Despite growing research on the perceived desirability and positivity of callings, there is intriguing evidence that while many experience personal benefits associated with viewing their work as a calling, others may experience detrimental effects. This discrepancy highlights the need to better understand when pursuing a calling might be positive or negative for individuals and to identify potential conditions under which such positive or negative outcomes may occur. In this article, the authors take a relational perspective on what they refer to as "healthy" versus "unhealthy" pursuit of callings, highlighting the conditions under which callings might be beneficial versus problematic for one's personal relationships, and relationships with coworkers and one's employing organization. Furthermore, our theoretical framework incorporates an identity perspective emphasizing work-identity flexibility as a critical factor that explains when and why pursuing one's callings might be associated with positive and enriching relationships for some, but negative and depleting relationships for others.