The Desert and What Holds Weight

Part Three of a Three-Part Conversation with Eric Pennington

There is a particular kind of man who can tell you, without flinching, exactly what a decade cost him — and then tell you, in the same breath, that he wouldn’t trade it. Eric Pennington is that man. I have known him for years now. I have watched him work rooms full of skeptical engineers and rooms full of grieving people and rooms full of executives who didn’t yet know they needed what he was offering. And nothing I have watched him do has prepared me for what it was like to sit across from him and ask him to open the desert back up, on camera, on purpose.

He calls it the desert. Sometimes the crucible — the older, harder word, the one that means the fire applied to ore until everything that isn’t the metal itself burns away. He doesn’t reach for that word for effect. He reaches for it because it’s accurate. The crucible doesn’t ask your permission. It doesn’t negotiate a timeline. It simply burns, for as long as burning is required, and you find out what you’re actually made of only after there’s nothing left to hide behind.

His began in 2006. It didn’t end, by his own accounting, until somewhere around 2017. Eleven years, give or take. I want you to sit with that number for a moment before we go further, because it would be easy to read past it. Eleven years is not a bad quarter. It is not a rough season. It is the better part of a man’s working life, spent not knowing, year after year, whether the ground would ever hold again.

“You can confidently say — yeah, I know I’m in the desert, but I’m sure probably next month we’ll be out of here,” he told me. “And then it’s not. And then you realize after a couple of years: yeah. You are in the desert.” He said it almost gently, the way people describe a wound long enough healed that they can finally hold it up to the light without flinching. But I watched his face while he said it, and I want to be honest with you: there was nothing easy underneath that gentleness. Eleven years of believing the end was near and being wrong, over and over, is not a small thing to survive with your faith intact. Most people don’t. Eric did.

I asked him what the desert took from him that he hadn’t expected to lose.

“A lot of that pride,” he said immediately. No hedging. No softening it into something more palatable. He traced it back through everything we’d uncovered in the two conversations before this one — a childhood where being right felt like the only available form of safety, a corporate career that rewarded the same instinct with money and promotions and the particular drug of applause, a company called Epic Living that he launched half out of genuine vision and half out of an old hunger still looking for its next hit. The desert went after all of it. “It birthed in me what I would say is authentic humility,” he said — and he meant the word authentic as a precise distinction, not a flourish. He has seen the performed version of humility up close. He knows it when he sees it, because he used to wear it himself. What the desert gave him instead was the kind you don’t get to choose. The kind that’s simply what’s left.

And then there were the mirages. I want to dwell on this, because I think it is one of the most honest things a person has ever said to me about suffering. A mirage in the desert isn’t an absence of hope — it’s hope, fully formed, arriving exactly when you need it, and then revealing itself as nothing. “You thought: I’m this close. There it is,” Eric said. “And then — gone. And another lesson to learn.” He didn’t say this with bitterness. He said it the way a man says something he has made an uneasy peace with, after enough years of practice, while still being honest that the peace was hard-won and is not the same thing as the pain having been small.

What grew in that soil, against every reasonable expectation, was something he attributes — without irony, in the middle of an interview about emotional intelligence — to Søren Kierkegaard. The idea of playing for an audience of one. Not performing for the room. Not measuring the work by who noticed it. Doing the work because the one true audience already knows the whole of your story, has already seen you at your most desperate and your most petty, and remains, somehow, still interested. I watched something settle in him when he said it. Like a man finally putting down something heavy he’d been carrying with both arms for over a decade.

This is the thing I most want you to understand about Eric Pennington: he refuses to simplify himself for your comfort or mine. In the span of a single answer he will move from Kierkegaard to the Enneagram to Miles Davis to a streaming television show, and somehow none of it is scattered. All of it is the same man, looking at the same wound from different angles, refusing to let any single lens claim the whole truth.

I asked him directly about the cost of being who he is — an empath, by his own naming, a self-preservation Four on the Enneagram, a man built to feel things at a depth this culture rarely makes room for, especially in men. His answer stopped me. “I’m an alien,” he said. “It feels like an alien.” Not with grief, though grief lives somewhere underneath it. With something closer to ownership. “I say that in recognition that I am here, and I’m here for a purpose.” He told me about a character on a television show he’d recently found himself drawn to — a figure who moves through the world differently than everyone around him, sees what others miss, is somehow both fully present and permanently a step outside. He used the word archetype without my prompting him toward it. He told me that the word “weird” used to land on him as wound, the way it landed on a boy who’d already survived more before age fourteen than most people survive in a lifetime. Now it lands as confirmation. “It added to my confidence and courage,” he said, “to continue to be who I know myself to be.”

I do not think most people get to that sentence. I think most people spend their whole lives running from the very thing Eric has learned to stand inside.

Then I asked him the question I had been most afraid to ask, because I suspected the answer would require more of him than any other question in three conversations: what is actually happening inside you, underneath, in the moment before you’ve found the words for something heavy?

He went quiet. Not an uncomfortable quiet — a deliberate one, the kind a musician takes before the next phrase. And then he gave me an answer I will be thinking about for a long time.

“It’s these notes,” he said. “If you’re familiar with music from a theory standpoint — you have quarter notes, you have half notes, you have whole notes, and then you have pauses that can be in between. That’s probably one of the gifts of music for me. It allowed me to process what’s happening underneath — that depth — and to be present with it. Because I can hold that note, and allow that liminal space to do what it does. And then play another note.” He brought Miles Davis back into it, the way he always eventually does — not the man’s sound, but his restraint. “It’s not how many notes. It’s what notes you choose. And the timing of them.” That, he told me, is the medicine. Not rushing toward resolution. Not explaining the ache before it’s finished teaching him something. Holding the note as long as the note needs to be held.

I have interviewed a great many people in my work. I have rarely heard anyone describe their own interior life with that much precision, or that much tenderness toward themselves.

We arrived, finally, at the question I had been saving across all three conversations — the one I think every other question had been quietly building toward. I reminded him of something he had told me himself: that his desire, underneath everything else, is to create things that will hold weight in eternity. And I asked him plainly: when you look back on this season of your life, what do you hope will have held that weight?

He answered slowly, on three levels, and I want to give you his words as close to whole as I can.

First — that he had been growing, across the whole of his life, into the person God intended him to be before he was ever formed in his mother’s womb.

Second — that his relationships would carry something real. That Jim, and Lynette, his wife, his children, the people he has walked closest to, would be able to say, without exaggeration: you did well there. We were helped. We were enriched by being near you.

Third — that the work itself, the podcasts and the articles and the coaching conversations no one ever sees the other side of, would have made a genuine difference in lives he will never personally know about. People who will never write him a message saying it mattered. He is not asking for the credit. He is asking that the giving was real, regardless of whether anyone ever tells him so.

The Desert And What Holds Weight Reflection Sheet

I have sat across from Eric Pennington enough times now to say this without exaggeration: I believe all three of those things will have been true. Not because he has learned to say the right words in the right order — he is far too honest a man for that kind of performance — but because eleven years in a desert burned away everything in him that wasn’t load-bearing, and what is left underneath is, simply, real. The boy who once watched his own life happen to him from a small distance, who found a lifeline in a hymn and a jazz record at thirteen, who carried a brother’s worst day into a school hallway where everyone already had a story about him, who chased the applause until it stopped feeding him, who walked eleven years of mirages and came out still able to play for an audience of one — that boy became, against very long odds, an extraordinary man. I am grateful to call him my friend. I think, by the time you finish reading this, you may understand why.

Where this meets you: what are you building right now that you hope will still mean something in a room you will never enter?

Peace and every good.

About the Author

Jim Vaive is co-founder of spirit of EQ, where he and his wife Lynette help individuals, leaders, and teams grow through emotional intelligence, the Enneagram, and contemplative spiritual formation. He writes at The Mystical Seeker on the inward life that makes the outward work possible.