Informed by considerations from medicine and wellness research, experience design, investigations of new and emerging technologies, and sociopolitical critique, HCI researchers have demonstrated that women’s health is a complex and rich topic. Turning these research outputs into productive interventions, however, is difficult. We argue that design is well positioned to address such a challenge thanks to its methodological traditions of problem setting and framing situated in synthetic (rather than analytic) knowledge production. In this paper, we focus on designing for experiences of menopause. Building on our prior empirical work on menopause and our commitment to pursue design informed by women’s lived experience, we iteratively generated dozens of design frames and accompanying design crits. We document the unfolding of our design reasoning, showing how good-seeming insights nonetheless often lead to bad designs, while working progressively towards stronger insights and design constructs. The latter we offer as a contribution to researchers and practitioners who work at the intersections of women’s health and design.