The chances of lightning striking twice are infinitesimal, at best. What are the odds, in middle age, of being struck with a jarring bolt of figurative lightning, then a few months later being an eyewitness as the same sizzle in the sky jolts a group of students--those decision-makers of tomorrow? The author describes two experiences that proved to be life-changing experiences. The first experience took place in the summer of 2013 at an annual seminar sponsored by Diversity Directions, an organization that addresses issues of diversity and inclusion in independent schools throughout the country. In six days in the gorgeous setting of a classic Massachusetts boarding school, he learned a lifetime's worth of lessons about multiculturalism and diversity in our schools. As a privileged white male, he was so moved by week's end that he felt the need to reassess his personal and professional priorities. With a clearer and more critical lens, he had the opportunity to take a fresh look at the environment at his school and even in his broader community. The second experience took place during a five-day community service trip with 23 ninth-graders in Washington, DC. Attending the trip as a chaperone, the author shared in the students' experiences of interacting with homeless people throughout Washington, DC. In addition to the profound socioeconomic lessons the students learned about why someone becomes homeless--and each story is unique and captivating--the students also saw that the face of homelessness, at least in their city, is predominantly black or Latino. Passive and institutional racism often play a part in the stories. In a very real way, the community service trip reinforced that, depending on your background, opportunity itself, let alone success, can be difficult to find.