This article discusses promises and pitfalls of employee-oriented workplace flexibility. The concept of employee-oriented flexibility applies to broad-based programs and individualized approaches. Here, the focus is on idiosyncratic deals (i-deals), individually negotiated work arrangements. Reviewing the literature, theory on characteristics, prerequisites, and limits of mutually beneficial flexibility is developed in the context of the neoliberal reconfiguration of work, employment, and societies. The dialectic construction of antagonistic types is used to differentiate employee-oriented i-deals from ideological counter-applications of economic rationalization. The latter reflect neoliberal ideologies of individualism, competition, and instrumentality, the former humanistic ideals of individuation, solidarity, and emancipation. Symptomatic for psychological governance through “subjectification”, self-enacted forms of rationalization threaten to undermine humanization prospects. Divisive management practices, politically motivated rhetoric, and inherently distorted theorizing are based on confounding “hidden modes” of workplace flexibility, the deconstruction of which advances scholarship.