Host Luke Burbank and announcer Elena Passarello reveal how their self-improvement goals have progressed; writer and Dear Prudence advice columnist Daniel M. Ortberg explains how his new 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 best-selling author Michael Arceneaux unpacks the hard truths of student loan debt; and doom-wop singer Prom Queen performs "End of the World."