Student debt is reaching new heights for many American students. Money host Tess Vigeland, senior producer Paddy Hirsch and personal finance expert Liz Weston listen to some particularly harrowing stories of student debt. One med student is faced with $440,000 in student debt, which he says is “not an uncommon number” among his peers. Grads and students shared similar stories of finding cheap and free ways to have fun and giving up material comforts to make ends meet.

Liz Weston — whose 9-year-old daughter was listening in — said that the conversation about student debt has to start long before the student even start applying for college: Their freshman year of high school. “You don’t have the conversation when they have the acceptance letter in their hands,” she said. Parents must clearly lay out how much they are willing to give towards their child’s education and how to manage debt responsibly.