A Thrill-Seeking CEO—Who Has Jumped Out Of Planes More Than 200 Times—Says Skydiving Is The ‘Greatest Mental Health Reset’

Fortune Well November 2, 2023


A Thrill-Seeking CEO—Who Has Jumped Out Of Planes More Than 200 Times—Says Skydiving Is The ‘Greatest Mental Health Reset’

When Isa Watson needs to clear her head, she jumps out of a plane. The Brooklyn-based author and entrepreneur considers skydiving her “greatest mental health reset.” And she may be on to something. Studies show that the adrenaline rush can help increase mental concentration, make you more alert and give you more energy.

“I’ve struggled with depression on and off since I was a kid, but what really made me have to address it was becoming a founder,” says Watson, who founded Squad, an audio-only social app, in 2018. “Becoming a founder is one of the most isolating experiences. It’s very anxiety-inducing and it’s a really hard path.”

In an effort to refuel her tank and learn how to take better care of herself and her mental health, Watson began experimenting with different self-care activities, such as guided meditation, traveling and skiing. But at some point during the early years of the COVID-19 pandemic, those tools were no longer working for her.

“I always wanted to try skydiving and it was the most serenity I’ve ever felt,” Watson says of her first jump at Mauritius, an island nation off the coast of Madagascar. “It was a mental health reset for me. When I go to the drop zone, I feel like I’m in a different world.”

Watson has completed more than 200 jumps since she started skydiving two years ago and she’s currently training to compete in the 2024 US Nationals for Skydiving. Although she’s often the only Black woman at a jump zone, Watson appreciates the skydiving community for being laid back—a stark contrast to the entrepreneurial world. Once on the plane, Watson is able to zone out as she takes in the world below her.

“It really sets the tone of ‘look at all of that down there, look at how beautiful the world looks from up here,” she says. “It’s like all of the horrible news, all of the shootings, all of the political infighting—I don’t see that up there.”

Freedom from intense daily pressure

“I feel like I’m constantly under an immense amount of pressure [in my everyday life],” says Watson. “When you’re a Black woman in this country, you’re expected to be twice as good to get half as much. It’s exhausting. I haven’t had the privilege of feeling free and when I’m skydiving, I feel so free. And once you feel free, you get addicted to feeling free.”

For other founders who may find themselves on the brink of exhaustion and burnout, Watson encourages them to experiment with what makes them feel free and what refuels your tank.

“Just because I parked the car doesn’t mean I’m filling up my tank,” she says. “A lot of founders may be like ‘oh my god, I’m adding another thing to my schedule.’ But it’s not about adding things to our schedule, it’s about using that experimental framework to invest in learning what makes you feel free and refuels you.”

That feeling of freedom is what inspired Watson to create and celebrate the Day of Intentionality on Sept. 20. The call-to-action was also influenced by her debut book, Life Beyond Likes, which launched earlier this year, and encourages people to spend more time connecting with others offline.

“Being intentional is part of your [self-care] toolkit,” she explains. “It’s about centering your joy and owning your happiness. Being intentional is not about changing all of your habits at once, it’s about doing bite-sized things. Intentionality is using the potential of your mind and the power of your actions to live a life rooted in joy.”

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