Seven Days Alone in the Dark
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When I worked for Facebook in Silicon Valley and lived in San Francisco, there were two routes to work; one was significantly shorter and the other significantly more beautiful.
Occasionally the direct highway would be so jammed that my map would send me the beautiful way. Picture me doing an elbow pull: “YAAAS!”
You guys. It probably took me a year to realize that I could simply choose to take the more beautiful way even though it was slower.
I worked for a company whose slogan was “move fast and break things.” I was conditioned for speed. I’m not blaming Facebook, I was totally aligned with this strategy.
When the option to take the scenic route finally occurred to me, I began shifting my drive.
I started slowly at first, opting for beauty when I really had no specific reason to rush. The more pleasant my commute became, the more I prioritized the longer way.
Yes, it took me 20% longer, but I was 100% happier.
One of the first things Vince and I did together was take a road trip. We turned on the “Avoid highways” for more scenic routes.

If there’s one word for seven days spent alone in the dark, it is ‘intimate.’
I learned about intimacy this past week. It is wild with paradox.
Intimacy is simultaneously deep and dark and spacious, while also being urgent and panicked and compressed.
It’s wild love and debilitating resentment. It’s brilliant insight and endless tedium.
Getting to know oneself intimately is a courageous act for its complexity.
The moment something is intimately known, it’s irrelevant, and that makes the experience of meeting one’s self an endless fall.
My time in the dark has been, on one hand, comfortable and pleasant: The room was warm, the meals were nourishing, everything I truly needed was available.
In that sense, this place is a foundation of safety and nurturance. A dark room is often compared to a womb, where there’s nothing one needs to do.
To a mind and body conditioned to “doing,” however surrender turns out to be a Herculean task.
No, Hercules is the wrong metaphor – I’ve felt more like Icarus in his fall.
Normally, my life is fueled by the pride of thinking I’m a separate self, responsible and in control of my life.
In the dark though, with distractions removed and habitual coping mechanisms unavailable, the wings of that pride melt, and my sense of doership plummets to the earth.
It is terrifying at times, as the mind desperately grasps for any sense of specialness, and finds none.
[Long pause]
‘Why on earth would you put yourself through that?’ some people have asked.
Of course I can’t speak for anyone else. But my own motive was a simple curiosity: could life feel even better? Radically better? And if so, what is in the way?
When my friend first suggested that I go alone into the dark, something in me lit up: a hunch, an intuition, a whisper of rightness. So here I am.
My first three-day journey was nearly intolerable, except for the way my life slowed down and expanded upon coming out.
And so I came back, not in search of anything specific, but simply because I was invited, and something in me knew to accept.
This week has been uncomfortable at best, and yet like sandpaper on rough wood, I can tell I am softening.
My heart is opening like the petals of a flower in a way they do not during my normally-contracted life. Like a flower, the process has been imperceptible, but the result is undeniable.
I will be back, I know this, for longer next time.
On one hand, coming in here is a dreadful prospect: what delights in life am I missing every time I go into the dark?
But how much of life is lost in the wash of daily light?
Andrew Holecek, one of the pioneers of dark retreat in the west suggests that the trouble of our age is not darkness but light.
24-hour factories, billboards, street lamps, charging lights, night lights, TVs, PCs, and phones. How much is all that light obscuring?
We already know that thanks to screens we do not sleep as deeply, we do not dream as vividly. We already know that in cities we’ve nearly lost the stars.
Among wisdom seekers it is common to experience spiritual bypassing: an obsession with light and a rejection of darkness.
[Long pause]
I say again, this is not a comfortable place to be.
In here, everything I spend my life avoiding, surfaces.

In that sense, it’s often a flavor of hell. But it’s my hell. And whether I know it or not, that hell shapes my waking life, running, often undetected, in the subconscious.
In the dark, I turn around and meet myself, honestly, maybe for the first time.
This week I have fought that meeting with everything I had, despite the intention and desire to let go and surrender.
My mind fought, my body fought.
I didn’t have a journal in here, but if I had, here’s what I might have written.
Day 1
Entry. This day, just like last time, was a time of enthusiasm, orientation, and napping.
I made it! Here we go! What’s gonna happen?
How many steps to the toilet? How do I get the right amount of toothpaste onto my toothbrush? Which end of this thermos is up? Where did I put my socks? Did I set my email auto-reply?
Napping on the bed. Napping on the sheepskin. Napping on the carpet. Napping with my legs up the wall and calling it Yoga.
Day 2
To distract or entertain, my mind obsessively rewatched TV shows, recounting plot lines and character names. I tried to stop. I couldn’t.
That night, I stayed up for hours trying to remember the name of Jamie and Claire’s adopted french son on Outlander. When Keen came for my morning check-in, I used my precious human contact to ask him to look it up. (Gratefully, he did. It is Fergus.)
Day 3
I began internally listing the names of people with whom I went to elementary, middle, and high school, then their siblings names, and parents.
My mind used anything to stay distracted, engaged, oriented; anything to stay out of quiet depths.
Even my dreams were endless, chaotic, and full.
In a place with nothing to do, I was always wondering what to do.
I peed more than I needed to just for an activity.
Taking my afternoon vitamins became a ceremonial event, just because it was something rather than nothing.
For all of this, I judged myself harshly. “Where is my big spiritual experience?” I wondered. “Where is my profound peace?”
“I am failing,” I thought, over and over and over.
It may sound as if all of this noise was in the way of me meeting myself, but I finally realized, rather humbly, that this is myself.
Not all of myself, of course, but busyness, resistance, doubt, and self-attack are the backdrop of my everyday life. I have learned to live with it all, rather gracefully, I might add.
But do I have to?
Day 4
During the morning check-in, I sobbed through the darkened door. “I’m failing.”
I was referring to my dark retreat, but that’s not all. “I’m failing creatively.” I said. “I’m failing at community and friendships. I’m failing professionally. I’m failing physically. I’m failing spiritually.”
This was when Keen suggested I could build a snowman.
I didn’t. But after they left, I finally realized that I wasn’t failing at my dark retreat, this was a success! I was seeing clearly, maybe for the first time, my constant life companion—the belief that I am a failure.
This is how the darkness illuminates.
Day 5
The internal TV watching and name recognition continued. So did the frequent showers and bathroom breaks. I sang mantras, not to God, but to pass time. The difference now was that I wasn’t judging myself nearly as harshly.
Seeing the “failure story” as a story, somehow drained its power.
Day 6
Peace emerged. It wasn’t spectacular or out of this world. It was just…ease. I had the thought “Wow. This is nice. I could stay here.”
It didn’t last, but it came and went, hinting at a quieter backdrop than the one with which I’ve lived.
Day 7
Today, on the very last day, I found myself on my knees.
This is a posture that could signify either defeat or devotion. In my case, it is both.
Though I tried all week, I never really let go of fighting. I yearned for peace, but it was not something I could do.
Yet still somehow peace had emerged.
Surrender took place, I realized, without my doing it. I am now left with the sense that this could not be a kinder design.
[here my voice breaks in the recording, streaming tears of gratitude]
For in the end I have learned that despite all my fears and incessant mental chatter to the contrary, Keen had been right: I cannot do this wrong.
“This” meaning my dark retreat, but also my life.
I cannot do it wrong, because I’m not doing it.
It is being done. And I am the unspeakably [more tears] privileged recipient.
</end recording>

Thank you so much for reading. It means a lot to me to be able to share these adventures with you. I’m honored by the gift of your time and attention, there is nothing more valuable. And as always, I welcome your reply if there’s anything you’d like to ask or share.
With love,
Leah
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Latest Mediation: Wanting to Slow Down (But Can’t)
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