Goodbye, Tough Guy

More executives are going on all-male retreats to open up, feel less lonely, and build empathy. 

-  ALEXA MIKHAIL

TO THE OUTSIDE OBSERVER, Matt Calderwood was the picture of corporate success. For over 20 years, he delivered results-no matter the circumstances. This mindset initially served him professionally, propelling him to the C-suite, where he oversees 150 employees as managing director of the Americas for multinational software provider SA Global. "I was very good at fragmenting my mind, segmenting the emotions, and putting them in different boxes just to be able to hit the goals at any cost," he says.

The cost became apparent in 2019, when Calderwood was newly divorced and had no one to open up to about it. He broke down crying when he read about a retreat that helped men find purpose and connection. A few weeks later, he was on an eight-day retreat in Glacier National Park hosted by Evryman, a men's wellness platform founded in 2016. There, he allowed himself to be vulnerable crying and sharing with 15 other men as they backpacked through the woods.

Each day, the men would hike for four hours, two of which were in silence. They had guided conversations about their relationships, work life, and past. One day was devoted to understanding their anger, followed by cold plunges and meditation.

Calderwood came back from this community feeling as if he were not only a more authentic person but also a better leader-more adept at being present for his team and leading with empathy. "I work in tech, but what gets me out of bed every morning is helping people become the best person that they can be," says Calderwood, now 43.