On the Other Side of Boredom
A conversation with Adam Ekberg
“I loafe and invite my soul”
— Walt Whitman, “Song of Myself”
***Update: The full conversation with Adam Ekberg is now live. Listen below or at theprincipaluncertainty.com/podcasts (or wherever you get your podcasts).***
Next week on the podcast, I’m publishing a conversation with Adam Ekberg--a photographer whose work involves spending years trying to make single images happen in the world. While editing the episode, one thread kept pulling me back: what he said about boredom.
A week ago, Adam Ekberg sat in his uninsulated studio in rural New Jersey, wood stove struggling against February cold, and told me something I’ve been thinking about ever since: “All that stuff happens on the other side of boredom,” he said. “If you can get yourself good and bored and sit with it and push past boredom, there’s like a fucking land within all of our minds, like right over there.”
He was talking about making art—specifically, about the iterative process of trying to photograph a disco ball on top of a mountain for thirty consecutive nights, or spending two and a half years figuring out how to get an arc of shaving cream to land in the center of a burning circle. But he could have been describing what I saw again and again in twenty-five years working in wilderness education, politics, nonprofits, and eventually studying therapists who sought out spiritual practices when their professional training proved inadequate for the suffering they encountered.
The pattern is remarkably consistent. Transformation doesn’t tend to happen in the urgent, productive moments. It happens in the course of gently sustained attention that our entire culture is organized to prevent.
Adam learned this from a neighbor named Tony King, a photographer and naturalist who lived across the street from him in Massachusetts. They would sit together—sometimes for twenty minutes before either of them spoke, sometimes for hours at a diner over coffee. They would go into the woods together and watch ants. Not study them, not photograph them. Just... watch them. For an hour and a half.
“It was like tuning into a frequency,” Adam said. “We’d just sit there--and then it would happen.”
When Adam was nineteen, driving cross-country with a friend in a battered Toyota Chinook, they got stuck in Ohio. Too young to buy alcohol, unable to score weed, bored as hell. They invented a game called Sink the Leaf. One person would wrap a leaf around a rock and throw it into the river, so that the leaf parted company with the rock, and the leaf would be left floating. The other person would then throw rocks trying to sink it. They played for hours. Later, in New Mexico, they invented Race the Tupperware—racing his friend’s mother’s orange Tupperware against a Cool Whip container down desert tributaries.
“Entertaining ourselves with that stuff was like the best,” Adam said.
Most people would call this wasting time. Our professional frameworks certainly would. Billable hours, productivity metrics, evidence-based interventions—the entire cult of self-optimization—these are the languages we’ve built to ensure that every moment counts toward some measurable outcome. The whole mental health apparatus is organized around symptom reduction timelines and treatment protocols designed to get people “better” as efficiently as possible.
But there’s a difference between what Whitman meant by loafing and inviting his soul—the productive emptiness where something genuine can emerge—and what most of us actually do, which is pursue adequate distraction. Sink the Leaf isn’t scrolling Instagram. It’s genuine play that emerges when you stop trying to be productive and let boredom take you somewhere.
And the people I studied weren’t actually getting ‘better’ through efficiency. They were getting better—or at least getting different, getting transformed in ways that mattered to them—through practices that sometimes looked an awful lot like doing nothing.
The therapists I interviewed for my dissertation had all reached a similar point. Their professional training had given them techniques for managing symptoms, frameworks for understanding pathology, and boundaries to protect themselves and their clients. What it hadn’t given them was any way to be deeply, personally present to existential suffering—their own or anyone else’s. So they went looking for something else. Some found Buddhism; some found contemplative Christianity; and some found their way to the Lakota Sun Dance ceremony—which could be easily described in terms of the dramatic piercing ritual at its center, but which actually involved days of just being present in community, hours of what looked from the outside like nothing happening at all.
What they described wasn’t learning new information. It was learning a different mode of attention. One therapist told me about spending three weeks at a meditation retreat where the instruction was simply to notice when her mind wandered and bring it back to her breath. For the first week, she was bored out of her mind. The second week, she was angry about being bored. The third week, something shifted. Not a dramatic spiritual experience, just... a different relationship to her own experience of herself, in her body, in a very specific time and place.
When she went back to her practice, she found it easier to sit with clients’ suffering without immediately reaching for an intervention. She could more readily tolerate not knowing what to do next. She could be more present to someone’s pain without trying to fix it, which paradoxically seemed to create more space for actual change than any technique she’d learned in graduate school.
This is, in part, what I think Adam means about the other side of boredom. The land over there isn’t filled with insights or revelations. It’s just a place where your usual relationship to time and productivity stops making sense, and something else becomes possible.
In my consultation practice, I work with people who have achieved everything they were supposed to achieve and still feel like something’s missing. They’ve done the therapy, read the books, optimized their routines. They know all the right frameworks. What they’ve done far less of is sit with themselves long enough to get bored, and then… keep sitting.
There’s a principle I’ve observed: the people most committed to efficiency are often the most terrified of what they might discover if they stopped being efficient. As long as there’s a plan, a protocol, a next step, they don’t have to encounter the deeper questions—questions that can’t be resolved through better time management or more strategic thinking. I’ve watched people who can teach seminars on emotional regulation, who’ve optimized their routines and done years of therapy, go completely blank when asked what they actually want their lives to be about. That question requires a different kind of attention than they’ve ever practiced—the kind that emerges not from doing things correctly but from sitting with uncertainty long enough that something genuine can bring to thesurface.
This is where Adam’s insight connects to the work I do. Making a photograph that takes two and a half years to execute isn’t about the photograph. It’s about living with an intention long enough to discover what it actually requires, what it costs, whether it’s genuinely what you want or just what you thought you should want.
Our professional frameworks want us to be productive with our uncertainty. Turn it into a SMART goal, break it down into actionable steps, measure progress. Spiritual practices—whether that’s watching ants with Tony King or spending three weeks at a meditation retreat or trying to launch a lawn chair twenty-five times until it works—require something different. They require duration without immediate payoff. They require tolerating boredom until something emerges that couldn’t have been planned.
Adam spent a month going up a mountain in Maine every night at dusk with a friend, hauling a disco ball, a flashlight that produced two million candlepower, a car battery, a power inverter, and a smoke machine. They had a fifteen-minute window when the light was right. Most nights, something went wrong. The wind shifted, the timing was off, they couldn’t get the smoke density correct. They would head back down the mountain, laughing at the absurdity of what they were attempting, and come back the next night.
“Does it matter?” Adam asked when we talked about this. “I mean, I could have made the exact same image in Photoshop in five minutes. But like, the experience of being there and the experience of being with that friend was all the stuff.”
I think about that a lot. The experience of being there is all the stuff. The therapeutic model wants the insight without the duration. The productivity framework wants the outcome without the process. The professional boundaries want the healing without the relationship. And none of it really works, because transformation happens in the sustained attention that our systems are designed to prevent.
When I ask people “What are you loyal to that you didn’t choose?” I’m not looking for an answer they can produce in the moment. I’m trying to create space for them to sit with that question long enough to get past the practiced responses, past the strategic thinking, past the efficient-maximizing problem-solving mode they’ve perfected.
Sometimes they sit with it for weeks. Sometimes months. That’s fine; there’s no protocol for this--there’s just the practice of staying with something past the point where it stops being interesting, past boredom, into whatever’s on the other side.
The people who benefit most from this work aren’t the ones who want quick insights or actionable frameworks. They’re the ones willing to discover that the question matters more than any answer they could generate through cleverness. They’re the ones who can tolerate looking foolish, wasting time, entertaining themselves with meaningless games like Sink the Leaf while something genuine slowly comes into focus.
Tony King gave Adam his pocket watch when he was dying, with a note that said “have a different relationship to time.” That’s the work: not better time management, and not more strategic use of hours. It’s about a different relationship to time entirely—one that makes space for the kind of attention that can’t be scheduled, optimized, or measured.
The land on the other side of boredom doesn’t care about your professional credentials or your strategic plan. It only cares whether you’re willing to sit still long enough to notice what’s actually there.
Our conversation ranged from Bluey to Walter Benjamin, from forest school to the ethics of riding your bike to work in Tampa. The full episode drops next Wednesday, February 12th.
I appreciated this piece, George. I was thinking about boredom and how productive I am on the other side, but didn’t have a way to put it into words. I also remarked to someone “I don’t think I’ve truly been bored since 1987. Attention deficit will do that to a fellow.” Thanks for sharing this one.