When Kim Foster was 17, she decided she was going to become a doctor.
It was a feat that no one in her family had accomplished. “I just strapped in and did what I needed to do to execute on that big goal,” she says. Foster worked toward getting into medical school, graduating, and all the subsequent training. Then she practiced medicine for 20 years. “It was great for a while,” she says, “until it wasn’t anymore.”
During the last few years as a family doctor, Foster noticed a pattern. She was often seeing patients when they were already experiencing problems—diabetes, chronic pain, heart disease. By the time they got in front of her, she says, “things were starting to fall apart.”
She began to feel a pull toward helping people make different decisions, and also yearned to do something creative. Eventually, she decided to walk away from her medical career. Now the 54-year-old helps those who are looking to make pivots or reinvent themselves in their lives through her YouTube channel and online courses.
Outgrowing your established career later in life
Like Foster, Alexandra Aileru knows what it’s like to outgrow one’s career. The 35-year-old had worked in the education sector for eight years. She’d already been thinking about leaving her field for a while. Then she became pregnant and realized she needed to make an exit.
Aileru transitioned into project management before realizing a few years in that she’d hit what she calls the peak of what she wanted to achieve in that role. At the end of 2023, she started posting on TikTok about her career pivot experience. She got a lot of questions from her audience and recognized that there was a market to help people with similar transformations. In 2024, she went all in on her business, Confident Career Switch. The company’s motto, she says, is to help people “get unstuck with their careers.”
Aileru and Foster might have made pivots during different stages of their lives, but both transitioned when they were more established and had responsibilities. Like Aileru, Foster had children to take care of. She was the main breadwinner in her family, so transitioning away from medicine required building what she calls an off-ramp.
For Foster, that meant operating in a half-in, half-out capacity. She reduced her hours as a doctor while building her income from various side projects. When she finally left medicine for good, she’d already made more money from her other projects than she had as a practicing physician.
Wrestling with an identity change and being a beginner
Practical considerations weren’t the only barriers Foster faced when it came to leaving medicine. She also had to wrestle with a change in identity—something that Aileru says is common among those who want to pivot their careers when they’re already established.
As a doctor, “I was very comfortable with being competent,” Foster says. “People came to me all day long, specifically to ask for my expertise. That was a big part of how I saw myself in the world, and I got a lot of satisfaction out of that.”
Starting an online business required Foster to be a beginner in something that doesn’t have the same prestige. A lot of those things, like making YouTube videos, “also needed to happen in public,” she says.
Then there was the marketing and drumming up business, something Foster never had to worry about in her career as a physician. Practicing medicine comes with set pathways, an ecosystem, and mentors, she says. The same doesn’t exist in entrepreneurship, where she had to figure out her own next steps, as well as search for people who could help her with various aspects of her business.
Foster also had to contend with the opinions of other people in her life, many of whom didn’t understand her decision. They wanted to know why she would throw away something she’d spent so long building.
Two things that helped Foster were working with a coach and enrolling in a coaching training program with others who were also building online businesses. Being exposed to different possibilities, Foster says, helped her realize that we don’t need to get locked into “one way of viewing ourselves.”
Leveraging your previous experience for the next role
As Foster transitioned into her new venture, she realized just how beneficial her previous experience was. As a primary care physician, she spoke to people every single day, and could also see the value of incorporating her medical experience in her coaching practice. Eventually, that led to a mindset shift where she says she began to see medicine as a “foundation, but not a cage.”
This mindset is something that Aileru sees many people struggle with when they switch careers, particularly those who are established. Because their background isn’t considered linear or traditional in their new careers, they see it as a hindrance, when Aileru says it can be a superpower. After all, she says, “You have a new lens and insights that other people don’t have.”
At Confident Career Switch, Aileru guides people through a multistage framework to help them get clarity about the transition. She begins by encouraging clients to dig deep into their identity before they start thinking about their skill sets and strengths.
Next, she urges them to consider their value. For this step, she instructs people to think broadly beyond what they’ve done in the office.
“This could be within an organization, a side hustle that you have, things you’ve done for friends and family,” she says. What you want to identify, she says, “is a repeated skill that keeps showing up.” Maybe you’re naturally great at organizing things, she says, which places you well to work in events. Or maybe you’re great at dealing with difficult stakeholders, which makes you a natural fit for leadership roles, she continues.
The importance of experimentation
Both Aileru and Foster acknowledge that changing careers at an established stage in your life comes with a set of considerations that may not apply to those who are earlier in their careers. That’s why Foster encourages a period of experimentation prior to making any major transition.
Not everyone knows what their path forward might look like, she says. However, being willing to experiment and explore different interests can reveal pathways or market opportunities. One piece of advice she often shares with clients is to “give themselves permission to question anything that they don’t currently believe about themselves and just say, ‘Well, what if I could learn this? What if I could actually acquire the skills to do that? What would that look like?’”
Foster says that for people who come from established careers with a delineated path, it can be difficult to embrace this period of uncertainty. But she urges them to try and be comfortable with not knowing what’s next, advising, “If you just jump into something that seems like a good idea and it’s got this clear path, you haven’t really given yourself an opportunity to experiment and play with it.”
When you do that, Foster says, there’s a risk that “you might just end up in the same situation again, where you’ve chosen something that really isn’t a great fit.”