadn’t been pushed to do it, I might have stayed in my low-paying art job, taken the path of least resistance, and let it confirm who I was.”

“It’s easy to get in a rhythm and routine for the job: getting your coffee in the morning, going to meetings, and someone else setting your movement forward each day,” Welch echoes, who says she misses parts of her former office-based life. “But the golden handcuffs are real. The security of a paycheck every two weeks, insurance, time off—all of it comes with security. We all want that, and it’s what we work for. It is a step of boldest to decide you want and love those things, but you are still going to try something different.”

Women tend to be defined by their obligations; how well they fulfill their duties to their children, aging parents, partners, and careers throughout their lives. But they feel more and more invisible as they age. Failing to see women over 40—which means we’re not hiring them, promoting them, not giving them raises or flexibility at work—is to our economic and social disadvantage. Institutional change is necessary to break down societal barriers to women having the opportunity to “do it all” without sacrificing their own wellness and happiness. And every woman has different incentives to change or not change careers, says Welch. “But life is short, I don’t think anyone should spend it feeling that they aren’t fulfilled, appreciated, respected, or working out of fear. If your heart is pulling you elsewhere, why wait?”