“Shadow Sailing” is a twenty-one minute psychological journey that charts one man’s downward spiral into madness as he tries to take the trip around Cape Horn that he and his father were never able to make together. In his father’s place, Brad brings his new wife and begins to chronicle his childhood, and the series of events that finds the two of them alone on the open ocean. Obsessed in writing his memoirs, he becomes increasingly oblivious of Emily, and her pleas to go to land. The more he delves into his traumatic past, the more Brad takes on certain aspects of his father that he’d rather forget. As the voyage stretches on and his psychosis deepens he begins to see his wife as an impediment to finishing a journey that began long ago and decides to quell the voices that torment him.