The “leaky pipeline” has become a popular analogy to explain the gender disparity in science, technology, engineering, mathematics, medicine (STEMM). The reasons for the “leaky pipeline” are varied and continue to be addressed in the literature, and entire sections of the pipeline are missing for Indigenous women, LGBTQ2S+, persons with disabilities, racialized minorities, and women who experience other forms of marginalization. In 2019, the authors were selected for Homeward Bound, a 12-month international leadership program that culminated in the largest ever all-women expedition to Antarctica. They joined 97 women from 34 different countries around the world where they explored and reflected on their leadership in the context of personal values, strategic planning, visibility, and team building. In this chapter, they explore current statistics that paint a clear picture that the “pipe” is still leaking. They also share reflections from their journey to Antarctica and offer strategies to “break the ice” and create a system that will enable all women to thrive in academia.