A familiar story about the evolution of alphabets is that individual letters originated in iconic representations of real things. Over time, these naturalistic pictures became simplified into abstract forms. Thus, the iconic ox's head of Egyptian hieroglyphics transformed into the Phoenician and eventually the Roman letter A. In this vein, attempts to theorize the evolution of writing have tended to propose variations on a model of unilinear and unidirectional progression. According to this progressivist formula, pictorial scripts will tend to become more schematic while their systems will target smaller linguistic units. Objections to this theory point to absent, fragmentary, or contrary paleographic evidence, especially for predicted transitions in the underlying grammatical systems of writing. However, the forms of individual signs, such as the letter A, are nonetheless observed to change incrementally over time. We claim that such changes are predictable and that scripts will in fact become visually simpler in the course of their use, a hypothesis regularly confirmed in transmission chain experiments that use graphic stimuli. To test the wider validity of this finding, we turn to the Vai script of Liberia, a syllabic writing system invented in relative isolation by nonliterates in ca. 1833. Unlike the earliest systems of the ancient world, Vai has the advantage of having been systematically documented from its earliest beginnings until the present day. Using established methods for quantifying visual complexity, we find that the Vai script has become increasingly compressed over the first 171 years of its history, complementing earlier claims and partial evidence that similar processes were at work in early writing systems. As predicted, letters simplified to a greater extent when their initial complexity was higher.