When Is It Time to Step Down?
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In a candid moment, John Mackey, the co-founder of Whole Foods, shared, “It wasn’t really exciting any longer.” This sentiment strikes at the heart of a significant turning point in the lives of many executives. When Mackey sold his business to Amazon in 2017, he had committed to a five-year tenure post-sale. Yet, as time passed, the cultural friction with the corporate giant weighed heavily on him. By the time the fifth anniversary approached, he informed Amazon’s leadership of his intent to depart.
One of the pivotal reasons for Mackey’s departure was the realization that he was “the last man standing.” The trusted colleagues who had helped him transform a modest Austin store in 1980 into a formidable brand had moved on. “Those were the people that I was in the foxholes with,” Mackey reflected. “We shared triumphs. We mourned together the losses.”
It’s fascinating, isn’t it? How the bonds built during moments of adversity become a cornerstone of our professional lives. Yet, for many CEOs, stepping back can feel like standing at the edge of an abyss. They wrestle with questions of identity, responsibility, and the void left by their absence. The transition to a life beyond the corner office is seldom smooth.
In conversations with a variety of executives, the consensus emerged: recognizing when to step aside is a nuanced journey. Every journey is unique, with each leader sharing tales that weave together struggles and realizations. For instance, in recent months, the Corporate world witnessed a significant uptick in CEO transitions. Linda Yaccarino’s departure from Elon Musk’s social media platform, X, after just two years, is a notable example in a landscape where the turnover rate for S&P 500 CEOs is projected to hit an astonishing 14.6%—the highest since 2001, according to insights from The Conference Board and ESGAUGE.
When It Doesn’t Feel Scary
Reshma Saujani, the founder of Girls Who Code, offers a compelling criterion for leaders contemplating an exit. She asserts: “When you walk into work and it doesn’t feel scary, you know it’s time to go.” Saujani stepped down in 2021, eager to launch a new nonprofit, Moms First. This decision echoed a realization that her strengths lay in the startup environment—solving problems, rallying teams, and fostering growth.
Reflecting on her journey, Saujani stated, “We were past that point.” Her vision for the organization had been achieved, essentially maturing from a startup into a well-established entity, a phase she likened to being a teenager. Despite advice from notable friends like Twitter co-founder Jack Dorsey—who counseled against staying on—Saujani has held onto her role as a board member. “This is my baby,” she proudly affirms.
A Journey of Humility
Rick Hammell, founder of Atlas, a human resources service, faced a similar crossroads. After nearly nine years, he grappled with whether he was still the right fit to guide the company into its next chapter. “It took a lot of humility,” he admitted. Yet, upon reflection, he recognized a stark reality: he was spending more time in meetings than engaging with customers, and that weighed upon him.
He’s not alone in this realization. Bill George, a former CEO at Medtronic, took a proactive approach to his upcoming departure. Knowing he wanted to serve no more than a decade, George met with a therapist to preemptively address the emotional toll of transitioning out of the CEO role. “You start to say, ‘Well, why would I give all this up?'” he candidly asked.
Leaving a Legacy
For George Guilmette, head of Alight, the mantra “Try to leave it better than you got it” guided his exit from a previous CEO role in 2023. This philosophy underlies a broader understanding that a successful transition is not merely about leaving but ensuring the organization thrives in the leader’s absence.
Life After Being the CEO
George Barrett, former CEO of Cardinal Health, meticulously planned his exit, valuing his energy and the opportunities that lie beyond leadership. He expressed the importance of stepping down to create space for successors and pursue personal passions like music—a desire nurtured since childhood. “I had a pretty strong sense that I wanted to do some things afterward,” Barrett clarified.
As Mackey embarked on new ventures, including the wellness company Love.Life, he confronted introspection, asking himself, “What does the company most need me to do now?” In 2021, that answer crystallized. “What the company most needs me to do now is leave.”
This leads us to an important question: Are you prepared to confront your transitions? Whether you’re bowing out or considering what lies ahead, understanding the indicators can pave the way for fulfillment, both personally and professionally. The journey of stepping back may be as profound as stepping forward.
As we reflect on these narratives, it becomes evident that leadership is as much about knowing when to hold on as it is about knowing when to let go. What legacy will you leave behind? How will you navigate your next chapter?
