["Journal of Management Studies, Volume 63, Issue 6, Page 2509-2577, September 2026. ", "\nAbstract\nWe extend the mixed gamble perspective to explain how family‐controlled firms frame and evaluate the difficult trade‐off between potential gains and losses in financial wealth (FW) and socioemotional wealth (SEW) when pursuing portfolio‐level strategic initiatives, as captured by competitive aggressiveness and complexity. Analyzing 570 public‐listed Korean firms from 1998 to 2017, we find that family‐controlled firms tend to avoid competitive aggressiveness and complexity in their strategic action portfolios. However, our broader perspective leads us to identify critical boundary conditions: this reluctance weakens when firms fall below historical and social performance aspiration levels, as the risks to FW and SEW become more apparent. Conversely, their reluctance strengthens when they retain many family business group affiliations that provide safeguards for FW and SEW.\n"]