A few weeks ago I completed the most difficult and, in many ways, the most rewarding trip I’ve ever taken. After an attempt that got derailed in June 2020, four years later my book club finally made it to Peru, to hike the Inca trail to Machu Picchu. While we were there, we also discussed our book, Turn Right at Machu Picchu, by Mark Adams. 

The trip and the discussion were beside the point.

On the surface, hiking Machu Picchu was about taking on a difficult challenge, having a peak life experience, and visiting one of the seven wonders of the world, all in the name of a quirky book club (it was hilarious to tell people on the plane about the lengths to which our group has gone for this book and, ultimately, each other). 

But beneath the planning and logistics, hiking the Inca trail was an excuse for our book club, a group of six guys who have been meeting monthly-ish for almost two decades, to deepen our relationships with one another. Whether we knew that going in or not. 

And I can’t imagine anything more important. 

Today I want to explore one of the most powerful, and vital, support structures for male leaders: the men’s group.

On Men’s Groups

There’s been a lot of research around the current plight of the American male. On the one hand, we’re taught a lot about avoiding anything that could be construed as toxic masculinity, scared shitless of being too assertive lest we get canceled. But on the other, we’re taught to be strong, determined, fearless providers whose bank balances are a direct reflection of our value as human beings. We have to deal with the pressures of work, family, and much more without ever showing any sign of the strain it puts on us. Even our self-help gurus advocate stoicism – emotional mastery – as the virtue to end all virtues. 

We’re put in a pressure cooker and told we cannot show any weakness. No emotions besides anger, and then only sometimes. And not too much.

And if you’re a leader, CEO, or founder, you have to navigate all this in the glare of a spotlight from all around. 

As a result of this unwinnable environment, is it any surprise that the American male withdraws into himself? That, faced with an impossible ideal, he does his best to project the stoic, accomplished exterior that is expected of him, while distancing himself further and further from himself, his own feelings, and the kinds of deep personal connections with others that might illuminate what’s going on underneath? Or (when what’s going on underneath is too painful) even aggressively leans into his masculine side, peacocking the kind of toxic, unfeeling caricature of a man against which society is rightfully pushing? 

In spite of so many cultural changes, the obligation of the American male is still to bear the stress of the pursuit of ever loftier goals, silently and alone. 

And we see the impact. Rates of self reported loneliness have skyrocketed among men. Suicide rates, too. And it’s getting worse, as young men replace roller hockey in the parking lot with PVP FPS gaming, social contact funneled through headphones as they sit alone in their respective basements.

No matter how successful they are (or perhaps because of it, as the pressures mount on the way up), men need the companionship of other men. And for the most part, they don’t get it. 

This is true even if they spend time with other men. I play basketball with men three times per week, but the only kind of communication that’s culturally allowed is banter and trash talk. Anything else, especially anything approaching vulnerability and feelings, is unmasculine and culturally unacceptable. You get metaphorical wedgies for that. 

And yet I talk with male clients every day about the depth of their feelings. Their pain, loneliness, grief, and their pride and love. Men feel as deeply as women. They’re just looked down on if they show their feelings in public, so I’m often the only other male they’ll be real with.

That’s why men’s groups are so important. And why our trip to Machu Picchu was about much more than seeing Incan ruins. 

What is a men’s group?

A men's group is a catch-all term for a group of men that meet regularly. These groups can be focused or started around nearly any common interest – faith, business, book club, etc – but whatever their focus, what differentiates a men’s group from a group of dudes hanging out is the express intention to lower their armor and connect deeply with one another, and themselves. 

We didn’t start our book club with that intention – initially we just wanted an excuse to read books regularly – but over the years, since its founding in 2009, that’s 100% what it’s evolved into. 

Men’s groups meet regularly, usually monthly, and often but not always center around a specific topic. Our conversations frequently begin with a nerdy topic like “subjective vs objective truth as framed by Hanya Yanighara’s masterpiece The People in the Trees,” but they inevitably turn to sharing what’s most important in our lives, our work, and our relationships. 

What’s most important is that I do not have to have my shit together at my book club. I can be sad, confused, or scared. I can let down the facade of perfection I’m asked to wear by our society, be truly seen by my peers without judgment, and be held accountable to becoming the best version of myself. That is a powerful thing.

That’s a men’s group. 

And it’s a key support structure for any man interested in doing more than shutting up and winning (or pretending to) every day until you die.

Why do guys join men’s groups? 

People join men’s groups for all sorts of reasons. Many times the topic itself compels them (parenting, business, relationships, book club), and sometimes they even join knowing that they want a space to go deeper. But I’ve facilitated dozens of these groups now, with hundreds of men, and whatever their initial reason for joining, any men’s group that stays together for any length of time does so because of the bonds they create with fellow members, and the way those bonds enable them to share deeply, be truly seen and understood by their peers, and contribute to making something greater than themselves.

I’ve talked many times before about CEO shit. CEO shit is the stuff you can’t talk about with your friends and family because they’re not in the business, and you can’t talk about with your investors or employees because they’re conflicted. The default for a long time was that CEOs would simply carry CEO shit on their own by shoving their emotions down or hiding them.. “It’s lonely at the top,” we’ve often said by way of twisted non-apology. 

The place to process CEO shit is within a CEO group – a safe, growth space of your peers. Many men’s groups are CEO groups as well (all the groups I personally facilitate fall into this category), but men’s groups go beyond CEO shit. 

They also cover Guy Stuff. The stuff you can’t share with your spouse or your female friend, because they don’t get it and/or they’re conflicted. Your spouse may be the most well meaning person in the world, but they don’t understand the pressure you put on yourself in the boardroom or bedroom. And even if they are CEOs themselves and do empathize with the pressures you’re under, your spouse’s perspective will never be objective. 

Guys join men’s groups for all sorts of reasons. But they stay in those groups, invest in those groups, and fly across the world in really inconvenient ways to meet with those groups, because men’s groups are the place, often the only place, they can truly express and discuss CEO shit and Guy stuff. 

(Fun fact, many groups take this space so seriously that they fine members up to $100 for every minute they’re late, donating the pool to charity at the end of the year. Yes, men like hard boundaries.)

What do people talk about in Men’s groups?

I still remember the moment when our book club deepened into a men’s group. We had read a book called The Second Mountain by David Brooks, and what had historically been a mostly intellectual debate turned into something deeper when a member brought up the challenges he’d been having aligning his career with what he truly felt he should be doing.

Like a rock chucked into a pond, the sentiment rippled throughout the group, each man expressing his own frustrations, his own longing, and his own efforts to align himself and his work to his deepest truth. There were no answers  – this is a personal journey in all cases – but I can’t overstate how important the conversation was to me, in the midst of consciously falling apart after leaving the company I’d built during the previous 10 years. I expressed my own secret insecurities about my capacity to provide for my family, my value as a CEO, my worth as a human being. And each was reflected back in turn, by men I immensely respected. Each of us was on his own journey, but I learned from all their experiences. More importantly, through their vulnerability, they gave me permission to fully allow mine. 

That’s the kind of conversation, in my experience now having started and facilitated a few dozen such groups in addition to my own, that you’ll often only find in a men’s group. Some other favorites I see often are:

  • Building an intimate, loving relationship over decades or wrestling with a relationship that has lost its spark

  • Confronting the loss of identity and virility which comes with exiting or retirement

  • Raising resilient kids, despite a life of wealth

  • Our relationship with ourselves, the ways we beat ourselves, and the cost

  • Finding your own spirituality, and sloughing off the religion of your youth

  • Becoming a man, despite or because of the father who modeled what that meant for you

  • Taking on the mantle of leadership from aging parents

  • And many more

Take a look inside. What is that deep, dark topic that you sometimes think about but don’t voice because of what that might mean? 

That’s men’s group material. 

That, and of course lots of topical, practical conversations as well. If your men’s group is a bunch of CEOs, that’ll include business strategy and tactics. If it’s a book club, that’ll include philosophical conversations about literature. 

Great men’s groups invite both the topical and near-term, and the deep, soul level topics. In other words, they invite all of you into the conversation. 

Options for Men’s groups 

If you’re a business exec or CEO, there are a number of pre-packaged CEO group options for you. 

If you can find a group inside one of these organizations that is A) all men, and B) is interested in emotional work, that’s golden. The role of CEO is so important to the identity of those men who play that role, that finding a men’s group of CEOs can be a critical part of enabling you to bring all of yourself to the conversation of leadership. 

But if you’re not a CEO, or are otherwise interested in a conversation focused entirely on the male experience, and less on the male CEO experience, my friend Jonny Miller created a wonderful resource called Find A Men’s Group, which is a fairly comprehensive look into the various men’s groups that are available. 

Starting your own men’s group

I was fortunate to find my group. I very wisely (read: completely by luck) chose a topic which attracted like minded men that I got along well with. And then, every month for over a decade, we deepened our friendship by degrees until finally someone was willing to make that first move into vulnerability. 

But most groups I run these days are engineered to create that space in a matter of a few sessions, rather than years. This is done by being extremely particular about three things: 

  1. Proper expectation setting and vetting of members

  2. Intentional, iron-clad commitments, rather than assumptions

  3. A conversation structure that requires emotional depth and exploration

Men respect hard edges to any container, so if any of these requirements are managed loosely, my experience is that the group is likely to atrophy and die. But if all of them are managed well, and if all members commit to each of them fully and equally, a special group can be created.

Each group will satisfy those requirements differently, and should because the group should serve its people, not any one specific structure. Two friends of mine – wonderful, deep men themselves – have created how-to guides I wholeheartedly recommend to any man looking to start a group. 

Playbook: Starting a Men’s Group by Jonny Miller

How to Start a Men’s Group, the Definitive Guide by Andrew Horn

They’re wonderful frameworks to start with, and have a lot in common with the way I facilitate the groups I lead. But they’re a starting point, meant to iterate from to create the edges that support the men in your group. 

I may create my own guide in the future, explaining how I’ve managed dozens of these groups. But see no need at this point to recreate the wheel when Jonny and Andrew have done such great work. 

That said, if you are interested in starting your own men’s group and would like some support, reply to this email and I’d be happy to chat, share best practices with you, and help you get situated. And if you really knew me, you’d know that I’m 100% serious about that offer.  

Intimacy amongst males

There was this moment, at a steak restaurant in Lima on the last day of our trip. We’d conquered the Inca Trail, abhorrent bathroom situations (I’m not typically a camper), and the Peruvian equivalent of Montezuma’s Revenge, and we were a couple drinks into reflecting on all that had led us to this point. There was a lull in the conversation, a comfortable silence, and then one of the other guys asked me what part of our trip was the most impactful to me.

As I reflected on the challenge we had overcome, the awesome sight of one of the seven wonders of the world, and all the years of friendship that had led us to that moment, the answer was obvious. “That I got to do all this with you guys. It feels like both the culmination of a lot of effort and planning over a long period of time, and somehow like a beginning at the same time. I’m really grateful for you guys. I can’t imagine doing this with anyone else.”

As I offered that intimacy, that depth of connection, I felt vulnerable. Still, even after all this time. Would they reject me? Would they bring things back up a level in that “yeah dude, totally” kind of way familiar to all men? Would they make light of it? 

My friends looked me in the eye, and told me they loved me. And they agreed wholeheartedly. 

That’s a men’s group. 

If you’re a man in this world, I can’t recommend anything more strongly.


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