A couple I’ve known for nearly twenty years sat across from me recently, and I could tell before they said anything that something had shifted. They’d built their plan fifteen years ago around the oldest — the daughter who was going to take over the business, who had the MBA, who spoke the language of the industry. The structure reflected that assumption. A significant interest in trust. Layered gifting. A buy-sell that assumed she’d be the buyer.
She moved to Colorado eight years ago. Started a nonprofit working with trauma survivors. She hasn’t mentioned the business in three years.
The youngest — the one who got the smaller allocation, the simpler structure, the “in case” provisions — is the one running things now. He’s good at it. The clients like him. The numbers are up.
“So what do we do?” the father asked.
But that wasn’t really the question. The question underneath it was different, and it was the one he couldn’t quite bring himself to ask out loud. The architecture of the plan had encoded a message about who was trusted to carry the family forward. That message landed, years ago, and it didn’t land the way anyone intended.
Inheritance and Heritage
English treats these as near-synonyms, but they point to very different things.
Inheritance is what moves — the assets, the property, the balance that transfers from one generation to the next. That’s the work most estate plans are built around. It’s the conversation about what passes, how it passes, and what the tax consequences are. It’s the technical work, and it matters. I’m not suggesting we stop doing it.
Heritage is something else. It’s the identity, the values, the meaning behind the transfer. The story the family tells about what the money is for and what it says about who they are. The unspoken ranking among the people receiving it. The expectations that get encoded into the structure, whether anyone intended to encode them or not.
You can transfer inheritance without transferring heritage. We do it all the time — that’s most estate plans. You can also transfer heritage without much inheritance, which is what happens in a lot of families with more to say than to give. But the families that come back years later and tell you the plan worked aren’t usually talking about the technical outcome. They’re talking about something in the heritage column. What got passed beyond the balance sheet.
The word “entitled” is a good example of how these two can get confused. To be en-titled is to receive the title — the name, the role, the place in the family story. That’s heritage. That’s what it used to mean. But “entitled” has come to mean something nearly opposite: the expectation of receiving without earning, the assumption that the resources will always be there. That’s the version most people worry about when they talk about trust fund kids.
The difference between the two isn’t the money. It’s whether the family transferred a title — a sense of identity, purpose, and continuity — or just a check.
Natives and Immigrants
James Grubman writes about this as the distinction between natives and immigrants in the land of wealth. People who grew up with money are natives — comfortable in the environment, fluent in the language, but sometimes lacking confidence in their own ability to navigate without it. People who built their wealth are immigrants — they may feel out of place, they may overcompensate or push back against the culture, but they know they can figure things out because they already did.
The planning challenge is that most wealth transfers turn the next generation into natives whether anyone intended to or not. The question is whether they’re also equipped to be navigators.
This is the parenting spectrum that plays out in every planning conversation, even when nobody names it. On one end, you have the parent who controls everything — every distribution runs through them, every decision requires approval, the kids never learn to drive because someone is always at the wheel. On the other end, you have the parent who steps away entirely — figure it out, here are the keys, good luck.
Most families know neither extreme works. The hard part is figuring out where you are on that spectrum and whether you’re there intentionally or by habit.
Cliff or Pothole
A colleague put it to me this way: if your child is driving toward a cliff, you grab the steering wheel. No question. But what about a pothole? Do you let them hit it? They’ll feel it. The car might need an alignment. But they’ll learn something about the road that they can’t learn from the passenger seat.
The problem is that every parent’s definition of “cliff” is different. And the things that feel like cliffs — a bad investment, a failed business, a reputational stumble, a choice we wouldn’t have made — are often potholes.
The supporting-vs-enabling question isn’t about whether to give. It’s about what the giving is teaching. A structure that absorbs every mistake teaches that mistakes don’t have consequences. A structure that demands perfection teaches that mistakes are catastrophic. Neither prepares someone to live a full life, make real decisions, and carry responsibility forward.
The plan my clients built fifteen years ago wasn’t technically wrong. It was built around an assumption about who their children would become. When that assumption didn’t hold, the plan didn’t adjust — because nobody talked about it.
The question I’ve started asking isn’t what came out of this. It’s what did this plan teach.
Not as a rhetorical device. As an actual diagnostic. Did the people receiving these transfers become more themselves, or less? Did the relationships in this family deepen, or fray? Did the next generation step into responsibility, or around it?
Sometimes the answer is “I don’t know yet.” That’s fine. But the question changes what we do next.
Over to You
When you look at the plans you helped build this year — or the ones you’re building right now — how many of them transferred assets, and how many of them transferred something the family can actually use?
What’s one plan in your book where you could already see, at the time, that the structure was encoding an assumption the family hadn’t talked about?
I’d be curious to hear it. Reply, or find me on LinkedIn. These conversations are where this work actually gets sharper.
Originally published on LinkedIn on 2026-04-24. View the LinkedIn version.