Founder of Toms shoes went on a men’s retreat with other entrepreneurs to combat his loneliness and depression: ‘I lost a lot of my clear meaning and purpose’

However, when Mycoskie sold a 50% share of the company, valued at $625 million, to Bain Capital in 2014 and stepped back from his leadership role to become the company’s “Chief Shoe Giver,” he learned that entrepreneurial success only gets you so far. 

“I lost a lot of my clear meaning and purpose,” Mycoskie tells Fortune. 

For the last decade, Mycoskie has dealt with periods of depression and loneliness, mainly due to how tightly he had tethered his identity to the brand he once helmed. In a 2016 op-ed in the Harvard Business Review, Mycoskie wrote that he began feeling “disillusioned” despite immense success. “I had lost my connection to many of the executives who were running daily operations. What had once been my reason for being now felt like a job.” At the time, he had taken a sabbatical to think about his next steps.  

He concluded the op-ed optimistic about his goal to expand Toms to a roastery business, donating water to those in need with every coffee bag sold, but his loneliness and depression persisted.

Mycoskie’s loneliness also stems from being somewhat of a nomad. Having recently settled down in the Bay Area with his family, he says he doesn’t have the close friendships he desires. 

His feelings of disconnection finally propelled Mycosckie, who, in March of this year, learned from a friend about a three-day all-men’s retreat in Austin, Texas, hosted by Junto, a community for men to improve their mental health. He signed up and packed his bags. 

He was introduced to other men, many entrepreneurs like himself. Mycoskie participated in exercises around emotional intelligence, relational leadership, and personal integrity—Junto’s three pillars of nonviolent communication. Facilitators talked with the men about how to have difficult conversations, especially with a partner, how to observe versus judge, talk about feelings rather than turn to anger, and how to articulate needs and requests. “That was something I had never heard of,” Mycoskie says. “We each brought up an example in our life where [conflict] would happen. It gave us a real model that we can use both in work and leadership, with coworkers, employees, and boards of directors.” 

Finding connections and community may have been more beneficial for Mycoskie than that sabbatical from work. 

“What caused me to go is just kind of feeling a little bit stuck and a little bit in a rut,” he says. The retreat didn’t focus on men’s physical strengths or professional resumés: They spoke of their challenges, not their titles. “We were asked not to talk at all about what we do,” he says. That was a really powerful thing.” 

Loneliness in the corner office 

Mycoskie’s experience is not an isolated one. Everyone, no matter their gender identity and title, can face loneliness, and underrepresented employees experience far more barriers to the corner office. However, male leaders say they feel disconnected and face immense pressure to represent the stereotypical, emotionless tough guy.

Andrew Horn founded Junto in 2017 after noticing a critical need for connection among men, which has become more apparent amid the broader loneliness epidemic—40% of men say they never talk about their mental health. 

Retreats are becoming one way to fill in the gap as more men are open to finding spaces to connect and be emotionally vulnerable—many for the first time. 

After hosting his first event with eight men in New York City, Horn saw the transformative power of feeling connected and aimed to help men show up authentically in the spaces they live, work, and serve in. 

“There was just a level of realness that came out of it,” he tells Fortune. “From that first moment, I felt so clear that there was something special about this type of space where men could come together to be completely transparent.”

Creating space for men to share their emotions helps them show up more authentically and cultivate purpose, Horn says, who hosts the company’s quarterly retreats. The alternative is damaging. Suppressed emotions can cause people to act out of anger and lead people to harmful alternatives to numb the pain, like self-medicating, says Matthew Hodgkin, a therapist at Lightfully Behavioral Health. 

“We become safer people to be around,” says Horn.

“Emotional mastery,” as Horn puts it, helps people manage emotions like loneliness in real time. Taking time to recognize and reflect on the less-than-glamorous side of life is a part of mastering the mind. 

“If I’m feeling angry, if I’m feeling sad, if I’m feeling shame, those things are going to imprint onto our thoughts and onto our actions,” says Horn. “Do I want that to happen consciously or unconsciously?”

Learning to open up 

Being vulnerable often feels scary at first pass, and Mycoskie was not immune to the phenomenon. 

“You’re kind of looking around the room, you’re kind of wondering, ‘Am I in the right place?’” Mycoskie says of the retreat experience. “There’s a certain set of doubts. Do the guys have the same challenges I have? Is this going to be meaningful?”

Eventually, though, Mycoskie shared what he was grateful for and his feelings of depression and loneliness after moving on from his business. “We all had some commonalities that we could really unpack together,” he says.  

After the retreat, while not naive to believe it’s a fix-all, Mycoskie, whose company has since been taken over by creditors to restructure debt, reflected on how to find more purpose. He is toying with starting a coaching business to help other entrepreneurs and plans to take the communication lessons into his marriage. He also sees spaces for men to challenge instilled narratives about masculinity as crucial for improving mental health outcomes, relationships, and leadership. “Anything that you’re going through, there’s a very good chance there’ll be a couple, other men, at least, going through the same thing,” Mycoskie says, who noticed how authentic communication can be the antidote to loneliness. “You’re not just thinking about it in a silo by yourself.” 

While men’s retreats can cost a couple thousand dollars for a weekend, Horn hopes to make “emotional mastery” more commonplace by giving groups of men the tools and curriculum to do this on their own time—in or out of the office.

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