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.”
Instead of divulging to a trusted friend or anonymously airing out her frustrations on Reddit, Nooyi looked inward. She was the only person she could trust, even if that meant embracing the isolation.
“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.”
“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.”
Apple CEO Tim Cook isn’t immune to the loneliness that often comes with the corner office. More than 14 years into his tenure, he’s acknowledged his missteps, which he called “blind spots,” that have the potential to affect thousands of workers across the company if left unchecked. Cook said it’s important for leaders to get out of their own heads and surround themselves with bright people who bring out the best in them.



