“What-if” Planning Blog

Conversations We Wish We’d Had Sooner — Stan’s Story

Conversations We Wish We’d Had Sooner — Stan’s Story

Our next ‘Til Death Do You Plan guest, Stan Lockhart, reflects on the importance of discussing "what if scenarios" as a family. He stresses that it feels like you're the only one when loss happens and shares the regret of feeling unprepared. Listen to his insights on family communication and avoiding mistakes by planning ahead.

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What Would I Do Without You? Let’s Talk About It

What Would I Do Without You? Let’s Talk About It

Most couples avoid the question, “What would I do without you?” because it’s painful. But having this honest conversation—about what happens if your spouse dies first—is one of the most loving and empowering things you can do together. In this post, we guide you through essential topics like life insurance, wills, advance directives, funeral wishes, and managing daily responsibilities. Use these questions to start the conversation, organize important documents, and protect your family’s future with confidence and peace of mind.

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From Shock to Action: Melissa Pierce’s Journey Through Sudden Loss

From Shock to Action: Melissa Pierce’s Journey Through Sudden Loss

When Melissa Pierce’s husband died suddenly in his sleep, she was thrown into a whirlwind of decisions she never imagined making so soon. From navigating the shock of loss to facing unexpected costs at the funeral home, Melissa’s story shines a light on the urgent, behind-the-scenes realities that so many grieving spouses encounter. In her candid ’Til Death Do We Plan interview, she opens up about the moments that caught her off guard — and the lessons she hopes others can take to heart before they’re in the same position.

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Be in the Room Where It Happens: Independence, Freedom, and End-of-Life Planning

Be in the Room Where It Happens: Independence, Freedom, and End-of-Life Planning

End-of-life planning isn’t just for later—it’s how you protect your family’s future now. As we celebrate Independence Day and reflect on what it means to have freedom and control over our lives, it’s the perfect time to start planning ahead. Inspired by the song “The Room Where It Happens” from Hamilton, this blog explores how taking control of your estate planning today ensures you’re not leaving your loved ones out of the most important decisions. Don’t wait for someone else to make the call. Be the one in the room where it happens—and secure your family’s financial freedom and peace of mind.

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What Early End-of-Life Planning Looks Like in Real Life.

What Early End-of-Life Planning Looks Like in Real Life.

When Kim Murray and her husband filled out their end-of-life plan before a quick trip to New York, it felt like a “just in case” precaution. Years later, after a devastating diagnosis, that early planning became her lifeline. In this honest interview, Kim shares how advance directives, life insurance, and one emotional conversation with their kids shaped her journey through grief—and why planning ahead truly matters.

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