Purpose: The purpose of this paper is to present a cybernetic way of seeing analog and digital along with a basic vocabulary for discussing assumptions underlying the use of both terms. Design/methodology/approach – Taking analog and digital not as properties of observed phenomena but as properties of observers, I ask not what is digital or analog, but what I do when I use these terms. I analyze introspectively, and report on, what I think my assumptions are when using the two terms. Findings: I develop a basic vocabulary to describe engagements that I describe as analog or digital. This vocabulary is applicable beyond technical contexts and suitable also for discussing social and creative processes. It includes a kind of observer who I call matchmaker. Research limitations/implications – The presented research is preliminary and subjective. Originality/value – While previous discussions consider analog and digital as properties of observed phenomena, they are considered here as properties of observers. The presented discussion is sufficiently abstract to account for the analog and the digital at various scales, including electronic signal processing and human interaction. The author argues that discussions of engagements described as analog or digital must account for observers of these engagements, including those who act as their matchmakers.