How the Great Wealth Transfer Is Redefining Philanthropy Across Generations
We’re in the middle of the largest wealth shift in U.S. history. Trillions of dollars are moving from one generation to the next. But what’s often overlooked in that headline is this: we’re not just transferring money, we’re transferring priorities, relationships, and legacy.
Now, you can look at the numbers $124 trillion over the next two decades, with around $18 trillion expected to flow into charitable causes. That’s a big pie. But what matters more than the pie is the recipe. How are families actually handling these transitions? How are values passed on, not just valuables?
Let’s talk about that.
It Starts With the Spouse, and Usually, She’s in Charge
Most folks think of generational wealth as parents passing money to kids. But the truth is, there’s usually a stop in the middle: the surviving spouse. In many families I work with, that person is the wife. She may not have been the one managing the financial picture day to day, but now she’s in the driver’s seat.
This transition can feel overwhelming. Grief, new responsibilities, and big questions about what to do next. I’ve seen it firsthand. The key is giving space to get clarity before rushing into decisions. One thing I always say: “Let’s not spend principal to generate income. Let’s grow and live off the cash flow.”
And when it comes to giving? The best place to start isn’t with a huge check. It’s with curiosity.
- Start with a learning portfolio. Try smaller grants. Get to know the organizations. Give yourself time to feel confident.
- Join a peer group. Philanthropy can feel isolating. Connecting with others doing the same thing helps build momentum.
- Work with an advisor who can connect the dots between your vision, your resources, and the tools that get you there.
Next Gen Wants to Help. They Just Don’t Know How Yet
Here’s something we’re hearing a lot: “I want to honor what my parents built, but I also want to do it my way.”
Totally valid.
The tension shows up when families haven’t talked about what “legacy” actually means. I’ve had three generations around a table before, each with a different idea of what “giving back” looks like. Some want to preserve, others want to innovate. That’s where we slow down and ask the right questions.
- What are your non-negotiables?
- Where do you want to see impact in your lifetime?
- Can we structure the giving in a way that gives everyone a lane?
One idea that works well: create a giving portfolio. You break it down into:
- One-third for family legacy gifts (like causes your parents supported)
- One-third for personal causes that light you up
- One-third for experimentation or one-time projects
You don’t need a foundation to start this. You just need a plan.
Why Timing Matters More Than Size
Too many families wait until a major event a death, a liquidity event, or a tax bill before starting the conversation about giving. That’s backward. Giving is most powerful when it’s part of your strategy, not a reaction to a crisis.
We’ve done this for years: create a financial model that supports “giving while living.” When your own plan is locked in retirement income, estate structure, insurance then you can start gifting assets confidently, without wondering if you're putting yourself at risk.
I’ll put it simply: The only thing we can control in the investment process is risk. So let’s model that first. Then we can talk about impact.
One More Thought
When we helped a family in Oregon walk through this process last year, the wife who had just lost her husband sat down with her adult kids and said, “This isn’t just about money. This is about who we are.”
We structured her giving around three themes she cared about: education, clean water, and helping single moms. Her kids each picked one group in those categories to support. They do a check-in every Thanksgiving. That’s legacy.
So here’s my question to you:
What would it look like to model your values, not just your assets, in the next chapter?
If you want to start exploring that, reach out. We’ll walk through it together, step by step.