From the days of Ben Franklin and his chart-obsessed “Autobiography,” the American self has been a perpetual work in progress. (Franklin recommended keeping careful records of one’s observance of such virtues as industry, temperance and cleanliness.) For the bemused, anxious and thoughtful writer Jessica Lamb-Shapiro, however, this mania has been especially pervasive. Her father, a child psychologist, has been writing self-help books for parents and children since before she was born, and even started a mail-order catalog of therapeutic toys and games, most of which he tested on her. Here’s Lamb-Shapiro’s recollection of the first time he coaxed his little...