This research aims to unpack how digital technologies can facilitate the flourishing of circular business practices in small- and medium-sized enterprises by structuring a detailed going circular path that explains businesses’ evolution toward circularity. In doing so, it outlines how the observed organizations have adopted – or are adopting – circular economy principles thanks to business digitalization. Following an inductive approach based on a multiple case study methodology, we investigated 16 small- and medium-sized enterprises operating in industries that put considerable pressure on the environment (e.g., manufacturing, chemical, construction, fashion, food, and beverage). Our findings confirm how digital technologies, as well as Industry 4.0 structures, play a fundamental role in shaping, enabling, enhancing, and refining circular products and processes development. Accordingly, we outline a generalizable step-by-step process to pursue circular economy by employing digital technologies. The present study represents a practical handout for guiding companies through their going circular path.