Since the COVID-19 pandemic, businesses have faced unprecedented challenges when trying to remain open. Because COVID-19 spreads through aerosolized droplets, businesses were forced to distance their services; in some cases, distancing may have involved moving business services online. In this work, we explore digitization strategies used by small businesses that remained open during the pandemic, and survey/interview small businesses owners to understand preliminary challenges associated with moving online. Furthermore, we analyze payments from 400K businesses across Japan, Australia, United States, Great Britain, and Canada. Following initial government interventions, we observe (at minimum for each country) a 47% increase in digitizing businesses compared to pre-pandemic levels, with about 80% of surveyed businesses digitizing in under a week. From both our quantitative models and our surveys/interviews, we find that businesses rapidly digitized at the start of the pandemic in preparation of future uncertainty. We also conduct a case-study of initial digitization in the United States, examining finer relationships between specific government interventions, business sectors, political orientation, and resulting digitization shifts. Finally, we discuss the implications of rapid & widespread digitization for small businesses in the context of usability challenges and interpersonal interactions, while highlighting potential shifts in pre-existing social norms.