The Great Wealth Transfer Is Already Happening: Here’s How Smart Families Are Getting It Right
We’re in the middle of the largest transfer of wealth in history. Trillions are moving from one generation to the next, and every family I talk to is asking the same question:
Are we ready for what’s coming?
The short answer for many is no.
And the reason isn’t lack of planning. It’s lack of preparation, not around documents, but around people.
The Real Risk Isn't Financial
A lot of families think estate planning is about taxes, trusts, and titles. And those are important. But the biggest failures I’ve seen don’t come from numbers, they come from communication breakdowns.
I worked with a family where a father had built a large collection of rare wine. Over the years, he’d made casual promises to each child about who would receive what. But when he passed, there was nothing in writing.
What followed was a three-year legal battle. The collection wasn’t even worth what they spent on attorneys.
That’s what happens when families don’t talk through the emotional side of wealth. And that’s more common than most people realize.
What Wealth Looks Like Today
The numbers are massive. More than $124 trillion will change hands by 2048. But here’s the part that matters more:
- Over half of that wealth will come from just 2 percent of households
- Nearly $40 trillion will flow to widowed women in the boomer generation
- New inheritors, Gen X, Millennials, and Gen Z, are bringing different values and expectations into the picture
This is no longer about just preserving capital. It’s about preparing for a generational shift in how wealth is viewed, invested, and used.
The Mistakes I See Too Often
Families don’t fail because of bad investments. They fail because they avoid the uncomfortable conversations. Here are the patterns I see play out:
- Heirs don’t know what the family owns
- There’s no clarity about who is getting what or why
- No one understands the thinking behind the plan
- Kids aren't taught how to make decisions with money, only how to receive it
This is where things unravel. Not in court... but around the kitchen table.
What Successful Families Do Differently
After more than 30 years working with business owners and multi-generational families, I’ve seen what works. It’s not about doing more. It’s about doing the right things early.
Here’s the framework:
1. Start conversations early
Not when someone gets sick. Not when the will is being drafted. The most successful families start talking when the next generation is still in their twenties. That gives you time to build clarity and trust.
2. Focus on education, not just execution
Your heirs need to know more than how to access an account. They need to understand how wealth works — taxes, cash flow, risk, strategy. That’s not a one-time lesson. It’s a process.
3. Document your values
The best families I work with create a family mission. Not just for show — it explains why the money exists, how it should be used, and what matters most. It helps guide decisions when you’re no longer there to answer questions.
4. Set up structure
This includes family meetings, shared decision-making models, and clear processes for when disagreements come up. It’s especially important when dealing with illiquid or emotionally charged assets like a family business, property, or collections.
5. Bring in a neutral third party
Sometimes, emotions get in the way. Having a trusted advisor in the room changes the tone. It turns a personal conversation into a strategic one. And it gives every voice a place to be heard without adding pressure.
The Human Side Comes First
We can build trust structures, allocate assets, and manage tax liability. But none of that matters if the next generation doesn’t understand how to use it, or why it matters.
The families who get this right take a different approach. They don’t just pass on money. They prepare their people.
Ready to Start the Conversation?
If this feels overwhelming, start small. One conversation. One meeting. One step toward clarity.
And if you want help creating that plan, one that protects your wealth and strengthens your family... just reach out. I’ve helped dozens of families walk this road with confidence. And I’d be glad to walk it with you too.