Pivot! 5 Tips for a Midlife Career Change

green and purple posterized image of ross geller yelling pivot on friends

image: Warner Bros
Story by Jen Cooper

For many, midlife is a time to re-evaluate everything from whom we spend our time with, to what we want to do with our lives. This semi-existential crisis isn’t uncommon. Even apes get bummed out in middle age. But for those of us currently in midlife, the natural decline in satisfaction we feel has been supercharged by a global pandemic. I know over the past two years I’ve questioned things both large and small: Can I pull off a middle part? Could I logistically move to another city? Will I ever write that book I said I would? Am I past the point of relevancy? What am I doing with my life? 

All of this is compounded by this specific point in our lives where we’re situated between the difficulty of childrearing and taking care of our parents. And then there are the college loans we’re paying off while we apply for new ones for our kids. Our life crises feel like whack-a-mole at this point. So it’s no wonder we’ve been collectively forced to reevaluate entire systems, especially our careers. 

In fact, half of us are thinking about switching jobs. And then there are many who are thinking of changing their whole career altogether. So I spoke with women who all successfully pivoted during a crisis—economic, political, and personal—to see what tips they had to offer to help those who are navigating a transition. 

Tip One: Remember that you’re resilient 

While we might have grown up thinking aging is the worst, it definitely has its benefits. One of its best aspects is that it comes with experience—personal experience you can draw from. Remember, this isn’t the first crisis you’ve lived through. You made it through 2008

There we were, left unemployed with a baby, in a place where there wasn’t a ton of industry for us. We were screwed.

STEPHANIE

Professional actor Stephanie Stearns Dulli liked her life in Los Angeles. Sure, the life of an actor is filled with rejection and competition, but Stephanie was lucky. It was the mid-aughts and she was going to auditions every day, regularly booking commercials, getting roles in plays, and producing a few plays of her own. She even met her husband, a fellow actor, on stage. As Stephanie says about that time, “It was wonderful.”

Then 2008 rolled around and Stephanie learned she was pregnant. Her husband felt he needed a more stable job to meet the needs of a young family. He found one in Akron, Ohio, managing a theater company. So Stephanie and her husband packed up their things, including their three-month-old baby, and that October uprooted their lives from Los Angeles to transplant themselves in the Midwest. 

A month later, the credit crisis hit. The fallout engulfed the country, including a theater company in Akron, Ohio, who’d recently hired a new director. 

“There we were, left unemployed with a baby, in a place where there wasn’t a ton of industry for us. We were screwed,” Stephanie explains. “I had no job, no identity, I had nothing. Even my cat died during the move.” 

She needed a new career plan and she needed it fast. 

That’s when Stephanie did something life coach Tami Hackbarth says to do when you want to change careers: she built her network. “You’re not going to find the job you want on Craigslist or Monster,” says Hackbarth. “You find them through networking.” 


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image: Christina Best Photography


Widening your circle, like Stephanie did, is one of the keys to finding a job, says Hackbarth. “It’s not the people in your immediate circle who will help you land a job. It’s the people on the outside ring. The ones you might see at a barbecue.” 

Stephanie and her husband moved in with his family in Washington, DC. There, Stephanie looked for jobs but couldn’t find any that paid enough to cover the childcare she’d need.

To battle her feelings of isolation and depression, Stephanie looked for connection. So she joined an internet board and started to talk to other women online. One of them had a blog and encouraged Stephanie to start one of her own. She drew on her experience doing stand-up comedy and her acting background to create something entertaining that other moms could connect with. But it was a friend from high school who gave Stephanie her big break. 

The friend ran a collective of writers and bloggers called Silicon Valley Moms that was starting a DC chapter. Stephanie wrote about her postpartum anxiety, and her name recognition started growing within the online community. Her writing got published in anthologies, and her circle kept expanding, eventually landing her a role as a director for Listen to Your Mother. Today Stephanie has written her first book and she’s writing a play. 

I struggled for a long time, but by losing everything, I learned so much about myself. I have talents and capabilities that I didn’t even know I had.

It’s a whole new career and one she feels grateful to have. “I struggled for a long time, but by losing everything, I learned so much about myself. I have talents and capabilities that I didn’t even know I had.”

While it was the 2008 financial crisis that set Stephanie off on a new career path, there are many reasons for a person to pivot in any given year: divorce, layoffs, general burnout, or a desire to take on new challenges.  

Lately, there’s been a lot of talk about the “Great Resignation,” and while the actual data doesn’t match up with the sensational headlines, the pandemic, much like the Great Recession, has helped people put things in perspective. It has pulled into focus the desire to find a balance between work and life—not just to survive, but to thrive. 

Tip Two: Determine the impact you want to have

One of the first questions Tami Hackbarth asks her clients is, “What impact do you want to have in the world?” Understanding what you want out of a career shift is key, she says. But it’s not just what you want out of the career, it’s also what you want to be doing in it. 

My physical therapist said my body had developed scar tissue from the stress I put on it at work.

CLAUDIA

That’s true for Claudia Towles. After more than 20 years as a small, independent shop owner who was on her feet all day, Claudia started experiencing pain. “My physical therapist said my body had developed scar tissue from the stress I put on it at work.” Claudia knew she needed another way to bring in an income, so five years ago she got her real estate license. She used her connections from her community to build a thriving career, but it wasn’t easy. There were some pretty big challenges. 

“I see crisis as an opportunity,” says Claudia. And it was a series of crises that got her involved in her next pivot: politics. Rising concerns in her neighborhood that weren’t being addressed by career politicians inspired Claudia, who had always been a community advocate, to do more for her community. So in 2024, she’s running for city council. 

In the U.S., women currently make up a far smaller percentage of representatives across local and national government. In fact, in Claudia’s city of Baltimore, women made up only 30% of the 2020 primary. That’s up from 18% from four years ago. 

That means she has a tough road ahead, but she’s not giving up. “You have to have resilience,” Claudia says. And that is something Claudia has proven to herself she has. 

The underlying theme in my life is to serve. It’s in everything I’ve ever done, so I’m doing the work to serve my community in a way that’s impactful.

The election isn’t for two more years, but Claudia is using this time to listen and learn about the important issues her neighbors are facing. One thing Claudia wants to make clear about her decision to enter politics is that, “It wasn’t on a whim. It has taken, and will continue to take, a lot of work.” As a Latina, Claudia used to having to create space for her voice. “I’m a first-generation American. I speak a different language. I’m not just a woman of color, I’m also a small business owner. The underlying theme in my life is to serve. It’s in everything I’ve ever done, so I’m doing the work to serve my community in a way that’s impactful.” 

Tip Three: Dare to dream

After determining the impact you want to make, the next question on Hackbarth’s list is, “If you could be doing anything, what would it be?” 

At 44 years old, I could have gone back to school, but I didn’t want to.

JENNIFER

For Jennifer Poe, the answer to “If you could be doing anything, what would it be?” surprised her. An American by birth and by culture, Poe had moved to France to raise her kids with her French husband. They wanted the kids to learn the French language and culture, something they couldn’t do living in Saratoga Springs, New York. “The initial plan was to do one to two years in a French-speaking country. My husband ended up getting a teaching job at a business school in Bordeaux, France.” So Jennifer and her family moved. 

While there aren’t official records for how many Americans emigrate from the U.S., the Association of American Residents Overseas estimates the number has doubled in the past 20 years to about 9 million. And while some do move for job opportunities, Americans are more likely than people from other countries to say they moved for a relationship

But what happens when you move to your partner’s home country, leaving your job and all your networks behind, and then find yourself getting divorced? That was the challenge Jennifer faced. U.S. studies estimate a woman’s household income in a heterosexual marriage can drop by 41% after divorce, twice the loss of income experienced by men. 

Back in New York, Jennifer was a school counselor with 17 years of experience. But her Master’s Degree wasn’t recognized in her new country, meaning that if she wanted to teach, Jennifer would have to get a French Diploma. “At 44 years old, I could have gone back to school, but I didn’t want to.” 

The year-long separation process bought her a little time to figure out what to do. Most Americans who move to other countries teach English. Jennifer investigated that, but it didn’t feel right. 

While she was searching for work, she networked with other English-speaking immigrants. She also started a blog that further widened her circle. Writing gave her an opportunity to share the history and culture of her new home, which she researched meticulously. 


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And then, as Jennifer says, “I got lucky.” Thanks to being in the right place at the right time, and the groundwork she laid by building her network, Jennifer saw an ad in her community newsletter. It was an employment ad placed by Viking Cruises. They were looking for native English speakers to train as tour guides. 

Jennifer experienced what many people consider a dream come true for many people: She became a tour guide in Bordeaux. She had to start at the beginning, but she took the long view. Because she was open to a new possibility, a job she’d never even considered has become a thriving career for Jennifer. She’s now the owner of My Bordeaux Tours, teaching clients about the wine, history, architecture, and culture of her region. 

Now instead of worrying about what she’s going to do next, she spends her days touring chateaus, villages, and vineyards while sharing her love for her adopted country’s culture. It’s a scene out of Under the Tuscan Sun, if it were set in Bordeaux, and maybe called something like Under the Bordeaux Skies. Either way, it’s a good lifestyle. 

Tip Four: Decide if it’s worth the risk

Before you decide to pack up and move to a new country, you should know you’ll probably have to make some sacrifices. And they can be pretty big ones. “By not going back to the States and working three more years to meet full investment, I cut my retirement savings by a very large amount,” explains Jennifer. “My retirement is going to be piecemeal.”

And that is a very real concern for many at midlife. Is the risk worth it? Can you afford to take it? 

“You have to know there’s inherent risk in changing careers,” says Claudia, the shop owner turned realtor and politician. “It’s not magically going to be okay. You have to work through the hard times and be willing to be uncomfortable. I think that part gets harder as you get older because you know what comfort feels like.” 

Don’t stop dreaming. It doesn’t matter if you’re 15, or 50, or 75, there are more opportunities that await us.

Tip Five: Remember, you can do this!   

You may be scared. You may have a negative voice in your head telling you that your time for something new has passed. But it’s not true. 

As Stephanie, the actress turned writer, explains, “When we were young, we were taught that we could be anything or do anything, but we weren’t necessarily taught the skills for it. And the world changed on us. It’s okay for your dreams to change and it’s okay for them to change before you accomplish the thing that preceded it. It is not a failure. Don’t stop dreaming. It doesn’t matter if you’re 15, or 50, or 75, there are more opportunities that await us.” 

Here in midlife, we’ve proven our resilience to ourselves—or at least, we should have by now. We have wisdom, we have experience, and we have people we can lean on: old colleagues, friends, family, even job coaches. And while these years might be at the bottom of the happiness curve, we can make the changes needed so the years ahead are our very best yet. 

Have you made a pivot or want to make one? Let us know in the comments below. We’d love to hear about your success, advice, or challenges.