Using two-level data drawn from franchisors and their franchisees, this paper explores how individual and work characteristics influence franchisee well-being. Franchising is an interesting context in which to examine well-being, given the boundary spanning nature of the franchisee role, both within the organization and across the employee-entrepreneur divide. Drawing on the Job-Demands Resource Model, we examine how a key tension in franchise systems – the desire for autonomy by franchisees and the need for standardization by franchisors – impacts franchisees' emotional exhaustion. We find that franchisees who self-identify as entrepreneurs and who are granted greater autonomy suffer less emotional exhaustion. Interestingly, our results also show that franchisees who are members of systems with strong operating routines (which should counteract autonomy perceptions) experience less emotional exhaustion, suggesting that routines can be important in reducing job demands. Our findings have a number of practical implications for franchisors. In particular, franchisors should favor franchisees with prior industry experience, which we found to be positively associated with franchisee mental well-being, and should not avoid entrepreneurial franchisees – as often suggested.