Why Some Families Choose to Give While They’re Still Here

There’s a particular kind of thinking that shows up somewhere in your sixties or seventies, usually without an invitation. You start looking at what you’ve built — the house, the savings, whatever else came together over a lifetime of work — and you start wondering what happens to it. Not today. Not urgently. Just… eventually.

If you’ve been thinking through your downsizing decisions already, this question probably isn’t new to you. It tends to show up right alongside the others — what to keep, what to let go of, what the next chapter actually looks like.

Most of us grew up assuming there was only one way this works. You save, you build, you leave it behind when you’re gone, and your kids sort it out then. That’s the default. Nobody really questions it.

But more families than you might think are doing it differently. They’re giving some of it now — while they’re still here to have the conversation, still here to watch what happens next. Not because waiting is wrong. Just because giving now is possible, and worth understanding before you decide it isn’t for you.

Video Transcript

There’s a conversation I have with people fairly often about what happens to everything they’ve built once they’re gone. But lately, I’ve been having a different version of that conversation. Not about what happens after, but about what could happen now while you’re still here to see it. For most of my life, I assumed the plan was simple. You work, you save, you build something for your family, and eventually when you’re gone, it passes down. That’s just how it works. But somewhere along the way, I started meeting families who did it differently. They didn’t wait. They gave while they were still here to have the conversation, still here to watch what happened next. Here’s what I’ve noticed. There are families who’ve had money for generations. And if you look closely, some of them still have it, and some of them don’t, even though they started with the same place. The difference usually isn’t the money itself. It’s whether anyone ever taught the next generation how to carry it. Warren Buffett once said he wanted his kids to have enough that they could feel they could do anything, but not so much that they’d feel comfortable doing nothing. I like that. Gifting during your lifetime, sometimes through a trust, is one way families try to get the balance right. It might mean helping with a down payment now instead of leaving it in a will. It might mean setting something aside with guardrails built in so generosity doesn’t mean losing all control. None of that is something you figure out alone or overnight. It’s worth sitting down with an estate attorney who understands your family, your assets, your goals, and can walk you through what’s actually possible. What I keep coming back to is this. The giving I’m proudest of in my own life started long before any money changed hands. It started with afternoons in the kitchen with stories, with just being present enough to teach what mattered. That’s not something a will can do. Only time can do that. I’m not here to tell you gifting is right for your family or that it is. It isn’t. That’s not my call to make. What I can tell you is this is worth thinking about and worth talking through with the right people at whatever pace feels right for you. You have more time than it might feel like, and you don’t have to figure it out alone.

Why Some Families Give Now Instead of Waiting

Here’s something I’ve noticed over the years, watching different families handle this in different ways. There are families who’ve had money for generations. And if you look closely at enough of them, you’ll find something surprising: some still have it, and some don’t — even though they started in roughly the same place.

The difference, almost every time, isn’t the amount of money. It’s whether anyone ever taught the next generation how to carry it. Money handed down with nothing else attached tends to behave a certain way. Money handed down alongside years of teaching — how to work, how to save, how to think about what you have — tends to behave very differently.

Warren Buffett said something once that’s stuck with me. He wanted his kids to have enough money that they’d feel they could do anything — but not so much that they could do nothing. That’s a hard balance to strike from a will alone, written once and executed after you’re not around to explain your thinking. It’s a much easier balance to strike while you’re still here, still able to have the conversation, still able to watch and adjust.

That’s really the heart of lifetime gifting. It’s not a trick, and it’s not for everyone. It’s simply the choice to give some of what you’d otherwise leave behind, now, while you’re present enough to be part of what it becomes.

You Don’t Need the Whole Plan Figured Out Today

If any of this is stirring something up, I want to say the same thing I’d say about almost any big decision in this season of life: there’s no deadline on this.

A lot of people assume that before they can even bring this up with their kids, they need a trust already drafted, a lawyer already retained, a whole structure already built. You don’t. You can start with something much smaller — a conversation about what matters to you, and why. The paperwork, if there ends up being any, comes after.

Stewardship doesn’t start with a finished plan. It starts with one honest conversation — with one of your kids, or with an estate attorney who can walk you through what’s actually possible for your family and your situation.

I want to be careful here, because this isn’t something I’m qualified to tell you how to do. Gifting during your lifetime, whether through a simple gift or something structured like a trust, touches real tax and legal questions that are specific to your family. That conversation belongs with an estate attorney, not a real estate agent and not a video online. What I can offer is the permission to start thinking about it — not the instructions for how to execute it.

The Giving That Happens Long Before Any Money Does

When I think honestly about what I’ve given my own grandchildren over the years, the things they remember aren’t the things with dollar signs attached. They remember afternoons at the kitchen table. Stories about their grandfather’s business — how we built it, what it cost us, what it taught us along the way.

That kind of giving happens years before any money ever changes hands. I didn’t always think about it that way at the time. But looking back, it’s the giving I’m proudest of — because whenever the money does eventually arrive, whatever form it takes, it lands on something. It lands on years of watching how you handled things. What you valued. What you taught without ever meaning to teach a lesson.

If you’re weighing whether to give now or leave it all for later, that might be worth sitting with for a moment. The timing of the money is one decision. The teaching that surrounds it is a separate one — and it’s already something you can start today, regardless of what you decide about the rest.

Where to Go From Here

I’m not here to tell you that gifting is the right answer for your family, or that it isn’t. That’s genuinely not my call to make, and anyone who tells you it’s simple probably hasn’t sat with a family through it.

What I can tell you is that it’s worth understanding, worth talking through with an estate attorney who knows your situation, and worth doing at whatever pace actually fits your family — not the pace anyone else is pushing.

If you’re already sorting through what downsizing looks like for your own life, this question tends to sit right alongside the rest of it. You can walk through what downsizing actually involves at your own pace, and there’s no reason this piece has to be solved before the others are.

And if you’d like to talk any of it through — the house, the timing, or just where to start — I’m always happy to have that conversation. You can reach out here whenever you’re ready.

You have more time than it might feel like right now. And you don’t have to figure any of it out alone.

FP13_Downsizing_00