December 2, 2025
Filed under: Wealth in Families
Most of the gifts I got as a kid? I couldn’t tell you what they were. I’m sure I said thank you. I’m sure they were given with love. But most of them faded.
Except one.
When I was twelve, I asked for a drum set. I imagined myself learning how to play, and playing in a band. My mom, doing her best, found what she thought was a solid starter set. What showed up was closer to a toy set for a young child.
I played it maybe a few times. Then it sat in a corner. But I still remember it.
Not because it was right drum set, but because she listened. She didn’t roll her eyes at the idea. She didn’t say, “maybe next year.” She said yes to drums in the house. Yes to the chaos of having drums in a house. Yes to me figuring something out.
That part has stuck with me.
That’s what James E. Hughes Jr. is getting at in The Cycle of the Gift. Hughes is a pioneer in the field of family wealth and legacy planning, known for his work on preparing heirs and creating lasting, values-based family systems. I’ve learned a tremendous amount about gifting dynamics from his writing.
In this book, he writes that a good gift isn’t about the object or the dollar amount. It’s about the spirit. The intention. What you’re trying to say when you hand it over.
Before I started working with families, I didn’t think much about what it felt like to be on the receiving end of a gift. But over time, I started to notice something, especially when the gift came without context.
Receiving isn’t always easy.
We talk a lot about the giving side of wealth. The strategy. The generosity. The pride that comes with being able to help someone you love.
What doesn’t get talked about is what it’s like to be on the other side of that gift.
It’s not always easy to receive. Especially if you didn’t ask. Especially if you’re not sure what it means. Especially if you’ve been told, in a hundred indirect ways, that needing help means you haven’t earned your place.
There’s a strange tension that can show up in wealthy families. Generosity is the culture, but so is achievement. Parents want to help their kids. At the same time, they want them to be independent. And somewhere in the middle, the adult child is sitting there holding a check, wondering what strings are attached, even if no one said there were any.
I see it happen. I’ve felt versions of it myself. This is the part of gifting that makes people squirm, but it’s also where the real stuff lives.
Over time, seeing this play out from both sides – the parent giving and the child receiving – has shifted the way I think about these moments.
Here’s what I see in my work with families.
Most of the families I work with are still in the active planning stage. No one has passed away yet. But the trust documents are getting written. And they’re detailed. Distribution language, trustee instructions, incentives, guardrails.
Meanwhile, the gifts happening in real time, the ones happening while everyone is still alive, come without instruction. A check to cover rent. Support for a first home. Tuition. All generous. But often given with little to no context.
And that contrast stands out to me. The legal structure is crystal clear. The emotional message in the gift? Not so much.
If you want to shape how your wealth is used when you’re gone, gifts give a really big opportunity. Something honest. Something that says, “My hope for you with this gift is…” It doesn’t have to be profound. It just has to be a connection.
Timing makes a bigger difference than we think.
Some of the most memorable gifts do happen at the big moments. A down payment. Support when a grandchild is born. They carry weight and often become part of the story a family tells for years.
But the gifts that sneak into your memory and stay there? Those tend to show up at less polished times. A move that felt like a leap. A career pivot that didn’t come with a salary. A time when someone was just trying to hold it together. No bows. No announcement. Just acknowledging there’s a need.
That kind of timing says, “I see where you are, not just where you’re headed.”
You don’t have to get it perfect. Just close enough to show you’re paying attention.
Say what you mean, while you still can.
As someone who works with the parents and adult children in families, I can tell you that you don’t need the perfect plan. It helps, but it’s not necessary.
That conversation might be more valuable than the gift itself. Don’t miss that opportunity.
The drum set missed.
But the message landed.
That’s what people remember.
If you want to think more intentionally about how you give, and how it’s received, I’d be glad to help.
jared