
I am sitting in the “Teacher’s Room” at the Lalit Hotel in London, sipping a Negroni and contemplating Naresh Kapuria’s In Conversation (seen above).
The Lalit was once St. Olave’s Grammar School. The “Teacher’s Room” is now the lobby bar. Isn’t that ironic? A place where I am sure alcohol was strictly forbidden (but maybe needed every now and then) is now encouraged. As I enjoy my drink and study Kapuria’s piece, I’m struck by how much I simply love being in conversation. The exchange. The way two or more people explore a subject, and in doing so, explore each other. Even small talk can be the spark for a connection. To me, there is nothing better in life.
The rows of black silhouettes in the art (I’m assuming these are male heads; those look like masculine chins, and I’m not saying that from a “looksmaxxing” perspective!) remind me of the many group conversations I’ve been in with men since 2018. As a principal at MenLiving, a Chicago non-profit, I’ve hosted and participated in hundreds of gatherings over the last seven years. We started with one monthly meeting; today, we host over 500 virtual and in-person sessions a year.
I’ve learned a lot in these spaces, but two things stand out.
First, there is a prevalent perspective that what we do is called “men’s work.” I’ve never been a fan of that designation. To me, it suggests something performative, a pseudo-therapy session where men follow prescribed rules of engagement and curated language to manufacture a “safe, authentic” conversation. I was skeptical. I wasn’t sure how much growth could come from a group of guys gathering primarily to “share their feelings.”
As it turns out, a lot of growth can happen. I saw healing and thriving. Yet I still believe the real magic happens when you strip the rules away and let conversation and connection take center stage. And let’s be honest: do most people even like work? Men are conditioned to repress every emotion except anger, but instead of framing emotional intelligence as another “job” to complete, why don’t we invite them to live another way?
Secondly, if groups were going to be convened for emotional sharing and growth, I carried a bias that true change couldn’t happen without the opposite gender. I believed we needed to be conversing with the other 50% of the population to truly navigate the human experience. I thought we needed to have these emotional conversations with women too so that when we left the room, we could function in the real world.
I was both wrong and right.
Hanging out with men willing to go deep was transformative; it enriched my life. But I had the sense that if we (now more “enlightened” humans?) didn’t leave these spaces and connect with others, both men and women, in curious, intentional conversations, these gatherings would only be serving half their job.
So, I am doing just that. I am starting new conversations.
Curbside Conversations.
After seven years of deep diving with men, I realized it was time to talk to women. I wanted the female perspective on all those subjects we explored in our circles.
After considering a variety of approaches, I decided to embrace a medium I was already familiar with: podcasting. For five years, my friend Chris and I have interviewed guests on If You’ve Come This Far. A year ago, we launched Pour It On with Ben Feller, our friend (and two-time IYCTF guest). But how to do this one? These shows were done virtually and while I love Zoom, it wasn’t going to work here. I feel the need to be in the same physical space as my guests to model what a curious, intentional conversation looks like. But how? Renting studios in every city would be difficult. I needed to take the studio to the guest.
The answer finally found me in a parking garage in Palm Springs, California.

Stay tuned for more details on Curbside Conversations