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Career Change Secrets: What I Know Now

Five successful reinventers share their insights—and their hindsight


by Sarah Mahoney

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It would be easy to hold Shelley Hunter up as a poster child for career reinvention. Earlier this year, the 46-year-old sold GiftCardGirlfriend, a website she founded, to a much larger company, negotiating herself a plum job as content manager in the process. “I like to call myself the Rachael Ray of gift cards,” she says, “and now I get to continue that, but with a wider scope, and a salary.”

But the reality is more complex. Since leaving her corporate IT job 13 years ago after her first child was born, Hunter's career path has been full of transitional detours. “I felt like I was throwing darts, freelancing here, small businesses there. I’ve had moments of greatness, and cushy, `We can go to Disneyland now’ times, but I still hadn’t found it, that perfect career. I wish I'd known that all those things I dabbled in—graphic design, marketing, Photoshop—were necessary stepping stones, and that I needed them all to get where I am now,” says Hunter, who lives in Danville, California. “I wish someone had told me I wasn’t failing, just adding essential skills to my toolbelt.”

We asked four other seasoned career changers for their road-tested expertise:

It’s up to you to find your “me” time When Laurie Itkin got laid off from her job as a corporate lobbyist last year, she decided it was time to launch a business based on her true passion: Trading options. Itkin, 44, is now The Options Lady, and her San Diego company teaches people how to buy and sell investments. “I wouldn't change anything about the path that led me here,” she says. “But I wish I had been more prepared for just how nonstop your own company can be. I work seven days a week, because the `project’—whether it’s a blog post or more networking or website revamping—is never done.” So Itkin has made a conscious effort to focus on the flip side: “Just as it’s fine for me to rewrite something at 10 p.m., it’s okay to play during the day sometimes. I have regular squash games. Before, I always had to leave yoga early to be at the office by 9. Now, I stay through every last pose.”

     See also: 9 Ways to Turbocharge Your Career Change

Mastering your new role may take longer than you expect… Before Chris Merrill decided to leave the world of biotech to become a life/career coach, he and his wife made extensive plans, including long-term budgets, prudent emergency reserves and a bailout date “so that if I wasn’t making enough money by a certain time, I’d look for supplemental income or another job.” While that hasn’t happened, he’s glad they entertained such worst-case scenarios. "It has been harder than I thought it would be to meet all my financial metrics," says the 43-year-old, who owns Shift Coaching in Boston. "You can plan as much as you want, but it almost always takes longer than you think. So even though you’ll be very enthusiastic in the beginning, temper that with planning for the worst. Optimism is great,” Merrill says, “but it’s very important to be realistic.”

but you’ll draw on old contacts more than you expected When Northwestern Mutual first recruited Chuck Volpentesta to be a financial representative at its McTigue Financial Planning Group in Chicago, he was hesitant. “I was doing really well in corporate sales at Ricoh, just as I had at Coca-Cola before that,” he says, and he worried about starting from scratch in a brand-new field. “I had to let go of those fears, and while I was a little nervous about tapping on the shoulders of past contacts, more of them have become current clients than I expected,” Volpentesta says. “And I love knowing I’m improving their lives. The connection between my past jobs and this one wasn’t what I expected. People I never would have imagined have become clients, and it has really warmed me.”

     See also: Failure: It's Not ad Bad as You Think

Trust your gut When Linda Amato started telling people she wanted to leave her job in investment banking to open an elder law and estate planning practice, “some people said things like, `Are you nuts? Don’t you know New York is full of unemployed lawyers right now?’” Amato had to remind herself that she was no stranger to career change: After spending much of her 20s and 30s as a social worker, where she often found herself advocating for elderly clients, she was 43 when she started law school. And while she has loved the years she spent in banking, “I really wanted to marry that healthcare and advocacy experience. Last year, I just knew the time was right,” says Amato, who is now in her 50s. “I had enough contacts and professional support. So I borrowed money to give myself a year to see how it would all develop, and it’s working out well. I’m not impulsive. I just knew, in my gut, that now was the time to hang out my shingle.”

Photo credit: Jayesh/Getty Images