How CEOs know when it’s time to quit

After more than four decades running Whole Foods, cofounder John Mackey’s heart was telling him it was time to go.

“It wasn’t really exciting any longer,” he told Business Insider.

When Mackey sold the business to Amazon in 2017, he committed to staying on for five years. Over time, however, struggles with the retail behemoth around culture took a toll, Mackey said. A year before the fifth anniversary of the sale, he told Amazon’s higher-ups that he intended to leave.

Mackey said another big factor behind his decision was his status as “the last man standing.” The colleagues who’d helped him propel the grocer from a single Austin location in 1980 to a natural foods powerhouse had moved on.

“Those were the people that I was in the foxholes with,” Mackey said. “We shared the triumphs. We mourned together the losses.”

For CEOs, it can be vexing to grapple with when — and how — to descend from what could be the pinnacle of their careers. Former chiefs sometimes struggle with a loss of identity, leaving behind work they care about, and letting go of big-time perks.

BI spoke to a half-dozen execs about how they knew it was time to move on. Their reasons varied, though all said giving up work they loved wasn’t always easy.

Nevertheless, more CEOs are stepping aside these days, whether by choice or otherwise. Last week, Linda Yaccarino announced she was leaving her job running Elon Musk’s social media platform, X, after just two years.

The number of CEO changes for S&P 500 companies is on pace to reach 14.6% for the year, according to data from The Conference Board and ESGAUGE. This would mark the highest turnover rate for CEOs since 2001.

When it doesn’t feel scary

Reshma Saujani, who founded the nonprofit Girls Who Code in 2012 to close the gender gap in tech, said leaders should look for the exit when they stop being afraid.

“When you walk into work and it doesn’t feel scary, you know it’s time to go,” she told BI.

Saujani gave up her CEO role in 2021, in part because she wanted to develop a nonprofit called Moms First, which began as a Girls Who Code initiative.

She said her strength is as a startup entrepreneur. That involves figuring out a problem, communicating about it, working to solve it, and building teams.

“We were kind of past that point,” she said of Girls Who Code. It had gone from being a startup to “basically being a teenager.”

Saujani said she rejected the advice of friend and Twitter cofounder Jack Dorsey, whom she said told her that most founders shouldn’t stay on as directors. Saujani maintains a permanent seat on the board of Girls Who Code.

“This is my baby,” she said.

Rick Hammell’s baby was Atlas, a human resources services company he started and ran for nearly nine years until 2023.

He said it was hard, but he eventually asked himself whether he was the right person to take Atlas to the next level.

“It took a lot of humility, I will say,” Hammell told BI.

Ultimately, he decided to leave because he found himself spending more time in meetings with his board and investors than with customers. Hammell woke up one day and decided he was done.

He left to start Helios, which helps employers manage global workforces, so he could get his “hands dirty again” by building something new.

Setting a deadline

Even for CEOs who aren’t founders, letting go of an all-consuming job can be hard. It was for Bill George, who was CEO at the medical device maker Medtronic until 2001.

George said he knew from the start he wanted to be chief for no more than a decade because, with few exceptions, he felt CEOs performed best in their first decade on the job. As his self-imposed deadline drew closer, he said he was unnerved by the thought of letting go.

It wasn’t just the work or colleagues he’d be leaving. Chiefs who’ve been on the job longer tend to have more influence than the newbies, George said, and longtime CEOs often get invited to take part in important events, fancy conferences, and White House gatherings.

“You start to say, ‘Well, why would I give all this up?'” said George, who is now an executive fellow at Harvard Business School.

In his final six months or so as CEO, he met regularly with a therapist to prepare for the ultimate hard stop: going from overseeing some 30,000 employees to having a head-spinning amount of free time.

“All of a sudden,” he said, “it’s you, and if you’re lucky, a part-time assistant.”

In the lead up, George said he also reminded himself that he was leaving the company “in good shape.”

That’s similar to what Dave Guilmette, head of the employee-benefits administrator Alight, thought when he left his previous CEO role at a division of the insurance brokerage Aon in 2023.

“I had this basic mantra: Try to leave it better than you got it,” Guilmette told BI.

Life after being the CEO

Like George, former Cardinal Health CEO George Barrett knew he wanted to limit his time running the medical products distributor to about a decade so that he’d finish the job with as much energy as he had at the start.

“That was really important to me, because I had a pretty strong sense that I wanted to do some things afterwards,” Barrett told BI.

Stepping down also carved out “opportunity and space” for successors.

Barrett said he knew he didn’t want to run another big company, in part, because he wanted to teach, mentor, and focus on policy work. He also wanted to spend more time making music, something he’d studied in his youth.

In his decades at Whole Foods, Mackey, who has since started the wellness company Love.Life, said he was able to grow the grocer by continually asking, “What does the company most need me to do now?”

In 2021, Mackey quizzed himself again and came up with a novel answer: “What the company most needs me to do now is leave.”

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