Sunday, March 15, 2026

From Brian Chesky and Tim Cook to the founding father of Toms Shoes, it’s lonely at the highest. Here’s why it matters and the way you may feel more connected

From Brian Chesky and Tim Cook to the founding father of Toms Shoes, it’s lonely at the highest. Here’s why it matters and the way you may feel more connected

While success has obvious advantages, it definitely doesn’t free you from the loneliness epidemic. We idealize rising to the highest, but there’s an unspoken struggle many business leaders face when that success is not coupled with feelings of connection and belonging. A 2022 survey by Deloitte found that one-third of top executives feel lonely. The researchers estimate that a big majority – 70% – of executives are considering quitting their jobs, partly as a result of feelings of loneliness and poor well-being.

“CEOs can be constantly surrounded by people and still feel lonely,” says Ryan Jenkins, writer of Connectable: How leaders can lead teams from isolated to integrated teamstold Assets in an email interview. Because the upper you climb the profession ladder, the more responsibility and stress falls in your shoulders to make decisions as a person reasonably than as a team.

Even CEOs of among the most prestigious firms admit that being at the highest is a lonely experience. Blake Mycoskie, founding father of the renowned shoe manufacturer Toms, which operates on the motto “buy-one, give-one”, struggled with depression and loneliness despite his company’s great successes. Tim Cook from Apple said being a CEO was a “lonely job,” and Airbnb’s Brian Chesky incessantly said his rise to power had only increased his loneliness.

“I started leading from the front, at the top of the mountain, but the higher you get to the top, the fewer people there are with you,” Chesky told Jay Shetty in an episode of Intentionally last 12 months. “Nobody ever told me how lonely it would be.”

Loneliness in the manager suite shouldn’t be a brand new phenomenon. In a study from 2012 Assets In an interview, Thomas Saporito, former chairman and CEO of RHR International, said: “The idea that it’s lonely at the top is not just a cliché. I’ve been around for over 30 years and have spoken to over 200 CEOs – there’s hardly anyone who hasn’t talked about loneliness in the privacy of our conversations.”

According to experts, tackling loneliness on the leadership level can have profound effects: it improves people’s mental and physical health and strengthens the well-being and engagement of employees who take guidance from their managers.

How to fight loneliness at work

Consider loneliness as a “signal”

Leaders often avoid addressing their doubts and insecurities, which may worsen their loneliness.

“When people face a problem with a lot of unknowns, they often withdraw and isolate themselves rather than seek the advice they need,” says Carter Cast, former CEO of Walmart.com, who’s quoted in Jenkins’ book. “People get scared and withdraw. I was the loneliest when I was managing at scale and just didn’t know if I was doing it right. I didn’t know who to talk to.”

However, if a manager feels lonely, experts recommend sharing their experiences – especially the challenges at work – with a partner, mentor or skilled.

“Loneliness is not a shame, it’s a badge,” says Jenkins, who develops revolutionary ways to enhance worker retention and engagement, including practicing emotional vulnerability. “CEOs should not be ashamed of their loneliness, but see it as an innate reminder that their influential presence matters to others.”

From manager to leader

While pervasive loneliness at the highest may end up from fear and uncertainty about business decisions, it might probably also result from not knowing how one can lead those that look as much as you. Nearly two-thirds of CEOs don’t receive coaching or leadership advice from people outside their organization, based on a 2013 survey by StanfordEven before they move into the manager suite, recent managers are rarely trained within the role of a pacesetter.

“New managers don’t understand what to expect,” says Dr. Rich Safeer, chief medical officer for worker health and wellness at Johns Hopkins Medicine. Assets. “Most companies don’t prepare new managers in advance.” According to a survey published by Spring Health this summer, only 33% of managers feel empowered to support their employees’ mental health. And yet research suggests that a boss can play a more vital role in worker mental health than a therapist.

When leaders take a look at their teams holistically, they value connection, combat their very own loneliness, and instill a way of community in others.

While leadership training is crucial, Safeer says leaders may also support employees by giving them opportunities to get to know their teams. They can hold office hours to be approachable and show that they care about people’s lives inside and outdoors of labor. Finally, more people find people-centered leaders to be supportive and approachable.

“Leaders need to start improving their relationships with those they lead,” Safeer says. That includes being more transparent about their successes and challenges. “They need to be better listeners. They need to be more open and reveal their challenges. They need to show more appreciation.”

Men particularly face stereotypical stereotypes about emotional vulnerability. However, many leaders who attended men-only seminars, for instance, reported that they felt connected to others after they shared their feelings and talked about their lives beyond their successes.

“People aren’t used to leaders being bold and opening up, and I think this is just a breath of fresh air,” says Craig White, founding father of Men without masksa retreat based within the UK, said previously Assets“If I’ve seen it, it gives everyone within the organization permission to potentially do the same thing.”

Reconnect with friends Outside of labor

Like everyone else, business leaders need the chance to be vulnerable by getting support from their friends. “So much of my life revolved around success… I thought that would make people love me,” Chesky Shetty tells the podcast.

Former President Barack Obama, a longtime mentor to Chesky, helped him discover the driving force behind his discontent outside of office.

“I think you’re a little lonely and probably need to renew your friendships,” Chesky recalls Obama saying in a 2021 conversation. Chesky says the previous president was able to take care of 10 to fifteen relationships, lots of whom he had been in touch with before taking office.

“They gave him stability and support, and roots are in the past, and the past is often the relationships,” Chesky says. “It’s hard to lose your mind when you have deep bonds and relationships… I realized I hadn’t been nurturing relationships.”

Keeping friends as you become old isn’t any easy task. According to an AARP survey, nearly half of individuals over 50 say it’s difficult to maintain friends.

“As we enter middle age, we are very busy,” says Marc Schulz, co-author of The good life and deputy director of the Harvard Study of Adult Development, said previously Assets“Some people wake up and realize they need to rebuild their friendships… many of their social contacts may revolve around work or other activities of their children.”

A CEO’s influence is a privilege and the best way he combats loneliness is critical to improving his well-being and the health of a company.

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