I’ve advised a lot of families on estate planning. Most of the time, those families have already built something substantial to pass on. I’ve observed a few things from those families, and I’ve combined that with a few principles from my financial experience.

Here’s the first thing I noticed. The families who successfully move wealth from one generation to the next don’t do one thing right. They do three. And almost nobody does all three.

They grow the money faster than it erodes. They put a structure around it and prepare the people who’ll receive it. And they pay attention to how it comes back out.

Miss any one of those and the other two won’t save you. So let’s take them in order.

Part One: The Risk Nobody Names

Start with the question underneath all the others.

What is the actual risk to your money?

Most people say losing it. I don’t think that’s right. The risk is outliving it — or more precisely, watching it quietly stop being able to do what it used to do.

Here’s the cleanest proof I know.

In 1976, a first-class stamp cost 13 cents. Today that same stamp costs 82 cents. Same envelope, same letter, same trip across town. Six times the money.

Nothing about the stamp changed. What changed is the dollar.

Now run that forward. At roughly 3% a year, the cost of everything you buy doubles about every 24 years. If you retire at 65 and live to 95 — and a lot of people now do — you should plan on roughly tripling your cost of living during your retirement. Groceries. Property taxes. Homeowner’s insurance. A roof. Care in the last few years, which is the expensive part.

That’s the enemy. Not a bad year in the market. A cost of living that never stops climbing while your dollars stand still.

So what actually beats it?

Over roughly two centuries of American financial history, here is what each major asset class returned after inflation:

Stocks — ownership of real businesses — returned about 6.7% a year after inflation. Bonds about 3.5%. Treasury bills, which is essentially cash, about 2.7%. Gold about 0.6%. And cash held as cash: negative 1.4% a year.

Read that last one again. Money held as money isn’t flat. It’s a guaranteed slow loss. The safest-feeling choice on that chart is the only one with a minus sign in front of it.

And that’s before taxes. Interest from a CD or a money market is taxed as ordinary income, at your top rate, every single year. Subtract inflation, then subtract taxes, and “safe” money has historically done little better than tread water. You can be certain of the number, or you can build wealth. Over a lifetime you generally don’t get to do both.

“But stocks go down.”

They do. And this is exactly where families lose the thread, so let me put real numbers on it.

Looking at U.S. stocks across about a century of rolling holding periods, the market was positive in roughly:

• 74% of one-year periods
• 88% of five-year periods
• 94% of ten-year periods
• 100% of twenty-year periods

And the one that matters most here: there has not been a single 20-year period in roughly 200 years in which stocks failed to beat inflation. Not one.

Something else worth knowing, because it runs against everybody’s instinct — bonds are not the refuge they feel like. The worst ten-year stretch for bonds after inflation was actually worse than the worst ten-year stretch for stocks. And over the decade just behind us, the 10-year Treasury returned roughly 1.5% a year against inflation of about 2.8%. That’s not safety. That’s a slow, quiet, reliable loss of purchasing power — accompanied by a very reassuring statement in the mailbox every quarter.

The declines in stocks are real. They are also temporary. In my experience nobody has ever been permanently hurt by a market decline. They were hurt by selling during one.

Volatility isn’t loss. Volatility is the admission price for the only return on that chart large enough to do the job.

Why this belongs in a conversation about generations

“A good man leaveth an inheritance to his children’s children.”

— Proverbs 13:22

Read that carefully. Not to his children. To his children’s children.

That verse is describing money that has to survive two handoffs and sixty-odd years of rising prices and still be worth something when it arrives. Over sixty years at 3% inflation, a dollar loses roughly five-sixths of what it can buy.

You don’t get money across that kind of distance by protecting a number. The number will arrive just fine. Its purchasing power won’t.

There’s one way across: owning good businesses — companies that sell things people need and that raise their own prices right alongside everything else — and holding them long enough for time to do the work.

That isn’t a stock tip. It’s the arithmetic of the assignment.

Part Two: Structure and Values

Growing it is the part most people think about. Here’s the part that actually decides the outcome.

There’s an old saying — shirtsleeves to shirtsleeves in three generations. The first generation builds it, the second maintains it, the third loses it. That happens often enough to have become folklore.

And here’s what surprises people about why.

Wealth almost never fails because of the documents. It fails because of the people.

I’ve watched beautifully drafted plans come apart, and I’ve watched simple ones hold for decades. The difference is rarely the paperwork. It’s whether the family was prepared to receive what was coming.

Which means this part takes two things working together, and most families only do one.

First: structure

Money left outright to a 26-year-old is money left to a 26-year-old’s judgment. And to a 26-year-old’s marriage. And to a 26-year-old’s creditors.

That’s not a knock on anybody’s children. That’s simply what the word “outright” means.

A properly drafted trust changes the terms of the handoff. It can say when. It can say what for. It can protect an inheritance from a divorce, a lawsuit, a business failure, or a bad season. It can keep what you built inside the family bloodline instead of watching it walk out the door with a former in-law.

Structure isn’t about controlling your children from the grave. It’s about putting guardrails around the money so your children don’t have to carry that weight alone at the worst possible moment.

And a note from the drafting side, because I see this constantly: a trust that doesn’t hold the asset doesn’t control the asset. Deeds have to be recorded into it. Accounts have to be retitled. Beneficiary designations have to line up with the plan — beneficiary forms override your will, every time. A signed trust sitting in a drawer while everything is still titled individually is an expensive piece of paper and nothing more.

Second: values

This is the part almost nobody does. It’s also the part that determines the outcome more than anything else on this page.

If your children don’t know how the money was made, what it cost you to make it, what it’s for, or what you hope it does — then it isn’t an inheritance. It’s a windfall.

And windfalls get spent.

Money without a story attached is just money. Money with a story attached becomes stewardship.

The practical version of this is unglamorous. Talk about it. Out loud. While you’re living. Tell your children what you did and why. Let them know a plan exists and roughly what it’s designed to do. Say plainly what you’d hope the money gets used for — education, a first home, a business, the church, the next generation after them.

A family that has never once discussed money is not going to suddenly get good at it during the week of a funeral.

“Train up a child in the way he should go: and when he is old, he will not depart from it.”

— Proverbs 22:6

Structure protects the money. Values protect the family. You need both, because either one alone eventually fails.

Part Three: How It Comes Back Out

Here’s the piece that quietly decides how much actually survives the trip.

You can spend forty years building something and hand a meaningful share of it away in the last few — simply by taking it out in the wrong order.

Most families hold money in three buckets, and they behave completely differently.

The tax-deferred bucket — the 401(k), the traditional IRA. You never paid tax on this money. Every dollar that comes out is taxable income. And it doesn’t stay voluntary forever; eventually the government requires you to take withdrawals whether you need them or not.

The tax-free bucket — the Roth. Already taxed once, grows without tax, comes out without tax.

The taxable bucket — the regular brokerage account, the land, the rent house. Taxed differently again, and frequently at the most favorable rates of the three.

The trap most families never see coming

That large traditional IRA doesn’t only belong to you. It’s a tax bill you’re handing to your children.

Under current rules, most non-spouse beneficiaries have to empty an inherited retirement account within ten years. Which means your child is likely draining it during their peak earning years, at their highest marginal rate, stacked right on top of their own salary.

You spent thirty years deferring that tax. They may end up paying it at a worse rate than you ever would have.

Meanwhile, there’s often a window — after you stop working, before required withdrawals begin — that is the lowest-tax stretch of your entire life. A lot of families sail straight through it without touching a thing, because no one ever told them it was there.

I’m not going to tell you what to do about any of that in a blog post, because the right answer depends entirely on your numbers, your bracket, and your children’s brackets. But the principle holds: the order you spend from, and the years you choose to do it, are worth real money — and both are decisions, not defaults.

Where Families Actually Lose It

Now put the three together, because that’s the real point.

You can invest beautifully and still watch it fragment in the second generation, because there was no structure. You can have an immaculate trust and still lose ground for thirty years, because the money sat in something that couldn’t outrun inflation. You can do both of those right and still hand your children an avoidable tax bill, because nobody looked at the order of withdrawals.

Here’s what I’ve noticed after enough of these conversations: the failures almost never happen inside somebody’s specialty. They happen in the seams between them.

Your attorney drafts the trust. Your CPA files the return. Your advisor manages the accounts. Each of them may be excellent at what they do. But if those three have never spoken to one another, nobody is watching the places where their work is supposed to connect — and the seams are where families lose the most.

That’s the gap I built my practice to close. I draft the documents myself, I read the tax return, and I work alongside your CPA rather than around them. Not because any one piece is complicated on its own, but because nobody was minding the space between them.

Building it is the first half. Keeping it — and handing it off intact, to people prepared to receive it — is the other half. And it’s the half most families never plan for.

If you’ve built something worth passing on, that’s worth a conversation. We work with a limited number of Arkansas families each year on exactly this — coordinating the legal, tax, and investment sides so the plan actually holds together. Reach out and let’s look at what you have.

“Without counsel purposes are disappointed: but in the multitude of counsellors they are established.”

— Proverbs 15:22