The meaning of work is influenced by the relationship between employees and organizations. In recent years, jobs outside the traditional boundaries of firms have grown considerably. Online platforms that connect contractors and clients for “gigs” are part of this trend. This study explored the process by which finance professionals who have become freelancers in online labor marketplaces make sense of meaning in work. Using an inductive, phenomenological approach, this study sought to understand and interpret qualitative data from 10 participants. The research adds a unique perspective to a vast body of literature on the meaning of work, largely focused on employment within organizations. It offers insights into how finance freelancers experience the meaning of their work as they adapt to their roles as gig workers. Findings show that freelancers initially perceive a sense of reduced structure in work and life, and often feel misunderstood by family and colleagues, which triggers a process of identity work. Freelancers then progressively develop resources and manage demands through goals, boundaries and routines, thus developing more control over their lives. They articulate narratives of themselves as independent, productive and adaptive individuals, who find meaning in solving problems. Although further research is warranted, findings suggest that, in a radically flexible working context, individuals who control variables such as tasks, time and location, tend to adopt a mindset focused on ongoing optimization and problem-solving. They set their own goals and manage resources, demands and uncertainty to optimize their work and their life.