AbstractIt is well researched that ideals of freedom and self-fulfillment through work are perpetuated by the neoliberal ideology that permeates subjective reasoning, meaning-making, and everyday practices. While these ideals may seem attractive and enticing to the subject, their pursuit usually leads to less secure working contracts and conditions. Thus, organizations can continue to enforce economic principles and increase pressure on workers while, at the same time, the mechanisms of liberalization and individualization make subjects — not organizations — responsible for their own success and existential survival, and for creating meaningful and happy lives. Striving to design and optimize their own personal and professional trajectories, subjects perpetuate these ideals and thus adopt the socially-validated view that opting out of a salaried job in favor of self-employment is the zenith of self-actualization. Existing research on the phenomenon of opting out emphasizes gender differences around this issue, i.e., women opt out to stay home, whereas men — if their role is even considered — do so to enhance their careers. However, this research is sparse and lacks a contextualized understanding of the phenomenon, such that we still know very little about who opts out and why. Following an explorative approach, this study looks at 20 single-case stories of subjects who opted out from corporate career tracks. We find that the decision to opt out worked out well for diligent subjects with high self-esteem, who already had successful career trajectories and who — independently of gender — viewed it as an act to free oneself from, and a fundamental critique of, corporate working conditions and values. We analyze this finding through the theoretical lens of critical psychology in order to shed light on the phenomenon of opting out and the extent to which individuals can pursue meaningfulness in life and work within the scope of neoliberal conditions, i.e., in contexts where liberal principles remain applicable to the living and working conditions achieved by subjects after they have left the corporate world.