A growing number of residents and faculty are becoming parents during their surgical training or early career years and, with this transition, face logistical, emotional, financial, and social challenges. A large proportion of Americans are caring for both their own children and aging family members; more frequently, these caregiving roles are borne by women, and they are often unacknowledged and lacking support from employers. Comprehensive systems of support at the departmental and institutional levels are essential to care for trainees and to build a strong, diverse surgical workforce. Emphasis should be placed on near-peer and peer support as systems are created to buoy surgeon parents and caregivers. Herein, we highlight our institution’s commitment to supporting trainees who are also parents or caregivers via the Parenting in Surgery Initiative. This comprehensive program provides multifaceted support to all members of the Department of Surgery who are planning for—or raising—a family or providing care to loved ones in their own home. Together with anecdotes from personal (AC) experiences that helped inspire this program, we describe how systems of support can be designed and propagated through an iterative process that necessitates both ideological and practical support and resourcing from leadership.