Most men spend the second half of their lives waiting to be invited into the right room. They’re waiting for the right network or right circle or right friendships or the right opportunities to magically come along. Well, I have news for you. It ain’t happening. Also, I think that mindset is backwards.
I believe you need to create the rooms you want to be in and here’s why:
There’s a certain point in midlife where you realize you’ve spent years walking into rooms that don’t actually fit you anymore.
Business dinners you don’t care about. Networking events that feel transactional. Surface-level conversations with people who are more interested in performing than connecting. You look around and think, “How did I even end up here?” Not because the people are bad, but because somewhere along the way you stopped being intentional about who you’re spending your time with and what kind of energy you actually want in your life.
I’ve become a lot more aware of that over the last few years.
At 53, I know exactly the kind of conversations I want to be having and exactly the kind of people I want to spend more time around. I want to sit with guys who are building things, evolving, struggling, succeeding, failing, learning and actually talking honestly about all of it. Men who care about being better husbands, fathers, leaders and friends. Men who have perspective. Men who have done interesting things but aren’t trying to convince everybody in the room they’re important.
And I realized something awhile back: if that room doesn’t already exist, there’s nothing stopping you from creating it yourself.
That’s really what these dinners have become for me.
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I hosted one in New York last week. Ten guys around a table at Cathedrale for a few hours and, honestly, it reminded me again how badly most men need this kind of thing in their lives.
The dinner started the way these things usually do. A few text messages. A couple reach-outs. Some guys I’ve known for years. A few I’ve interviewed. A couple I only knew through their work or mutual friends but respected enough to say, “Hey, you should come to this.” And the funny thing is, once people realize the room is going to be filled with thoughtful, interesting men, they almost always say ‘yes’.
Because everybody is craving it.
And once we sat down, the conversation went exactly where you hope it goes when you get the right people together. Fitness. Business. Marriage. Parenting. Recovery. Money. Style. Stress. Aging. Ambition.
One guy talked about navigating life with an autistic child. Another talked openly about divorce. One sold his company for hundreds of millions and rode his bike to dinner. Another has become so obsessed with bagels he’s probably reviewed more bagel shops than anyone alive and now wants to build a bagel museum while helping run one of the biggest music companies in the world.
That’s the stuff I love.
Not because any of it is particularly impressive, although some of it is, but because it’s real. Nobody’s curating themselves at that point in the night. Nobody’s posting clips from the conversation or trying to win the table. Guys are just talking. Sharing stories. Asking questions. Learning from each other. Laughing. You can almost feel everybody relax a little once they realize they don’t have to perform.
I honestly think we’ve lost a lot of that.
Most men have friendships built almost entirely around convenience now. School friends. Work friends. Parents from their kids’ sports teams. But very few are intentionally creating environments where meaningful conversations and real connection can consistently happen. And then they wonder why they feel isolated, uninspired or disconnected even when they’re constantly around people.
When you spend enough time around thoughtful, disciplined, interesting people and eventually it raises your own standards. You leave wanting to take better care of yourself. Be more present at home. Think bigger. Loosen up a little. Dress a little better. Travel more. Try something new. It all starts bleeding together in a positive way.
And the good news is this doesn’t require some exclusive dinner in New York.
You can create this anywhere.
A monthly breakfast. A standing golf game. A group workout on Saturdays. A walk with a couple guys you respect. A simple dinner reservation and a text that says, “You free next Thursday?”
That’s really how this stuff starts.
Most men are waiting for somebody else to organize the kind of life and community they say they want. I just don’t think it works that way anymore.
At some point you have to take ownership of it yourself. You have to decide what kind of people you want around you and then make the effort to bring them together.
That’s what I’m trying to do more of.
And every single time I do, my life gets better because of it.
In Health,
Greg Scheinman
Founder, Midlife Male
Husband. Father. Entrepreneur. Coach.
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