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The Unraveling of Midlife and The Welcoming of Elderhood

Men at forty
Learn to close softly
The doors to rooms they will not be
Coming back to. 

– Donald Justice, excerpt from Men at Forty

I turned 60 this past December. It was just days before my youngest son, Mike, got married, the two mile markers of a life well-lived colliding in a cloud of love, excitement and just a tinge of bittersweet terror.  On the morning of his wedding day, when he would go on to exchange vows with his long-time girlfriend Neve, we stood at a mirror as I helped him slip into his tuxedo.

I stood behind him as he adjusted his bowtie. My place, behind and slightly to the right, and no longer in front, clearing the way nor directly behind pushing him forward. No. I was slightly behind and off to his right–the proper place of a father who is now more of a guide than the protector and provider he once was. As Mike fumbled with his tie, I thought of Donald Justice’s poem, Men at Forty:

Men at forty
Learn to close softly
The doors to rooms they will not be

Coming back to. 

At rest on a stair landing,
They feel it moving 

Beneath them now like the deck of a ship,
Though the swell is gentle. 

And deep in mirrors
They rediscover

The face of the boy as he practices tying
His father’s tie there in secret…

Deep in the mirror, I see the faces of a father and his son as, together, they rediscover the face of the boy as the boy ties his tie on the day he’ll commit his life to his beloved.

The bittersweet pain of aging is sharp and undeniable. This pain was present for me during a recent conversation with my friend, Chip Conley. 

After my birthday and just days after the wedding, Chip reached out over LinkedIn. I had known of Chip for years. We’d crossed paths at a few different companies including one where a former client had benefited from his advice and counsel and shared his wisdom in our sessions. What’s more, beyond hearing of the positive effect he was having on the life of a dear client, I’d been a fan of a book he’d written, Emotional Equations: Simple Steps for Creating Happiness + Success in Business + Life. 

Chip was reaching out, he explained, because he was interested in seeing how we might collaborate, as part of his work with the Modern Elder Academy. After a laughter-filled first brainstorming conversation, we agreed to co-facilitate a retreat on the art of growing up, the art of navigating transitions, the art of becoming–if you will–a modern elder.

But, more importantly, what I heard in Chip’s suggestion of our working together was a call; I felt called by an elder whom I admire to be an elder myself. “The Council of Elders is calling,” I joked with my therapist, “and I must listen.”

Trusting the instinct to listen, I then read Chip’s latest book, Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age. Reading, of course, is just another form of listening. When I was through with his book, I invited Chip to join me on the Reboot podcast.

At the start of our podcast conversation, I asked why midlife is such a challenging transition. Behind my question was the remembrance of my own journey through what the poet David Whyte calls “The Great Unknown.” My own journey was marked by a deep depression that forced me out of the cocoon of my previous life. I remember how like the protagonist in Justice’s poem I felt, feeling the swell beneath the deck of a ship, however gentle the waves seemed to be.

“Why do we have a hard time with midlife?” I asked him. 

“Well, it’s a great question,” he responded. He went on to answer by dividing the experience into two parts: a personal one and a societal one. 

“Personally,” he began, midlife was  like “a lurker in a back alley…one day it jumped on me and just said, ‘Hey, I’m here, notice me, and I’m dangerous.’” 

That was in his forties, he said, noting that his late forties “were rough.”

Rough, because, he explains, that “if disappointment equals expectations minus reality, it is often around our mid-forties to later forties where we can see the future and some of the expectations we had in our life may not be coming to pass.”

The expectations of our life not coming to pass and the rooms we will not be coming back have their doors closed softly. When the doors to our old lives start to close, the modern elder, Chip, says.

“[W]e have to do something that my friend, Brene Brown, calls the midlife unraveling. We have to actually unravel ourselves from our emotions and expectations. And not from our emotions, we have to face the emotions, but we have to unravel our expectation.”’

I’ve told the story of my own unraveling often enough. At 38, I walked out of the chapter of my life marked by my life as an investor and into the next chapter, as a coach. But that statement belies how arduous the journey was. I spent much of my midlife anxiously wondering about who I had been, who was it that I was becoming and, most anxiously, whether I was a good man. “On a walk on a hill in Marin, thankful for the gift that is California, I met an ancient tree, toppled by age, blight, and wind,” I wrote in my first book, Reboot,

…Stopping in my tracks, I realized, Here lies a good man. If, at the end of my days, as this current meat bag starts its inevitable transition to the Earth that birthed me, I can lie as majestically about the soil as this elder, I’ll know that I earned my manhood. His body ragged with the scars of actions he may not always have been proud of but resting in the knowledge that for fifty, sixty, or one hundred years he grew into his purpose: sheltering others, providing them a respite from the glaring sun, the toppling wind, and the painful vagaries of life. 

Gnarled and twisted by inaction, decisions taken and not taken; scarred by selfishness, with limbs stretched by acts of kindness, generosity, and gentleness; I wish to end my days stretched out on the side of a hill, welcoming the slow decomposition of my anxieties and my flesh into nourishing earth. Years ago, I had an epic dream—the kind that teaches you about yourself. I had returned to a past job, the place where I became an adult and a father. Working this gift from my innermost being, I found myself articulating fiercely my purpose: to serve others in their pursuit of their own becoming.

That purpose became a lodestone helping me navigate the rough seas of my own unraveling. That sense of purpose helped my anxieties decompose. The lodestone of purpose powered the compass I used to find the land of my next life.

Revisiting this conversation with my fellow elder, Chip, it’s clear we have a simple yet powerful message for those in the middle of that place: You will pass through, you will be okay, and, eventually, you too will join the council of elders. 

Pulling together my thoughts for this piece, I was brought back to something I wrote about in my second book, Reunion: Leadership and the Longing to Belong. In seeking to understand my own longing to belong,  I wrote of the necessity of re-membering those who had come before us so that we might turn them from unremembered and disregarded ghosts into ancestors. And, more, in doing so they could become elders, guiding us to what is right and true. 

After speaking with Chip, I now see that more than anything, my own unraveling was merely preparatory work for me to become an ancestor and elder to my descendants and those who come after me. Folks, perhaps, such as you. The work for me now is to become that which I wish I’d had when I was in my thirties.

Even more, radically inquiring into my life as it is now, my next life transition, has helped me better understand a poem I wrote while in the wilderness with my dear friend and colleague, Jim Marsden (himself a fellow modern elder). Written just months after the release of Reboot, I understand now that I had already been hearing the calls from the council of elders.

Welcome Wild Elderhood
Written at Green River canyons in Utah October 25, 2019

Out of the shame came
the good boy. And the bad.

For the shame,
borders were lost,

boundaries asunder.

Because of the shame,
there was only separation;

no individuation.

Secret compartments burst.
No longer is the need to
keep things apart.

Things fall apart into wholeness.

The sandstone kiva whispers,
“The true sin, the only sin, is
failing to see that the wild in you

is the wild in me.”

The wholesome wildness of
earth, air, water, and fire
is the wild of the true elder.


Welcome to your own next stage of your life and may you hear your own versions of these calls with the fierce bravery of your elders.


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