You can’t achieve a dream that you’ve never dreamt. This chapter’s goal is to broaden your trajectory and options as a leader in medicine by raising awareness and promoting introspection. Here, we share two journeys, present lessons learned via diversity, equity, and inclusion leadership, and highlight the expanse of academic medicine leadership options that exist. Our hope is that this can help you reveal options, generate new questions, and expand your possibilities. Being intentional in personal development—establishing relationships and engaging in areas of work focusing on refining your mission-based craft or niche—are all best achieved with a blueprint. This chapter shares tips and suggestions to consider along your journey. Skill building exercises will help you anchor important areas of development including strategic planning, mentorship, and relationship building. Finally, we consider the future of diversity, equity, and inclusion for those called to serve and facilitate change in academic medicine.