Psychoanalysts have written about synchronicity, or meaningful coincidence, from the beginning of the field, yet the topic remains controversial and relegated to the edges of clinical work and research due to lack of a scientific framework. This paper presents a way to conceptualize resonant patterning between inner and outer processes derived from the mathematics of fractal geometry. Considered the “geometry of nature” since its inception, nonlinear fractal models, methods, and metaphors reach beyond reductionism, Cartesian dualism, and traditional linear notions of causality to accommodate porous, interpenetrating boundaries between inner and outer domains as well as self-similar relational patterns. A fractal epistemology is sturdy yet flexible enough to accommodate paradox, ambiguity, uncertainty plus other complex, fuzzy processes of the ordinary analytic experience. Clinical examples also illustrate that fractal framework applies more broadly to the occasional extra-ordinary experience of synchronicity and other “uncanny” nonlocal phenomena in clinical work.