“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

“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

Memory, Doubt, and Regret

Dear Aiden,

There will be many significant transitions in life, so I offer some ideas that might be helpful when things are confusing and unclear. 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. I also know that the recommendations come out of my own personal preferences and oddball way of seeing the world so some may not resonate at all.

The existential reckoning I experienced was not a stereotypical mid-life crisis because from a technical perspective I’m already past mid-life, and it certainly wasn’t the first time I’d found myself forcibly evicted from life as I knew it. Like Dante, I found the straight way completely lost and was gripped by an acute sense that this was much more than a crisis. It was a sudden stripping away of reality as I knew it, and the forest I awoke in wasn’t just dark, it was haunted.

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

The experience has led me to conclude that men don’t have just one mid-life crisis that predictably occurs around 40 and features a divorce, 23 year-old girlfriend, and red sports car. For some men, especially the most narcissistic and least self-aware (meaning, most of them) this happens, but many don’t make it out of the wilderness at all.

I believe that as we grow older, men in pursuit of an authentic life face many crises, disruptions, and upheavals. I don’t even know if I’m actually out of the woods yet (pun vigorously intended). yet. 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 hasn’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.

I’ve always loved the work of David Whyte and Mary Oliver, and their books were helpful as I wrestled with my identity and the fact that reality seemed 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. You know as well as I that there is little left unsaid about effective living or the masculine journey, and that most purported ‘new’ thinking is just repackaged ancient wisdom. I stopped looking for new perspectives and have settled in with people like the Stoics, Plato, Socrates, and more recently, Hobbes and Noam Chomsky.

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.

Ad Astra,


Complete Annihilation

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

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

Can you spot the real Tolstoy?

“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. 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.

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.

The truth was that life is meaningless.

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.”

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