The Chronology of a woman determines numerous transitions across her lifespan. Menopause is a transition that begins with subtle changes that may not be noticeable several years prior to menopause; yet, it impacts the ageing experience. Design and participatory approaches have demonstrated how we can collaborate to define and determine pathways that offer innovative solutions across social, work, and health settings. ‘Design Your Menopause Life’ encourages autonomy, curiosity, and support as a woman documents, diaries, and expresses her experience with an awareness of support and empowerment through peers, technologies, and professionals. This chapter will discuss the rationale for instigating, designing, developing, and delivering three concepts aimed at encouraging a call to women to create their journey as they navigate perimenopause and menopause with an awareness of peer and professional support through innovative digital and analog tools and events. These solutions are conceived to offset and alleviate some chronic or age-related conditions, enhancing quality of life and informing policy in work and social settings.