There are as many meanings to drawing and painting as there are cultural contexts for them to exist in. But this is not the end of the story. Drawings and paintings are made, and in their making embody unique meanings that transform our perception of space-time and sense of finitude. These meanings have not been addressed by art history or visual studies hitherto, and have only been considered indirectly by philosophers (mainly in the phenomenological tradition). If these intrinsic meanings are explained and further developed, then the philosophy of art practice is significantly enhanced. The present work, accordingly, is a phenomenology of how the gestural and digital creation of visual imagery generates self-transformation through aesthetic space.