Role Model spent years writing songs about his heartbreak — until his new album made him realize he might be the problem
The 29-year-old singer has just started therapy and says once a week might not be enough.
Tucker Pillsbury has spent the better part of a decade turning his emotional life into music, moving from rap to indie-pop, writing songs about heartbreak that he makes sound breezy enough to play at a summer barbecue. You may know him as Role Model, or as the guy who got Hilary Duff, Olivia Rodrigo, and Kate Hudson to dance onstage during his viral hit “Sally, When the Wine Runs Out.”
His third album, Chuck Timely & the Hourglass, is out now, and he admitted he had started seeing a therapist for the first time. “I don’t know if once a week is enough for me,” he told NYLON this week. “I feel like since I’ve got 30 years of sh*t I’ve got to start dealing with, I need more therapy.”
Pillsbury spent around 2 years writing Chuck Timely & the Hourglass, his third studio album. “You start to question if maybe you’re the problem,” he said, “and I think maybe there are things in myself that I need to change.” He was clear about what a relationship alone could not fix: “I don’t think dating or finding love can fully heal that.”
The self-examination had been building for a while. He attended his first wedding as an adult last year and found himself unexpectedly moved, then his sister got married shortly after, which he called “a double whammy” of reflection on his own stagnation. “I was like, there’s obviously deeper things going on,” he said, so he booked the appointment with a specialist.
He had spent a decade processing emotion through music, turning his inner life outward into songs, and the album forced the lens around. “Making the album and writing all those songs,” he said, “I think me going to therapy now is a result of that.” By the end of the interview, he was staring at the ceiling of his LA home surrounded by paintings of Maine, the small oceanside town he grew up in and still calls home in the way that matters. “I’m trying to set myself up to be happy,” he said.
What men carry into their thirties without examining
Most go to therapy after something breaks: a marriage, a health scare, a career that falls apart. Starting before the crisis is a different move entirely.
By thirty, most men have habits around conflict, intimacy, and self-worth that were built in the first two decades of life and have never been examined directly. Those habits run underneath everything: how you handle someone pulling away, how you respond to a setback at work, and how much of yourself you bring into a relationship versus how much you manage on your own. Left unexamined, they do not fade with age; instead, they accumulate.
The idea that therapy is for people in crisis is one of the most costly misconceptions men hold onto. Executives hire coaches. A musician goes into the studio with a producer to hear what he cannot hear from inside the song. Therapy is that kind of tool, a structured space to identify patterns you cannot see from inside.
