Befriending shame

I’ve written half a dozen drafts of this essay since the start of the year. All of them stalled out, mostly due to me being a scaredy cat and getting stuck in the swamp of perfectionism. So I’m starting fresh. Gonna write this bad boy in one sitting with minimal editing. LFG.

If I had to summarize the last few years of my life with one phrase, it’d be “I fought the shame, and the shame won.”

For as long as I can remember, I’ve had a persistent nagging voice in my head, telling me that something in me is irreparably broken, and that I need to hide it from others. It shows up as a burning, clenching sensation in my chest, a tightening of my jaw, a physical constriction that signals it’s time to bolt. The only viable path to safety, shame tells me, is to run, hide, and numb.

I’ve expended a great deal of energy over the years trying to outwit, outrun, or outright defeat shame. My decade long obsession with “personal development” and productivity and business/marketing education has, in retrospect, largely been one attempt after another to prove shame wrong, to show it that I’m the boss, and that I actually am worth something. Maybe, just maybe, if I learn the right strategies and try harder, I can banish this darkness once and for all, and finally feel okay, like I, too, belong in this world.

This strategy of going to war with shame, to put it mildly, has failed spectacularly. I won’t get into the details, but late last year, after crashing and burning once again, I found myself in the deepest pit of despair of my life to this point. I daydreamed daily, sometimes hourly, about driving up into the Catalina mountains, along those long winding switchbacks, finding a good steep overlook with rocks below, and gunning it right over the edge. So it goes.

By the grace of God, I’m still here. But so is the shame. Yet this time around, also by the grace of God, I feel pulled towards relating to this darkness, which nearly consumed me, in a new way. Maybe, just maybe, I can make a friend of it.

One of the silliest, most profound spiritual experiences I’ve had came on a scorching summer afternoon in Brooklyn.

I was walking around with Dan Hunt after joining Foster, and we were talking about moving the email list over to Substack. And at that moment, the word “CONVERSATION” dived straight out of the sky and landed in my chest, penetrating my heart with a burst of insight. I saw how all of our writing, and all the writing in history, is part of one larger, more beautiful conversation. I saw the tapestry of conversations and relationships binding everything together—an essay, a platform for writers, the internet, the trees, birds, and mountains. I saw the unbroken line of dialogue tracing from this strategic business decision all the way up to God, and the intimacy of true relationship at the heart of it all. Our birthright is to participate in this Great Conversation, and connect ever more deeply with all that is.

It felt all kinds of profound, like the nature of life and the inner workings of the universe had been revealed to me in the snap of a finger. But when I tried to share this momentous insight with Dan, it came out as a series of banal platitudes about how our writing would be more conversational on Substack. He looked at me, probably wondering if I was having a stroke, and said something along the lines of “yeah, conversations are good.” So it goes.

That was three years ago, and while my life has been turbulent as fuck since then, the insight hasn’t left me. It feels stronger and truer and more urgent than ever right now. That said, I’ve had the hardest damn time living it instead of just thinking about it.

There’s a book I’ve had on my shelf for years called Metaphors We Live By. I’ve never actually read it, but the title alone goes incredibly hard. As I’ve attempted to live more conversationally these past few years, in messy fits and starts, I’ve come to see how there’s a different metaphor lodged at the core of my being. One that stands in direct opposition to conversation.

For me, life is battle. Life is war. Life is a never-ending series of zero-sum fights that, according to my shame, I have already lost or am in danger of losing, and therefore need to armor up and double down on strategy, such that I might stand any chance of winning a place at the table. Belonging and love must be fought for.

The metaphor I live by is war, and I want, more than anything, to change that. I’m so tired of fighting. I’m painfully aware that it’s a battle I cannot win, and I want my brief flash of existence on this planet to be in service of something more joyful. I want to participate and contribute to the web of conversations that make up my little patch of the world. I want, for the first time, to feel connected to life instead of alienated from it.

I am perpetually annoyed by how fucking difficult and messy it is to live and embody insights like these. It’s so much easier to write about them on the internet and seem really smart and like you’ve got it all figured out. God I wish writing about these things was enough to truly live them. But alas, that has not been my experience.

I renamed this publication “The Living Question” last year because I want this to be a place where I don’t have to pretend to have all the answers, as is generally the case if one follows the Best Practices of Internet Writing. I want this to be a container for sharing the messy, uneven, often unflattering truth about my extremely human attempts to live the questions that matter to me.

And the most important questions I’m dancing with right now, and probably will be for the remainder of my days, are “How can I build a life-giving relationship with my shame? How can I befriend something that I’ve long perceived as trying to destroy me?”

I don’t have the answers, of course. But I’m living into the question as imperfectly as I can. My journey is increasingly centered around 12-step spirituality (and potentially even a return to actual religion, which is something I’d never thought I’d say), learning how to actually meet my physical, emotional, and relational needs, along with a great deal of friendship and fellowship, because I’m increasingly convinced I cannot do any of this on my own. But I do want to share the intention that this will be an ongoing series of writings, as I keep

I feel like I should end with some some pithy and poignant takeaway that leaves you all nodding your heads and being like “gee that Rob fellow sure is a great writer.” I recognize now that’s the shame talking, telling me I have to control how I’m perceived. I have to hide what’s true and convince others of how great I am despite not feeling that way.

So I guess I’ll just end with this.

Hello darkness, my new friend. I come in peace, and my sincerest hope is that we can start a conversation, a real one. Maybe it’ll lead us somewhere new. So let’s start again. Hi, I’m Rob. What’s your name?

get my emails, you coward.