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How to plan for two or three (or seven) different careers in your lifetime

That path to retirement has been replaced by far more complex scenarios and, for many, delayed retirement. Here’s how to manage your professional life through myriad phases.

How to plan for two or three (or seven) different careers in your lifetime
[Source Photo: DI/iStock]

When Qadirah Bridgeman was 22-years-old, retirement was the furthest thing from her mind. A dance major when she earned her undergraduate degree, Bridgeman was transitioning pretty dramatically into the real world. “I had just changed my religion, got married, and was pregnant,” she says, “so it was hard to say where my career would go, but I knew I wanted it to go somewhere.”

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So Bridgeman taught for a while but switched to customer service as her family grew to include four more children. As she got older, she knew retirement was an option but understood that working as long as possible was best for her mentally, physically, and financially. “My father worked until he was 81, and I believe it is what kept him going for so long,” she says.

What she hadn’t planned for either was landing a job at T-Mobile at the age of 45, 14 years ago. “I had done customer service roles for other companies, so I was familiar with the work,” she says. “But it was definitely a different experience going through onboarding and training as one of the oldest of the bunch.” Bridgeman didn’t even own a mobile phone at the time. “From a tech perspective, there was a learning curve,” she recalls. But the company’s training process was inclusive, putting everyone into teams right away.

Despite a tough transition, Bridgeman maintains her age was a huge benefit. Not only was she seen as a natural leader, but her experience also gave her the stick-to-itiveness required to get through the training. “When everyone would pull out their fancy tech, which was great for them, I used my trusty pen and paper to my advantage, because I knew it was what worked for me,” she says.

Now at age 59, Bridgeman is a T-Mobile customer care senior-level expert based in Nashville, TN., who recently completed her master’s and has no plans to retire for at least another 30 years.

Bridgeman is not alone. The traditional arc of a career that lasts 25 to 30 years–usually with the same company–has become exceedingly rare. This translates to most workers having two, three, or more phases of their career during their lifetime. This can involve switching industries, gig work, or even entrepreneurship. The conventional strategy of mapping out a single career path needs a radical rethink.

An aging labor force

The number of people who 65 and older in the workforce is the highest it’s been in 55 years. And that’s not going to change soon. The Bureau of Labor Statistics found that 36% of 65-to-69-year-olds will be part of the labor force by 2024. Part of this is due to financial considerations. Lisa Marsh Ryerson, president of AARP Foundation, says that as many as 42 million adults who are 50 or older struggle with some aspect of their financial lives. “There’s a misconception that most people older than 50 are comfortably heading toward retirement by putting money away in savings and paying down their debts,” she says. “Today, that path to retirement has been replaced with far more complex scenarios and, for many, delayed retirement.” Longer life expectancy, stagnant wages, and the shift from pension plans to 401(k)s are impacting how long many people stay in the game. “From research, focus groups, and conversations with individuals, we know these challenges force older adults to make difficult decisions, including career changes,” she says.

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As Marsh Ryerson points out, older adults need to have tools and resources to make informed financial decisions–from determining if the gig economy is an option to identifying and learning new skills to compete in today’s job market–to achieve the financial freedom required to find a job that provides intellectual and creative stimulation, to pursue their passions, or to quit working altogether.

Follow your passion, no matter where it takes you

Take McAfee’s current chief consumer security evangelist, Gary Davis, who switched careers and industries to pursue his passion–all while staying relevant working with current technologies.

The self-professed “farm boy” launched out of a high school graduating class of 32 students into the U.S. Navy, where he landed his first job as an avionics technician. During his service, Davis completed both his bachelor’s and master’s degrees.

His thesis for the master’s was based on a comparison study of the voting habits for two different military bases in Hawaii. “It was during that work that my passion surrounding the importance and effect of influencing people by informing and educating them came into strong focus for me,” says Davis.

From there, Davis held a variety of roles in marketing before moving into security at McAfee in 2009. “The work on my thesis taught me the value of implementing compelling programs intended to educate and inform a target audience and measuring the efficacy of those programs,” says Davis, who never thought he’d end up in the tech industry. But it was the best fit for his personal passion.

Stay curious

For those who do remain in one industry, it can be challenging to stay relevant as they age. Sheila Talton, the CEO of Gray Matter Analytics and a 30-plus year veteran of tech companies like Cisco, puts it this way: “If you are in this industry, change is inevitable.” Talton watched colleagues who didn’t like change and often professed nostalgia for “the good old days” inevitably get passed over and phased out. “You have to be keeping your skills updated,” says Talton, who is an avid reader and researcher, as well as a keen observer of trends.

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“Most of my staff are much younger,” says Talton, “I learn a lot from them.” One thing she says stymies older workers from progressing is that they mistake their age and experience for knowledge. This can come across as being obstinate or resistant to change–and can paint the older executive into a corner of being hard to deal with.

Experience has taught Talton to recognize patterns in situations, and she credits her time working internationally for helping her learn to work with all different types of people. “When you’re the only [African-American woman] in the room, you have the ability to learn and listen,” she explains. Talton says this taught her the importance of gaining trust. “You can be successful in gaining trust by showing your human side, exposing where you made mistakes.” As she’s advanced in her career, Talton says that this ability to be humble combined with being intellectually curious has served to keep her career advancing, with no end in sight.

If you have a good gig, stick with it–but keep educating yourself

Being willing to learn is a vital ingredient for navigating the vicissitudes of an episodic career. “I am most definitely a student for life,” says Vince Digneo, who has been Adobe’s sustainability strategist since 2013. Digneo says he still takes classes on topics related to his role or that simply pique his interest. “Adobe has been very supportive of continuous learning,” he notes.

Digneo’s career shaped up unconventionally, after earning an MBA at Berkeley while in graduate school in biophysics at Stanford. From there, he followed a series of opportunities including at HP Labs on their biosciences team (what is now Agilent Technologies). He initially thought that he might eventually launch his own biotech startup. “I did end up working for a number of startups and along the way transitioned from a biotech business professional to a corporate tech sustainability lead,” he explains.

Entrepreneurship is not for everyone, and Digneo was no exception. “I realized a few years ago that I was not going to be a retired startup billionaire, and I’m good with that,” he states. “I really believe that I continue to contribute and to do good for Adobe, the environment, and the communities where we work and live,” he says, “My role is a happy reality.” And one that he’s not planning to quit any time soon.

Study a company’s culture

Whether it’s continuing to take the opportunities that present themselves, sticking with a passion, or doing the work necessary to put food on the table, Bridgeman–who’s looking to put her newly earned master’s degree to good use as she climbs T-Mobile’s customer care ranks– says it’s important to look at a company’s culture before deciding to take a job there as an older adult.

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“Look for a company that has a proven track record for diversity and inclusion,” she says, clarifying that it needs to be one that’s open about age diversity. “It is one thing to say you are accepting of all ages, it is another to specifically seek out older generations as part of your hiring process and give all ages the tools to advance their careers,” she says.

Know your strengths

Bridgeman, like Talton, urges older workers to lean into their strengths. “Our leg up is knowing exactly what those [strengths] are, whether that is working with people, or helping innovate behind the scenes,” says Bridgeman. “Find a role that will highlight these strengths, so that you can succeed in a competitive workforce.” Chip Conley is a great example of this. At 52, the veteran of the hospitality industry found himself being scouted by Brian Chesky, the cofounder and CEO of the nascent Airbnb. “We were able to combine Brian’s impressive design skills and visionary leadership with my know-how and know-who of the hotel industry to turn home sharing from a peripheral to a mainstream part of the hospitality sector,” he writes.

Just don’t forget your personality along the way, says Talton. Intellectual curiosity and intellectual capability are key she says, but “a lot of it is your spirit.”

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About the author

Lydia Dishman is a reporter writing about the intersection of tech, leadership, and innovation. She is a regular contributor to Fast Company and has written for CBS Moneywatch, Fortune, The Guardian, Popular Science, and the New York Times, among others.

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