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In this deeply personal and intergenerational episode of Sandwiched, host Paul H. Richardson Jr. is joined by someone who has shaped his life in profound ways: his grandmother, Diane Aden, affectionately known as “Gram.” Closing out Season One, this conversation offers a rare perspective on caregiving told not only by the person who provides care, but by someone who has lived on both sides of it. Diane reflects on a lifetime marked by responsibility, resilience, and quiet strength. From losing her father at a young age and stepping into caregiving for her mother, to later navigating distance caregiving as her mother faced Alzheimer’s and cancer, Diane shares how caregiving responsibilities followed her through every stage of adulthood. She speaks candidly about managing grief while raising children, balancing work with care, and making impossible decisions when memory, illness, and safety collide. The conversation also turns inward as Diane describes aging herself and becoming a caregiver again later in life, this time for her sister. Living together for years, Diane recounts the emotional and physical realities of in home caregiving, the limits of what one person can do alone, and the weight of deciding when additional care becomes necessary. She offers hard won insight into hospice, long term care, financial tradeoffs, and the importance of having conversations about wishes before crisis arrives. Throughout the episode, Diane emphasizes dignity, autonomy, and legacy. She speaks openly about planning for the end of life, organizing legal and medical affairs, and making sure family members know who she was beyond her age or diagnosis. Her reflections underscore a truth often left unspoken: caregiving does not end with youth, and aging does not erase identity. This episode is a powerful reminder that caregiving is not a single chapter, but a lifelong thread woven through families and generations. It is for anyone caring for a parent, a sibling, or themselves as they age, and for those who want to understand what it truly means to care with intention, honesty, and love.