The proposed article is an attempt to look at the problem of the authorship of the works of William Shakespeare (Shakespeare authorship question), as if from the outside, since the author, considering this problem to be real, is not, however, a staunch supporter of any one approach. Shakespeare's question is two hundred years old. This is generally thought to be a problem with the authorship of Shakespeare's works. But in fact, the question lies in the very reason for the emergence of doubts about the authorship — in the discrepancy between the image of the real person — Will Shakespeare from Stratford, the image of the playwright and poet William Shakespeare, which is formed in the reader under the influence of his works. And with this approach, the Shakespearean question can be resolved not only by proving one or another alternative authorship, but also if, within the framework of traditional authorship, the reasons for this discrepancy are explained, or if it is shown that the discrepancy is apparent. However, instead, supporters of traditional and alternative authorship further increase this gap between the two images: on the one hand, an opinion is created and maintained about the unprecedented erudition of the playwright Shakespeare, and on the other, about the lack of education of the real Shakespeare. Moreover, representatives of both approaches show dishonesty in their research, and at the same time they reproach the other side for the unscientific approaches. The article points out that any solution can be convincing only if it explains the nature of the contradictions between the personality of the real Shakespeare and the world of Shakespeare's works. And for this it is necessary to answer the main question: at what moment and how Shakespeare from Stratford became close to high society. The author comes to the conclusion that the known facts can be explained and reconciled only by the assumption that the connecting link could be one of the "candidates" for the role of the author of Shakespeare's works, the Earl of Rutland, and that Will was recommended to the Earl's family by a very influential person. Moreover, it seems that there is only one candidate for the role of such a person — his mother — Mary Arden. The stated hypothesis makes it possible to explain the main oddities associated with the personality and work of William Shakespeare, who thus combined two worlds — each with its own system of values.