The Infinite Conversation: A Therapist’s Case for Reading as a Tool for Raising Emotionally Fluent Boys

My work as a therapist is, at its heart, a conversation, but never a tidy one. Words exchanged in session spill into the car ride home and hover at the edge of sleep.  Franz Kafka’s image remains sharp: a book should “be an axe for the frozen sea within us.” Sometimes reading soothes; sometimes it cracks something open. Many of the boys I sit with carry a rich inner world that is unnamed, unmapped, and, at times, creatively defended. Neuroscience suggests that stories help organize that inner landscape, giving structure to emotion and thought. Ryan Holiday suggests that books can be a superpower for boys, one for them to enter an ancient conversation with the sharpest minds who have ever lived. And as Mortimer Adler argued, to read well is to join that enduring dialogue.

When I was in 7th grade, I found escape in books that might have been considered obscure for a boy growing up in a hard-knock Jersey city that had outlived its industry. Beowulf was the nickname I went by on our basketball team. It was after the book, not because I was a warrior on the court by any means. And eventually, reading helped me get a full scholarship to a private high school. Books were a hard-won solace for me as I was always a slow reader. In college, I had neuropsychological testing and was diagnosed with dyslexia. It was also in college that I immersed myself in the great works of philosophy, particularly the phenomenology of ethics. Perhaps reading challenging texts felt natural to me because all reading is difficult to me, always laborious, a work of love.

Mirror Neurons and Empathy — Fiction is a Stealth Theory of Mind Lab

Mirror neurons are the neural mechanism by which your brain doesn’t just observe someone else’s pain or joy—it quietly rehearses it, giving empathy both a heartbeat and an address in the brain. In fiction, when we read about a character’s actions and experiences, the brain simulates them — the motor cortex, somatosensory cortex, and emotional processing areas all show activation. But the theory of mind layer goes deeper than simple mirroring.

Theory of mind is what develops when your son moves from “everyone sees what I see” to “other people have their own thoughts and feelings, and I can learn to read them.” Psychologist Raymond Mar’s research found that people who read more fiction score higher on theory of mind measures, and crucially, the relationship appears to be more than correlation— fiction seems to train the capacity. The reason likely lies in what fiction uniquely demands: you must simultaneously track your own perspective and the inner lives of multiple characters, update your beliefs about characters as new information emerges, and tolerate ambiguity. This is mentalizing in a highly practiced, iterative form. 

For boys specifically, this is therapeutically significant. Many boys haven’t had enough practice reading social and emotional cues, and many boys with ADHD are too overwhelmed or hyperkinetic for the slow work of learning to understand others. It takes lingering and stillness to develop these skills. Fiction is a low-stakes, non-threatening way to build that capacity. A boy who would never discuss feelings in conversation might spend hours inside the head of a morally complex character, doing the exact cognitive-emotional work that therapy tries to support. In this sense, fiction can be a “stealth theory of mind laboratory.”

The Vocabulary-Emotion Connection — “You Have to Name It to Tame It”

Daniel Siegel famously wrote that phrase in a book—The Whole-Brain Child—that I remember reading when I first moved to the Bay Area well over ten years ago. When your son, or any of us, “name” emotions, the prefrontal cortex gets activated and “tames” what might be an intense emotional response on the part of the amygdala’s threat detection. This is the work of therapy — supported by the affect labeling research of Lieberman and colleagues at UCLA—putting feelings into words leads to neural integration. Lisa Feldman Barrett’s work on emotional granularity deepens this understanding — the richer your emotional vocabulary, the more precisely your brain can predict, construct, and regulate emotional experience. Monosyllabic boys tend to experience emotion as an undifferentiated flood. As they develop higher granularity, they can distinguish between feeling disappointed, humiliated, and melancholic, and that distinction itself is regulatory.

To tie this to the theory of mind concept from earlier, your son cannot accurately infer others' mental and emotional states if he lacks the vocabulary to represent them internally. A boy who only has access to “fine,” “mad,” and “whatever” is working with a profoundly impoverished mentalizing toolkit—not because he lacks empathy, but because he lacks the conceptual infrastructure to represent emotional nuance in himself or others. Reading builds that vocabulary in a neutral context, which is far more effective than rote learning. When a boy reads that a character feels “a gnawing sense of injustice” or “a hollow kind of loneliness,” his brain is filing new emotional concepts that become available for future mentalizing.

Words spoken in session or read once in a book continue to work on us.


I debated whether to share this list of books I’ve read in 2025. I’ve seen friends and colleagues do something similar. This isn’t exhaustive, and some are re-reads. I share it not as a credential but as a practice. These are the books that informed my thinking, challenged my assumptions, and kept me in conversation with ideas larger than my own. They are grouped by category. The first grouping is the most clinically relevant, and those titles were often a mix of reading and audiobook (while hiking). Audiobooks are a legitimate form of engagement, and I’d recommend them to any boy who resists sitting with a physical book.



Clinical & Contemporary

ADHD Is Awesome - Penn & Kim Holderness

The Power of Strangers - Joe Keohane

Four Thousand Weeks - Oliver Burkman

Meditations for Mortals - Oliver Burkman

Mastery - Robert Greene

The Explorer’s Gene - Alexander Hutchinson

Endure - Alexander Hutchinson

Death By Comfort - Paul Taylor

The Hardiness Effect - Paul Taylor

Raising Mentally Strong Children - Charles Fay & Daniel Amen

Deep Work - Cal Newport

No Bad Parts - Richard C. Schwartz

The Anxious Generation - Jonathan Haidt

Furiously Happy - Jenny Lawson

Extreme Ownership - Jocko Willink & Leif Babin

Can’t Hurt Me - David Goggins

Never Finished - David Goggins

Ceremony - Brianna Wiest

The Mountain Is You -  Brianna Wiest

The Molecule of More - Daniel Z. Liebermann, MD & Michael E. Long

Time Anxiety - Chris Guillebeau

This Is Water - David Foster Wallace

Sapiens - Yuval Noah Harari

Peak Performance - Brad Stulberg & Steve Magness

Training for the New Alpinism - Steve House & Scott Johnston

Man’s Search for Meaning - Viktor Frankl



Philosophy & Ethics

The Daily Stoic - Ryan Holiday

Wisdom Takes Work - Ryan Holiday

Discipline Is Destiny - Ryan Holiday

Courage Is Calling - Ryan Holiday

Meditations - Marcus Aurelius

Dialogues - Seneca

Moralia (various essays)- Plutarch

On the Shortness of Life - Seneca

The Enchiridion - Epictetus

On Truth - George Orwell

The Power of the Powerless - Vaclav Havel

The Myth of Sisyphus - Albert Camus

Various Essays from Minima Moralia - Theodore Adorno

On Escape - Emmanuel Levinas

Trust - Alfonso Lingis



Byung-Chul Han

The Burnout Society - Byung-Chul Han

Saving Beauty - Byung-Chul Han

The Palliative Society: Pain Today - Byung-Chul Han

In the Swarm: Digital Prospects - Byung-Chul Han

The Spirit of Hope - Byung-Chul Han

Psychopolitics - Byung-Chul Han

The Agony of Eros - Byung-Chul Han

The Transparency Society - Byung-Chul Han

The Scent of Time: A Philosophical Essay on the Art of Lingering - Byung-Chul Han

Vita Contemplativa: In Praise of Inactivity - Byung-Chul Han



Literature

The Idiot - Fyodor Dosteyevsky

Notes From Underground - Fyodor Dosteyevsky

The Adolescent - Fyodor Dosteyevsky

White Nights - Fyodor Dosteyevsky

A Funny Man’s Dream - Fyodor Dosteyevsky

The Trial - Franz Kafka

Various Short Stories and Letters - Franz Kafka

Bartleby the Scrivener - Herman Melville

The Death of Ivan Illych - Leo Tolstoy

Family Happiness - Leo Tolstoy

The Stranger - Albert Camus

The President - Georges Simenon

Travels with Charley - John Steinbeck

Men Without Women - Ernest Hemingway

The Sun Also Rises - Ernest Hemingway

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