The midlife period introduces a complex array of developmental challenges for most adults, representing a span of time in which expectations for stability and achievement are high despite ongoing evolutions in identity development, family relationships, health, and social roles and responsibilities to the outside world. Under the best of circumstances, positive attachment relationships and a mature sense of self developed earlier in life can provide firm footing for navigating this complex terrain; in the face of either early life adversity, new obstacles or traumas, or other forms of developmental interruption, the midlife period can feature special challenges that require consideration from both psychological, socio-historical, and cultural perspectives. In this roundtable, three experts in the field of midlife development and psychosocial functioning offer their perspectives on the particular issues and opportunities facing adults as they navigate the midlife period.