We use the viewpoint of the formal calculus underlying vertex operator algebra theory to study certain aspects of the classical umbral calculus. We begin by calculating the exponential generating function of the higher derivatives of a composite function, following a very short proof which naturally arose as a motivating computation related to a certain crucial “associativity ” property of an important class of vertex operator algebras. Very similar (somewhat forgotten) proofs had appeared by the 19-th century, of course without any motivation related to vertex operator algebras. Using this formula, we derive certain results, including especially the calculation of certain adjoint operators, of the classical umbral calculus. This is, roughly speaking, a reversal of the logical development of some standard treatments, which have obtained formulas for the higher derivatives of a composite function, most notably Faà di Bruno’s formula, as a consequence of umbral calculus. We also show a connection between the Virasoro algebra and the classical umbral shifts. This leads naturally to a more general class of operators, which we introduce, and which include the classical umbral shifts as a special case. We prove a few basic facts about these operators.