Leading a major corporation offers numerous advantages: executives gain control of globally influential businesses, forge lasting impacts as industry innovators, and receive substantial billion-dollar paychecks. However, as individuals ascend the corporate hierarchy, they might not recognize the colleagues who were outpaced until they've reached the summit. This position can be isolating and singular.
TL;DR
- CEOs like Tim Cook and Brian Chesky find leadership roles isolating and lonely.
- Many executives consider quitting due to lack of energy and feeling alone.
- Leaders like Indra Nooyi and Carol Tomé describe the solitary nature of their positions.
- Entrepreneurs are advised to seek peer connections and support for well-being.
Leaders at some of the world’s largest companies—from Airbnb and UPS to PepsiCo and Apple—are finally opening up about the mental toll that comes with the job. As it turns out, many industry trailblazers are grappling with intense loneliness; at least 40% of executives are thinking of leaving their job, mainly because they’re lacking energy and feel alone in handling daily challenges, according to a Harvard Medical School professor. And the number could even be higher: About 70% of C-suite leaders “are seriously considering quitting for a job that better supports their well-being,” according to a 2022 Deloitte study.
To ward off feelings of isolation, founders and top executives are stepping outside of the office to focus on improving their well-being. Toms founder Blake Mycoskie struggled with depression and loneliness after scaling his once-small shoe business into a billion-dollar behemoth. Feeling disconnected from his life’s purpose and that his “reason for being now felt like a job,” he went on a three-day men’s retreat to work on his mental health. And Seth Berkowitz, the founder and CEO of $350 million dessert giant Insomnia Cookies, cautions bright-eyed entrepreneurs the gig “is not really for everyone.”
“It can be lonely; it’s a solitary life. It really is,” Berkowitz recently told Coins2Day.
Airbnb's cofounder and CEO, Brian Chesky
Airbnb's cofounder and CEO Brian Chesky stands out as one of the most vocal business leaders highlighting the issue of loneliness. Chesky recounted a solitary upbringing, torn between his passion for creative design and athletics, never quite finding his place. However, his mental well-being deteriorated significantly after he took the helm at Airbnb. His two other cofounders, whom he referred to as his “family,”, spent all their time working, exercising, and socializing together, but they became distant once he reached the top of the executive suite.
“As I became a CEO I started leading from the front, at the top of the mountain, but then the higher you get to the peak, the fewer the people there are with you,” Chesky told Jay Shetty during an episode of the On Purpose podcast last year. “No one ever told me how lonely you would get, and I wasn’t prepared for that.”
Chesky recommends budding leaders actually share their power, so no one shoulders the mental burden of entrepreneurship alone.
“I think that ultimately, today, we’re probably living in one of the loneliest times in human history,” Chesky said. “If people were as lonely in yesteryear as they are today, they’d probably perish, because you just couldn’t survive without your tribe.”
Indra Nooyi, who previously led PepsiCo as CEO
Executives at Coins2Day 500 powerhouse PepsiCo are continually challenged by customers, shareholders, directors, and their workforce. Yet, it's also difficult to express frustrations to colleagues who might not grasp—or even comprehend—the difficulties of managing a $209 billion enterprise. Indra Nooyi, the company's previous CEO, mentioned that she frequently felt alone with no one to share her thoughts with.
“You can’t really talk to your spouse all the time. You can’t talk to your friends because it’s confidential stuff about the company. You can’t talk to your board because they are your bosses. You can’t talk to people who work for you because they work for you,” Nooyi told Kellogg Insight, the research magazine for Northwestern’s Kellogg School of Management, earlier this year. “And so it puts you in a fairly lonely position.”
Rather than confiding in a close friend or venting anonymously on Reddit, Nooyi turned her focus inward. She recognized that she was the sole individual she could rely on, even if this path necessitated accepting solitude.
“I would talk to myself. I would go look at myself in a mirror. I would talk to myself. I would rage at myself. I would shed a few tears, then put on some lipstick and come out,” Nooyi said. “That was my go-to because all people need an outlet. And you have to be very careful who your outlet is because you never want them to use it against you at any point.”
Carol Tomé, CEO of UPS
Prior to Carol Tomé assuming the position of UPS CEO, she was warned the leadership role is inherently isolating. This warning didn't deter her initially. However, her perspective shifted once she assumed control of the $75 billion logistics enterprise.
“I would say, ‘How lonely can it really be? It can’t be that lonely?’ What I’ve since learned is that it is extraordinarily lonely,” Tomé told Coins2Day last year.
“When you are a member of an executive team, you hang together…Now, my executive team will wait for me to leave a meeting so that they can debrief together. It’s the reality and you have to get used to it. But it is super lonely.”
Tim Cook, CEO of Apple
Even Apple's CEO, Tim Cook, experiences the isolation common to those in top leadership roles. After more than 14 years at the helm, he's admitted to errors, which he described as “blind spots,” that could impact numerous employees company-wide if not addressed. Cook emphasized the necessity for leaders to step outside their own perspectives and be surrounded by capable individuals who foster their strengths.
“It’s sort of a lonely job,” Cook told The Washington Post in 2016. “The adage that it’s lonely—the CEO job is lonely—is accurate in a lot of ways. I’m not looking for any sympathy.”
Seth Berkowitz, the founder and CEO of Insomnia Cookies

Entrepreneurship can be a deeply fulfilling and rewarding journey: an opportunity to trade a nine-to-five job for a multimillion-dollar fortune, if all the right conditions are met. And while Insomnia Cookies’ Seth Berkowitz loves being a CEO and all the responsibilities that come with it, he cautioned young hopefuls about the weight of the career. He, like Cook, advises aspiring founders to counter loneliness with genuine, meaningful connections.
“It can be lonely; it’s a solitary life. It really is. [During] the harder times, it’s very solitary—finding camaraderie, mentorship, some sense of community, it’s really important,” Berkowitz recently told Coins2Day. “Because I go so deep, it’s sometimes hard to find others and let them in.”
