5 Game-Changing Career Change Strategies From People Who Have Already Done It

Making any sort of career change can seem daunting, even if you’re just moving from one specialty within your field to another. But if you’re totally starting from scratch, transitioning into a completely new thing? That can feel downright impossible.

But it’s not, and we’ve got proof. The five people below successfully made pretty massive career changes, and not only lived to tell the tale but are now happily working in jobs that truly match their values, interests, and skill sets.

For those of you hoping to do the same, we chatted with them to learn a few smart strategies for getting through the transition. Whether you’re trying to figure out your next step or know exactly the change you’re looking to make, the advice below should help you get closer to a career you’ll really love.

Strategy #1: Figure Out What Motivates You

The Change: Health Analyst to Real Estate

After feeling disheartened in a traditional 9-to-5, Sahar Pezeshki took the time to figure out what motivated her as a person. She knew she didn’t want to work in a cubicle or as a healthcare analyst anymore—but from there, she had to find the best way out.

Rather than jumping straight into a new career, Pezeshki went back to her values. She asked herself questions that would serve as a guide for her career choices, questions like, “Who am I? What do I want? Who do I serve?” Her advice: “Write it out—marinate in your answers and get to the point where you can answer these questions with unwavering confidence and speed.” Pezeshki believes that by trying to understand what motivates you, you can set a solid foundation for a major career move.

“From there,” she recommends, “you can choose a career path that aligns with your values and goals.” Based on her answers to these questions, she knew she would find fulfillment helping people through monumental milestones, like buying a home, and became intrigued by real estate.

With the help of Redfin’s impressive training program, which includes classroom learning, on-the-job training, and mentoring, Pezeshki was able to get up to speed quickly and become a trusted, established agent. Although Pezeshki’s successful transition depended on her hard work and determination, it started with a willingness to dig deeper with a meaningful inquiry about her values.

Strategy #2: Translate Your Skills to a New Context

The Change: Social Work to Community Manager

Molly Berry worked as an intensive care coordinator for children with mental health challenges before she realized she needed to make a change. Despite years of investment in her work—including a master’s degree—Berry lacked the license she needed for a promotion (and wasn’t sure she wanted to get it). She had no clear way forward.

“Ultimately, I looked at my own career path and had to decide if I wanted to progress or remain stagnant at that level,” she says. “Anyone who knows me knows that I’m not one to settle for something when I know I can be doing better.” After some research, Berry decided to look for jobs in different fields that built on the skill set she developed as an intensive care coordinator.

Berry knew from her work with kids that she wanted to engage with people, provide resources, and act as a voice for a community that needed extra support. Her sister worked in marketing, which helped her to broaden her perspective, and thinking about her skills and the marketing world brought her to an unexpected role: community manager. “The more I talked about my skills and my passion for building community, the more natural it seemed,” she explains. Now, at content marketing platform Skyword, Berry thrives in her role facilitating relationships and advocating for freelance writers.

Berry recommends that people who are looking to make a drastic shift see the value of their skills within a bigger framework: “If I only looked at my skills as providing mental health care, coordinating doctors’ appointments, attending school meetings, and helping teens find jobs, this never would have worked. I had to step back and look at what I could offer from a different perspective.”

Strategy #3: Transform Your Side Project Into a Career

The Change: Technology to Real Estate

Jason Aleem always knew that he wanted to be his own boss. So, while working at Dell as an account manager, he started an apartment-locating business on the side.

“The business gave me an opportunity to be out in the field, face-to-face with people, working on a team, and learning real estate in an intense environment,” he remembers. After doing some research, Aleem realized that his interest in real estate wasn’t coincidental. It allowed him to marry two of his passions, branding and entrepreneurship. “The business was a springboard to understanding real estate, and it opened up doors to other areas of the industry that interested me.”

As a licensed real estate agent, Aleem made the leap and opened his own brokerage. “I had a great job at Dell and a clear path on how to excel there. Leaving that perceived comfort and structure seemed outlandish for some, but I knew it was something I wanted to do,” he shares.

Aleem got creative and diversified his business during the recession, and ultimately joined the national real estate brokerage Redfin to help open the company’s Dallas office. He continues to work for Redfin as an agent, broker, and district manager.

Based on his experience, Aleem recommends that anyone who wants to transition a side project into a full-time career build a nest egg. “Create as much financial runway as you can before making the leap. You want to be able to focus on learning and growing in your new capacity and not on paying the bills.”


Learn More About Working at Redfin


Strategy #4: Meet a New Demand

The Change: Investment Banker to Full-Stack Developer

Rex Salisbury worked for five years as an investment banker. During that time, he felt like his work had little to no real impact on people’s lives. “You’re really far removed from the actual customer,” he says. “Why would I spend 10 or 15 years doing a job that doesn’t make a difference?”

So instead of hunkering down in the traditional banking sector, Salisbury started exploring alternative models. “I was reading about customer-based, financial-technology companies, the majority of which are based in San Francisco,” he explains. Although he initially considered working on the business side of a fintech company, he soon realized that he could maximize his impact as a developer.

“When you have people who are working in technical roles for customer-focused companies, they are adding value, solving real issues, and they’re not replaceable parts because there’s so much demand for this kind of work,” he says.

From there, Salisbury invested his time and resources into learning to code at a nine-week developer bootcamp program. While gaining technical skills, he tapped into existing networks in San Francisco. “Being successful is about being surrounded by people and networks that are really powerful,” he shares.

Now a full-stack developer, Salisbury works at Sindeo and founded a fintech Meetup that includes 1,200 members. By adapting to the demand for technical roles, Salisbury believes professionals can not only transition into dynamic careers, they can also maximize their impact in their desired field.

Strategy # 5: Monetize Your Passions

The Change: Acting to Life Coaching

Claire Byrne built a successful career following her passion as a commercial actress in New York and Los Angeles. But when the economy tanked in 2008 and work started drying up, Byrne needed a new source of income as she continued to audition for acting gigs.

Byrne found her next step in an unexpected place. “I started taking yoga after an awful breakup—sometimes I would go twice a day. Teachers had recommended I take a teacher training course, but I wasn’t ready to commit. Then it dawned on me that I could give private yoga lessons, which would give me extra income and the flexibility to keep on auditioning,” she says.

Byrne credits the downturn with giving her the momentum she needed (“Realistically, I was 28, and I needed income stability”), and she got creative and built her yoga teaching business from the ground up. At the time, she was diving into self-help books out of personal interest, and it rubbed off on her clients and friends too.

“I felt like my clients were paying me to be Claire—for me to listen to their problems and share my perspective—rather than for a guided yoga practice. And in acting class, people always wanted to talk to me about their issues. All of a sudden, I was the ‘class guru.’” Without knowing it, Byrne’s peers and clients mirrored her emerging passions back to her.

After some research, she signed up for Martha Beck’s intensive Life Coach Training and evolved her business into Claire Your Mind. Byrne has successfully changed careers not once, but twice, by getting creative about turning her passions into businesses. Now, she gets to help others do the same.

Regardless of the nature of your career, there are always options to transform it into a job that pays the bills and brings you a sense of fulfillment. As you chart a new path, find inspiration from others who have gone before you, and know that with hard work and some smart strategies like these, you can make it happen.

Photo of man in road courtesy of LaraBelova/Getty Images.

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About Alyse Kalish

Alyse Kalish
As an Associate Editor for The SalesJobInfo, Alyse is proud to prove that yes, English majors can change the world. She calls many places home, including Illinois where she grew up and the small town of Hamilton where she attended Colgate University, but she was born to be a New Yorker. In addition to being an avid writer, Alyse loves to dance, both professionally and while waiting for the subway.

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