Silent mode: Why the stars of Silicon Valley are turning to silent meditation retreats

It’s not just Twitter CEO Jack Dorsey doing silent meditation in Burma; more tech execs and business leaders are signing up for vipassana retreats, and million-dollar compounds are going up in Silicon Valley.

Silent mode: Why the stars of Silicon Valley are turning to silent meditation retreats
[Photos: Drew Angerer / Staff/Getty Images]

Our Burmese video guru, speaking from beyond the grave, emphasized that all “intoxicants”–everything from alcohol to Ambien–were strictly forbidden. We repeated the vow, eager to make an honest attempt at the ancient practice of Burmese vipassana meditation.


When the “noble silence” was lifted 10 days later, the truth of what really goes on at some retreats like ours was laid bare. One attendee split on day seven, explaining that a mid-retreat mushroom trip had already opened “all the doors” to “all the universes.” Another was microdosing LSD. To kill time, people made art from food and invented primitive games. When blank-faced participants took “exercise” by slowly circling a rain-drenched field, it looked like a scene from The Walking Dead.

Greetings from the intersection of ancient spiritual tradition and tech-infused lifestyle engineering: the American silent retreat. Meditation has gone mainstream–and it’s a booming $1 billion industry. The number of Americans who meditate spiked to 14.2% in 2017, up from 4.1% in 2012. Apps like Headspace and Calm proliferate, some with valuations in the hundreds of millions of dollars.

Ten-minute morning meditations on one’s phone are a gateway drug to silent retreats like vipassana, which are increasingly popular. Courses are booked months in advance, and new facilities are under construction near tech hubs around the country.


Last December, I scored a coveted spot at a vipassana retreat in rural Oregon. Based on a series of VHS tapes recorded by S.N. Goenka, an eccentric Burmese millionaire, attendees committed themselves to what he called “surgery of the mind.” Over 10 days I stared deeply at tree bark, tried to avoid scratching that itch on my face, and reached astral planes of boredom.

I also learned that not everyone comes in search of enlightenment.

Pulling up to a rustic compound deep in the heart of logging country, I was unsurprised to find the standard New Age crystal-healing types and bearded hipsters. What jarred me was the preponderance of refugees from “Silicon Valley North”–coders and capitalists in the ambit of Microsoft and Amazon.


The clientele at entry-level retreats increasingly skews less Thich Nhat Hanh, the celebrated Vietnamese monk, and more Tim Ferriss, the hyper-productivity guru. For some participants, the experience is yet another life hack, like drinking bulletproof coffee or KonMari-ing your garage. A grueling daily schedule began with a 4 a.m. gong blast and only ended–some 11 hours of focused, eyes-closed contemplation later–with a lugubrious evening “dharma talk.”

For me, the retreat was meant as the capstone to a year of mental health that included a 2,700-mile thru-hike. For most of my life I have struggled with breathless, nail-biting, pain-in-the-chest anxiety. It gave me the work ethic to get into a fancy law school but also produced restless dissatisfaction with all my life choices. I was sold on the retreat by a hiker friend who claimed: “Vipassana is the most powerful tool available to humanity.”

During check-in, there were multiple conversations about software and startups, but I found myself sipping tea with a chemistry teacher from Colorado, a stout man with a handlebar mustache whose wife finished a course over the summer.


He warned me that by the end of the first “motionless sitting” his wife had tears running down her face from pain. But we were interrupted by a thirtysomething techie in a puffy vest, who reassures us that we are on the right side of the research.

“All the studies show that the strongest benefits correlate not with the total number of hours in meditation, but with the number of hours spent in retreat.” he said, explaining why he had flown up from San Francisco.

By the second full day he was gone, his cushion discreetly removed from the cramped meditation hall during a break.


“Your mind is not as much in control as you realize”

Alexis Santos, a former monk and instructor for the Insight Meditation Society, which facilitates a constellation of retreats nationwide, said that high achievers who attend retreats to “become more efficient or effective” often end up going “deeper” by confronting their own restlessness and suffering.

“Once someone comes on a retreat, they may not know what they’re getting into, but the discoveries are pretty universal,” Santos said. “You learn that your mind is not as much in your control as you realize.”

Some Insight centers are booked out to next December. Santos noted an “incredible growth in interest over the years” and said that a recent 100-person course had around 500 on the waitlist.


My retreat was not a gentle introduction to the practice. Goenke joked that we had signed up for meditation prison. The men were housed in 4-person dorms with thin foam mattresses and cold concrete floors. And yet like Al Capone’s luxurious stay at Eastern State Penitentiary, one of my roommates subscribed to the theory that prison need not be uncomfortable. Though he wanted to “remain anonymous” and wouldn’t even tell us his first name, he declared we were “doing it wrong” because we had not, like him, brought our own mattress, bathrobe, and Brita water filter.

[Photos: Kalen Emsley/Unsplash; Eidy Bambang-Sunaryo/Unsplash; Fortyozsteak/Unsplash]
As we discussed the grueling schedule, Anonymous said he planned on skipping most of the sittings.

“I’m mostly looking forward to being without a phone for a few days.”


At the start of each group sit, our flesh-and-blood “assistant teacher” sat on a dais before around 60 novitiates, solemnly wrapped in a blanket. He pushed play on the iPod and suddenly Goenke was among us, his voice dripping with vocal fry: “Staaaart with a caaaaaaaalm and cleaaaaaaaar miiiiiiind.” He held the teachings out as completely “scientific” and non-religious, but there was ample talk of reincarnation and the Buddha’s supposed anticipation of quantum mechanics, not to mention an egregious amount of chanting.

Goenke–a strict video taskmaster–cautioned that the “weak-minded” might try to “run away,” and he was right about the running. There were numerous escapees, including the guy with a Tibetan tattoo encircling his arm who sped off in his Subaru on Day 6, and the fellow who brought his own folding leather throne–a veritable meditation Laz-E-Boy–but flew the coop on Day 8.

Jack Dorsey’s quest to hack the mind

Despite its no-compromises approach to meditation, there are 12 Goenke-style centers around the U.S.–and the organization is expanding in the places you might expect. The Bay Area Vipassana Trust purchased land last year for a new facility just south of Silicon Valley in Gilroy that will cost more than $10 million to build. And a compound with 130 individual soundproof “cells” is slated for construction outside Seattle.


Though the program was donation-based, there’s no such thing as a free vegetarian lunch: you are expected to “pay” with your efforts. During breaks, I cleaned toilets and stole catnaps. The last full meal was served at 11 a.m., though a piece of fruit and cup of tea were allowed–for new students only–in the afternoon. By the end, some participants were crafting mandalas from apple slices, out of sheer boredom.

The strenuousness of retreats stands in some tension with the mobile app industry, which seeks to demystify meditation to neophytes. The 10% Happier app, $99.99 for a year’s subscription, calls itself “meditation for fidgety skeptics.”

10% Happier cofounder Ben Rubin said that the broader mindfulness movement is drawing a new demographic to retreats, and he told me: the “performance optimizer.”


“This is that ‘four-hour body,’ executive, sort of life-hacker type, more male than female, 25 to 45,” said Rubin, who is also a board member of Insight. “Their goal is to get a performance edge in work and sport and relationships.”

Twitter CEO Jack Dorsey, who flew to Burma to complete his second 10-day retreat this winter, framed his experience in software-friendly terms: “Vipassana’s singular objective is to hack the deepest layer of the mind and reprogram it.”

The risk of punishing ennui

On the fourth day, we learned Goenke’s version of the technique. It was essentially a mental MRI scan. Goenke advised us that all group sits–around 16 hours–should now be practiced with a “strong determination” to remain perfectly motionless.


About 20 minutes into the first vipassana sit I felt waves of anxiety as pain flooded into my legs. I can’t do this, I thought, and yet, as the minutes continued to pass, it became apparent that I could. For the rest of the hour, at least, my anxiety dropped away like a stone. It was a minor breakthrough.

But the emotional vacuum was soon filled by a punishing ennui. Every morning I made a point of walking few yards out into the empty forest road, to remind myself there was an outside world. Anonymous, my luxury-minded roommate, took to “shooting” sticks and twigs into the basketball hoop, standing at the free-throw line in his bathrobe.

The retreat center did double duty as a summer camp, and someone came up with the idea of “bowling” with the old semi-deflated basketballs littering the surrounding woods. It turns out that when you knock a bunch of deflated basketballs into one another, precisely nothing happens. But we were mesmerized. Heads turned to admire our Prometheus, who stole back Sport from the void.


“For the vast majority of people, [the first time] will be incredibly frustrating,” said Rubin, who makes a point of attending a retreat at least once a year. “You’re going to be cooped up and going crazy in your own mind.”

The retreat experience can become so intense that people with a history of mental health issues are often precluded from participating. One attendee of a vipassana retreat in England recently wrote about leaving in handcuffs after falling into psychosis.

[Photos: fizkes/iStock; Jeremy Thomas/Unsplash]
Given that the Headspace app alone has reached over 40 million downloads, it seems inevitable that a “spill-over” into retreats will continue. But many first-time participants either don’t know what they are getting into or come with their own agendas.


Narayan Liebenson, an instructor with the Insight center in Cambridge, Massachusetts, and author of a new book on meditation, said that while retreats used to attract more of the “counter-culture,” she has been seeing a more from the “conventional culture” of late.

“There are more people coming not completely knowing the difference between stress reduction and the teachings of the Buddha,” Liebenson said. “We’re trying to do a little more education around that so people will know what will be expected of them and what they will be there for.”

She said that, while retreats may not be for everyone, “for most people in this world I think to sit in at least one week-long retreat in their life would be really positive.”

On the ninth day, Anonymous Roommate finally packed up his Brita. The day before I had seen him talking to his jacket. Breaking silence, he explained: “I think I got the gist of it.” He left a hundred-dollar bill on his bed and drove his car through the center of the compound to collect his big cardboard box, leaving a long, muddy gash in the grass.

On the 10th day, the vow of silence is lifted. Within minutes, a Microsoft coder in an “Oxford University” shirt was asking the course manager for his phone. He looked desolate when he was told we must wait one more day.

In the noisy dining hall, people were already networking and swapping business cards. I was eager to chat with the young man who had been coughing next to me all week. From his baggy sweatshirt and baby face, I had him pegged as a college student, but in fact he was a venture capital investor living in China. He talked a lot about drugs and said his curiosity about meditation was piqued after taking ayahuasca at an illicit ceremony on the outskirts of Shanghai.

“I wanted to go to the next level, you know?”

Things don’t always go smoothly at the next level. In a podcast interview, ur-performance optimizer Tim Ferriss described microdosing ‘shrooms during his retreat. “I decided I would rather overshoot than stay suborbital.” He overshot, reliving childhood traumas for hours on end.

As for our own Mushroom Man, before he left he dropped a note to one of the women, saying that he had been watching her all week and that she “looked sad.” This did not go over well.

An earnest woodsman with a thick beard told me he recently escaped a religious cult in Pennsylvania. He became interested in “contemplative states” after trying legal marijuana in Oregon, but our teacher’s heavy-handed approach triggered him.

“The whole thing–the chanting, the ritual, the isolation from other people. I mean, it’s just an elder male telling you what to think and how to act. That’s religion to a ‘T’!”

Even so, he said he achieved something like a revelation, if not a strictly Buddhist one.

“I realized it doesn’t matter,” he said. “None of it matters, because it’s all fine, we’re all going to be fine!”

Nearby, the China VC guy had fully moved back into the modern world. He was telling the fledgling startup founder that he specializes in “taking companies to their Series A.” Without any irony, he added: “We should talk.”