These 8 Women Made Major Career Pivots — & So Can You

Photographed by Eva K. Salvi.
What do you do if, on paper, your job seems perfect, but you still feel like something is missing?

You might be getting bored. Maybe you’re approaching burnout. Or maybe this plateau is a product of your success — which is a signal that you’ve outgrown your current role and are ready to move in a new direction.

As I conducted research for my new book, PIVOT: The Only Move That Matters Is Your Next One, I came across a category of people for whom money and financial gains — accruing a high net worth — are not their primary motivators in life. Financial security is important, but this group aims more for high net growth and impact instead. They will happily bootstrap a business or side hustle, or make a lateral move if it will keep them learning, growing, and making a difference.
Counter to what it may seem, this pivot point is a good thing. It means you are on the brink of a breakthrough for your personal growth and broader career. So how do you start mapping what’s next? How do you bridge the gap between where you are now and where you want to end up? Read on to find out.
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1. Plant by creating a foundation from your values, strengths, and interests, and your vision for the future. The most successful pivots begin from a strong base of who you already are, what works, and how you define success for this next phase of your life.

2. Scan by researching new and related skills, talking to others, and mapping out potential opportunities. This is the exploration phase: identify and plug knowledge and skill gaps, and have a wide variety of conversations.

3. Next, run a series of pilots — small, low-risk experiments to test your new direction. Pilots help gather real-time data and feedback, allowing you to adjust incrementally as you go, instead of relying on blind leaps.

4. Eventually, it is time for a bigger move, or launch. The first three stages of the Pivot Method, repeated as many times as necessary, help reduce risk and give you a greater chance of success — often taking you 80 to 90% of the way toward your goal. Launch is when you pull the trigger on the remaining 10 to 20%. These are the bigger decisions that require commitment, even in the face of remaining uncertainty.

The Pivot Method is a cycle, not a one-and-done process. Some pivots take one month, while others can take years. And sometimes it takes several smaller pivots to reach your destination. Just as an 18-wheeler cannot turn on a dime, bigger pivots often require several smaller turns. Repeat the Plant-Scan-Pilot process as many times as necessary for clarity and feedback before advancing to the fourth stage, Launch.

Ahead, learn about how eight real women used the Pivot method to relaunch their own careers.
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Photo: Courtesy of Brooke Siem.
Brooke Siem, 30
After cofounding Prohibition Bakery in New York in 2011, Brooke Siem was looking to break away from running daily operations and move into a more creative role.

“I was developing recipes at the bakery and also writing every day, for personal work and professional work. After I finished writing a piece or developing a recipe, I realized I felt like I'd actually accomplished something, as opposed to just moving another part down the assembly line. I wanted to keep creating,” said Siem. She explored a career in writing by first ghostwriting about food, fitness, and travel for major sites. She is now writing under her own byline, and has a few potential books in the works.

Siem explored new passions and projects through freelance. And when her gut told her it was time to make a change, she knew she was ready. Siem is now on a yearlong trip around the word with Remote Year, a paid service that brings together 75 digital nomads to work in and explore 12 different cities worldwide. She'll also have time to focus on her own writing and projects.
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Photo: Courtesy of Lisa Lewis.
Lisa Lewis, 28
Lisa Lewis had been working in marketing since graduating college, and while she was great at the work, she was feeling empty.

“I was craving work where I could see my effort making a meaningful difference in people's everyday lives,” Lewis said.

She also realized that her favorite part of her marketing job was supervising her direct reports and helping them to become successful. Lewis loved connecting one-on-one with people and developed a reputation for being great at offering personal branding advice.

It was time to pivot. Lewis started piloting a few opportunities in therapeutic work, like applying to grad school programs and being a volunteer counselor for the Crisis Text Line. These paths would offer her one-on-one connection with others, while making a positive impact on their lives.

These small experiments helped Lewis realize that her sweet spot is actually in helping people work through finding career fulfillment — and not the larger mental health questions. With this foundation, Lewis started a career coaching business in 2015 on the side, while maintaining her full-time marketing job. She has since been able to strategically grow this business and safely leave her former job.
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Photo: Courtesy of Stephanie Huston.
Stephanie Huston, 30
While she was moving up quickly at the startup she was working for, Stephanie Huston was looking for something more — both short-term and long-term. Her strong strategic partnership and planning skills just weren’t being put to good use where she was.

First, Huston took stock of her strengths and where she wanted to grow. She has a passion for volunteering, event planning, and supporting women in business. She also started to attend non-profit events to scan for open opportunities.

After finding an organization that she loved — The United Women in Business Foundation — Huston started getting involved by volunteering at events and joining Board of Directors meetings to see how things worked. Her involvement steadily grew, and she now serves as the organization’s NYC chapter president, while still maintaining her full-time job as an account director at AdTech.

Pivoting to focus on her passions has opened up many more opportunities for Huston to develop her thought leadership, grow her social media presence, freelance for The Huffington Post, and create a partnership to travel to Antarctica with Oceanwide Expeditions.
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Photo: Courtesy of Mandi Holmes.
Mandi Holmes, 27
When the company Mandi Holmes was working for failed, she found herself out of a job and needed to pivot fast. Instead of being discouraged, she used this turn of events as a sign to finally do something she’d always wanted to do: start a business.

“I've always had the entrepreneurial itch. For years I had studied, researched, and just watched other people ‘do the thing.’ I had recently uncovered my passion for helping equip other people to do the work to make their dreams and goals reality. So I took all of the tools, resources, and training that I had and created my own business.” said Holmes.

To do this, she ran a series of pilots by taking on every client that came her way and experimenting with different pricing breakdowns of her services.

Throughout this process, Holmes was very intentional about checking in with herself. Was running her own business working? Was this the right move to make? Through these pilots, Holmes slowly honed in on her ideal client, the type of work she wants her team to do, and the right pricing. Just a year later, her business, She Can Coterie, a team of virtual assistants for women entrepreneurs, is going strong.

“I've developed a diverse team and we are able to reach many more women entrepreneurs. Our clients are incredible women who are doing great work. We are helping them publish books, release online courses, and achieve several five-figure months in a row!” said Holmes.
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Photo: Courtesy of Wade Brill.
Wade Brill, 27
For years, Wade Brill taught Pilates and meditation classes, and while she loved being able to support people physically and mentally, she wanted to go deeper and offer emotional support as well.

So she decided to double down on her strong people skills by enrolling in coaching school. There, she received more formal training on how to deeply listen and support people to take positive, purposeful action in their lives. Brill further scanned her interest in the “helping” field by reaching to people in the coaching world to learn more about it.

“In the end, it was a right match. I loved that it was all about moving and growing forward with intention,” said Brill.

After becoming a certified coach, she started offering one-on-one coaching and focused on getting herself out there as much as possible. Each time she recited her elevator pitch for others, there’d be a new tweak, and this helped her narrow down her niche and better understand her strengths.

Since launching her own coaching business, Brill has been able to make her desired impact in many other ways, including hosting in-person workshops for urbanites, leading corporate meditation sits, and leading virtual group coaching programs. She also launched Centered in the City, a coaching collective working to bring mindfulness and self-development into concierge service buildings and corporate spaces.
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Photo: Courtesy of Casey Pennington.
Casey Pennington, 27
Two years out of college, Casey Pennington was doing great. She was accepted to a top business university and landed a full-time job at a large corporation. She thought she was set for life, but then she started to feel stuck.

Pennington began her pivot by first identifying the “known variables” of what she ultimately wanted in a career: challenge, autonomy, flexibility, relationship building, and something more aligned with her interests. While she wasn’t quite ready to venture out on her own just yet, Pennington decided to pivot within her company from accounting to IT. This way she could better explore her interest in software development and systems. She scanned for opportunities by making her interest in moving to the IT team known among her coworkers and managers, and soon enough, she was working on a new software project.

In October 2015, Pennington pivoted again by leaving her corporate job and starting her own business systems consulting business. But the pivot wasn’t over — after four months of self-employment, she started working on the side for Less Doing Virtual Assistants. Over time, she's gradually grown her role to become part of the internal management team and be their finance process expert.

“The funny part is that when I was initially looking to pivot from my corporate job, I was looking for a role like the one I have now with Less Doing. But I couldn't find it at the time, so I started my own business. However, being self-employed gave me the flexibility to grow into this role over time. And of course, I may pivot back toward entrepreneurship again in the future,” said Pennington.
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Photo: Courtesy of Amy Schoenberger.
Amy Schoenberger, 33
Amy Schoenberger had been working as a senior creative strategist in a public relations firm for four years. She was starting to feel uninspired by the work, but had no desire to leave the company and coworkers she loved.

Instead, she sought to prove her value at her PR firm by taking on the projects that no one else wanted to do. In 2009, when it became increasingly clear that social media and blogger outreach were important for PR strategy, she volunteered to learn more about it. This was a job others in the company avoided, for fear of lowering their status by working with bloggers — instead of marquee clients.

Schoenberger soon developed a reputation as the company’s social media expert, consulting on all the biggest accounts, and parlaying this expertise into a new role as a digital strategist.

Schoenberger’s reputation and expertise led her to being invited to join a new company in a bigger role. She was approached by a former manager and mentor to be the vice president of social strategy at M Booth, working across practices to help clients find creative ways to stand out as new communications platforms emerge.
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Photo: Courtesy of Julie Clow.
Julie Clow, 41
Julie Clow was an executive who had outgrown her role as a senior vice president in HR at a hedge fund, and felt capped in her trajectory. But with a family to support and great compensation at her job, leaving was an easy choice.

After exhausting her options internally, Clow opened herself up to the idea of pushing past a career plateau by switching companies.

Clow was perfectly positioned to be poached for a new role because of the platform building she had done: continually achieving great results at her company, writing a book based on her expertise in organizational behavior and company culture, taking on a board position with a prestigious global learning and development organization, and co-hosting a Work Revolution conference. This platform building was not for the purpose to run her own business, but it made her remain discoverable by others in her industry who might want to work with her.

In the end, Clow was able to leverage all of her experience into a better fit job. One day, she received a message through LinkedIn, asking her to interview for a job that exceeded her wildest dreams: head of global people development for Chanel.
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