From Brian Chesky And Tim Cook To The Founder Of Toms Shoes, It’s Lonely At The Top. Here’s Why It Matters And How To Feel More Connected | Old North State Wealth News
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From Brian Chesky and Tim Cook to the founder of Toms shoes, it’s lonely at the top. Here’s why it matters and how to feel more connected

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While success has obvious perks, it sure doesn’t exempt you from the loneliness epidemic. We idealize the hustle to the top, but there’s an unspoken struggle many company leaders grapple with when the view isn’t coupled with feelings of connection and belonging. A 2022 survey from Deloitte found a third of the c-suite feels lonely. The researchers estimate that a vast majority—70%—of executives consider quitting their jobs in part due to the feeling of loneliness and poor well-being. 

“CEOs can be constantly surrounded by people and still experience loneliness,” Ryan Jenkins, author of Connectable: How Leaders Can Move Teams From Isolated to All In, tells Fortune in an email interview. After all, the higher you climb the corporate ladder, the more responsibility and stress rests on your shoulders to make decisions as an individual rather than as a team.

Even CEOs of some of the most prestigious companies admit that being in the top seat is an isolating experience. The founder of renowned buy-one-give-one shoes company Toms, Blake Mycoskie, grappled with depression and loneliness amid his company’s major successes. Apple’s Tim Cook said being CEO is a “lonely job,” and Airbnb’s Brian Chesky frequently said that his rise only perpetuated his loneliness. 

“I started leading from the front, at the top of the mountain, but then the higher you get to the peak, the fewer people there are with you,” Chesky told Jay Shetty during an episode of On Purpose last year. “No one ever told me how lonely it would get.”  

Loneliness in the C-suite is not a new phenomenon. In a 2012 Fortune interview, Thomas Saporito, former chairman and CEO of RHR International, said, “The notion that it’s lonely at the top is not just a trite phrase. I’ve been at this for over 30 years, and I’ve spoken with 200 plus CEOs—there are precious few that didn’t, in the privacy of our discussions, talk about loneliness.”

Experts say that addressing loneliness at the top can have profound impacts—improving people’s mental and physical health—and strengthening the well-being and engagement of employees who look to their leaders for guidance.

How to combat loneliness at work

See loneliness as a ‘signal’ 

Often, leaders avoid addressing their feelings of doubt and uncertainty, which can catalyze their loneliness. 

“When people face a problem with a lot of unknowns, they often pull back, isolating themselves rather than seeking the advice they need,” says Carter Cast, former CEO of Walmart.com, quoted in Jenkins’ book. “People get scared and retreat. The loneliest I have ever been was when I was managing at scale, and I just did not know if I was doing it right. I did not know who I could talk to.”

But, if a leader feels lonely, experts recommend that they share their experience—particularly their challenges on the job—with a partner, mentor, or professional. 

“Loneliness isn’t shameful; it’s a signal,” says Jenkins, who works to create innovative ways to improve employee connection and engagement, including practicing emotional vulnerability. “CEOs shouldn’t be ashamed of loneliness but view it as their innate reminder that their influential presence matters to others.” 

Pivot from manager to leader 

While pervasive loneliness at the top can stem from fear and uncertainty about business decisions, it may also result from not knowing how to lead those who look up to you. Almost two-thirds of CEOs don’t get coaching or leadership advice from those outside their organization, according to a 2013 survey from Stanford; even before getting to the C-suite, new managers are seldom trained on being a leader. 

“New managers don’t realize what they’re about to take on,” Dr. Rich Safeer, the chief medical director of employee health and well-being at Johns Hopkins Medicine, tells Fortune. “Most companies don’t prepare new managers beforehand.” Only 33% of managers feel able to support their employees’ mental health, according to a survey released this summer from Spring Health. And yet, research suggests that a boss can play a more significant role in employees’ mental health than a therapist.

When leaders see their teams holistically, they prioritize connection, combat their own loneliness, and help others feel a sense of community.

While leadership training is crucial, Safeer says leaders can also support their employees by making space to get to know their teams. They can host office hours to be approachable and show care for people’s lives in and outside of work. After all, more people find human-centered leaders supportive and relatable.

“Leaders need to start improving their relationship with those they lead,” Safeer says, which includes being more transparent about their triumphs and challenges. “They need to be better listeners. They need to be more vulnerable and share what their challenges are. They need to show more appreciation.” 

Men, in particular, face stereotypical conditioning around emotional vulnerability. However, many executives who attended all-men’s retreats, for example, reported feeling connected to others when they shared their feelings and talked about their lives beyond their successes. 

“People are not used to seeing leaders courageously open up, and I think it’s just a breath of fresh air,” Craig White, founder of Men Without Masks, a retreat based in the U.K. previously told Fortune. “When I’ve seen it, it gives permission for everybody within the organization to potentially do the same.”

Reconnect with friends outside of work

As does everyone, corporate leaders need room to be vulnerable by having support from friends. “So much of my life was about being successful … I thought that would make people love me,” Chesky tells Shetty in the podcast. 

Former President Barack Obama, a long-time mentor of Chesky’s, helped him realize the driving force behind his dissatisfaction beyond the office. 

“I think you’re kind of lonely, and you probably need to renew friendships,” Chesky recalls Obama telling him in a 2021 conversation. Chesky says the former president was able to maintain 10 to 15 relationships, many of whom he had a connection with before he took office. 

“They kept him grounded and rooted, and your roots come from your past, and your past is often your relationships,” Chesky says. “It’s hard to lose your mind when you have deep connections and relationships … I realized I hadn’t maintained relationships.” 

Maintaining friends as we age isn’t an easy, breezy walk in the park. An AARP survey found nearly half of those 50 and older say keeping friends is difficult. 

“As we approach middle age, we have found ourselves busy,” Marc Schulz, coauthor of The Good Life and associate director of the Harvard Study of Adult Development, previously told Fortune. “Some people wake up and realize that they really need to rebuild their friendship connections…a lot of their social connections may revolve just around work, or just around other sorts of activities that their kids do.” 

A CEO’s influence is a privilege, and how they combat loneliness is integral to improving their well-being and the health of an organization.  

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