Growing up in Kenosha, Washington, Jackson initially aspired to work as an illustrator with the goal of becoming a painter. He began exploring painting during his sophomore year in college.
These early paintings include abstracted portraits of people Jackson knew, signaling to the ways that figurative painting felt imposed on him during his undergraduate experience. After realizing these portraits were more symbolic of larger communities than the subjects they portrayed, Jackson reinvented his practice in graduate school by removing referential materials and working from a creative space of invention and world-building. Narratives became more intrinsic to his paintings, and he began to explore global painting traditions, namely Indian miniature painting, as a method of grounding his practice. During this time, Jackson started writing a fictional text that has become foundational to his work. This text narrates the story of “E,” Jackson’s protagonist, who arrives at a Maroon village via a starfish; he eventually implodes into a black hole. The resultant compression of matter into a singular space is the place from which Jackson’s paintings depart. “Lookers” and “Seers,” supernatural characters drawn from “E,” recur in Jackson's paintings, drawings, and prints as ways to depict otherworldly themes.
