This thesis grew out of my own experiences of the sudden loss of a loved one. It turns to the philosophy of Martin Heidegger and Paul Tillich to examine how vertical and meditative thought, respectively, aid in interpreting art to overcome such a tragic event. The first section of this thesis begins with an explanation of how I came to realize that my capacity to understand and interpret life had been restricted by a lens of calculative thought. The second section of this thesis addresses the philosophical lessons about depth in thought in the vertical plane that Paul Tillich teaches us about, and is combined with Martin Heidegger's teaching about the difference between being studying in meditative versus calculative thought. Following their explication on the importance of our elusive capacity, the third section is reserved for becoming aware of how to practice our capacity of meditative and vertical depth in thought through the art of poetry. The final section concludes with a discussion of the importance of involved thinking, along with a poem I created using a meditative mind frame.