In this insightful interview, Dr. Jacqueline Winkelmann shares her inspiring journey from growing up in Puerto Rico to becoming a successful pediatric hospitalist for over 20 years. Recently, she transitioned into the tech and development space, eventually founding the non-profit organization, Scrub Sisters. Dr. Winkelmann emphasizes the importance of community and mentorship in her personal and professional life. She also introduces her ‘joy or paycheck’ policy to decide on commitments, aiming to avoid burnout. The conversation delves into the challenges she faced, the steep learning curves, and the joys of giving back. Finally, Dr. Winkelmann provides valuable advice for starting a non-profit and highlights the significance of surrounding oneself with supportive mentors and communities.