It is widely reported that somewhere between $90 and $120 trillion will be transferred to the next generation over the next 20 years or so.

What fascinates me is that this means there is probably over $100 trillion of wealth sitting in older Americans’ accounts, waiting.

And most of the people holding it worked incredibly hard to build it. They were disciplined. They sacrificed. They deferred. Which raises a question worth sitting with: what if the best version of your financial legacy isn’t what you leave behind — but what you do with it while you’re still here?

The Shift That’s Already Happening

Something quiet is already underway. Affluent parents are covering down payments, preschool tuition, rent, family vacations. Not estate planning moves. Just love in action.

I was reading a recent article where one man gave away an estimated $700,000 over his lifetime to his kids and grandkids. When asked why, he said it plainly:

“They can use the money now more than we can use it to watch our stock portfolio go up.”

Another dad paid for his sons’ rent, doctoral programs, and annual family trips abroad. His take?

“Who wants to be 60 years old and your parents die and you get a bundle of money? It’s a little better to travel with your parents.”

I don’t know if either of these men are people of faith. But I recognize the spirit behind those words. There is something deeply biblical about being a generous, living participant in the lives of the people you love — not just a posthumous check.

Proverbs 11:24 says “One person gives freely, yet gains even more.” I’ve always loved the counterintuitive nature of that verse. It doesn’t say you give and break even. It says you gain. The returns just don’t always show up on a balance sheet.

Two Stories

I have a client in his mid-50s — successful, healthy, full of life — whose adult daughter and her husband are on a great trajectory. Good jobs, solid future. But they’re trying to buy a home in an expensive market, and the down payment gap is real.

He decided to help. His reasoning is hard to argue with: Why wait until she has more wealth, when the impact of this gift is greatest right now? And just as importantly — he gets to feel the joy of a first home purchase again — not as the buyer, but as the father standing behind her. That’s not a small thing.

Another client made a decision that their grandchildren would graduate college debt-free. Their adult children — the students’ parents — are doing well. They don’t need a rescue. But not having to save aggressively for college has freed them up in ways that ripple through the whole family: summer vacations, a better neighborhood, better schools. One act of generosity became a gift to three generations simultaneously.

These stories don’t make the financial headlines. But they’re happening every day in families who have simply decided to be intentional with what they’ve built.

The Permission Problem

Here’s what I observe most often with people who have reached financial independence: they don’t have a money problem. They have a permission problem.

Marshall Goldsmith wrote a book called What Got You Here Won’t Get You There. The premise is simple and a little uncomfortable: the very strengths that made you successful can become your biggest obstacles in the next chapter.

Think about what it took to build real wealth. Discipline. Frugality. Delayed gratification. Not spending. Those aren’t just habits — they’re deeply wired beliefs. And they served you extraordinarily well.

But if your goal has shifted — if the mission now is to maximize joy, create memories, and deploy your resources with purpose — those same strengths can quietly become weaknesses. The discipline that built the number is now the thing keeping you from enjoying it.

Give yourself permission to enjoy what you built. That’s not reckless. That’s the point.

John D. Rockefeller, one of the wealthiest men in history, said: “I have made many millions, but they have brought me no happiness.” That is a haunting sentence. And it is a warning. Wealth without intentional deployment toward the things that actually matter is just a larger number on a screen.

Sometimes people just need a nudge. I have a financial advisor friend who puts it perfectly: “If you don’t go first class, your kids will.” It’s said with a smile — but it’s true. And in my experience, it’s exactly the kind of reframe that finally gives people permission to enjoy what they’ve spent a lifetime building.

Smart Ways to Think About It

If this is stirring something in you, here are a few practical angles worth considering:

• Give experiences, not just assets. The memory dividend is real. A trip your grandkids will talk about for decades outweighs a slightly larger inheritance check. Experiences keep paying off long after the moment is gone.
• Give while you can witness it. There is something irreplaceable about watching your daughter close on her first home with your help, rather than having an estate attorney distribute the funds after you’re gone.
• Give to causes now, not later. Your favorite nonprofit needs resources today. The impact compounds differently when you give a meaningful gift at 65 versus a bequest at 85.
• Put tax rules in your favor. You can give up to $19,000 per year to any individual completely tax-free. The federal estate tax exemption is now $15 million per person ($30M for married couples). You can also pay tuition or medical expenses directly to the institution — no gift tax, no limit. There are ways to give more by giving smarter — and most people are leaving those opportunities on the table.

The Real Question

At the end of your life, you will not wish you had protected the number longer. You will wish for more memories. More moments. More mornings watching someone you love benefit from something you gave them.

Ecclesiastes 5:19 says: “When God gives someone wealth and possessions, and the ability to enjoy them, to accept their lot and be happy in their toil — this is a gift of God.”

The wealth is not the gift. The enjoyment of it is.

So — what are you waiting for?