Inspired by burgeoning scholarly interest in the role of digitalization in the COVID-19 pandemic, this paper examines how the COVID-19 pandemic is driving or constraining the digitalization of businesses around the globe. We contend that COVID-19 is “the great accelerator” in fast-tracking the existing global trend towards embracing modern emerging technologies ushering in transformations in lifestyle, work patterns, and business strategies. Thus, COVID-19 has evolved to be a kind of “catalyst” for the adoption and increasing use of digitalization in work organization and the office, alongside presenting foreseen and unforeseen opportunities, challenges, and costs-leading to negative and positive feedback loops. In this article, we develop and advance a conceptual model by linking the different forces for and against digitalization in response to the pandemic. Our analysis indicates that adoption of emerging technologies may be hindered by vested external interests, nostalgia, and employer opportunism, as well as negative effects on employee well-being that undermine productivity, work-life balance, and future of work. Whilst digitalization may bring new opportunities, the process imparts risks that may be hard to mitigate or prepare for. Finally, we draw out the wider theoretical and practical implications of our analysis.