This course offers a deep clinical and theoretical exploration of the peri-menopausal transition, examining not only the decline of estrogen and kidney yin but also the fluctuating surges of LH and FSH and the critical role of the liver in regulating these changes. We will explore how these biomedical and traditional frameworks intersect, informing more precise diagnosis and treatment. Participants will examine the role of hormone replacement therapy (HRT), including how to effectively support patients whether they choose to use HRT or not. Special focus will be given to disharmonies of the Chong channel and strategies to harmonize hormones and internal systems during this transition. Beyond symptom management, this course reframes peri-menopause as a meaningful physiological and psychological threshold—a portal that influences long-term health and vitality. In contrast to the prevailing cultural emphasis on productivity and constant output (yang) during the prime of life, with all the hustle and things we are encouraged to do to improve women’s health outcomes, we will explore the importance of engaging yin processes of restoration, introspection, and even entering the darkness that can lead to beneficial transformation for healthy long-term outcomes. Integrating classical theory, modern endocrinology, and clinical application, practitioners will leave with practical tools for treatment planning, point selection, and patient guidance. We will also consider the broader developmental context of this life stage, including the evolutionary role of the grandmother/elder as a carrier of wisdom, culture, and continuity, both in our mentors and in our own coming to wisdom, and how this perspective can inform and deepen clinical care.