Is It Time to Reinvent Yourself? Four Ways to Know You’re Ready for a Career Pivot

A few short years ago, the pandemic set off a wave of soul-searching about the role work plays in our lives. Some lost their job and had to reskill, some retired early, and some left for better opportunities. In general, there’s been a collective realization that life is too short to stay in an unfulfilling job. Hopefully, the worst of COVID-19 is behind us—but here in 2023, many of us are still feeling a nagging sense of discontent.

Robert L. Dilenschneider says we absolutely need to heed that quiet voice whispering that it’s time for a change.

“Work is meant to be meaningful,” says Dilenschneider, author of Wall Street Journal and USA TODAY bestseller The Ultimate Guide to Power & Influence: Everything You Need to Know (Matt Holt Books, July 2023, ISBN: 978-1-6377429-3-8, $28.00). “We’re not supposed to endure a boring or unfulfilling career until it’s time to retire. Sometimes we need to pivot—and that’s a scary prospect.”

A life-altering career move can be controversial, notes Dilenschneider. It’s so much easier to stay snugly in your comfort zone. But when you take that leap, you’ll feel better about yourself—sometimes much better, and you actually might do some good along the way.

When faced with these heavy choices, it’s always helpful to take inspiration from others’ success stories. Below, Dilenschneider provides some accounts and advice from other entrepreneurs who took a chance—and succeeded.

First, here’s how to know when to make a move:

You’re bored. Have you ever dreaded going back to work the next day? Does the thought of your daily tasks in the office make you long for something—anything—else? Perhaps you have a talent or skill that you’re not getting to employ. Are you searching for a way out?

James Patterson did too, notes Dilenschneider. Before the author became a household name, he was a copywriter working in a Manhattan-based advertising agency, J. Walter Thompson. Even while leading the creative team, he garnered little satisfaction from the simple ads he was writing for green beans and playing cards, and he knew he had to quit.

“Patterson hasn’t stopped writing books,” says Dilenschneider. “His career change was good for him—he’s sold more than 400 million copies—and for his legions of loyal readers.”

Your conscience is nagging at you. This was the case for Dilenschneider when he worked for Hill+Knowlton as a fresh graduate. He adored his work and quickly rose through the ranks, eventually becoming president and CEO. That is, until he was asked to do something he considered unethical by upper management. Without any safety net to fall into, Dilenschneider quit his job.

“This was September 1991, and newspapers wrote about my departure,” he writes in his book. “I refused to say why I’d suddenly left, and this is the first time I’ve talked publicly about the reason. Personal integrity is important to me.”

Eventually, with some advice from trusted partners, he started his own hugely successful public relations agency. Today, The Dilenschneider Group is going strong, with top companies and individuals as clients for more than three decades.

You see an opportunity to make a difference. Dilenschneider includes a Rosalind “Roz” Brewer, former COO of Starbucks, in his book. She had a satisfying career before 2020. But as she watched communities being slammed by the effects of the virus, she knew she had to step in.

In 2021, she left her stable job and became CEO of Walgreens Boots Alliance, which helped to administer the COVID-19 vaccine to communities. With this single move, Brewer became the highest-ranking Black CEO on the Fortune 500 list of top executives in the country, where she is now using her position to bring attention to multiple concerns and crises concerning women.

One day you realize your career no longer “fits.” Maybe you can feel your priorities changing. Maybe you’re getting older and want to make meaningful, lasting relationships with coworkers. Or perhaps you want to become an advocate for a community.

Kim Malek, weary from her weekly trips between Seattle and New York for her corporate job, was longing for something closer to home. She wanted to know her employees, coworkers, and neighbors, and wanted to be able to walk her dogs.

“She didn’t let the risk of failing stop her,” says Dilenschneider. “With a cousin, she cofounded Salt & Straw, an ice-cream shop with specialty flavors that quickly became a hit. That was 2011. By 2022, she had over thirty locations and annual revenues reaching the millions.”

If you’re thinking about making a career pivot, Dilenschneider offers the following advice:

Don’t worry about going backward. When you shift gears while driving, there’s always going to be a second or two of lag, but ultimately, you get where you are trying to go. The same can be said for careers. Dilenschneider quotes Sheryl Sandberg, who early in her career went from a team of tens of thousands at the U.S. Department of the Treasury to a team of just four at Google, on the fear of moving backward:

“There are so many times I’ve seen people not make that jump because they’re afraid they’ll…‘move backward,’” she said in the When to Jump podcast in 2017. “If you can financially afford it, and you’re gonna work the next, I don’t know, thirty years, who cares about ‘going down?

It’s fine to try something completely different. Dilenschneider cites Ina Garten, the host of the Food Network’s Barefoot Contessa, as an example of what can happen when you’re willing to follow your gut and make a move that’s completely unexpected. He writes:

Fans of her many cookbooks might be surprised to learn that in her twenties she was a staff member of the White House’s Office of Management and Budget. “There’s got to be something more fun than this,” she recalled in a 2016 TIME story.

“And then I saw an ad for a specialty-food store for sale in the New York Times, and it was in a place I’d never been before: West Hampton. So my husband, Jeffrey, said, ‘Let’s go look at it.’ To say that I knew nothing about what I was getting myself into was an understatement. I’d never run a business before, never even had employees working for me. But when I saw the store, I thought, ‘This is what I want to do.

“Being willing to take a risk, and listening to that inner voice, led to an astonishing career for one of America’s most prolific cookbook authors,” reflects Dilenschneider.

Come up with a pivot plan. Start by simply focusing on what you enjoy doing. Why do you enjoy it? Does it give you satisfaction? Are you willing to commit yourself to it? Will it require further education? But before you enroll in an expensive program, do your research to determine whether that degree is truly necessary. If it is, can you pursue it after joining a company that contributes to its employees’ education? Is there other training that will position you to get into a new field? Find a mentor who can advise you on what you need.

You’re going to feel fear (and for good reason). Push through it and make the leap anyway. Dilenschneider recalls his “terrified” state of mind when he left Hill+Knowlton. His main concerns were his wife and children. “What was I going to do?” he asked himself. “How was I going to tell my wife, Jan, that I had walked away from a powerful and lucrative position? We had two young sons to raise.”

As it turned out, his (seemingly very valid) worries turned out to be unfounded. By the time he got home after lunch with a couple of trusted colleagues, he had received calls from Chase, W.R. Grace, Dun & Bradstreet, and Ford Motor Company—they all wanted to do business.

“Sometimes when you decide to take control of your own fate, the universe opens up for you,” he says. “It’s funny how that works.”

Even if it doesn’t all come together immediately, Dilenschneider says that if you’re doing what makes you happy rather than what others expect of you, you won’t regret the hard work.

“There may be moments of fear and doubt and even despair that come with the exhilaration,” he says. “That’s life. But the brand of growth and resilience that come from reinventing yourself and building a career that means something can’t be earned any other way.”

Robert L. Dilenschneider, author of Wall Street Journaland USA TODAYbestseller The Ultimate Guide to Power & Influence: Everything You Need to Know, formed The Dilenschneider Group in October 1991. Headquartered in New York, Miami, and Chicago, the firm provides strategic advice and counsel to Fortune 500 companies and leading families and individuals around the world, with experience in fields ranging from mergers and acquisitions and crisis communications to marketing, government affairs, and international media.

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