Oliver Cromwell was a stern, Puritan dictator from the seventeenth century, and Kylie Jenner is a twenty-first-century pop culture princess and lipstick mogul. They could not be more different, yet they have in common that they’ve been tagged with the provocative and powerful label “self-made.” Their stories bookend the history of how what was once a sin became an accolade. For Cromwell, a claim of self-making would have endangered his social and political standing, as well as his soul. Jenner, in contrast, proudly accepted this label as a badge of esteem, a reward for being a “selfie-made success.” Over the centuries between them, the concept of self-making evolved, always serving storytellers as a tool for judgment. It became socially and politically destructive along the way because storytelling based on its false assumptions and judgments has fostered policies and cultural attitudes that advance inequality and absolve the affluent of community obligations. Although much of its modern persuasiveness comes from claims that it belongs among core American values, the myth’s history reveals that there is nothing intuitive, stable, or tied to the real world about the idea of self-made success.