Thinking out loud

On staying present in the messy middle

Photo by Patrick Perkins on Unsplash

In a recent-ish newsletter,

Anne Trubek

included a brief preamble. She wrote: “My thoughts on this topic are very sketchy and preliminary, obviously—I’m using this newsletter to formulate my thoughts.” I loved her caveat because it perfectly summarized what writing often is: Writing is thinking out loud.

Often, we don’t write because we have the answer(s) and are bestowing them to the reader; we write because we are seeking the answer(s), wrestling with a topic, and drawing connections in conversation with the audience (and with ourselves). The thinking doesn’t always beget the writing. The writing sometimes begets the thinking. Or, often both—at the same time. And the process can be awfully untidy.

Sure, lots of great writing arrives at a crisp conclusion with supporting evidence—clean essays that obscure the muck in the middle. But what if we’re not there yet? What if we’re still in the messy midpoint and we haven’t arrived at a neat finale? And what if there is no palatable endpoint to reach at all because thinking, like life, takes place in the grey, in nuance, in contradictions, in tension. In the dirt.

I often delay posting here because of the nagging worry that I must have a sparkling product complete with sharp, actionable conclusions in order to be worthy of your inbox. But many of the newsletters I enjoy reading most are grappling aloud with the human experience, without always offering a sanitized “takeaway.”

Maybe it’s because I’ve worked in the content marketing/thought leadership space for so long—a space where (sometimes) the most saleable ideas are the ones that distill a complex concept into a sticky soundbite or catch phrase—that I balk at allowing room for imperfection, flaws, bruises. The banana with the spots.

So—welcome to ‘Thinking Out Loud,’ a segment where we talk about ideas even if they are only half-baked. And in a meta turn, the first idea is the topic of deeming our thinking worthy even when it’s in the messy middle: Giving ourselves permission to be seen, warts and all, unfinished product, a work in progress. Finding the bravery and patience to reject the shine of insight and roll around in the muck.

Summer Brennan

talks sagely about this in her (also recent-ish) newsletter essay, “The Wisdom Trap.” After hearing another writer describe wisdom as “so boring,” Brennan reflects:

When many of us sit down to write about ourselves or the things we have experienced, we want to tell everyone that we’ve grown, that we know better, and that we have it all figured out now.

But she reminds us that striving to impart insight often has the opposite effect:

When we start from a place where our primary goal is to be wise or insightful, before actually embarking on the difficult process of discovery through writing, we will not usually arrive at a place of real wisdom. To do this, whether through arrogance or ignorance, is to try and cheat the genuine work of creative excavation. More often than not, this path leads not to insight but to cliché. In speaking with students about this all-too-common writing pitfall, I have come to call it “The Wisdom Trap.”

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I see this “wisdom trap” as a kind of self-protection. No matter how much we might sputter and delay in our writing process, if we at can at least muster a pleasing endpoint to work towards—a “wise” conclusion—(maybe) we can shield ourselves from shame: The shame of being wrong, or foolish, or too exposed, or sloppy. When we calibrate our efforts towards insight, we are trying to control the outcome, to keep ourselves safe. Because creative work is a risk, isn’t it?

Any time we share our output with the world, there is the chance of being ridiculed, misunderstood, disliked, or challenged. And even the thickest skins aren’t immune, especially in the digital age where people feel emboldened to spit vitriol at strangers for the unforgivable sin of thinking out loud. So we fall into the “wisdom trap” as prophylactic, as armor against the fear. If our conclusions are brilliant enough, or our art is polished into resplendence, maybe it can shield us from the discomfort: The naked peril of putting ourselves out there.

But this attempt at self-protection does us a disservice. When we’re only focusing on the future—on how our writing will be perceived—we’re pulled out of the present, shirking our duty to be alert in the here-and-now.

In her essay, Brennan goes on to say that creators ensnared in the wisdom trap are “sleepwalking through the writing process,” thereby betraying the cardinal task of the writer, which is “simply to show up, pay attention, and tell the truth.”

How can we “show up, pay attention, and tell the truth” when we’re skipping ahead to the end—so beleaguered by doubts about being witnessed that we forget the writer’s task of bearing witness?

Unpacking the Dread

In a discourse earlier this year on Twitter (sorry, I will never call it “X”), one thoughtful writer talked about how the fear of being perceived sabotages them; I have not been able to track it down again (if you remember the link, please send it to me!) but I recall their worry was along the lines of, “What if my friends see me taking myself seriously?” I deeply felt this writer’s dread. And I wasn’t alone. Many creative people were retweeting across disciplines—writers, painters, illustrators, actors—sharing their own struggles with imposter syndrome and perfectionism as they worked through the public pursuit of their craft.

The discourse struck a chord because sometimes the thing that pulls me out of the present is a pang of embarrassment. I’m embarrassed for trying, ashamed of talking openly about my writing, work(s) in progress, and passion projects that I pursue outside work hours: My novel (THE SHREWDNESS), this newsletter, my intermittent adventures in freelance etc. For reasons I haven’t quite been able to crack until I started noodling with them here, there is something vaguely humiliating about “taking myself seriously.”

When my therapist recently challenged me to articulate the pain point, asking “What is embarrassing about doing, and talking about, what interests you most?,” I floundered. I couldn’t say why exactly, only that there is an inner voice that scolds, “who the hell do you think you are?” and hounds me into negative rumination. And that voice is definitely part of the shame equation: A run-of-the-mill fear of not being good enough, which is pretty standard writerly stuff. (And a healthy aversion to being insufferable and self-important is part of it too.) But when I thought more about it, I realized that’s only half the story.

Another thing that holds me back is the fact that all effort carries a terrifying admission: “I care.” And there is a tacit understanding among people roughly my age (born in the 1980’s) that we are not supposed to admit we care about things unless we shroud it in irony, or humor, or anger, or endless caveats. Caring is “cringe.” Unless that caring is made palatable by being filtered through indignation or self-deprecation, in which case it becomes acceptable again. And this is tiring too. Another attempt at self-protection.

My sense is (whether it’s accurate or not): When writing to make sense of the world, we are allowed to be angry, we are encouraged to be disaffected, we are sanctioned for nihilism. But there is less permission for hope. And I’m over it. I see it as another trap: The pressure to perform disillusionment is as boring as the compulsion to assume a pose of wisdom.

When we posture as disillusioned, we can end up presenting a false reality devoid of joy, offering diatribes packaged as facts. When we posture as wise, we can end up presenting a false reality devoid of suffering, offering feel-good pap packaged as enlightenment. Both default to lies. Both are presumptive about the conclusion—presupposing either doom or redemption—at the expense of any meaningful excavation of the messiness in the middle. They obscure rather than reveal.

Saying ‘Yea’ to It All

I recently came across a quote from Joseph Campbell’s famous work about the archetypes of myths, The Hero With a Thousand Faces, that bowled me over:

“Participate joyfully in the sorrows of the world. We cannot cure the world of sorrows, but we can choose to live in joy. The warrior's approach is to say ‘yes’ to life: ‘yea’ to it all.”

As artists, we can look at a broken world and think what’s the point, why bother and turn away from the joy. Just as easily, we can live in denial about the ugliness and turn away from the sorrow. Or, we can try harder to see more of it, all of it. We can stop trying to find tidy truths in a world that’s inherently messy.

Paying attention is a practice; writing can be that practice. It is one way to revel in the full breadth of this planet and its living beings—the joy and the suffering and all the messiness in between. But to really see it, we have to first release our own fear of being seen, rejecting the protective armor of deprecation about how terrible it all is (and we are), and discarding the shield of grandiose punditry which imparts “look on the bright side” platitudes.

To find truth, not in the extremes but in the details, we have to be alert enough to see it, patient enough to capture it, and brave enough to share it. Which means we can’t skip to the end, can’t sleep through the middle.

A Leap of Faith

Earlier this year, in my post “I want to be the fool,” I wrote about my aspirations for 2023:

I want to be more committed to writing and brave and generous with the work I create. To be less afraid of being seen. To allow the world to witness my work—and to make work that is reciprocal such that the world, too, feels witnessed by it.

Many months later, I’m still bumping my head against the same desire and the same attending fears, and all I can say is this: Making art is a leap of faith in a climate that wants you either pissed off and aggrieved or blissfully unaware. Creation is a rejection of despair and a bid for connection. It’s a vulnerable act, an invocation: “I want to be seen,” and reciprocally, “I want to see you too.” And it is a lifeline bringing us back to awareness, to presence, so we don’t sleepwalk through our short time on Earth.

Right now, for me, being present means trying to step away from self-protection and into the gooey guts of the middle. And it requires welcoming hope; I’m calling it in. I shouldn’t feel humiliated to admit that when I share my work, it comes from a place of optimism: A desire for connection, a wish for a deeper understanding of the human experience, a little prayer cast into the air. I shouldn’t be embarrassed to admit that I’m most alive, engaged, and alert when I’m pursuing the things that matter to me most.

I don’t want a curmudgeonly life, sulking and lamenting and waiting for some elusive “perfect” flash of insight to share with the world. Life, the real shit, happens in the in-between; it’s happening right now. If we default to defeatism or idealism as a way to protect ourselves, we’re not fully engaged with reality; we’re seeking safety over discomfort. And these traps don’t shelter us anyway. Nothing can immunize us from criticism. So we might as well clear our throats and say what needs saying—now.

When we release our expectations for perfection, we are affirming our worth. We are declaring: My ideas are not earth-shattering, flawless, or complete but they are good enough to be considered as they are.

The longer we wait to be visible because we are pursuing the “wisdom trap,” or plummeting into disillusion, the more we risk slipping away from the present, severing our connection to ourselves and the universe.

It’s ridiculous how many times I’ve had to learn this lesson (and maybe someday it will stick): Self-protection is a blindfold. There is no virtue in hiding in the shadows, hanging back, waiting to bestow perfect answers to the world’s pain. All we can do is “show up, pay attention, and tell the truth,” saying, “‘yes’ to life: ‘yea’ to it all.”

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So, that’s what I’m thinking out loud about this week—how about you?

And—what should the next Thinking Out Loud segment be about? Answer the poll below and let me know.

P.S. In an effort to practice what I preach and share my work in the messy middle, I made a zine as part of

Clementine Morrigan

’s zine challenge. It’s called CHAPTER ENDINGS and it includes 13 chapter endings from my work in progress, THE SHREWDNESS, each as a self-contained, poetic little vignette. You can get it here:

Zine