The nuts and bolts (and joys) of reinventing yourself for a career change.

By Lesley Alderman
Illustration by Julie Houts

I remember the moment it hit me. I was in my cozy (read: cramped) home office, gazing out the window at the leafless December trees. I’d been sitting for hours and hadn’t talked to a colleague in days. “I’ve got to get back into the world,” I thought. 

After being a freelance journalist for five years, I felt isolated and oddly bored. It was hard to pinpoint why, as the work was engaging—I wrote about health and wellness for The New York Times and national magazines—and I had the flexibility to pick up my young son, Charlie, from school and go to yoga at lunchtime. While I missed the energy and camaraderie of my previous job as a magazine editor, I had no interest in returning to it. What I craved was a new chapter. 

I had reached an inflection point—a term coined by Howard Stevenson, a leader in the field of entrepreneurship and a professor emeritus at Harvard Business School, to describe a moment when one has both the opportunity and the motivation to head off in a new career direction. At any given time, millions of women are right there with me: restless, ambitious and ready to switch things up. If you’re one of them, you may be ripe for reinventing yourself. You just need to know where to start.

Pinpoint Your Passion

It’s not that hard to recognize what you don’t want to do, but identifying what you do want out of a career can take some time and soul-searching. Start by asking yourself, “What excites me? What do I feel drawn to?”

Tara Prasad Nagabhyru, 43, had a solid job as a financial planner but constantly felt guilty about not spending more time with her kids, Arya, now 16, and Rhea, 12. A diagnosis of thyroid cancer in 2010 spurred her to action. “Let me do something more fulfilling,” Tara thought. “Let me make the years I have count.” 

Tara had always been interested in the arts but never thought of art as a viable career. “One day I took my then 2-year-old daughter to a pottery studio, and I felt a connection to the place. I thought, ‘Why don’t I do this?’ ” That sense of excitement stuck with her. Two years later, when she saw a Color Me Mine pottery-painting franchise for sale close to her home in Summit, NJ, she didn’t hesitate. Turned out she liked being a business owner so much that a few years later she bought two more franchises. 

It can even be helpful to think back to your childhood. What excited you when you were in high school or college? When I was 15, I wanted to be either a ballet dancer or a psychologist. By the time I was ready to envision myself in a new career, I’d clearly missed my window on the whole ballet gig. But being a psychologist? That was a definite possibility. I’d been writing about mental health for years, so I already knew a lot about the field. I started looking into graduate programs in psychology and social work and eventually enrolled at New York University. That connection to my past helped me plot out a new future.

Illustration by Julie Houts

Dip a Toe in First 

Once you have an idea or two, consider the practicalities. Wendy Raizin, 48, was earning a great salary as an arbitrage trader in NYC, but she spent 10 hours a day tethered to a computer screen. “I felt like a dog on a leash,” she says. After 9/11 (her office was just blocks away from the Twin Towers), her mind-set shifted. “I started to question everything I was doing.” 

“My husband kept saying, ‘You spend a lot of time reading Architectural Digest !’” Wendy recalls. While reading I Could Do Anything If I Only Knew What It Was: How to Discover What You Really Want and How to Get It by Barbara Sher, Wendy decided to “try out” a career in interior design. While still at her arbitrage job, she took a few design classes, and doing well in those gave her the confidence to quit her job and enroll full-time. She finished design school a year later and, after a brief stint at a big design firm, opened her own design company. Wendy now works on new construction projects, both residential and commercial. “I like seeing a place take shape from the ground up,” she says. As a sideline, Wendy also helps other creative types get their new businesses off the ground. “Creative people often have great ideas, but they’re not so good with the business side. I like to help them figure out a way to become profitable.”

The goal is to build an on-ramp to your career switch. “Read up on the career, learn the lingo, adopt the dress code,” advises Priscilla Claman, founder and president of Career Strategies and a contributing writer for Harvard Business Review. Tara spent the two years between realizing she wanted to run an arts-related business and actually buying her first pottery franchise doing tons of research. She pored over the listings on BizBuySell and read up on financing, competition and small business administration. The research led her to decide that buying into a franchise was the best way for her to enter the business world. (“There’s a formula and a set of rules,” she says—helpful structure for a first-time business owner.) So when the Color Me Mine shop went on the market, she was ready to take the leap.

Talking to people who work in your field of interest can also help you figure out whether you have the right temperament and skills. Ten years ago, Lisa Sicilian, 52, and her husband, who live in Rockaway, NJ, adopted two young girls from Ukraine: Victoria, now 18, and Natalia, 15. Lisa was thrilled to be a mom but eventually realized mothering was not enough. “It was the loss of professional identity that hit me,” she recalls. She worked as an administrative assistant at a business close to her home, but “it wasn’t really what I wanted to do.” One day a close friend who’s a longtime nurse suggested Lisa might enjoy nursing. “I’ve always been interested in science and medicine,” she says. “My friend told me, ‘You’re so good with people,’ and a lightbulb went off in my head.” That friend’s encouragement sealed the deal: Lisa enrolled in nursing school and never looked back. She scored her first job at the New Jersey Firemen’s Home, a nursing home 10 minutes from her house. After a year on the job, she says, “I’ve got this. The career transition was terrifying, but my confidence has built up over time.”

Illustration by Julie Houts

Be Prepared for Some Bumps

Starting a new career can be tiring and scary. Lisa was working full-time and going to nursing school at night and says there were times when she asked herself, “Am I being selfish or foolish? But friends would remind me that I was being a good role model for my girls. I was showing them what’s possible if you work hard. Now that I’m working and happy, they see how my bravery paid off.”

Along with encouragement from friends and family, one good way to smooth the transition into your new career is to join a network. “Networks offer support, community and a tribe,” says Wendy Sachs, author of Fearless and Free: How Smart Women Pivot—and Relaunch Their Careers, who herself has made at least six career pivots. Tara joined a local chapter of B.I.G., an organization for women entrepreneurs with members across the Northeast. Lisa’s nursing support group formed spontaneously while she and some classmates were studying together. Once they graduated they created a Facebook page for support, career guidance and job-hunting leads.

And don’t rule out a little professional help: If you feel stalled or overwhelmed, consider hiring a career coach to help you tackle roadblocks. You can find coaches on Landit (see “Resources,” at right).

Remember, Any Career Has Challenges 

It can be tempting to assume that switching to a career you’ve been dreaming of will mean leaving behind not just your old job but its challenges as well. Not necessarily. Every job has its drawbacks—it’s just easier to deal with them when you’re happy with your direction overall. Wendy admits she works as many hours as she did when she was on Wall Street, but “because I am so interested in what I’m doing, it doesn’t feel like work.” And she can switch her phone off and take an early morning yoga class, something she could never do in her old life. Her kids, now 11 and 14, are happier too. “They like that I have my own business; they’re proud of what I do.”

If you feel like an impostor at first, recognize that it’s totally normal. Especially as you launch your new career, work on projecting confidence—even if you don’t truly feel it yet. Begin to craft a narrative and convey excitement about your new direction, advises Lisa Skeete Tatum, founder and CEO of Landit. “Let people know what your goal is. If people don’t know where you are trying to go, they can’t help you.” Your confidence (real or faked) will create a virtuous cycle: Friends will start to believe in what you are doing and their confidence in you will reinforce your decision. Once your business gets going, that confidence will help you attract clients and vendors, says Wendy. “No one wants to hire someone who is wishy-washy. Most of my business is now word-of-mouth.”

Above all, keep reminding yourself of why you made the switch and of the eventual benefits for yourself and your family. Within a few years of that first I-want-something-more moment in my home office, I was able to mesh my new expertise with my old career: working as a psychotherapist while continuing to write about mental health for newspapers and magazines, a combination I find thrilling and fulfilling. As Lisa describes her transition: “I worked my whole life being a diligent employee, but the jobs didn’t feed my soul. Nursing does. What better way to nurture myself and my children?”

Resources

Books

TED Talks

Websites

  • Landit is a bit like LinkedIn for gals—but more personal. It helps guide your career transition, prompting you to keep track of your accomplishments and create a board of advisors. The site also offers résumé reviewing and coaching, although those services cost extra. 
  • Après is an online job marketplace for women heading back to work.
  • Coursera (from $39 per month) offers online classes in everything from effective communication to social media marketing to robotics. 
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