For the next three weeks, I will be blogging about my post-military retirement trip to the Sierra Nevada mountains. This first post explains the project. You can subscribe to my blog posts here (it’s free) and follow my author page on Instagram.
“Midway upon the journey of our life I found myself within a forest dark, for the straightforward pathway had been lost.”
So begins Dante’s Inferno. The lines are quoted in almost every book I’ve read on midlife; Dante’s description captures the midlife passage with archetypal power. The Forest Dark. I personally spent years in that dark wood, that “forest savage, rough, and stern”, wondering how I got there and how I might get out again. I describe much of that journey in my book Eating Glass. I write about wilderness experiences, of deserts where prophets are forged, of hard lessons about acceptance and the release of control.
Dante’s Forest Dark is not a place we seek, but rather one we sleepwalk into. Dante describes himself as full of slumber “at the moment, in which I had abandoned the true way.” In midlife, we confront all the ways we have abandoned our true self. The dreaded forest gives a gift: consciousness. We wake up to life.
Yet there is another tradition of wilderness passages: the journey consciously chosen, the voluntary exile, the compulsion to lose and then discover oneself. The forest becomes a place to find wisdom, to train, to prepare for the next ordeal. The traveler is explorer and pilgrim.
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My upcoming three-week trip to the Sierra Nevada mountains is, I hope, in the latter category. I’ve already done my time with Dante, trudged through the hellscape of my own Inferno. Professional setbacks and a sense of lostness. Divorce. Learning to date again, feeling it go sideways. Supporting my children through the upending of their lives.
Now I’m on the other side of that first wilderness journey. I’m in a loving, healthy new relationship. Recently, while sitting around a campfire after a day of climbing and rock-jumping at a remote swimming hole, my children told me they are happy. It has been a really good year, they said, making an implicit contrast with the damnable year before. Professionally, it was a good year too. I ended my Air Force career in exactly the right teaching assignment, passing on everything I’ve learned about defense innovation to a new generation of entrepreneurs in uniform
Now it’s time for a more joyful kind of wilderness journey.
My years in Dante’s wood woke me up, taught me to listen. I read such good books during those years: about the soul, and unlived lives yearning for expression, and subconscious energy breaking through the surface with violent ferocity. Something within me is trying to be born.
I’m at a crossroads: down one path lies safety and stability in a continued government role, at the price of sameness. It’s a good path. Many of my colleagues choose it, for good reasons. But I’ve learned to trust my energy, and the compass needle points elsewhere. I need a new beginning, new challenges. A reinvention.
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I train hard in the weeks leading up to my wilderness trip. Older people remind me that I’m not old, but when I was young, 44 looked positively ancient. In any case, the wear and tear is getting real. A partly-failed shoulder surgery patched up some damage but also left me with a torn rotator cuff and a long rehabilitation process. I’m still getting strong again and testing my limits. I run and climb stairs. The better my fitness, the greater the adventures I might enjoy.
I’m also helping Hannah get ready. Before we met, she had never climbed–only dreamed of it. She devoured climbing documentaries, which is what brought us together in a chance coffee shop conversation. My friends and I had her on a rock wall just a couple weeks later. A year on, she’s making her first outdoor lead climbs and I’m teaching her multi-pitch climbing skills at mock belay stations in my garage. Also, we’re dating–another subplot in this great division of my life into Before and After.
We spend our last weekend in Alabama climbing at Sand Rock, our local crag, practicing multi-pitch skills on stubby rocks that probably don’t even need ropes. We move slowly, meticulously, practicing every step of our belay transitions until they’re perfect. Better to work out the kinks here, ten feet off the ground, than five hundred.
Our upcoming trip is supposed to be a joyful retreat, but as it draws closer, I feel immense pressure. Three weeks in the mountains is exceedingly rare for me, made possibly only because my children are overseas with their grandparents. I want my trip to count. I want it to mean something. It feels like my life depends on it.
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Life typically progresses in a continuous line. That line makes great big ups and downs, and sometimes careens in wild drunken loops, but the pen never lifts from the page. Each event sets the stage for the next. Skills compound, networks expand, we progress through adjacent jobs and friends. Momentum carries us downstream like a river, until one day…
“I felt like I was living someone else’s life.”
That’s another recurring line in books on midlife. One day, many of us wake up to realize we have abandoned something precious in ourselves. We could have everything in the world going for us, and yet we crave some kind of renewal.
That’s the puzzle I’ve been stuck on: how to lift the pen from the page. How to create a discontinuity.
Everyone in my professional life knows me as a defense innovator. That is true. I am a defense innovator, and I will still be a defense innovator when I descend from the mountains and begin my next job in a defense technology startup. I’m excited about an amazing opportunity ahead.
But I’m something else too. I’m a writer, with a deeply spiritual nature and a profound love of the natural world. I use words like “soul” and “belonging” that don’t compute in my professional circles. I read books by psychotherapists and meditations on landscapes. I use precious vacation time to make pilgrimages to Thomas Merton’s monastery and Wendell Berry’s town in rural Kentucky. I write as a way of perceiving, experiencing, and understanding the world. So much of my writing is an effort to answer my own biggest questions: how does one construct a well-lived life? How does one find a sense of belonging in the world? How do we reconcile our deepest human needs with our dehumanizing technological society?
I never really harmonized my personal writing with my military career, which is one reason I finally felt compelled to hang up the uniform. Military leadership demands a certain persona, especially as one advances through the ranks. The kind of writing I like to do demands almost the opposite qualities: a penchant for solitude, an inclination for observation over action, a temperament that asks hard questions rather than provides confident answers, a willingness to distill life experiences into narrative rather than bullet lists.
Collisions came with increasing frequency. The Air Force wanted and needed the Colonel, so I kept the writer quiet.
Now it’s time.
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So: military retirement. An interlude. Three weeks around Donner Pass, Yosemite valley, Tuolumne Meadows, and Bishop.
On the surface, it’s about getting outdoors for a few weeks. But it’s really about personal reinvention, which is very hard to do. It’s difficult enough overcoming twenty-two years of career momentum and social expectations. What makes this even harder is that I’m taking myself with me, with all my habits, self-doubts, and distractibility.
My strategy is this: for the next three weeks, I am going to live as that alter ego. No defense innovation. No coding. No military persona. No responsibility, real or perceived, to write the way a Colonel or technologist is supposed to write.
Instead, I will give that other persona free expression. I am attempting to craft a temporary new life, in the same way I might craft a short story. Hannah and I will be living in a van, going where the winds blow. We’re seeking a kind of simplicity, although that will entail its own complexities, like where to empty sewage or do laundry. My reading list encompasses soulful nature writing, like Robert Macfarlane’s Landmarks and Kim Stanley Robinson’s The High Sierra: A Love Story, and rich psychology books like Rollo May’s Love and Will. I am a do-er and Hannah as a be-er, so I expect our days to exhibit a healthy fusion of our natures: leisurely hours sitting in beautiful alpine landscapes, and rigorous hikes or ascents of rugged rock faces.
And writing. Writing, writing, writing. That is the heart of it all, my real motivation, the thing I’m trying to set free. I’ve spent two decades feeling wound up too tight, worried about readership and positioning and branding. I’ve never felt comfortable making the leap into writing because I don’t have a business strategy. Walt Whitman said, “I contain multitudes.” That celebration of eclecticism resonates powerfully. It’s a great way to live and a terrible way to craft a value proposition to buyers.
Enough of all that. My goal, in these three weeks, is to let go of that need for control–to live lightly upon the earth, to write for the love of it and for no other reason. I will write for myself.
And then I will share it.
Thats the catch, the terror-inducing crux of this long ascent. I’ve always had a paralyzing fear of sharing my personal writing, especially if I haven’t spent weeks rigorously editing and polishing. That has held me back for two decades. So my commitment, for these three weeks, is to write what I want and then share it. Whether anyone reads it, likes it, or hates it doesn’t matter. It’s all flint on steel, a shower of sparks, the hope of igniting something.
I only have a small readership, and I expect I’ll shake some of you loose, especially those who came looking for defense innovation writing. That’s fine; no hurt feelings. I’ll do more of that writing later in other forums. But I hope I’ll gain a few new readers as well. I give you absolutely no promises concerning what I will write about, except that it will be important to me. You can subscribe to these posts by e-mail (it’s free) and see shorter updates on Instagram. If this is too much, you can unsubscribe below or–better–switch to an infrequent newsletter, so you’ll know when I release new books.
What will happen after those three weeks? That’s a three-weeks-from-now problem.