Jack Burns was not one of those silent majority baby boomers. He was one of those who helped to make them the hippest generation, if not the greatest. He went to the Fillmore, marched in anti-war protest, and watched Yellow Submarine on acid. Jack had no interest in his own pedigree when he read of Lee Melon's search for his Confederate General ancestor of Big Sur, he saw only the symbolism of a war against the status quo, a war he was a veteran of. Like Melon, 21st century Jack values the past and has pride in his Southern heritage, but it is just one more anchor around the neck of an aging baby boomer. He once trusted no one over thirty, but now at more than twice that age has difficulty accepting the new world. He sold out and embraced materialism claiming he did so for the sake of family. He has fulfilled his duties and there is still time to chase the ambitions of his youth. His wife of more than forty years, trying to balance career and family, forces him to choose between her and his dream. The situation is complicated by their son Aaron who has disappeared into a drug culture and their Harvard grad lawyer daughter Amanda battling her own demons. The clock is ticking and the end is near, a man must do what a man must do. Like Agamemnon he assembles a band of friends willing to follow him in his quest. He accomplishes his mission, but not in the way he imagined when he started. In Tribulations of an Old Hippy, armed with the attitude that "if a baby boomer can't do it then it can't be done," one man finds his answer to the meaning of life.