Trouble Met Me Halfway records Thomas Conway Maas' memories, observations, and youthful indiscretions from his upbringing in Milwaukee, Wisconsin, in the fifties, sixties, and early seventies. These essays relate the sometimes rocky path Tom took to adulthood, as well as reaffirm some universal truths about growing up. They provide not only snapshots of Tom's childhood, but offer a time capsule of ordinary life and changing cultural norms of that time period. Tom actively reflected about his life through his journals, his speechwriting, and his essays, a habit encouraged by his involvement in the Catholic Church's Schoenstatt Movement during his formative years. These particular essays reveal not only Tom's phenomenal memory, they show the confidence and aggressiveness that were present from early-on, which assisted him throughout his career as a lawyer.