Men and boys are struggling with loneliness, isolation, anxiety, depression, and meaninglessness more than ever. The situation is dire. With our culture’s deeply embedded expectations for men and boys to be tough, unemotional, self-sufficient, and avoid anything considered feminine, they’re offered little to no support or means to live outside of a restrictive, rigid male persona (AKA the Boy Box and the Man Box). It doesn’t need to be this way. In this panel, we explore various aspects of a paradigm shift away from the rigid-based masculinity beliefs and behaviors toward more prosocial, integrated and sustainable expressions of masculinity. In particular, we highlight the profound, yet often overlooked, importance of compassion and self-compassion in the daily lives of men and boys.