Why Every Business Leader Should Take a Silent Retreat Every Year

—Below is a passage from my journal, written at a small retreat house in Flagstaff, Arizona, 2009.

I haven’t eaten in 2 days, I haven’t heard a human word in 3. If I found a cigarette, I’d smoke it.

The weight of this particular life decision is now apparent; the weight of all of my decisions is now something I feel. That feeling is liberating; remaining numb is not. Satisfying one desire after another is not satisfying; rushing from one thing to the next is not progress. Why am I here? What unknown desire brought me to this little place?

I found the library tonight. I handle-checked a door which I thought was a small closet at the end of my hallway. It opened up into a large room with floor-to-ceiling books and two reading chairs. After browsing the philosophy and history sections (there were no business books in this library, which made me happy), I went to the literature wall and settled on “The Old Man and the Sea.” It was calling my name in some strange way. Or maybe I just liked the way it smelled. I really don’t know.

I took it back to my room and read it. All of it. I had to set it down and look out the window every 10 minutes because the energy building inside of me seemed to want more time to coalesce. ‘Slow down, Luke,’ I kept telling myself. ‘Let it happen. Let it build.’

I had to remind myself that I was not reading this book to tell someone I had read it, nor to make myself feel good that I had read it, but to read it. I was reading it to stir my soul. Maybe to break it open.

In the front of the book, someone named Thomas had dedicated it to someone named Anthony in November 1974 with the words (now barely visible in number 2!? pencil): “A book must be the axe for the frozen sea inside us.” — Franz Kafka.

I wondered who these two men were. Who did they love? What is their relationship? Are they father and son? Brothers? Friends? I’ll never know them in person, I doubt. But I know something of them, even now. Something personal.

When I finished the Hemingway book, the woman who runs runs this place (‘Mercy’ is her name, seriously) asked me if I’d already visited the small chapel down the hall. Yes I had. It seemed like a converted dining or living room with a tabernacle at the front and 9 or 10 rows of chairs. She asked if I’d like to sit there for two hours…between the hours of 2–4am…because it’s necessary that someone is there in the chapel all the time, 24 hours/day — perpetually! — to keep watch. She had planned to take that time slot herself tonight (which she does if nobody else signs up), but she ‘thought I might like to have it’ instead. How sweet. This perfect stranger asking me if I’d be willing to sit there, in the middle of the night, entirely on my own, between the hours of 2 and 4 in the morning, as if she were offering me a great gift. There was almost a sparkle in her eye when she asked. A wry smile. Does she not know that I work 80 hours/week? Of course she does. She can sense it. And maybe that’s why she asked.

What does she know? What happens to her in the middle of the night? Who is she?

I showed up when I said I would. I had fallen asleep around midnight but set my alarm for 1:55am. When the alarm rang, I immediately lamented and cursed my ‘yes’ to Mercy, but I rolled out of bed, threw on my jeans and a hoodie, splashed some water on my face, and made my way down the hall. And I just sat there. I listened to the creaking of wood in this old house, the occasional tapping of what sounds like demons in the water pipes, and the clock ticking, and the low humdrum of the A/C. Though I’ve never felt less alone.

I finally nodded off near the very end of my session, peacefully, after struggling valiantly to stay awake for 90+ minutes. I finally succumbed. I must have only been asleep for 10–15 minutes when heard someone enter the side door and come into the room behind me. The clock said 3:50.

I opened my eyes and looked at the person who had entered the room and kneeled a few rows ahead of me. He was a guy about 55 years old, wearing what was clearly a mechanic’s outfit. His name patched onto the shirt, the kind of thing you’d see from the guy you talk to when you’re getting your brakes done, who normally tries to upsell you on window washing fluid and other fluids, but not this particular guy. He looked as if he’d just smile and hand you back your paperwork. He’d been doing it too long. I needed an oil change, I remembered.

He looked gentle yet weathered; tired, but alive. He wasn’t wearing a wedding ring. I wondered if he was widowed, or if maybe he wanted to protect it from the grease and the grime of his day job. This, apparently, was his night job.

He turned around and smiled at me, nodding as if it to tell me that it’s okay for me to leave now if I wanted to. I did not. I wanted to stay there. I wanted to stay with him. At the same time, I need (want) to get some sleep.

I have “a call” tomorrow morning. I have to “be prepared.” I have to re-insert myself back into a different rhythm of life, a rhythm that doesn’t give my soul time to rest in people and things. [writes in margin, with an arrow pointing back to this sentence: ‘must solve this problem right away.’]

Could it be that this man freely chose to come here at 4 o’clock in the morning to sit in silence for an hour by himself before he goes to his job and works his ass off for 8–10 hours? Does he do this every week? Every day? What kind of love is this? Who is this man, with this hidden life? What acts of heroism has nobody ever told me about? It’s okay to cry. I have to change my life. It’s 4am.

One of the unfortunate byproducts of our Cult of Experts: 99% of the content that I stumble upon — or at least content that is marketed at me — is aimed at my head and not my heart.

Nearly every podcast markets the “knowledge”, or gnosis, that it’s going to impart through interviews with subject-matter experts, authors, or other Really Interesting People.

The man who entered the chapel at 4pm would not be one of them.

But the heart knows things that the mind cannot. “For myself, it was not logic, then, that carried me on,” write John Henry Newman about the different between a ‘notional’ and ‘real’ assent to truth. “It is the concrete being that reasons; pass a number of years, and I find my mind in a new place; how? the whole man moves; paper logic is but the record of it.”

Newman coined the term?illative sense: a power in the soul that collects, combines, and engages in sense-making out of the mysterious moments of everyday life, of lived experience, and of the multitude of probabilities that all converge and give us the ability to ‘know’ something or assent to some truth in a real way — with the whole of our being: a whole-person way of knowing which affects our whole life, or causes us to change our life.

(Perhaps Iain McGilchrist is talking about this in some sense, even if he doesn’t use the term ‘illative sense,’ when he describes the whole brain — both the calculating and the meditating parts — working together to shape our relationship with reality. In my view, the illative is a spiritual organ, like?the conscience .)

The affective sphere of life has been ravaged, and that’s not good for the intellectual sphere either.

As I’ve been trying to put my finger on what seems so off to me about the Contentverse — even the very?best?of it — it’s that it lacks that personal knowledge and tenderness of the heart, covered up in intelligence-signaling or access to better sources or studies or more credentialed people, whether from Ivy League Institutions or from the Intellectual Dark Web (which has its own very serious set of credentials. Can you guess what they are?)

It was in the silence of those days and in the silence of those nights that I came to know things, both about myself and the world, which convinced me of the truth of Pascal’s observation that “All of humanity’s problems stem from man’s inability to sit quietly in a room alone.”

Not long after my 3-day retreat in Flagstaff, I was thrust back into my 180 mph life in Las Vegas. The very next week, I also received an invite to a prestigious ‘conference’ that promised to be a Good Networking Opportunity with Interesting Speakers and made up of an Exclusive Gathering of The Most Promising New Founders and Investors.

I just wanted to be with normal people. Why did it seem like every conference or event in my world was marketed to appeal to a desire to be in some kind of C.S. Lewisian?inner ring ?

What I really craved was a place where I could just?be?— along with other people who wanted to do the same thing. No speakers, no panels, no talking heads, no keynotes, no contrived or manufactured socialization or games. Just good food, natural conversations, and total silence for at least one full day — a day on which we could wake up in the morning and wander around the beautiful grounds of a retreat center in our sweatpants and sweaters, t-shirts and shorts, with a book under our arm and access to a library full of beautiful and rare books, with antique writing desks in each room and our devices locked in boxes somewhere. Silent meals, silent hikes, silent games.

Things happen in that silence. They just do. Things that none of us could’ve ever predicted and certainly not engineered. This is part of the work of transforming desire that I tried to articulate, perhaps inarticulately (because it is?inarticulate knowledge) in?Wanting .

I’ve engaged in the work of silence for well over a decade now. The retreat in Flagstaff was one of the first. This year, I’ve realized that I want to do something to bring this kind of experience to more people who might not have sought it out, or may not have even known to, partly because it’s so inconvenient to do so on a number of levels.

I believe that this type of experience should be attractive; it should be as convenient as booking an AirBNB, with hospitality and food that rivals the best hotel stay you’ve ever had; with a strong sense of community — bound by a powerful, shared experience; and the (optional) opportunity to immerse oneself in classical education on par with a small-group seminar at Oxford or Cambridge.

That’s the type of intimate experience that just might act as an antidote and counterforce to the Content-Brained destruction of the Default Mode of the current world, which none of us really opted into with our full consent. It just sort of happened to all of us.

This is one way that I plan to put my time and my money where my mouth is — to bring something new into the world at a time when I believe it is sorely needed. You might say that my illative sense is sensing that there is a thick desire for this, even if it is an inarticulate one for most. I know that it’s there. It was for me, and I know I’m not alone.

I have been thinking deeply about this for months, and I’ve started having conversations with potential partners. My hope is that one of these experiences (which still don’t have a name) would be available sometime in 2023 for anyone interested and daring enough to come.

It will likely be a long weekend to start with — Friday-Sunday — with Saturday being the day of silence, and Friday evening/Sunday morning as time for wonderful meals, unstructured play, and conversations, with several different learning tracks to embark on as ‘take home’.

These experiences should be opened up to corporations, schools, and organizations who want a curated, tailored retreat, grounded in silent reflection, which gives people an opportunity to connect more deeply with their personal sense of mission and their thick desires than they would ever be able to if they were being talked at and compelled to participate in happy hour drink-fests that only bring false catharsis. (Not to worry, though, there will be plenty of ways to imbibe: I’ll make you a martini or tea or unpretensiously pour-over coffee from Guatemalan beans at a water temperature of exactly 195 degrees myself if needed.) Sure, anyone can take time for a reflective getaway on their own; but few do. And a structured experience, guided by 2,000 years of monastic tradition (though nothing about this needs to be explicitly religious), with community accountability, is extraordinarily valuable, as is a consistent experience across the various locations these will be held.

I’ve come to a point in my life where I wouldn’t dedicate myself to building anything that I wouldn’t be a regular and avid partaker of myself. More importantly, I wouldn’t invest my time or effort in anything that I didn’t know I would desire doing and participating in 50 years from now just as much as I do now.

Maybe that’s called a thick company — a company built on thick desires.

Or, as one venture capitalist who is meme-ing his way into my twitter feed far too often these days might put it: It’s time to build something that is not the Current Thing.

— Luke

Archaic Torso of Apollo

by Rainer Maria Rilke

“We cannot know his legendary head

with eyes like ripening fruit. And yet his torso

is still suffused with brilliance from inside,

like a lamp, in which his gaze, now turned to low,

gleams in all its power. Otherwise

the curved breast could not dazzle you so, nor could

a smile run through the placid hips and thighs

to that dark center where procreation flared.

Otherwise this stone would seem defaced

beneath the translucent cascade of the shoulders

and would not glisten like a wild beast’s fur:

would not, from all the borders of itself,

burst like a star: for here there is no place

that does not see you. You must change your life.”