The Retention Problem No One Wants to Admit
Habit builds intimacy. Intimacy builds return.
Spend enough time talking with conference founders, festival producers, association chiefs, and brand-side experience leaders and you start to hear a tone change — not in public, not onstage, not in the glossy recap decks — but in the private conversations where the curtain comes down and the room is finally honest. Registration isn’t dead. Sponsors still show. The lanyards are still printed. But renewal — that quiet vote of confidence, that moment when a person chooses to come back without being courted like a first-time customer — has stopped behaving like a foregone conclusion. The reflex is weaker. Every season feels slightly more provisional. Every year feels like it needs to re-argue its own existence.
The research world has language for this. Companies like Freeman have been describing the post-pandemic attendee as more selective, more intentional, more emotionally discerning — less impressed by volume, less willing to tolerate friction, less inclined to “go because we always go.” I’m not quoting numbers here because the exact percentages shift from report to report, but the directional finding is unmistakable: satisfaction alone is no longer a guarantee of return. In other words, the business model that used to ride on habit is now being forced to re-sell itself every cycle.
That is the real anxiety. Not attendance. Not buzz. Return.
There was a time when return didn’t require persuasion because culture itself trained us in ritual. My generation lived inside broadcast appointments the way you live inside weather. Monday night wasn’t “a programming option.” Monday night was Monday Night Football — not merely a game, but a weekly synchronization device. You could feel the country briefly align around the same hour, the same soundtrack, the same shared references for the next morning. During my early days,
Saturday night on CBS had its own gravity: All in the Family was there, The Mary Tyler Moore Show was there, The Bob Newhart Show was there — not because we were analyzing a menu of entertainment choices, but because the menu didn’t exist. You showed up where the culture already was. You didn’t decide each week whether it was worth it. You resumed.
That’s what habit is, when it’s functioning at full strength. It’s not just repetition. It’s repetition that lowers the cost of life. Familiarity strips out evaluation. It reduces social uncertainty. It quiets that constant background hum of “How do I behave here? Do I belong here? What’s the vibe?” When people say they want “belonging,” they often mean something more practical: they want the emotional labor of orientation to be handled for them. They want to walk into something that already knows how to hold them.
This is why so many organizers are seeing renewal soften. The world has turned everything into a decision, and decisions accumulate like dust. Another login. Another platform. Another RSVP. Another agenda. Another set of social rules. Another “figure it out.” When an event asks people to re-decide, re-learn, re-calibrate every year, it is quietly adding cognitive tax to an already over-taxed audience.
If you want to see what the opposite looks like — what disciplined intimacy looks like as an engine of return — you can find it in a place that event people would do well to study with more respect: podcasts, particularly the ones that have mastered cadence, chemistry, and ritual.
I’ve been a fan of Kara Swisher for years — through all her renditions. I watched her when she was a journalist who could walk into the rooms where power lived and ask questions that made powerful people visibly uncomfortable, not for sport, but because she understood something essential about credibility: it’s not granted, it’s earned. I watched her on conference stages, where she treated moderation like an art form rather than a courtesy, building a container strong enough that the truth could survive inside it. Kara has always been an event person in the deepest sense: she understands that the format isn’t the wrapper around the content — it is the condition that makes the content possible.
That’s why Pivot matters here. Pivot is a twice-a-week podcast co-hosted by Kara Swisher and Scott Galloway, and on paper it’s “a business and tech news show.” In reality, it’s a relationship you return to. The cadence is dependable. The segments recur. The emotional temperature is consistent enough that listeners don’t have to spend energy learning how to listen. Scott plays provocation with the confidence of someone who knows he’ll be checked; Kara plays precision with the authority of someone who has done this long enough to cut through fluff without losing the room. The friction isn’t chaotic. It’s patterned. That pattern is the point.
Twice a week is not incidental. That frequency tightens the bond. The emotional thread doesn’t go slack. The show occupies a slot in the week the way old broadcast television used to occupy a slot in the week. It becomes part of someone’s life architecture. People don’t return simply because the topics are relevant. They return because the container is familiar and the intimacy feels earned.
And when that relationship goes live — when a podcast becomes an event — the mechanism becomes visible. The private ritual becomes communal. Hundreds or thousands of people discover they’ve been keeping the same rhythm separately. Laughter spreads faster. Tension synchronizes. The audience moves as one organism for stretches of time. That’s emotional contagion. The electricity isn’t created on stage. It’s released in the audience — because the bond preceded the ticket.
Long before podcasts, I learned what recognition does to a community from a different angle.
Decades ago I started Washington Dossier, a society magazine that chronicled Washington’s social choreography. It became a phenomenon because it reflected people back to themselves — not merely photographed, but placed. Readers didn’t casually flip pages. They scanned. They searched. They used it as a map. And once people rely on a map, they expect the map to keep showing up.
Then the Washington Star folded, and Washington lost one of its daily rhythms. I had just sold Dossier. My entrepreneurial spirit was flying high. The idea of launching a new newspaper felt thrilling. The capital of the United States should have more than one dominant voice, I thought.
That’s when Dean Singleton stepped in.
“You’re not in the newspaper business,” he said. “You’re in the habit business. And habits can take a hundred years.”
He wasn’t being poetic. He was being precise.
Instead, I spent twenty-five years running BizBash, which, in hindsight, was the back-of-house counterpart to what Dossier had been in the front-of-house world. If Washington Dossier reflected the social choreography of the visible room, BizBash reflected the invisible world that made the visible possible: the planners, producers, lighting designers, caterers, stage managers.
Marjorie Merriweather Post understood continuity as emotional architecture at the pre-Trump Mar-a-Lago she built decades ago. Guests returned not only for spectacle, but for continuity. The same staff. The same choreography. Familiarity wasn’t sentimental. It was structural.
Even the largest gatherings — SXSW and Cannes Lions among them — depend on rhythm more than they admit. The first visit overwhelms. The fifth feels like reunion.
Some gatherings feel transactional. Others feel narrative. Over time, narrative becomes identity. The gatherings that endure don’t relaunch themselves every season.
They resume.
For readers who want to go deeper
If this way of thinking resonates and you’re inclined to dig into the underlying ideas, there’s a deeper body of work worth spending time with — not because it offers formulas, but because it explains why habits, return, and recognition mattered long before anyone applied them to events or retention.
The Presentation of Self in Everyday Life — Erving Goffman- A quiet explanation of why people need to know how to be in a room before they feel comfortable returning to it.
The Ritual Process — Victor Turner -A foundational look at repetition, ritual, and why meaning stabilizes through return rather than performance.
Bowling Alone — Robert D. Putnam -A broader cultural view of what happens when shared habits of gathering erode — long before the effects show up as churn or disengagement.
The Power of Habit — Charles Duhigg -A useful reminder that most behavior is driven by structure, not intention.
Atomic Habits — James Clear -More individual in focus, but helpful for understanding why consistency outperforms ambition.
None of these books are about events. All of them are about return.