As we head into the holidays, many of us will be spending extended time with family — which also means that those meaningful conversations we tend to avoid might finally have space to surface. One of the hardest and most universal? Talking about death, aging parents, and what we want to happen at the end of life. It’s uncomfortable, but it’s also something every family will eventually need to navigate.
This season, I sat down with Emily of Plan Big Sleep, who helps people document what they want before, during, and after they die. Our conversation was anything but grim. Instead, it was honest, thoughtful, and surprisingly comforting. Emily brings a unique perspective that blends the emotional, logistical, and relational sides of end-of-life planning — the parts that often get overlooked in traditional estate work.
We talked about why these discussions feel so taboo, why millennial adults often feel stuck between caring for children and supporting aging parents, and how to gently start these conversations with loved ones who may be hesitant or overwhelmed. We also explored what a “death plan” actually includes, the financial considerations around long-term care and funeral planning, and modern trends like green burials and celebration-of-life services.
If you’ve ever thought, “I really should ask my parents about this…” but stopped short because you weren’t sure how, you’re not alone — and this conversation might be exactly the starting point you need.
👉 Listen to the full conversation
Whether your family leans practical, sentimental, or avoidant, you’ll come away with ideas for how to open these important conversations in a way that’s grounded, compassionate, and doable — this holiday season or whenever the moment feels right.