Male mentors rarely teach you to sit and watch when you’re growing up.
They teach you to achieve. To earn more. To improve yourself. To optimize. To move faster, work harder, and squeeze a little more productivity out of every hour of the day. The entire infrastructure of modern life seems designed to keep men in motion. There is always another goal to pursue, another problem to solve, another person telling you what you should be doing next.
But some of the most valuable lessons I’ve learned in midlife haven’t come from books, podcasts, courses, or experts. They’ve come from observation.
I’ve spent years sitting across from successful men, interviewing them, traveling with them, working out with them, sharing meals with them, and watching how they move through the world. If you pay close enough attention, people will show you exactly what’s working in their lives and exactly what isn’t. They’ll show you what they value, what they prioritize, and where they’re still performing.
This past weekend reminded me of that lesson again.
My wife Kate and I traveled to New Jersey for a wedding. The bride has a large social media following, and everyone was asked to keep photos and videos off social media until after the wedding. There was essentially a media embargo in place so the couple could tell the story on their own terms.
I respected it, but I didn’t think much about it.
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What I didn’t realize was how quickly putting my phone away would change the entire experience.
Without a device constantly pulling at my attention, I started paying attention to everything else. I listened to the bridal party speeches instead of checking messages. I had conversations with people I’ve known for years but had never really spent meaningful time with. Instead of evaluating every moment based on whether it was worth photographing, I simply experienced it.
It struck me how much of our life is spent looking down. Remove that distraction and your attention naturally shifts upward. The world doesn’t suddenly become more interesting. You simply become more available to it.
The following day, Kate and I drove to Long Island to stay with close friends. I’ve known this friend since third grade, and we’ve known them as a couple since our twenties. We spent a day on their boat circling New York City, watching planes descend into LaGuardia, cruising past the Statue of Liberty, the Freedom Tower, and the skyline stretching in every direction. When people think of New York and New Jersey they think of subways and skyscrapers and traffic, but out there on the water, both are quite beautiful. It was a perfect afternoon with friends.
By the end of the day, everyone was tired. Of course, we could have gone out to dinner and treated the evening like another event that needed maximizing. In a past life, I would have done that.
Instead, we all independently arrived at the same conclusion. We were going to shower, put on sweats, order takeout, watch the Knicks game, and sit around the kitchen talking.
And it was perfect.
What I observed in that moment was something I’ve noticed repeatedly among the happiest men I know. At some point, they stop performing. They stop making decisions based on how they’ll look to other people and start making decisions based on what they actually enjoy.
One of the great advantages of getting older is realizing how little of your life needs to be optimized. A great evening isn’t always the reservation everyone wants. Sometimes it’s takeout with people you’ve known for decades. Sometimes it’s a conversation that goes nowhere in particular. Sometimes it’s simply being exactly where you are.
I’ve learned more from observing people than almost anything else I’ve done. I’ve watched how men treat waiters, talk about their wives, handle success, disappointment, and boredom. I’ve watched who checks their phone every thirty seconds and who stays engaged in the conversation happening right in front of them.
Some of what I’ve seen, I wanted for myself. Some of it I wanted no part of.
That’s why observation matters, it reveals what deserves your attention and what doesn’t. It helps you recognize the habits worth adopting, the relationships worth investing in, and the unnecessary complexity you can leave behind.
Most of the answers we’re looking for are already sitting right in front of us. They’re in the friend who’s fully present. They’re in the couple whose marriage still looks easy after decades together. They’re in the people who seem genuinely content with their lives rather than endlessly trying to upgrade them.
You just have to look up long enough to see them.
Life should get easier as you get older, not harder. If it’s getting harder, it’s worth paying attention to why.
Every once in a while, it helps to put the phone away, look around, and remember that the people and moments worth paying attention to have been there the whole time.
In Health,
Greg Scheinman
Founder, Midlife Male
Husband. Father. Entrepreneur. Coach.
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