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The ongoing “digitalization of work” is one of the major phenomena shaping contemporary organizations. The aim of this study is to explore linguistic constructs of white-collar workers (WCWs) related to their use of digital tools.

The framework of ideological dilemmas (Billig et al., 1988) is mobilized to investigate the conflicting demands WCW interviewees construct when describing the ongoing digitalization of their office work.

This study shows how “digitalization of work” is enforcing an organizational ideological dilemma of structure and flexibility for WCWs. In the digital workplace, this dilemma is linguistically expressed as the individual should be, or should want to be, both flexible and structured in her work.

The use of language exposes conflicting ideals in the use of digital tools that might increase work–life stress. Implications for managers include acknowledging the dilemmas WCWs face in digitalized organizations and supporting them before they embark upon a digitalization journey.

The study shows that the negotiation between competing organizational discourses is constructed irrespective of hierarchical positions; the organizations digital maturity; private or public sector; or country. The study confirms contradictory ideological claims as “natural” and unquestionable in digitalized officework.