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How to Make the Choice to Change Careers

A career checkup in your 50s might help you make the decision, experts say

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You’ve worked hard and established a solid career, but now you find yourself yearning for a new direction. If you’re not quite ready for retirement, either financially or emotionally, do you maintain the status quo or do you pivot?

The COVID-19 pandemic served to deepen many people’s desire to change their career course. A 2021 CNBC Catalyst report showed that as many as 50 percent of workers want to make a switch. Location flexibility was a driver for about 40 percent of respondents, but that wasn’t all they were seeking. Almost a quarter of those surveyed said they “want a job with more purpose.” They cited changing career fields (33 percent) and starting their own business (20 percent) among their alternatives.

There is, of course, a big difference between changing jobs and making a major career transformation. If you’re leaning toward the latter, how do you decide whether, when or how to change?

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Give your career a checkup

Wharton professor Adam Grant suggests that his students follow health care advice and schedule regular checkups ― in this case, career checkups. Grant, the author of Think Again: The Power of Knowing What You Don’t Know, describes how self-assessments and asking introspective questions can help someone determine if their career has just stalled or whether a bigger change may be in order.

In your 50s and beyond, the criteria you use to measure your career health may differ from earlier decades. But like medical exams, the need for regular career checkups is important.

John Tarnoff, career transition coach and author, says, “As we hit 50 or thereabouts, we start to realize, ‘I don’t have forever. How do I want to spend my days? Do I want to really focus on what is most meaningful and fulfilling and purposeful to me?’”

He likes to describe this proposition using the Japanese term ikigai, the concept of living with our meaning and purpose. To help clients apply this idea to their career choices, Tarnoff recommends practical exercises that ask, “What can I do that I love to do, that I am good at doing, that the world needs and that I can get paid for?"

How two people made their decisions

During the three decades that Andrea Young worked as an interior architect, in her personal life she honed her skills in a different area ― culinary craft. “My passion for cooking goes back to being in the kitchen as a child with my grandmother. She made everything beautiful and fun.”

It was an accident that led Young down a new career path. After her mother fell in 2006, she recuperated in Young’s apartment. Young hired a chef to prepare nutritious plant-based meals for the family, and she helped the chef with food preparation. This inspired her to enroll in the Natural Kitchen Cooking School. After graduating, Young worked part time as a personal chef but decided she didn’t want to do that full time.

When she was 57, the interior design firm where Young worked started downsizing. A couple of years later, she launched Sweet Vegan Chocolates, an organic, plant-based, gourmet chocolatier based in Harlem. Today, Young, 65, goes by the title of Chef Andrea.

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Another New Yorker, Phil Gautreau, found a way to turn his passion into a second career in his early 50s. Gautreau, 61, had a successful 25-year career in health care administration but found that his work had become less fulfilling.

“I started asking myself, If I am going to work for another 10 or 15 years, is this what I want to keep doing?” Gautreau explains. “But I didn’t know what I would do instead.”

Roughly four years earlier, he had taken a woodworking class and loved it. Gautreau started spending most of his available off hours developing his craftsmanship in that field. By fall of 2011, he had enough items to exhibit at his first art show at Lincoln Center, where they sold well.

“I had started having discussions with my financial advisor about making a career change, but I still hadn’t made up my mind exactly what I was going to do next,” Gautreau recalls. He turned 51 the following year and developed a plan to transform his woodworking passion into his new career. Gautreau has since exhibited his designs at prestigious events like the Philadelphia Art Show and the Smithsonian Craft Show.

Switch to your side gig 

Tarnoff advocates the benefits of developing a side gig as a possible career alternative, as they were for Young and Gatreau.

“We hear a lot more about side gigs today than ever before, because it’s so easy to start a new business,” Tarnoff says. He points to the ease and abundance of online resources like free YouTube videos that can spark business ideas and/or serve as a road map.

According to Tarnoff, another alternative to abruptly quitting your job is a phased retirement.

“This is something that you can plan in your 50s where you look at ways of reducing your hours at your main job or changing your responsibilities to give you time to seek the side gig or the eventual second act career. This gets into the idea that all work today is more entrepreneurial than it’s ever been,” he says.

Add new skills throughout your career

To help them realize successful career transitions, both Young and Gautreau acquired new business skills.

To boost her business acumen in areas like finance and business development, Young enrolled in a program through the New York City Small Business Development Centers. Her creative marketing ideas, like donating 1,000 pieces of gourmet chocolates to first responders, led to Sweet Vegan’s increased visibility, sales and business success.

Gautreau spent a couple of years learning the products and places with the best return on investment for his time and talent. His designs are now carried by 40 stores in the U.S. and online.

He still loves woodworking and embraces being an artist, but he is also a serious small business entrepreneur.

“I’m not retired. It’s not a hobby. I run a business,” Gautreau says.

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