What I Took Away from My First Men's Retreat

Borrowed

"Vulnerability is at the core of shame and fear and our struggle for worthiness, but it appears it is also the birthplace of joy, of creativity, of belonging, of love."

Brené Brown, quoted in "An Everyone Culture" by Robert Kegan & Lisa Laskow Lahey [Book]

Learned

Yesterday was my birthday, and while I didn’t plan it this way, I spent the weekend before it on my first men’s retreat. It was four days. No rushing between meetings. No backlog of notifications. And… no showers! Just space to take it all in and feel immersed in nature. Afterward, the guys joked about how those four days felt more like four weeks. Maybe even months. It’s incredible what happens when you’re fully present to experience the day.

The past year has been full of new experiences, growth, and responsibilities. Every day, I carve out time to journal, read, and exercise. While it feels like I make space to sit with my thoughts, part of me wondered what it would be like to step outside the daily rhythm and ask, how am I really doing?

I like to think I found the retreat by chance. My flight to the Shopify conference in Toronto got delayed by just 10 minutes or so, and while going to respond to a message on Instagram, I came across Michael Chernow’s post. I was familiar with Chernow’s story of overcoming addiction and admired the life and businesses he’s built. I’d also heard him describe his first breathwork experience with Michael Gazzo and what it uncovered for him. Gazzo’s work would be central to the retreat.

Normally, I’d overthink an application like this, but this time I hastily filled it out and submitted it just before takeoff. A few days after returning home, I learned I’d been accepted. With Dana’s encouragement, I decided to go for it.

On our group intro call the week before the retreat, Chernow mentioned how this experience can be powerful for people whose lives are 95 percent great, but there’s still 5 percent keeping them from fully appreciating it. That 95 percent looks different for everyone, could be more or less, but still, this concept resonated. I was curious to understand what that last percentage might look like for me.

The retreat brought together twenty-some men. Some entrepreneurs. Some artists and athletes. Some veterans. Mostly strangers. What surprised me wasn’t our differences, but how quickly those differences stopped mattering. There’s something powerful about being with people who aren’t trying to fix each other or give advice. Just being there. Listening. Seeing one another.

That first night, we sat around a fire and shared why we had come. What we were carrying. What we were hoping to release. Some had a clear reason. Others didn’t know yet, but felt called to be there. And over the next few days, those reasons kept revealing themselves.

There were sauna and ice bath sessions, a ruck, great food, among other things, but many of the most powerful moments came from hearing each other share after breathwork.

Every breathwork session peeled back a new layer. For me, it was fear I didn’t realize I’d been holding onto. Judgment I’d worn like protection. The pressure of trying to hold it all together. I remembered experiences I hadn’t thought about in decades - from being bullied on the playground to the joy of feeling seen after my first talent show. But underneath it all, there is a part of me that still holds back. While I’ve built a life I’m proud of, I’ve also quietly carried stories about who I need to be to feel safe and respected. I saw the ripple effects of that, not just in my own life, but in the way I relate to the people closest to me.

There was discomfort in confronting all of this, but there was peace in how honest it felt.

One night, I shared a song I wrote years ago called Young at Heart. Outside of singing nursery rhymes to my son Mylo, I hadn’t played music in a long time. But I felt called to share it and it felt incredible to release. The song is about carrying the passion, wonder, and curiosity of childhood through life’s transitions. The kind I see in Mylo’s eyes every day. Playing it reminded me that some parts of ourselves don’t need to be left behind. They can come with us, if we make room. I fell asleep that night reminded how much I’ve missed this part of myself.

I kept returning to Mylo throughout the trip. To how much he’s already learning by watching me. Not just how I treat others, but how I treat myself and connect with people. I want him to grow up knowing it’s okay to feel. That strength includes softness. That being open and steady go hand in hand. But if I want him to believe that, I have to model it.

During one of the final breathwork sessions, I saw my Pop-Pop. He passed years ago, but his presence felt close. I thought about the joy he brought into people’s lives. The line out the door at his funeral. How he made others feel welcome. His own quiet kind of kindness. How he held our family together in ways I probably won’t ever fully understand. I realized how much of that I’ve tried to carry forward, and how important it is to me to keep his spirit alive in how I lead, live, and show up for the people I love.

Toward the end of that session, I saw white light and felt my body lifting off the ground. I was overcome by fear and bliss all at once. You’re told to lean into those emotions during breathwork, so I did. I checked my Whoop data after and saw my heart rate reached 160. It was unlike anything I’d ever experienced. And it felt incredibly special.

All week, I’ve been reflecting on the retreat and debating whether or how much to share. It’s hard to put into words just how meaningful it was, and uncomfortable to commit to the words. There's so much more to say. I chose to share because if there’s one thing I’ve learned, it’s that when one man does, it opens the door for others to do the same. And sometimes, that’s enough to create real change.

We don’t talk about our emotions much as men. It’s funny how we can spend hours with a friend and never go beyond the surface. But we’re taught to stay in motion. To keep it all inside. To be strong. Over time, that builds up. Eventually, we disconnect from how we feel, or worse, feel nothing at all.

What I saw on this retreat is what becomes possible when men make time to slow down and speak openly. Not because we solve each other’s problems, but because we remind one another we’re not alone and our challenges are not unique. That what we can lighten what we carry. That letting it out doesn’t make us weak. It brings us closer to who we once were and want to be.

For as long as I can remember, I’ve been a bit of a lone wolf. I keep a tight circle. I try to figure things out on my own. While there’s been value in that, these four days showed me how good it feels to connect with other men. A kind of brotherhood where you don’t have to perform or size each other up. Where certain things don’t need to be explained because they’re just understood.

I’m starting to see how much this kind of connection matters. Especially during challenging seasons or times of transition. I still value my independence, but the thought of having others walk alongside me through life’s big questions feels good.

I’m grateful to Michael Chernow, Michael Gazzo, and his council, Anthony Escobar, David Brown, Ricky Baldonado, and Scott McDonald, for bringing this crew together. For the generosity, care, and intention behind every moment. For giving us the chance to step back and ask, who am I becoming? And of course, lots of love to the guys who showed up so fully and made the space what it was.

On our retreat intro call, we each shared something from childhood we wished we did more of. I said performing music. A couple days later, a friend invited me to play a local show he was putting together. I played it this past Saturday at a venue that holds a special place in my heart, from years of playing there in High School. It was the evening before my birthday, and it just felt right. I’ve always told people I’d return to music one day when I felt drawn back in.

Standing on that stage again, I thought, maybe this is that calling? I can’t thank the guys enough for their encouragement after hearing me sing around the fire and my friend Pat for inviting me to perform. I have to believe this all came together for a reason.

As I step into another year around the sun, I’m not claiming to have everything figured out. But I feel a quieter kind of clarity. A deep commitment to the work. And to keep showing up for this never-ending journey of becoming better.

To be a better husband to Dana. A better father to Mylo. A better son. A better brother. A better friend, leader, and so on. And to live in a way that invites other men to do the same.

Thought

What’s the 5, 10, or 15 percent holding me back from fully appreciating the rest of my life?

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If you're curious to check out my song, Young at Heart, you can listen on Spotify.