Conversations We Avoid: Death, Money, and Planning Ahead

Talking about death, money, and planning ahead can be uncomfortable—especially with the people closest to us. But avoiding these conversations doesn’t make them go away; it just leaves our loved ones in the dark when they need clarity the most.

In Episode 4 of The Death Readiness Podcast, I spoke with Megan Malick, founder of A New Path, about why these topics are so difficult to discuss and how we can approach them in a way that is meaningful and productive. Megan brings a background in grief education, counseling, and after-loss support, helping people navigate both the emotional and logistical burdens of loss.

1. Why Do We Struggle to Talk About Death and Money?

Despite knowing that death is inevitable, many of us struggle to acknowledge it. Megan highlights reasons for this, including:

• Societal shifts: In past generations, people often died at home, making death a visible and familiar part of life. Today, most deaths happen in hospitals or care facilities, distancing us from the reality of mortality.

• Emotional weight of planning: Estate and end-of-life planning forces us to confront not only our own mortality but also potential loss of independence due to illness or aging.

2. How to Start these Difficult Conversations

Megan shares five small steps that can help make conversations about death and money more approachable:

✅ Make the Unseen Seen – Recognize the hidden beliefs that make these topics difficult. For example, many people believe talking about death will somehow make it happen.

✅ Go Low and Slow – Instead of diving straight into heavy topics, start with small, approachable questions. For example:

• “I was listening to The Death Readiness Podcast, and they talked about passwords—how do you keep track of yours?”

• “If something happened to you, have you thought about who would take care of your pet?”

✅ Get Concrete – Focus on one specific and manageable topic at a time, like where someone banks or who their financial advisor is.

✅ Practice Good Communication – Ask open-ended, curious questions rather than making demands. 

✅ Model by Doing Your Own Planning – Show your loved ones that you’re not just asking them to do something—you’re doing it, too.

3. Why Money is Often the Hardest Topic

Estate planning isn’t just about death—it’s about money, and for many families, money is an even more taboo subject than death. Some families have unspoken rules about never discussing finances, while others worry about who gets what after a death.

Megan emphasizes that even basic financial information (like where accounts are held and advisor contact information) is better than no information at all. You don’t have to share dollar amounts—but ensuring someone knows where to start is crucial.

4. Grief and Estate Administration: The Double Whammy

Megan shares her personal experience of losing both of her parents in quick succession. She explains that every piece of paperwork, every estate task, and every legal form can trigger fresh waves of grief. That’s why breaking things down into small, manageable tasks is so essential.

Practical Next Steps: Free Downloads

To make planning easier, I’ve created three essential worksheets to help you organize key information in advance. These documents ensure your loved ones won’t be left searching for details if something happens to you. They’re also useful for everyday situations—whether you need a friend to watch your child for the day or a pet sitter while you visit a sick relative, you’ll have all the important information in one convenient place.

📌 Home Information Sheet – For household management in an emergency
📌 Pet Information Sheet – Ensures your pets are cared for
📌 Child Information Sheet – Helps organize key details for caregivers

The most difficult conversations are often the most important ones. Planning ahead doesn’t just make life easier for your loved ones—it gives them peace of mind knowing they’re honoring your wishes.

To learn more about Megan Malick and her new book, A New Path – A Practical Workbook and Planner for the First Year of Grief and Settling Your Person’s Affairs, visit her website.

🎧 Listen to the full episode here: