Want to Be a Better Boss? Try Playing Hooky. How a midday Mets game became a formative leadership experience
This story appears in the November 2023 issue of Entrepreneur. Subscribe »
My team was two weeks away from hosting a big event. There was a lot left to do. But my boss, Lisa, had just learned of a more imminent big event: a midday Mets game, where one pitcher had the rare chance to win his 20th game.
"We have to go," she said.
I was skeptical. It hardly felt like an ideal time for an afternoon adventure! But Lisa insisted that we could tackle the work later, because this Mets game would only happen once. She got tickets for herself, me, and a junior team member. When that pitcher secured his win, the three of us were there. And weeks later, when we hosted our successful company event, all was well — with nothing sacrificed from our outing.
This experience underscored a lesson I'd learn repeatedly from Lisa: Work benefits from time away from work. And team outings — particularly ones that remove hierarchy — are underrated ways to bond.
Three years after that game, Lisa's lesson would extend much further: Not only does work benefit from time away from work, but people benefit from the bonds that go beyond work. In 2015, I was diagnosed with cancer. The timing was especially unfortunate because I'd recently resigned from our company to pursue an entrepreneurial venture. But as soon as I told Lisa my biopsy results, she reversed my resignation to give me a paid medical leave, even though it meant she could not fill my headcount. She also gave me the names of both surgeons I consulted, one of whom I ultimately hired.
"All of your executive skills will come to bear now," she told me the morning I was diagnosed. Again, she saw that thread of connection: Our careers and personal lives complement each other.
After completing my treatment, at a team lunch the following year, Lisa toasted my health and bright future. Then she gifted me a circular gold and diamond necklace as a symbol of the light she saw in me. Three weeks later, she herself received a devastating pancreatic cancer diagnosis — and 16 months later, the same week I learned that my own cancer had returned, Lisa passed away.
Five years later, I run a well-being company that empowers executives and their teams to flourish, and I regularly think of Lisa and pay her lessons forward. She is present in how I value play alongside work; in how I include others regardless of title or hierarchy; and most of all, in how I have leaned into the work of patient advocacy and become a champion for health equity. And as I do, every morning, I put on the necklace Lisa gifted me. Whatever awaits me that day, she stays close to my heart (literally), there with me to celebrate every win.
