Considerable academic attention has been dedicated to Michelangelo’s purported self-portraits in the Last Judgment, Pauline Chapel, and Florentine Pietà. It is perplexing, then, that scholarship has fallen largely silent on the artist’s portrait medal (1560) and has dismissed its elusive impresa as having ‘no obvious application to Michelangelo’. This article considers how Michelangelo’s portrait medal, and its impresa especially, should be understood as one of the artist’s most public instances of self-fashioning. Taking Psalm 50:15 as his motto and a blind pilgrim as his image (likened to the soul and body, respectively, by Paolo Giovio), Michelangelo presents himself through the medal as a penitent artist-evangelist in the tradition of the Old Testament King David. The impresa also makes a bold statement of Michelangelo’s potential as a religious artist, bearing witness to his belief that he would only be able to render service to God after he had been redeemed in the eyes of heaven. This conception of self is not unique to the medal, however, and explores similar themes to those found both in the writings of Savonarola and the artist’s late poetry. Michelangelo’s poetry and portrait medal are thus evidence of the artist’s attempt to reconcile the conflicting interests of art and religion at the end of his life.