Gavin DeGraw mans the mic at a Starwood Preferred Guest event
07/30/2013 at 12:00 PM EDT
For Gavin DeGraw, heartbreak is bittersweet.
The singer says some of his darkest moments have inspired his greatest hits, including 2004's "I Don't Want to Be" and 2011's "Not Over You."
"If [the song] becomes successful, suddenly you're not quite as angry singing it anymore because you're like, 'Wow, I paid my college loans off with that song!' " DeGraw, 36, told PEOPLE Thursday at Starwood Preferred Guest's "Hear The Music, See the World" concert series in N.Y.C., where he performed for a crowd
that included actor Stanley Tucci.
"You're singing 'I Don't Want to Be,' and you're just not quite as frustrated as you were when you were writing it because ... it really changed my life."
He adds: "It changed my career and altered my reality in a very positive way."