On Solitude

Note: I am releasing myself from the obligation to write weekly. I will publish more sporadically now, perhaps with breaks in between. I will be putting more time towards my team-oriented pursuits, so it’s fitting that I close this phase of weekly posting with a post about solitude. Writing this newsletter has been rewarding for me. Thank you for reading.

Over 15 years ago, I took my first device-free, silent, solitude experience. 15 years and 100s of “solos” later, I can say the following with confidence: If I could give any bit of advice to my younger self, it would be to spend one or two Saturdays a month in device-free solitude (keywords: “device-free” and “solitude”).

Backstory: In college, I took an 8 week study abroad trip to Maine (no phone or computer) and channeling our inner Thoreau, we all took what we called “Solos” — a weekend without talking to any people or, of course, using any devices.

When I first began my solo, I remember being restless, playing with branches, kicking leaves — I was bored. I was hungry. I wanted to come back to mainland. Then, two hours later, I experienced my first solitude high — a feeling I’d seek out for the rest of my life.

It came out of nowhere. I was journaling, and suddenly, I came up with a nice thing to say to someone. Then another. And another. I couldn’t stop. One was an apology. Another was a note of gratitude, far overdue. I started fiercely writing letters, with a clarity of spirit that I hadn’t felt before. I also started to untangle the knots in my head and my heart. with my parents. A friend I didn’t talk to anymore. 

I began to cultivate what John Keats calls negative capability — when a man is capable of being in uncertainties & doubts, without any irritable reaching after fact and reason.

I have always been happier when I have kept my solitude practice regularly. I have improved my relationships, come up with my best ideas, and generally acted with more integrity when I have taken time for myself.

Although it can seem daunting to “waste” a day—the time you save in having less fights, less stress, and less bullshit is priceless.

It’s the strangest thing: When I am alone for extended periods of time, I feel closer to others. When I am offline, away from devices, I feel like I am connected to something bigger than myself. 

Paradoxically, solitude begets solidarity. 

“Labor is a craft, but perfect rest is an art.”

OK. So what do I do during the “solo”? Literally nothing. During the week I am held hostage by inputs: Texts. Notifications. Podcasts. No moment goes un-utilized. On sabbath, no inputs. No podcasts while eating. No checking my phone during down time. No people. No conversations. 


At first, it’s really f-ing boring. It reminds me of David Foster Wallace’s book on boredom (“The Pale King”), where he describes the accountant lifestyle just to give you a sense of what boredom truly is, and it bores you in the process of reading it. I’m bored just thinking about it.

But then the thoughts come. At first they’re mundane: Did I get back to this person. Respond to that email. Overthinking a (unnecessary) comeback to some small thing someone said months ago. Then the ideas come. Compliments (& apologies) you should give people. Ideas for hangouts. Lists of things I should start or stop doing. 

And then the questions come: Why am I still friends with this person? Why am I not in touch with this other person? Do I still want to work or live in the same place? What are the important but not urgent things in my life that, if I did more of, would make me significantly happier? How can I act with more integrity?

Overtime, you untie the mental knots that keep popping up. Tensions you have with people. Limiting beliefs you have about yourself. Other bottlenecks that are preventing you from connecting with yourself, and thus, other people. Then the feelings come. Regret at mistakes you made. Anger. Pain. Sadness. You haven’t felt actual feelings in so long. Some feelings sink so deep into the heart that only solitude can help you find them again.

You emerge with more sympathy, because you can now separate observations & judgments Maybe when he said that hurtful thing he was going through something of his own, you reflect. You forgive. Hearts & minds are reclaimed during solitude. Perspective shifts—they happen here. So does healing. 

You become more compassionate, untethered, and proactive: How can you be a better friend to her, better partner to him, better colleague to them? You ask these questions, brainstorm solutions, and then enact processes to operationalize the solutions

The process takes time. The thoughts are sporadic and are surface level before going deeper. It’s as if you’re hacking at a tree, several trees at a time. Whack-a-mole. With enough hacks, you get at the root. Normally, an input blocks a deeper hack. But with silence, you hack away…

Or maybe it’s like fishing. Just wait. You’ll catch the Good Thoughts—the ideas, feelings, the paradigm shifts. Or, more accurately, they’ll catch you.

Sometimes you will lie there for hours. Other times you will be seized with a desire to write something down. You trust the process. With enough time, Your mind reconfigures your thoughts, like a Rubik’s Cube solving itself. Or puzzle pieces. Or Tetris.  Sometimes it's painful. You sit with this harrowing memory. It hurts. It’s hot.

Your heart becomes like Wolverine’s body — the wounds heal themselves, if you let them. “Time heals all wounds”, they say, but they forget to say that it’s the right kind of time--solitude.

Normally when my brain is about to go deeper, it gets distracted. One notification here, one “like” there. Alone, there’s nowhere to run to. You have to face your thoughts. Some are pleasant, some are sad. They flit by. You bide your time, until the cycle begins again. Like clockwork.

You’re like - “How can I uplevel myself—what if I had a virtual assistant?”

Or OH—Remember the idea of spaced repetition? Maybe you should do that

Or OH—why don’t you hang with college friends anymore? You should plan a retreat.

Or OH—it’s your friend’s birthday! You should plan a surprise.

I have to admit—the whole thing sounds random. It feels random. If someone looks at you, it sure as hell looks random

It’s not even meditating. It’s just sitting there. Zoning the fuck out. Sometimes I meditate. Other times I fall asleep. 100% not judging the process.

Not judging the process is key. I try to do it weekly - but realistically it’s like every 2/3 weeks for me. Sometimes it’s one day. Other times, it’s 3. I try to alternate between sabbath and weekend trips/experiences.

Unlike meditation retreats (which are great & serve different purposes), I don’t focus on the mind. I just let it wander. Unlike religious sabbath, not strict or historical, although the fact that people have sought solitude for thousands of years is another indicator of its importance

The only rules are *no phone* and no*people*. Do I follow these rules? No. I end up checking my phone a couple times. I remember I was on a 3-day self-imposed meditation but I needed to know whether Kawhi Leonard had gotten traded. (He had.) But that’s OK. The fact that my device is off for most of it is what matters. Also like meditation, the key is to not to judge yourself during the process. 

One interesting side effect is that it makes you conscious of what you put in your mind. A conflict can drive you crazy.  A passive aggressive remark can eat at you. Even a simple song could get stuck in your head.

Want new ideas? Spend one full day alone doing nothing. Want to be more in touch with yourself? Spend one full day alone doing nothing. Want to have greater appreciation and connection with others? Spend one full day doing nothing.

Don’t think it’s worth a full day? Spend two days.

Of course, if you have kids or other responsibilities, device-free solitude may be impossible. Like any retreat in general, It’s a privileged thing to be able to do it, and if you're unable, maybe take little bouts of deliberate solitude when one can.

When do you know you’ve had a good “solo”? When you’re hungry to see people again.

Hence another paradox of solitude : the problems that solitude can help you overcome often make it hard to take the time to do the solitude in the first place.

But the time I take gives me back double. I’m so much more effective, so much more precise. So much more in tune, in sync.

With that, I’ve just scheduled my next one for next Saturday. I haven’t taken one in months, and needed to write this to keep me accountable.

Until next time,