Famously renowned as William Shakespeare’s imaginary sister, whose life Virginia Woolf sketched out in her 1929 landmark feminist essay, A Room of One’s Own, in order to compensate for the silences of history and to explain women’s presumed literary silence in the Elizabethan era, Judith Shakespeare was, in fact, the playwright’s illiterate youngest daughter. In fiction and on stage, Judith Shakespeare’s life has been, since Woolf, repeatedly rewritten in various novels and plays, among which Shakespeare’s Sister (a period drama written by young British playwright and lecturer in Shakespeare studies, Emma Whipday) stands out as it not only offers a rewriting of Judith Shakespeare’s fate but also tackles the issue of women’s professions in the Elizabethan renaissance while implicitly negotiating Woolf’s thoughts and writings on the matter. This paper offered to analyse how Whipday’s play both rewrites and restages Judith Shakespeare’s life in order to question from our contemporary standpoint (both in terms of historiography and feminism) women’s professions in Shakespeare’s world, most notably through the figure and fate of Judith, aspiring playwright and actress, but also thanks to other women, be they the daughters of theatre men or prostitutes, who attempt to accompany Shakespeare’s sister in her endeavour to tread the boards, in a world where, as Whipday’s Judith argues: “it is easier for [her] to die as a writer. [She has] no chance of living as one”.