The Slippery Slope Nobody Warns Older Men About
It’s an inner thing I’ve been working through myself
Digital watercolor rendering of the Pacific Ocean from Cross Hill by the author
It was 75 degrees and bright in Cabo San Lucas, Mexico, when Enrique Morales asked us the question. We were standing at the foot of Cross Hill, a legendary, steep, unforgiving pile of rock that rises above the Cabo marina, daring you to hurt yourself.
There were maybe forty of us, plus at least thirty-five dogs. Enrique owns a local dog training camp at the base of the hill. He is one of those people whose love for what he does radiates off him before he says a word. Before we started the climb, he stopped the group, looked around at all of us, and asked: What is the only real thing?
Nobody answered right away. I wanted to guess, but it was too early to sound stupid. Then he told us. The now. This moment. Nothing before it, nothing after it. Just this.
The now. We’ve all heard the reference before, but living it, feeling it, being it is the entire purpose of it. Letting go.
I’m 64 years old. I’ve heard some version of that idea a hundred times. But something about hearing it from a super-fit man surrounded by dogs at the base of a hill I wasn’t sure I could climb, on the morning of our 40th anniversary, in a place my wife had dreamed about for years. It landed differently this time.
It landed like something I’d finally earned the right to understand.
We celebrated our 40th anniversary late
We’d planned it for October, and life moved it to now, which felt appropriate once we got here. Janice has wanted to come to Cabo for as long as I can remember. I’m more of a homebody; the idea of an all-inclusive resort, the crowds, the noise, and the organized fun.
It’s not my domain. But within twenty-four hours, something shifted. And I don’t use that word casually.
I sat with my coffee the morning after we arrived and felt something I hadn’t felt in a long time. Not productivity. Not a purpose in the professional sense. Just presence. The water. The light. My wife is deservedly resting, the complete absence of anything I had to be by nine o’clock.
A year ago, a decade ago, that feeling would have unnerved me.
The reason I’m telling you all of this is that when we got back to our resort room, I read an article about a tragic trend for older men. I was reading about myself, my father, and all of my buddies who are older than I am.
The news for men isn’t good
A geriatric psychiatrist recently published something that stopped me mid-scroll. She’s spent decades sitting across from older men in crisis. Not the dramatic kind, not the kind that announces itself, but the slow, quiet, desperate kind.
When you ask not what is wrong with older men but what we have lost as we age, four things consistently surface: autonomy, belonging, dignity, and meaning. Lose one, and the structure wobbles. Lose two or three in close succession, which retirement, illness, and life transitions have a way of doing, and something more fundamental gives way.
Because I recognized all four. Not abstractly. Personally.
Within the last year or two, I let go of past identities I’d been carrying for decades, the need to compete, scale, grow, win, earn, promote, hustle, network, and sell my consulting solutions. It left me almost as fast as my brief obsession with becoming a national Pickleball champion. What replaced it wasn’t emptiness, exactly.
It was more like the beautiful silence at sunrise. You don’t know whether to jump for joy or sprint up the empty beach chasing seagulls, or sit grounded in the sand, breathing, basking in the glory of a Creator we struggle to understand.
My father went through his version of this in his mid-seventies. Oh, how I love and miss that beautiful man. My first hero. A man who had been a leader in his business community, whose identity fused with what he did and who knew him for it, found himself on the other side of all that. He was still the same man, but without the scaffolding that had been proving it.
The last time I flew to Florida to see him, in 2012 or so, I watched him describe that slippery slope he was on. Shorter off the tee box. Less of a desire to be among the popular crowd at his golf club and an inability to be relevant in the business community.
I didn’t fully understand it then. I do now, ten years younger than dad was, sitting in Cabo with nowhere I have to be.
The losses men experience are real
But they’re not the end of the story. And the reason I’m writing about men is that I’m not qualified to write about the experience of women.
The needs of men don’t disappear when the scaffolding of business life and career comes down. They go underground. They become the ache that doesn’t yet have a name. And they can be met in different forms, through different structures. But if you feel you are slipping, you’ve got to be willing to let go and shift your perspective before the old ones have been gone too long.
That willingness starts with one thing. Honesty. Not the kind you perform for other people. It’s the kind you look in the mirror, asking what is actually real right now. Not where you want to be. Not where you were. Where are you actually?
Most men I know, myself included, for most of my adult life, are far quicker to troubleshoot a problem in their business than to sit with the question of whether they feel like they belong somewhere anymore.
Men are wired to fix, not to feel. “Honey, let’s solve this problem!” That training carried us a long way. In this season of life, our later years, it’s the thing most likely to get in our way.
Enrique led us up Cross Hill, a man clear on his mission
He was at the front. His alpha dog is beside him. Forty people and thirty-five dogs scrambling up loose rock in the Cabo sun, nobody entirely sure what they were doing up there, all of us doing it anyway.
At the top, the marina spread out below us. The water caught the light. Boats and a cruise ship passed by. I stood there breathing hard, Janice beside me, and I thought about my father. About the men I mentor, younger guys, half my age, building businesses and chasing the same things I once chased. About the research sitting on my phone. About Thursday afternoons with nothing scheduled.
And I thought: this is the work. Not the climbing. The willingness to stop at the top and actually look.
And to wait for what’s next, if anything. For me, not knowing what was next felt normal. One of my mentors taught me the power of not knowing, being okay not knowing, waiting, being patient, until knowing what’s next is crystal clear. That’s clarity. When clarity is radical, something within us lights up, and that becomes the beacon for our next calling: to serve others. Every day we are blessed to be here in a school called life.
If you had asked me one or two years ago what I’m up to, I would have said, “Not much. Void. Winding down the consulting. Chilling out. Riding bikes. Letting money work for me instead of the other way around.”
Out of the void emerged a new way of helping myself shift my perspective on what really matters at this stage of life. Any stage of life. We shift all through life, different seasons, different bodies and minds, whether we are willing to train them or not.
I have a five-step method. It helps me stay present. To shift my perspective on when a person, place, or thing begins to set me off, agitate me. I tested it on myself for a few years and played with the concept. I wrote about it. Then, I started sharing the method with others. It helped some of them, only the willing. You have to be willing to shift yourself.
It feels like riding a bicycle with a tailwind once you get it
The first step is S — Self-Awareness. You stop and ask the hardest question most men avoid: What is your reality right now? Not where you want to be, not where you were — where are you actually when you look in the mirror?
From there, H — Higher Understanding. You deliberately lift your perspective above the noise, the fear, the story you’ve been telling yourself, and look at the situation from a wider view.
Then I — Introspection. You go inward quietly, honestly, without judgment, and ask what this moment is asking of you.
Next, F — Focused Intention. You choose your next move with clarity. What outcome do you want, and by when? You stop drifting and get intentional — writing a new script, a new affirmation, a new way of seeing yourself that you can practice morning and night until it becomes the story you actually live.
And then T — Transformation. Not the dramatic kind. The quiet, durable kind that happens when a man stops fighting what is real and starts building toward what could be — and finds himself, almost without trying, back in the only place any of it is possible, the now.
That’s not self-help. That’s self-honesty. And once you’ve done it once, you know exactly how to find the tailwind again.
I built it because I needed it. I share it because I keep meeting men who need it too and don’t know yet that what they’re feeling has a name, and that the name isn’t failure.
It’s a transition. And transition, when you stop running from it, is the beginning of something.
The psychiatrist ended her piece with a simple image
A man in a chair, hands on his knees, describing the void that lies ahead of him on Thursday afternoon. The clock reads 10:43 in the morning. He sits there reflecting in my mind, practicing the five steps, finding the now, inner peace, and serenity.
That is, in fact, the beginning of something very real. It is presence, the ultimate gift and ageless wisdom.
I know that man sitting in the chair. I’ve been that man, wondering what’s next. I am here, present, writing this for you from Cabo on our anniversary morning.
What I know now, having returned from the pinnacle of Cross Hill, is that the question Enrique asked at the bottom wasn’t rhetorical. It was an invitation.
If you’re still with me, consider yourself invited to the now. That’s when you become part of the solution.
If you’re stuck in the business of life, start your shift here.