When to Pivot in Your Career

Do you believe in yourself? Are you willing to take a risk?

Don’t be afraid to take a jump out of fear of going backwards, says Sheryl Sandberg, who early in her career went from a team of tens of thousands at the US Department of the Treasury to a team of just four at Google.

“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?’”

George Steinbrenner had it made. He didn’t have to worry about “going down” in income. An industrialist, he ran a shipping company purchased by his great-grandfather out of Cleveland. He made a lot of money. (He also misused some of that money and was convicted of making illegal campaign contributions to then-president Richard Nixon; later, President Ronald Rea- gan pardoned him.) But Steinbrenner decided he’d had enough of the shipping business, pivoted, and ended up acquiring and running the New York Yankees.

It wasn’t just a matter of spending money but also a way of conducting himself that brought excitement to Yankee Stadium and players. Back then, when the national anthem was played, the teammates would mill around in the dugout. I asked him, why not have players stand at the first-base line, holding hats? Steinbrenner was a real patriot; he made it happen. He understood the significance of a gesture.

Rosalind “Roz” Brewer, the former COO of Starbucks, had a satisfying career with increasingly higher responsibilities. But then the COVID-19 pandemic happened.

“The pandemic was really hitting me at a certain point in my life at a time where I saw the virus impacting communities that needed some form of, first, education, and then to actually really get behind being vaccinated,” she told USA Today. “So that first of all touched me, but what’s most important is looking at it through a much longer-view lens and thinking about the health inequities across the United States.”

She left her stable, well-placed job and in 2021 became CEO of Walgreens Boots Alliance, just as the drugstore chain got involved, as other chains did, with helping to administer COVID-19 vaccines to save lives.

With her move, she became the highest ranking Black CEO on the Fortune 500 list of top executives in the country in 2022, ranks that surely need to grow, as the list includes only six Black CEOs. She is using her prominence to draw attention to women who have had to leave the workforce during the pandemic because of responsibilities such as childcare.

Excerpted from The Ultimate Guide to Power & Influence: Everything You Need to Know, copyright © 2023 by Robert L. Dilenschneider. Reprinted with permission from Matt Holt Books, an imprint of BenBella Books, Inc. All rights

Robert Dilenschneider

Robert L. Dilenschneider has hired more than 3,000 successful professionals, and advised thousands more. He is founder of The Dilenschneider Group, a corporate strategic counseling and public relations firm based in New York City. Formerly president and CEO of Hill & Knowlton, he is the author of the bestselling books Power and Influence, A Briefing for Leaders, On Power and newly released Decisions: Practical Advice from 23 Men and Women Who Shaped the World. For more information, please visit https://robertldilenschneider.com