It was half past midnight when Demi Lovato announced that it was time to take her clothes off. In the streets below her Manhattan hotel room, the crowd of dedicated fans waiting for a glimpse of the singer/songwriter/actress/pop star couldn’t possibly imagine what was about to transpire behind closed doors. Quite frankly, neither could I.

That morning I’d stepped off a plane from Los Angeles to shadow 34-year-old Phil McIntyre, C.E.O. of music talent-management firm Philymack, who has launched the careers of several major pop stars, including Nick Jonas and Lovato, whose new album, Confident, is set to be released on October 16. After shuttling from meeting to meeting, we ended up at the Greenwich Hotel to meet with the Philymack team.

The topic at hand was Lovato, whose great-grandfather Buddy Moore had died the day before. Lovato considered him one of the most important people in her life, and McIntyre and his team were concerned. At midnight, an emotionally drained Lovato arrived sans makeup, hair pulled back, carrying her Yorkiepoo, Batman. I had photographed Lovato once before, so she smiled and said hello, then plopped down in a chair. Batman came over and jumped in my lap. She spoke about her sadness, and then she got an idea.

“If there’s one thing I’ve learned in the past day, it’s that life is too short,” she said. “I’m about to launch an album that finally represents who I truly am. How do I embrace this new chapter in my life? How do I really walk the walk? What does it mean to be confident? It means letting go, being authentic, saying I don’t give a fuck and this is who I am. I want to show the side of me that’s real, that’s liberated, that’s free. What if we do a photo shoot where it’s totally raw? Super-sexy, but no makeup, no fancy lighting, no retouching, and no clothing. Let’s do it here, let’s do it now.”

The room emptied, and I wondered how I’d fallen into this situation. With only her assistant remaining, Lovato and I worked in near silence, making our way through the hotel room, communicating with subtle gestures, nods, and tilts of the head. Lovato had rarely posed nude before, so I had to be respectful of that and tread lightly. When I left her at three in the morning, she gave me a quick hug and thanked me for making her feel pretty. I thanked her for her confidence.