Digital technologies have deeply pervaded the economy and society, and, in turn, the world of work. Twenty-five years ago a worker would have been amazed by some of the current characteristics of the labor market and company practices. Thus, progress in information technologies has potential effects on the number of workers who telework. Some technology-based practices of present-day companies can unfavorably affect their employees’ wellbeing. In addition, there is a new labor market, the digital labor market, where individuals work through Internet platforms. Simultaneously, there is a debate about automation because there are signs that the traditional labor market is being shaken by the more advanced information technologies. This article addresses these topics in an attempt to portray new aspects of the contemporary world of work.