via The Mostly Occasionally Show
How Scott Rogowsky—HQ Trivia’s iconic host—used a life-altering psychological retreat to transform his cynical inner critic into a grateful Phish fan, finding himself in the process.
There are two Scott Rogowskys. The first is the one you almost certainly remember: “Quiz Daddy,” the razor-sharp, unflappably charismatic host of the HQ Trivia app that, for a meteoric moment in 2017 and 2018, captured the cultural zeitgeist. He was a digital ringmaster, beamed into millions of phones, a symbol of a specific, frenetic moment in internet history.
The second Scott Rogowsky is the one I spoke with on a recent afternoon. This Scott is a deeply introspective writer and comedian enjoying his 40th journey around the sun, newly engaged, and embarking on a surprising academic journey into depth psychology. He is also a massive Phish fan. And for him, the two Scotts—the public persona and the private self—have been on a profound journey of integration, a path that led him through the mountains of Sonoma, California to explore one of the most storied personal development programs in the world, and deep into the improvisational heart of his favorite band.
Our conversation was sparked by an essay he penned on his Substack following Phish’s 2025 spring tour, titled Key Notes No. 5: Phish. First, read it. It wasn’t the typical fan review of 2.0 jams and breakout songs. You can find that kind of heady show breakdown, multiverse analysis, and “what does it all mean?!” scholarship in every nook and cranny of the hyperconnected Phish interwebs.
Rather, it was a vulnerable exploration of personal growth, gratitude, and a conscious decision to shed the snark that had defined his fandom for years.
In the process, Rogowsky found a new way to listen, not just to the music, but to himself. And it all started with a week of radical self-confrontation.
In a nutshell, he read the book.
I spoke with Rogowsky on the Mostly Occasionally Show, where I explore subjects near and dear to my millennial heart, and the weird corners of music, media, culture, and internet randomness.
You can watch it on YouTube, or listen to it on Apple or Spotify.
My Intent Is All for Your Delight
A year before our conversation, Scott checked himself into a retreat for a program called the Hoffman Process. Before he left, he provided a simple public explanation for his upcoming week of disconnection. “I was calling it a digital detox retreat,” he tells me. But the reality was far more profound.
“What it does, just in a nutshell,” Scott explains, his voice earnest, “it allowed me to, like, meet myself. And I was only able to do that without the distraction of the outside world.”
The Hoffman Process is a week-long, intensive psychological program designed to help participants identify, understand, and ultimately resolve the negative patterns of behavior, thought, and feeling learned in childhood. It’s not about blaming parents or one’s upbringing as much as it’s about recognizing the unconscious “agreements” we make to win their love and approval, and how those agreements continue to run our adult lives. For seven days, there are no phones, no news, no music. The goal is to quiet your thoughts and eliminate distractions so that you can focus on inner transformation..
“It’s more just like, I’m distracting myself from my true self,” Scott clarifies. “And it’s not just the phone, right? It’s literally, it could be music, it could be anything… anything you do that is taking your thoughts off of yourself and putting it onto some other object or concept is a distraction from the self. So that’s what this process did. It took away all distractions.”
In that space of quiet, guided by therapists and coaches, Scott was compelled to sit with the thoughts that had shadowed him throughout his life. “Why do I feel so shitty all the time, and why do I think I’m a piece of shit?” he recalls wondering. “All the negative, dark thoughts that I have had all my life were allowed. I was allowed to, sort of, like, sit with them and reason with them and process them… and go, ‘Okay, I’m not my thoughts. I’m not my feelings.’ Like, there’s a deeper, higher self in there that is sitting behind all of it. And, boy, that’s a hell of a realization to have.”
Everything’s Wrong
That inner critic didn’t just manifest in Scott’s private life; it was a defining feature of his generation’s cultural posture, and it bled directly into his experience as a Phish fan. Scott and I are the same age, and, in his late 30s, he started noticing the ways his attitude was poisoning one of his favorite things in the world: Sharing in the groove with Phish.
The roots of that cynicism, he explained, were a perfect storm of personal history and a historical moment.
Raised by “children of the 50s,” Scott felt he grew up with a certain kind of idealism. “I was kind of being raised with those values, very, very old school… I was raised with optimism,” he says. But that foundation began to erode as our generation came of age. We were old enough to remember a pre-9/11 world but young enough to have our formative years defined by the ensuing wars, the rapid growth of technology, and a constant stream of public scandals involving leaders on both sides of the political spectrum, which created a “complete, complete shattering of the moral compass,” as Scott puts it.
The older I get, the more it seems like this unique historical gumbo is crucial to understanding the millennial worldview. Straddling the analog optimism of our parents and the digital cynicism we inherited, we learned to process the world through an entirely new, and often skeptical, lens. Why do millennials use snark as a defense mechanism and come across as bitter as they are? Time and place, man. It’s really as simple as that.
This societal cynicism collided with Scott’s personal upbringing. “I was raised with a sense of, there’s a right way and there’s a wrong way,” Scott explains. “That sort of creates a complex, at least it did for me, where I was again, I was so freaking neurotic… I’ve got to do things right, and if I don’t, I’m a failure. And then that gets reflected onto me, I’m a failure, and then I point to others, because it makes me feel better.”
This became his default lens—a shield of ironic detachment. And for a Phish fan at that time, there was plenty to be cynical about. After a triumphant return from a mini-hiatus in 2003—Scott’s first show was the legendary 2/28/03 Nassau Coliseum gig, featuring a monster 27-minute “Tweezer” to open the second set—the band’s playing grew inconsistent, culminating in the messy, emotional Coventry festival in 2004 that marked the beginning of a five-year breakup.
The snark was easy. It was fun. It was a way to feel smart. For Scott, this manifested as a rigid, judgmental attitude toward the band’s music. It’s something I deeply relate to, as someone who also spent a lot of time in high school attending Phish shows during that same era, and then had my Phish worldview partially shaped by the edgelord, chronically online nature of Phish fans, including myself.
“I was so caught up in the judging and criticizing, comparing,” he says. He hated the new material. “Undermind? Are you kidding? Like, what is this shit?” The looping Trey Anastasio was doing in 2004, a sound we now understand as a cry from a man deep in the throes of addiction, was an affront. “That wasn’t the Phish that I got into that I liked.”
Eventually, the constant snark sucks the joy from the very thing you once loved, until you’re the fan who notices every flubbed note in “Stash” and complains that every “Ghost” was better in ’98. Basically, this guy:
Many people get stuck in this train of thought and let it run them off the tracks.
Scott, however, realized he needed to adjust his attitude.
See The Vultures Moving In
The core of this critical mindset, as Scott came to understand through his work at Hoffman, was a simple, destructive habit: expectation. He went to shows wanting to repeat the pure bliss of his first, transcendent experience. He wanted the band to play the songs he liked, the way he liked them.
“Expectations are nothing but premeditated resentments,” Scott says, slowing down to let the weight of the sentence land.
It’s a powerful statement he learned, and it became a key to unlocking his new perspective. Let me write it again so you can read it again, and really process it. Hopefully it sticks with you.
“Expectations are nothing but premeditated resentments.”
“You’re going into this experience… and if he doesn’t match this, if he doesn’t ask me this, I’m gonna be pissed. No, I had no expectations [for this podcast], and I’m having the time of my life. But when you set expectations, whether it’s like for the Mets to win, for Phish to play your favorite song, for this meal to taste as good as it did last time, you’re inevitably setting yourself up for disappointments and ultimately, resentment. Like I started to resent this band, the thing I love the most.”
This realization reframed everything. The goal was no longer to judge the show based on a personal scorecard but to appreciate it for what it was: a unique, unrepeatable moment in time. “If I go to a Phish show now, it’s just like, holy shit, I get to see this band do this incredible thing that only this band can do,” he says. “It’s all appreciation. It’s all gratitude.”
This shift from expectation to appreciation is the essence of the implicit contract Phish has with its audience. It’s the acceptance of the band’s unofficial, four-word life cycle, hollered during the deepest, most euphoric moments of a “You Enjoy Myself” jam: Boy, Man, God, Shit.
To be a fan is to live that cycle. To show up for the transcendent “God” moments when the music peaks and wows you with feel-good chemicals and deep introspection, but also to accept the occasional “Shit” nights without letting it sour the whole journey from the innocent joy of “Boy” to the wisdom of “Man.”
The Trick Was To Surrender To The Flow
For Scott, learning to hear differently was a process. Sober for his first 20 or so shows because he was a “good” kid growing up, he initially struggled to connect with the band’s long, abstract improvisations. He had trouble focusing. It wasn’t until he began to experiment with psychedelics at shows that the music fully opened up to him and his musical world expanded.
“What I found that psychedelic drugs do for me,” he says carefully, “is that… it brings me to presence. It brings me to a place where my mind can actually focus on this, this art that’s unfolding, and I feel connected to it in a deep, deep, visceral way.” He finally understood why they wrote a song called “Split Open and Melt.” He was doing it too, which tracks as a common Phish experience for many-a fan who’s dabbled with LSD and similar psychedelic drugs.
But this also wasn’t about escapism. It was about access. The psychedelics were a tool that helped him break down the ego-driven need for control and simply be present with the art. It was a chemical way of achieving the state of mind he would later cultivate and carry with him at Hoffman. It was, in the parlance of the band, a way to surrender to the flow.
Today, Scott sees that phrase as the ultimate ethos. Phish’s own journey mirrors his own. They were kids who found creative liberation through acid, writing nonsensical, joyous epics. Then, as darker drugs infiltrated the scene, the music reflected a growing paranoia and mistrust. Finally, after a painful bottoming out and a commitment to sobriety, Trey Anastasio emerged with a new message, one of unabashed gratitude and presence, captured in songs like “Everything’s Right.”
“They’ve unlocked new levels. More so than even when they started. They’re so present, and they’re coming from a place of gratitude and appreciation, all that fuzzy Christian rock stuff. Like, I call it Christian rock, Trey,” Scott jokes.
“Everyone does!” I laugh warmly. It’s all from a place of love and light.
“My cynical younger self would have been like, that’s terrible, fuck that,” Scott laughs. “I love it. I appreciate that I understand where it comes from. I understand the journey he went on. Maybe it’s just being older, getting older, maturing, whatever it is. I got there, I finally arrived, and I’m meeting them on a level where I’ve never been before.”
He has learned to love himself in a way he never had before, which has allowed him to find the love of his life. He is applying to graduate school to study the very psychological principles that changed his life. He is no longer a writer who doesn’t write, thanks to his Substack. He is living a life of intention.
“That’s why I love this band, like never before,” he says, his voice filled with a quiet, confident joy. “I love myself like never before. I love psychedelics like never before. I love it all, dude. The world is good.”
And in that simple declaration, the two Scotts become one. Two versions of me, alas, as Phish’s Page McConnell might pipe from his nest behind a keyboard.
The performer and the seeker, the fan and the man, finally in the same key, surrendered to the same beautiful, unpredictable flow.