Eric Flannagan Jr grew up in Charlottesville, Virginia, where The Madison House Big Siblings Program became a pillar of his youth. He recalls the single decision he made to raise his hand in a class, not realizing how this transformative experience would shape his adolescence. Flannagan recounts the impact of those siblings on his upbringing, weaving together his personal experience with broader social and cultural issues. He reflects on the intersections of race, class, and privilege that impacted his childhood and how these continued to influence his outlook into adulthood. Following him through his teenage and university years, Flannagan, a natural linguist and avid traveler, discusses his life's highs and lows, his periods of growth and transformation, and how he has emerged on the other side of the decision he made over thirty years ago.