Earlier this summer, I had the joy of traveling to Bermuda with my family — children, grandchildren, the whole crew. The island's beauty is breathtaking, with its pink sand beaches, calm turquoise waters, and that easy rhythm that makes you slow down, breathe deeper, and appreciate what really matters. But while it was a vacation in every sense, it also became something more: a moment to reflect on legacy, and to begin a conversation I believe every family should have.
One of my favorite memories from the trip was hearing my 3½-year-old granddaughter, full of energy and wonder, ask me — not just once, but many times — "Grandpa, this is fun! Where are we going next year?"
Every time she said it, it warmed my heart. Her joy was contagious, and it reminded me that while we may plan for the future with spreadsheets and legal documents, the true legacy we leave behind is found in moments like these, in the laughter, the bonding, and the sense of continuity that flows from one generation to the next.
Finding the Right Space for Important Conversations
As a father and grandfather, I've reached a point where my focus is less on accumulation and more on preservation — not just of wealth, but of values, relationships, and stories. Sitting by the sea or sharing quiet dinners, I found the right space to talk with my family about inheritance planning. We didn't talk in formal terms - it was a natural, heartfelt conversation about what really matters and how we want to support and guide future generations.
Bermuda gave us the gift of uninterrupted time. With no meetings or distractions, we could speak openly — not just about assets, but about responsibilities, philanthropy, and the emotional side of legacy.
That one simple question from my granddaughter — "Where are we going next year?" — stayed with me. It wasn't just about the next destination; it was a beautiful reminder that legacy is forward-looking. It's not just what we leave behind, but how we live together now, and what we build toward as a family.
If you're wondering when the right time is to talk about inheritance planning, my advice is this: don't wait for the perfect moment. Just find a meaningful one. A quiet afternoon, a family gathering, a trip like ours — any of these can be the right setting to begin the conversation that helps secure your family's future with clarity, love, and intention.
By David Schaeffer
Founder of American Retirement Advisors, David has spent decades helping retirees and pre-retirees build secure financial futures. His straightforward approach to retirement planning has guided hundreds of families toward confident, well-prepared retirements.
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Easy Eddie's Take
David's story really captures something I see all the time: the best estate planning conversations happen naturally, not in a lawyer's office. Here's the good news — you don't need to have everything figured out before you start talking. Most people are surprised to learn that family conversations about inheritance planning are often more about values and wishes than they are about specific dollar amounts or legal documents.
Think of it this way: with the federal estate tax exemption at $13.99 million per person in 2026, most families aren't dealing with complex tax issues. Instead, they're working through questions like "How do we prepare our children to handle an inheritance responsibly?" or "When should we involve the grandkids in family financial discussions?" The SECURE 2.0 Act has also changed how inherited retirement accounts work, making it even more important to have these conversations while everyone can plan together.
One question that comes up all the time is "What's the right age to start involving adult children in estate planning discussions?" The answer is usually simpler than people think: when they're mature enough to understand that family wealth comes with both opportunities and responsibilities. A little preparation today can make a big difference tomorrow.