September 13 is National Grandparents Day. In our house, that usually means an eye roll from me while my wife turns our dining room into a mess of arts and crafts as the kids hand make their special, customized presents. But as I get older I find myself thinking more and more about something I talk with clients about: what we actually pass down when we pass down wealth.
Most families spend a lot of time planning how assets transfer: who gets what, when, and under what structure. Far fewer spend time on the why behind it. Why did you build what you built? What did you want it to make possible? What do you hope the next generation does with it, beyond simply having it?
I've found that families who are intentional about that "why" tend to have very different outcomes than families who aren't. Wealth transferred without context can feel like an inheritance to manage. Wealth transferred with context such as a story, a set of values, and/or a shared cause tends to feel more like a responsibility to carry forward. That distinction matters more than almost any technical planning decision.
Giving is one of the clearest ways to pass down the "why."
Charitable giving isn't just a line item on a financial plan. For a lot of the families I work with, it's one of the most direct ways to show the next generation what actually mattered through action rather than a lecture. A grandparent who involves grandchildren in choosing where a family gift goes each year is teaching something that no amount of explaining net worth ever could.
A few ways I've seen families put this into practice:
- Making giving a conversation, not a transaction. Some families set aside an annual amount and let the kids or grandkids help decide where it goes. The dollar figure matters far less than the discussion it creates.
- Attaching a story to the cause. A gift tied to a family member's history with a school, a hospital, or a cause that shaped their life carries meaning that an anonymous donation doesn't.
- Starting small and staying consistent. You don't need a foundation to teach stewardship. Even modest, recurring giving builds the habit and the conversation over time.
- Letting older generations lead by example. Grandparents, in particular, often have both the perspective and the standing to model what generous, values-driven giving looks like. Grandparents Day is as good a nudge as any to have that conversation out loud.
None of this replaces a well-built financial or estate plan; it complements it. The technical side makes sure the wealth transfers efficiently. The conversation makes sure it transfers meaningfully.
If you're a grandparent, parent, or simply someone who's thought about what you want your generosity to represent someday, this is worth sitting with. You don't need all the answers today. You just need to start the conversation.