Scholars have observed workers combining multiple work roles to earn a living to cope with the vicissitudes of the labor market. In studies of creative labor markets, this trend of workers broadening of their skills is termed “occupational generalism”. Previous scholarship has focused on the structural factors that push and pull workers into generalizing and combining multiple work roles. But we lack an understanding of the subjective experience of work as a generalist. I introduce the concept of dilemma work: a form of problem-solving wherein workers who have generalized their work portfolios, attempt to rationalize their professional practices to overcome conflicts that arise from occupying multiple work roles. Drawing on in-depth interviews with professional writers who also freelance as book reviewers, I find that these generalists use three dilemma work strategies: anchoring another role to guide action in the current one; incorporating multiple roles under a higher role or purpose; and compartmentalizing roles in order to act exclusively within a single identity. I propose the general value of a typology of dilemma work for understanding workers’ experience both within artistic labor markets, and beyond.