Men’s Work #3: The Courage to be Authentic
“Intimacy is sharing those most private thoughts, feelings, and secret parts of ourselves over a long period of time. It is something we all need and crave—and few of us men have known the comfort or experienced the joy of true intimacy, especially with other men.”
— A Circle of Men by Bill Kauth
Most men long for deeper, lasting connections with other men—relationships where they feel understood by men who truly know where they’re coming from. Yet many of us don’t know how to create those kinds of friendships.
We can spend years talking about work, sports, politics, or the latest project while carefully avoiding the conversations that reveal who we really are. I call these conversations “coffee talk”—the comfortable, surface-level conversations that rarely reveal what’s truly happening inside us. And I’m just as guilty of it as anyone. The truth is, I crave something deeper.
Why don’t we just open up?
For many of us, it simply wasn’t modeled growing up. We learned to be capable instead of vulnerable, to solve problems instead of sharing our struggles, and to protect ourselves from rejection by keeping the deeper parts of ourselves hidden. Over time, those habits become walls. We can be surrounded by people and still feel profoundly alone.
The irony is that what many men are searching for isn’t more advice, more success, or even more activity. It’s to be truly seen, accepted, and known. That kind of connection doesn’t happen by accident. It begins when one man is willing to be authentic enough to go first.
Not every relationship will go deep—and that’s okay. I have friends and family members with whom that level of connection simply isn’t there. Over the years, I’ve learned not to force it. Some people genuinely want to explore life’s deeper questions, while others may not be at a place in their own journey where those conversations feel natural. Depth requires curiosity, self-awareness, and a willingness to be vulnerable. It begins with a genuine desire to know another person and to be known yourself.
I’ve also noticed something interesting: sometimes it feels easier to have a meaningful conversation with a stranger than with someone I’ve known for years. With people we have long histories with, there can be unspoken expectations, familiar roles, and patterns that make it difficult to show up differently. Strangers, on the other hand, have no preconceived ideas about who we are or who we’re supposed to be. Without those expectations, it can feel safer to speak honestly and allow deeper conversations to unfold.
That’s one of the gifts of our men’s circle. We create a space built on trust and confidentiality. What is shared remains confidential. We speak our truth. We listen without trying to fix one another. This can be challenging for many of us men because our instinct is often to solve problems and offer advice. But sometimes what another man needs most is not a solution—it’s to be heard, understood, and reminded that he doesn’t have to carry everything alone.
Trust isn’t created in a single conversation; it’s built over time as men consistently show up with honesty, vulnerability, and authenticity. That’s where real connection begins.
“The new knights [Aaron Kipnis’s own men’s group] don’t have any special chemistry or magic. We’re not particularly brave, smart, cool, or lucky. We’re essentially ordinary men who took the risk of reaching out to one another. We asked each other for help and offered it in return. We didn’t pay anyone to be our expert healer. We just took turns. Fools and wise men all, stumbling along through the dark, being steadfast companions to one another in quest of masculine soul.”
— Aaron R. Kipnis, Ph.D., Knights Without Armor
A challenge
This week, choose one man you trust. Skip the coffee talk. Ask him a question that can’t be answered with a word or two:
How are you really doing?
What’s been weighing on you lately?
What’s bringing you joy?
Then, when he asks you the same question, have the courage to tell him the truth.
Someone has to go first. Why not let it be you?
-Dwight
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