“I became famous when I was 22 and it was quite the rollercoaster ride,” Posner said. “It was very overwhelming at first, but I look at it now as a blessing because it helped me become who I am now. I love who I am now.” Like most people, Posner believed that achieving certain goals, including launching a successful music career and reaching a certain tax bracket, would make him happy. “But when you then achieve that thing and it doesn’t solve your problems, the hope disappears and that’s when disillusionment sets in,” he said. “And disillusionment is not a bad thing in and of itself. It really is what we do with disillusionment. … I set out on a quest. I thought, ‘Well, OK, this stuff that I thought — the fame and the money and the popularity and all stuff — that I thought was going to change my moment-to-moment experience of life didn’t. So if not that, then what?’ And that’s what the second chapter of my life has been about.”

In 2019, Posner reached a major inflection point. “I felt the pain of not getting this equation, right—having all this external success and knowing like, ‘I have everything, but deep down, I kind of know I have nothing.’” Even though his management team told him he was “crazy,” he decided to walk across America. “That was quite a departure, quite a left turn, from the things that were on my CV before that, which were being a pop star,” he says. The journey “changed my life,” he said. “I’m not saying everyone here should walk across America, but sometimes there’s an internal walk we need to go on. There’s an internal feeling like there’s more inside me then I’m letting out. There’s an element of waiting sometimes that I felt in life, like there’s this beautiful part of me that I’m keeping to myself, and I’ll let it out when the time’s right. And what I’ve learned on that journey is the time’s never right. The time is now.  You don’t want to have a life imbued with waiting for later. The reason I think some artists see me that way is I had everything and I walked away.”

At mile 1,797 on his walk across America, Posner was bitten by a rattlesnake. He took it as a deeply significant sign. “I was on a journey to shed a layer of skin; not to show people who I was, but to find out who I’d become on this journey,” he says. “I was injured and hurt by a thing that also sheds layers of skin. And I look back at that venom that was coursing through my veins as the most powerful medicine I’ve taken to date. I’ve taken some powerful medicines and that’s my favorite one.” Posner spent five nights in the hospital and almost lost his foot, if not his life, as his leg swelled to the size of “an elephant trunk.” But then, after a long recovery, he picked up exactly where he left off and walked the remaining 1,000-plus miles.  “It was the only way for me to become the version of myself that I know I’m meant to be [was] to finish this walk.”

When asked by Applefeld how the music industry can help creative people realize their journey, Posner stressed that artists need to understand their own agency. “I don’t like the narrative of like, ‘I’m an artist and my label and my manager made me do all that.’ They didn’t make you do anything. They work for you. Sorry. And you always can say no. If you don’t feel like you can say no, you have to learn that. And that’s not anyone’s fault but yours. … I think an industry where more people are healthy, happy and fulfilled is ultimately probably a more abundant industry. You have better pieces of art being made for longer and I think that results in prosperity for everyone.”

Posner has more than 775,000 followers on Instagram, not that he’s likely to know. When asked how he deals with the anonymous keyboard warriors to endless try to take down celebrities, Posner joked, “I have this hack. It’s called not reading the comments. It’s pretty good.” Posner, who gets deeply profound on his Instagram, writes what he wants posted and turns it over to his team and they post it for him. “I don’t have the actual apps on my phone,” he says, acknowledging that’s a privilege most people don’t have. “These things are a little addictive,” he said of social media. “And that’s the reason the algorithms work. There’s a part of me at least, and I suspect in other people in this room, that really loves the drama of someone saying something nasty about me. … There’s a really addictive nature to depression, negative thoughts, cynicism, self-pity. I mean anyone whose spent time in those spirals knows that there’s a part of you that like kind of loves it, like wants to go there. And so, for me, it’s been a practice of loving that part of myself, but not letting it steer the ship of my life any longer.” 

Posner has a new album coming out, which he says will serve as a “soundtrack” to his spiritual journey, and he’s also writing a book about his walk across America. To finely illustrate how far he has come in his quest, he ended his session by playing “I Took a Pill in Ibiza” acoustically, which really brought out the song’s painful, poignant lyrics about feeling like a has-been in his 20s, sabotaging all his relationships and finding nothing but emptiness in spending all his money on “girls and shoes”; he then played a song from his new album, the uplifting, hopeful “It’s a Beautiful Day to Be Alive.” He also led the room in a breathing exercise and, as parting advice, added, “There’s some people in this room dealing with something real, challenging. I want to remind you this is just the beginning and you’re right where you’re supposed to be.”