ABSTRACT. In this article, I focus on Wittgenstein's view of self-understanding as a necessary part of the attempt to live an ethical or responsible life especially focused on his description of our use of pictures in this regard. Wittgenstein shows how we construct and use pictures to highlight or express certain features of our particular way of being; pictures that may be revealing but may also prove to be a source of misunderstanding about ourselves. In the final part of the paper, I use a minor digression into Wittgenstein's account of a philosophical problem to show how pictures in this way mirror, and thus may help us to understand, an inherent dynamic dimension in the acquisition of self-understanding.