Applying a demands–resource approach, the present empirical study among 1395 individuals researches how flexibility and self-employment affect work–family conflict in Germany. Specifically, gender differences regarding work interference with the family and family interference with work are examined on a strain-based and time-based level. The multivariate results reveal a differentiated but surprisingly non gendered picture of the effect of self-employment and job flexibility regarding work–family conflict. Due to greater flexibility, self-employed people perceive a slightly lower time-based work-to-family conflict while their strain-based work-to-family conflict is higher than among employees. Regarding family-to-work conflict, self-employment leads to a higher level of time-based conflict, possibly because of higher expectations regarding availability. Thus, self-employment can be seen as a demand or a resource depending on the type of conflict. This study therefore contributes to a more refined understanding of the role of flexibility and self-employment in the light of literature on demands and resources.