Many women stay silent about health challenges at work due to stigma, even as issues like perinatal mood disorders, perimenopause, and disproportionate caregiving responsibilities drive female attorneys out of the profession at far higher rates than men. Up to 2 in 5 mothers experience perinatal mental health conditions, and 1 in 3 women consider leaving or retire early due to perimenopause symptoms, a transition that can often begin during peak career years. The consequences of silence are significant, but so is the opportunity to change it. This roundtable discussion, hosted by Phoebe, the leading working parent coaching and support platform, brings together experts in perinatal health, working motherhood, and perimenopause to explore the health transitions that most impact women's careers, why stigma keeps them hidden, and what companies can do to build environments where women don't have to choose between their health and their career.