Host Luke Burbank and announcer Elena Passarello share some financial advice penned by listeners to their younger selves; writer and Slate advice columnist Daniel Lavery explains how his latest book, Something That May Shock and Discredit You, revisits the media and myths of his past through the lens of his transition; New York Times bestselling author Michael Arceneaux unpacks the hard truths of student loan debt in his newest essay collection I Don't Want to Die Poor; and Jonathan Russell from indie folk group The Head and the Heart performs "Glory of Music."