Boatwright had enjoyed a loving childhood with his father, mother, and sister. After Harvard, however, he was rejected from the military because of poor eyesight. There ensued a lifetime of bouncing around. Boatwright found work equipping navy ships with radar equipment. Then he moved to Vermont to manage a tree farm. In Vermont he helped build a lumber cooperative, an egg cooperative, and a high school. He worked as a journalist, a milk deliverer, a carpenter, a painter, an accountant for a gas station, and an artificial inseminator of cattle. In the 1950s, an interviewer for the Grant Study noted that Boatwright had “persistent difficulty in establishing a career,” and yet Boatwright also struck the interviewer as one of the most stable men in the study—a paradox that took Vaillant a lifetime to unravel.