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This book will provide a guide for medical students to self-reflect, build a portfolio, and select a career path equipped with the knowledge to make an informed decision that is the best for them. The editors comprise a diverse spectrum from background, stage of training, type of practice, to career path. This is a timely update taking into account new situations such as the virtual environment for residency applications, the spotlight on residency wellness, and incorporating diversity, equity, and inclusion in our personal and institutional missions.