Dear Aiden,

There will be many significant transitions in your life, so I offer some experiences, reflections, and ideas that I hope will be helpful when things are confusing or unclear. The seed of what follows was planted in 2019, shortly after I’d lost a job at PayPal, but aided by the wisdom that only comes with the passage of time, I’ve made extensive additions and revisions to the material.

“In the middle of the journey of our life I came to myself within a dark wood where the straight way was lost. Ah, how hard a thing it is to tell what a wild, and rough, and stubborn wood this was, which in my thought renews the fear!”

Dante alighieri – The Divine comedy

If I quote a book, provide a video clip, include artwork, or cite some type of source material, it’s because I find these things helpful when I feel lost and recommend them to men who find themselves experiencing what I call an existential reckoning.


Of or relating to existence.

“And so I asked myself, ‘has my choice of career created an existential threat to my wellbeing?'”


Time when one is called to account for one’s actions, to pay one’s debts, or to fulfill one’s promises or obligations.

“I knew I had to change; there would be a reckoning and it would require all the courage I had.”

It is a constant encouragement to me that I have a son who shares similar tastes, interests, humor, and histories, so I’m betting some of what I’ve included here will be of interest. You’ve always demonstrated an ability and willingness to grapple with ideas that many adults either ignore, avoid, or don’t understand, so I’ve tried to avoid truncating ideas or concepts simply because you’re young. You’re well aware of my less-than-favorable views on American education, but I also feel adults tend to assume young people can’t engage with sophisticated subject matter without bothering to test that belief.

I also know that some of these thoughts come out of my own personal preferences and weird way of seeing the world, so may not resonate with you at all. We’re all unique and that’s just fine. I’m also not the first person to use the phrase existential reckoning to describe a challenging life transition. The band Puscifer even wrote a great album about the idea.

The existential reckoning I experienced after Paypal was not a stereotypical male mid-life crisis, primarily because I was already past mid-life and it certainly wasn’t the first time I’d found myself suddenly without a job. Granted, this time the company treated me in a shockingly unfair manner, so much so that despite being an at-will labor state where it’s legal for employers to treat workers as disposable garbage, the Nebraska Department of Labor investigated the matter and found PayPal had unjustly terminated my employment. This meant PayPal had to fund my unemployment claims, but again, I’d experienced job transition before so the event itself, while gut-wrenching and dreadful, was not new to me.

What was new was where I found myself emotionally and intellectually after the fact. This wasn’t the first time I’d been forcibly evicted from a life I thought I wanted but was in reality driving me insane. After nearly losing everything in Michigan, I thought I’d learned to stop building a life around corporations and people I had nothing in common with and whose priorities were so vacuous, unimportant, or unethical to me that I spent years biting my tongue or trying to not laugh out loud. If Dante were writing the Divine Comedy today, it’s likely Virgil would guide him through a plane of hell filled with cramped cubicles, badge readers, and meetings that could have been emails.

I’d burned far too many precious hours creating complex widgets for others that seemed to have no intrinsic value at all and at the time believed I’d matured beyond making unhealthy investments in what I did to put a roof over our heads or food on the table. I was wrong. Again.

Like Dante, I found the straight way completely lost and was gripped by an acute sense that this was much more than a jarring job loss. It was a sudden stripping away of reality as I knew it, and the forest I awoke in wasn’t just dark or wild, it was haunted. This forest was home to monsters, demons, and the ghosts of Depression, Anxiety, and Shame.

Depression, Anxiety, and Shame

This particular reckoning, coupled with a lifetime spent—often to my sincere displeasure—around males of the species, has led me to the conclusion that men go through a few distinct types of life crises, and the shape of these experiences depends on largely on how the individual relates with his internal and external world.

“I felt that what I had been standing on had collapsed and that I had nothing left under my feet. What I had lived on no longer existed, and there was nothing left.”

leo tolstoy – a confession

The most well-known of these disruptions is the traditional mid-life crisis. This often occurs around 40, and features a divorce, 23 year-old girlfriend, red sports car, or, in the more tragic cases, hair plugs.

“My life came to a standstill. I could breathe, eat, drink, and sleep, and I could not help doing these things; but there was no life, for there were no wishes the fulfillment of which I could consider reasonable.”

leo tolstoy – a confession

Some men, especially the most narcissistic or least self-aware aren’t even cognizant of the fact that they’ve lost their way, and some don’t make it out of the wilderness at all. Men who aren’t curious about why they’ve reached a certain age and suddenly feel a gnawing sense of doubt or are blindsided by the panicked realization time is running out will mistake a new car or beautiful young replacement for the woman they once loved with some kind of renewed freedom and autonomy.

“If I desired anything, I knew in advance that whether I satisfied my desire or not, nothing would come of it. Had a fairy come and offered to fulfil my desires I should not have know what to ask.”

leo tolstoy – a confession

Men who live what Socrates called “the unexamined life,” will mistake everything from addiction to adultery as signs they’ve taken charge, faced down midlife, and emerged the victor. These are the hollow victories men often confuse with progress or proof they’ve left all their disappointment, boredom, and bitterness back in the dark wood, when in reality nothing has changed at all.

“If in moments of intoxication I felt something which, though not a wish, was a habit left by former wishes, in sober moments I knew this to be a delusion and that there was really nothing to wish for. I could not even wish to know the truth, for I guessed of what it consisted.”

LEO Tolstoy – A Confession

The message here is simple: Be curious. Be a voracious student, not just of ideas in books, but of the words written in your heart. Don’t assume you know everything or have all the facts. I tried that for a long time and it wasn’t true at all. When you wake in the dark wood, after the initial disorientation passes, reflect honestly on what might have put you to sleep in the first place.

Part of any existential reckoning involves doing what the Swiss psychiatrist Carl Jung called “shadow work.” Shadow work is the process of exploring and integrating the unconscious aspects of one’s personality, known as the shadow. The shadow represents the parts of ourselves that we have repressed, denied, or disowned because they are deemed unacceptable or incompatible with our self-image. This can be a humbling process, which is why many men avoid it like the plague.

Tolstoy’s Existential Reckoning

Despite having written “War and Peace” and “Anna Karenina”, at the age of 51, Leo Tolstoy looked back on his life and considered it a meaningless, disappointing failure. A Confession provides insight into the Russian writer’s movement from the pursuit of the aesthetic ideals of art toward matters of religious and philosophical consequence.

Can you spot the real Tolstoy?

After years of literary and financial success, Tolstoy woke in the dark wood, but unlike many of his contemporaries, he began a painful process of self examination. The only immediate benefit of this work seemed to be that it revealed to the writer he’d grossly underestimated just how ‘wild, rough, and stubborn’ the woods were, and that the thick, tangled canopy of branches above allowed only the most thin, transitory threads of moonlight through to serve as illumination.

I highly recommend ‘A Confession’ to any man who wakes in a dark wood but is at a loss for how to articulate their experience. The book provides an clarifying depiction of how an existential reckoning can lead to shadow work, and how shadow work can help us find our way out of the dark wood. The ideas in the book are also useful if we suspect we’ve overvalued the valueless and are ignoring the essential.

Existential Exploration

Without self-refection or curiosity you’ll think you’re on solid ground when the earth actually gave way a long time ago and you plummeted into a dark canyon below.

“A Confession” helped me feel less alone in the struggle, and it’s a very short read. I’d also forgotten how much I love Russian literature and philosophy, so the book was and remains a welcome companion.

I believe that as we grow older, men in pursuit of an authentic life face many disruptions, and upheavals. As for myself, I’ve come to accept that the violence and abandonment I experienced as a young boy—experiences that bred monsters like depression, anxiety, and PTSD—may prevent me from ever reaching the place where the dark wood finally meets a well-travelled highway or some other clear sign of civilization, but I keep trying. That’s my commitment to you and your mom.

To confront what Tolstoy calls “complete annihilation,” you must examine your life and subject your values, motives, desires, talents, and shortcomings to thoughtful, honest scrutiny. Live in wonder and distrust of yourself, others and the world around you. Things are often not what they seem, but we only discover this through existential exploration. Reflect on what you really love and what you find boring. Explore why certain things anger you, and why others bring you joy. Do this with a therapist or psychiatrist if necessary, but find a good one. A lot of them sincerely want to help, but aren’t very good at it. Never mistake a degree or certification with competence.

“I had as it were lived, lived, and walked, walked, till I had come to a precipice and saw clearly that there was nothing ahead of me but destruction. It was impossible to stop, impossible to go back, and impossible to close my eyes or avoid seeing that there was nothing ahead but suffering and real death—complete annihilation.”

leo tolstoy – a confession

Without honest self-refection you’ll think you’re on solid ground when the earth actually gave way a long time ago and you plummeted into a dark canyon below. You won’t know you’re bleeding out or your leg is broken until the animals show up and lurk just inside the tree line waiting for their chance at a free meal.

Our sense of what constitutes a meaningful existence changes, and these shifts are unpredictable and chaos-inducing, like two massive tectonic plates smashing together beneath what appears to be solid ground. Thankfully, the fact that this has happened to me before didn’t led to me beating myself up for not learning the lesson the first several-hundred times. I also know it’s likely to happen again and Stoicism has helped me come to a simple acceptance of this eventuality.

In Extremis

“In extremis” is a Latin phrase that translates to “in extreme circumstances” or “at the point of death.” It is often used in legal, medical, or military contexts to describe situations of great urgency or severity. My favorite, more literal translation is “in the farthest reaches” because it characterizes both the dark wood’s isolating physical geography and the intense psychological dislocation that can occur following a traumatic event. It’s safe to say the figure in Edvard Munch’s painting “The Scream,” is in extremis.

The film “In Extremis” is an original, thought-provoking cinematic achievement that captures much of what Tolstoy explores in “A Confession”‘ With its compelling plot, exploration of psychological themes, and outstanding performances, the film succeeds in leaving a lasting impression on the viewer. Movies about mental health are often little more than a collection of shopworn plots and stereotyped characters, but “In Extremis” provides an authentic portrait of the complexities of the human psyche and the delicate balance between the conscious and the unconscious.

Themes: trauma | unmoored from reality | impending catastrophe | grief

I’ve always loved books, movies, art, and music, as they’ve always been a source of grounding and comfort as I wrestle with my identity or at times when reality seems to be coming apart right in front of me. I’ve taken to the deep study of material that resonates with who I am as a man, and for every man this is different.

There’s little left unsaid about authentic living or the masculine journey and most purported ‘new’ thinking is just repackaged ancient wisdom. I’ve found the ‘self help’ book category to offer little in the way of meaning or direction, so more often than not turn to philosophy, literature, art, and more abstract forms of sense-making for guidance.

I hope some of this is of interest and helpful to you. I treasure the time we have together as father and son, and am here to support you however I can.

With love,


Art Credits

The Scream

Edvard Munch

Norwegian – 1895


Ami Mehta

United States – 2016

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