Although technological innovation has often been met with dire—and usually overblown—warnings of job displacement and economic fallout, many theorists consider the ongoing digitization and automation of work one of the most pressing social and economic issues of our time (Benanav, 2020; Srnicek & Williams, 2015; Stiegler, 2016). Described by World Economic Forum (WEF) founder Klaus Schwab (2016) as “the Fourth Industrial Revolution,” the growing predominance of machines and artificial intelligence in the workplace has been accelerated by the global COVID-19 pandemic, which forced many organizations to increase their reliance on digital tools and software (WEF, 2020). Although researchers, scholars, and policy makers in diverse fields have devoted significant attention to this phenomenon, it has been curiously neglected by vocational psychologists, despite its potential to dramatically impact vocational behavior (Hirschi, 2018). The field has been even quieter on the topic of a “post-work” future, a hypothetical but nevertheless plausible outcome of current trends that, if realized, would carry profound implications for the study and application of vocational psychology. This presentation aims to start a dialogue regarding the vocational implications of future work (e.g., increased precarious work, changing workforce demands, the blurring of work and nonwork roles, the possible institution of universal basic income) and their impact on the practice of career counseling. We synthesize a transdisciplinary overview of recent scholarship on the future of work, followed by a discussion of associated challenges and considerations for career practitioners. To start remapping the field, we suggest drawing from Cognitive Information Processing (CIP) theory (Sampson et al., 2004), an approach to career development which emphasizes strategies for effective decision-making—an increasingly critical skill in light of the rapid workplace changes and frequent career transitions associated with the Fourth Industrial Revolution.