The mission of the Society for Investigative Dermatology (SID) is ‘To advance and promote the sciences relevant to skin health and disease through education, advocacy, and scholarly exchange of scientific information.’ Part of this mission is to ensure there is an adequate pipeline of educators and researchers to foster the next generation. Over the past few decades, there is a notable shortage of Academic Dermatologists in the United States. Among the 127 ACGME accredited Dermatology residency programs in the US, a relatively small percentage of graduating residents indicate an interest in academic medicine and teaching the next generation. Members of the SID represent a significant percentage of U.S. dermatology faculty. The SID is uniquely suited to address the problem given its access to both faculty and resident physicians. The SID mission and that of the National Institute for Arthritis and Musculoskeletal and Skin Diseases (NIAMS) are largely overlapping. Both are committed to supporting skin disease research and training basic and clinical investigators. The two organizations have a vested interest maintaining a pipeline of dermatology educators and researchers. To leverage potential synergy in the missions of the SID and NIAMS, the SID Retreat was developed. The SID Retreat is an annual conference presented by the SID for a select group of first, and second-year dermatology residents and PhD-trained post-doctoral fellows who have expressed an interest in a career in academics. The program tests the hypothesis that early and sustained exposure to like-minded residents, post-docs and seasoned faculty will have a positive effect on a decision to enter academia. To achieve our goals, we will continue to expand upon the format utilized over the past 20 years, which included discussions of grant writing, finding mentors, negotiating a job (and protected time), economics, work-life balance, developing an interest area, integrating academics into dermatologic specialties, finding funding, and how to form meaningful collaborative liaisons between MD- and PhD-trained scientists, educators and clinicians. New recruitment strategies will be used in this iteration of the SID Retreat to enhance and grow our Diversity and Inclusion (D&I) initiatives, to increase the URM pipeline, to retain people of color, and to synergize with existing D&I initiatives ongoing within in the SID. This retreat provides scientific and educational opportunities for future leaders in dermatology and supports the core values of the SID. Outcome analyses measured by retention in academia supports the SID Retreat as effective at promoting increases in academic retention.