Dirty Underwear, Howling, and the Future of Podcasting

What On Air Fest Taught Me About Fear, Vulnerability, and the Nonlinear Path to Your Most Authentic Creative Self

I knew On Air Fest would be small. I’d done my homework. I knew the footprint would be intimate, the attendance modest, the whole thing more curated gathering than a massive industry expo. What I wasn’t prepared for was the care.

My first clue came before I’d even found my seat. I’d been mildly anxious about where to check in. On Air Fest is spread across multiple venues in Brooklyn, and the logistics of a multi-location festival can get messy fast. Turns out they had check-in at every single location. You just showed up, got your armband, and walked in. No central registration bottleneck. No lanyards with corporate sponsors dangling from your neck. Just an armband and a warm body pointing you in the right direction.

That simplicity set the tone for everything that followed.

Because here’s the thing: what On Air Fest didn’t spend on organizational infrastructure, they poured directly into the experience itself. The stage lighting. The screen displays. The music cues. Every single presentation felt like a million bucks. I didn’t see a single tech hiccup across the entire festival, and if you’ve been to enough conferences, you know how rare that is. They’re a production company, and it showed. The production was flawless. And there were people everywhere, actual human beings, guiding you, making sure rooms were set, making sure you knew where to go.

There weren’t any name badges. Which meant you were constantly asking, “What’s your name? What’s your name?” and honestly, I wonder if that was on purpose. Because it forced a different kind of interaction. Not the conference scan where you glance at someone’s lanyard and decide if they’re worth your time. An actual human introduction. Eye contact. A real exchange.

Simple. Intentional. Deeply cared for. And it set the stage for what turned out to be one of the most transformative creative experiences I’ve had in years.

THESE ARE MY PEOPLE

Before I get into the sessions that rewired my brain, I need to talk about the humans.

I love storytellers. I love podcasters. I love people who live in that particular frequency where a conversation isn’t small talk—it’s an event. And On Air Fest was wall-to-wall with them.

These are people who will stop dead in their tracks in a hallway to have a twenty-minute conversation about something real. Not a pitch. Not a networking play. A genuine, leaning-in, I-see-you-and-I-want-to-hear-more conversation. These are people who will thrust their phone into your hands and say, “Call yourself on my phone, now you have my number.” No QR codes. No LinkedIn requests. Just the beautiful, impulsive, deeply human act of saying: I want to stay connected to you, and I don’t want to lose you in the shuffle.

There is something about audio creators, people who have chosen the most intimate medium, the one that lives inside someone’s ears while they’re driving or doing dishes or falling asleep, that makes them wired differently. They listen harder. They ask better questions. They understand, on a cellular level, that connection isn’t a metric. It’s the whole damn point.

And the looks! God, I love Brooklyn fashion. But I love these people more.

SOME OF US ARE MAKING ART

Blake Pfeil and I originally met when he graciously lent his time and expertise to a webinar I was hosting for The Podcast Academy. He’s one of those people you respect immediately through a screen, so to meet him in person was a genuine delight. But watching his presentation was something else entirely.

Blake and Dylan Thuras performed a live production of an episode of abandoned: The All-American Ruins Podcast. In a small, dark room lit only by the audio tracks displayed on the screen behind them, they took us on an immersive adventure. It was like watching an old radio play being recorded, except it felt more like art than production. Following along with the audio track, getting lost in the sounds, the layering, the pacing, it was mesmerizing. The kind of experience where you forget you’re sitting in a conference venue, and you’re just… there. Inside the story.

And it gave me a new, deeper respect for the work that audio creators do. Because here’s the thing we don’t say enough: while some of us are making podcasts, some of us are making art. And the line between those two things isn’t about budget or production value or the size of your team. It’s about how deeply you’re willing to inhabit your own creative vision. It’s about craft. It’s about care. It’s about giving yourself over to the work completely.

That kind of creative surrender? It requires something most productivity frameworks don’t account for. It requires the willingness to go somewhere you can’t fully control.

THERE IS NO STRAIGHT LINE TO YOURSELF

“Carl Jung once wrote that the goal of psychic development is the self and that there is no linear evolution. There is only a circumambulation of the self. Uniform development exists, at most, at the beginning. Later, everything points toward the center.”

I heard those words at On Air Fest, spoken and echoed between two voices like a ritual incantation in a session called “Ritual for Creative Destiny.” And something in my chest cracked open.

Circumambulation. It means walking in circles around a sacred center. Not a straight line. Not a ten-step plan. Not a “just niche down and post consistently” trajectory. A spiraling, looping, sometimes maddening orbit around the thing that matters most: who you actually are.

We’ve been sold this lie that success is linear. That if you just follow the formula, you’ll arrive at some gleaming destination called “making it.” But anyone deep in creative work knows the truth: it’s circles. It’s revisiting the same fears, the same questions, the same doubts, each time from a slightly different angle. Each time a little closer to the center. That’s not failure. That’s the work.

PERMISSION TO BE A COMPLETE AND TOTAL BUFFOON

The Ritual for Creative Destiny session presenters, Zak Rosen and Sharon Mashihi, named two forces that govern the creative life: fear and connection. They embodied these forces by giving half of the presentation with dirty underwear on their heads (talk about vulnerable). Then did something I’ve never seen at a professional event: they made a room full of adults close their eyes, clutch a piece of white fabric, and repeat an incantation out loud.

Sharon had described her own creative process with an honesty that made the room collectively exhale: go into a room, hate yourself, scream and cry a little, add a few minutes to whatever you’re working on, and if you’re lucky, do it again the next day. She named the fear most of us carry but never say out loud, the terror of entering the irrational creative space where your rational self can’t protect you, because it’s your irrational self that has the best ideas.

And then came the incantation. The part I haven’t been able to shake:

“I can walk that fucking road. I can have self-acceptance. I can allow myself to be a complete and total buffoon. In the privacy of my own singular and sacred creative process. Anything is possible.”

A complete and total buffoon in the privacy of your own singular and sacred creative process. I spent decades trying to be anything but a buffoon professionally. Trying to be polished, taken seriously, proving my unconventional approach was legitimate. And here was someone saying the thing that took me decades to figure out: the path forward isn’t through more polish. It’s through more permission.

Zak and Sharon also introduced a concept I carried out of that session like stolen treasure: the idea that art is a process of “being with.”

Not making. Not working. Not optimizing.

Just hanging out with the thing you’re working on and trusting that if you stay long enough, the work will emerge without you forcing it into existence.

I had just experienced this very thing. I’d arrived in Brooklyn a day early, intending to do some sightseeing in Manhattan, and instead I got snowed in by a blizzard. That snow day turned out to be some of the most productive and creative work I’ve done in months, because I’d been sitting with these big ideas for a long time, and in the middle of a New York blizzard, they all came pouring out. No forcing. No optimizing. Just being with the ideas until they were ready to move.

This concept of “being with” is the opposite of the grind-and-optimize approach that’s burned out an entire generation of creators. It’s the permission to trust your own creative rhythm instead of someone else’s productivity framework.

KILL YOUR DARLINGS

Journalists Rachel Martin and Brian Reed sat down for a conversation that took everything the Creative Destiny session had opened up. They drove it straight into the real world of professional stakes, public criticism, and the actual cost of leading with vulnerability.

Brian Reed created S-Town, one of the most talked-about podcasts of the last decade. It also drew a lawsuit and a searing critique from an Australian career journalist named Gay Alcorn, who called the work “morally indefensible.” Not boring. Not poorly reported. Morally wrong to have been made.

When Brian launched his new show, Question Everything, he wanted it to be a space where people felt comfortable being self-reflective and self-critical. But he knew he had to go first.

So he did something most of us would never consider. He flew to Alabama to sit on the couch of the man who had sued him. A lawyer of twenty-five years who said he’d never once spoken to someone he’d sued. They talked for five hours. Brian was certain this would be the episode that launched his show.

His editors listened and said, “This is something you needed to do for yourself.”

It didn’t work as an episode. It was too inside-baseball, too mired in legal specifics that mattered deeply to Brian but wouldn’t land for a listener. All those years of questions, all those hours of conversation, and the thing he needed most turned out to be something he couldn’t package for anyone else.

If you’ve ever poured yourself into a creative project only to realize it was for you and not your audience, you know exactly how that feels. And if you’ve ever dared to accept that truth and pivot rather than force it, that’s a kind of professional bravery that doesn’t make anyone’s highlight reel.

What Brian launched with instead was the scarier conversation, the one with Gay Alcorn herself. The critic. He couldn’t even call it an interview because it was genuinely unclear who was interviewing whom. They didn’t agree in the end, but they found common ground, and the conversation went somewhere neither of them expected, all the way down to how you feel about death and legacy, what it means to tell the stories of people who are gone.

He went first. Not because it was comfortable, but because he understood something essential: you cannot ask others to be vulnerable if you’re not willing to go there yourself. You can’t build a space for authenticity while keeping your own walls up.

That’s exactly what we’re asking our clients, our audiences, and our communities to do every single day. And this conversation made me think about how often we’re willing to ask it of others without doing it ourselves.

The conversation between Rachel and Brian kept circling back to the difference between genuine curiosity and performed professionalism. Brian put it plainly: the minute you start asking questions you think you’re supposed to ask, it’s over. Even when there are questions you feel obligated to ask out of duty, out of professional expectation, the work is finding what you genuinely want to know within that obligation. Not the performed version. The real one.

Think about how radical that is in an industry that runs on formulas. We have templates for everything now. Sales call scripts. Content frameworks. Engagement strategies that tell you exactly what to post and when. And none of it, not a single word of it, accounts for the fact that the most powerful thing you can do is ask a question you actually care about the answer to.

Rachel said something that I want tattooed on the inside of every content creator’s eyelids: it’s amazing what will happen if you just sit in silence.

She learned this as a news journalist, where the job was specifically not to emote, not to share your own loss, not to make it about you. The work was to allow silence, to be a safe place, and to let your body language and your listening do the heavy lifting. When you stop trying to fill every space, people share.

Now, on her current show Wild Card, she’s built a different model, one where mutual vulnerability is the architecture. She shares, the guest shares, and together they build something. By the end of an hour, they’ve gone somewhere real. And maybe someone listening hears their own experience reflected back.

But here’s the critical balance she named: you don’t want it to be the you show. Vulnerability isn’t content. Vulnerability serves the conversation. You share not for the sake of sharing but because it’s embedded in a question: “I’ve been thinking about this, here’s why, how have you made sense of it?”

That distinction matters enormously for anyone building a personal brand. There’s a difference between performing vulnerability for engagement and genuinely sharing your experience in service of connection. One is performance. The other is presence. And your audience can always tell the difference.

YOU’RE NOT DOING IT WRONG

I need to interrupt the inspiration for a moment of honesty, because I think it’s important and because nobody else seems to want to say it.

The people making money in podcasting are the outliers.

I posted this during the festival because the gap between what we see celebrated on stage and what most creators experience behind the scenes was impossible to ignore. Most shows, even the ones from larger studios and networks, are still trying to figure out consistent funding. Public radio is looking at how to be profitable for the first time. No one has solved the funding problem. Not the big players. Not the indie creators. Not the networks with teams and budgets and institutional backing.

And yet somehow, independent podcasters walk around feeling like they’re the ones failing.

You’re not. You’re not doing it wrong. The model is still being invented. The rules haven’t been written yet because the old rules, the ones borrowed from radio and television and traditional media, don’t map cleanly onto a medium this intimate, this decentralized, this stubbornly resistant to scale-at-all-costs thinking.

This is actually liberating if you let it be. If the biggest players in the industry haven’t cracked the code, then the playing field is more level than anyone wants to admit. Your scrappy, authentic, recorded-in-a-closet show isn’t behind. It’s just operating in the same uncertain landscape as everyone else, with the added advantage of not having institutional overhead and shareholder expectations dictating your creative decisions.

Rachel talked about organizations needing to stop duplicating efforts and double down on their core competency instead. She was talking about NPR. But she could have been talking about every creator I’ve ever coached who’s spreading themselves across seven platforms instead of going deep on the thing only they can do.

The lesson is the same at every scale: stop trying to be the New York Times when you’re actually doing something they could never pull off. Big media can outspend you, but they can’t out-YOU you.

ONE LISTENER AT A TIME

Across multiple sessions, a theme kept emerging that flies in the face of every growth-hacking playbook: audiences are built one listener at a time.

One person who discovers your work and thinks, “Where has this been all my life?”

Not through viral moments because what goes viral is not up to you to decide. Not through algorithmic manipulation. But through the slow, patient, deeply human work of being so authentically yourself that the right people can’t help but find you.

The Patreon Discovery Panel discussed listener communities as the modern equivalent of old internet forums, places where people gather not because of an algorithm, but because of genuine connection. Give people a place to go beyond the hour they spend listening to your show. Create a space that’s theirs, not just yours. That’s how communities grow, not from the top down, but from the center out.

This is where conventional marketing advice falls apart for people like us. The playbook says optimize, scale, hack, automate. But the evidence keeps pointing to something simpler and scarier: be undeniably yourself, and give people a place to gather around that.

YOUR WEIRD IS THE POINT

Here’s what I keep coming back to, days after leaving Brooklyn.

Brian Reed flew to Alabama to talk to a man who sued him, then sat sweating through a late-night conversation with a critic who called his work morally wrong, because he believed that going first was the only way to build something honest. Rachel Martin admitted that distance made hard questions easier, because pretending you’re not human doesn’t make you more professional. A roomful of strangers howled together and chanted about being complete and total buffoons, because sometimes the most sophisticated creative strategy is permitting yourself to be ridiculous. And in the hallways between sessions, people were shoving phones into each other’s hands and stopping mid-stride to have the kind of conversation that changes how you see your own work.

None of this looks like a growth strategy. None of it fits in a content calendar template. None of it follows a formula. And that’s exactly the point.

Jung was right. There is no linear evolution. There’s only this spiraling orbit around the center of who we are. And the center holds. It always has.

So here’s your permission slip:

You’re not doing it wrong. The model is still being invented, and your way of doing it is as valid as anyone’s.

You don’t need a straighter path. You need a more honest relationship with the one you’re on.

You don’t need to ask the questions you think you’re supposed to ask. You need to find the questions you genuinely care about the answers to.

You don’t need to perform vulnerability for engagement. You need to show up with enough presence to let silence do its work.

You don’t need to be everywhere. You need to go deep on the thing only you can do.

And you don’t need to tone it down. You need to turn it up—on your terms, at your frequency, in your singular and sacred creative process.

Allow yourself to be a complete and total buffoon. Allow yourself to get stuck in a blizzard and let the ideas pour out. Allow yourself to shove your phone at a stranger in a hallway because you just had the kind of conversation you refuse to let end. Allow yourself to spiral, circle, loop back, and try again.

Because everything points toward the center. And the center is you.