The order you draw from your accounts.

The first surprise of retirement isn't a market crash.

It's the first blank line on a form that asks where the money should come from.

For thirty years you got good at the opposite. You filled the accounts. You trained yourself not to touch them. And now, one Tuesday, the job flips inside out, and nobody ever taught you this half.

This is A Considerate Retirement. I'm Josh Mangoubi, and I spend my days helping people near retirement decide how their money should support the life ahead.

Today, one small choice that most people make on autopilot.

The order you pull money from your accounts.

It feels like a bookkeeping detail. It's quietly one of the biggest tax decisions you'll make. And the obvious answer isn't always the right one.

Let me show you why.

Picture a couple. Let's call them Margaret and Tom. Both sixty-three. The paychecks have stopped. The accounts are still full. And now they have to decide which one to touch first.

Here's the thing to understand about their money. It sits in three different piles, and the tax code treats each pile by a different rulebook.

Pile one is the ordinary account. A regular brokerage or savings account. That's money they already paid tax on years ago. When they sell something, they owe tax only on the growth, often at a gentler rate. And under today's rules, if money is still there when they die, their kids may inherit it with much of that old tax problem reset.

Pile two is the big one for most people. The traditional four-oh-one-k, or the traditional I-R-A. This money has never been taxed. Not once. So every single dollar that comes out counts as ordinary income, taxed like a paycheck. And here's the catch — starting at seventy-three, the law makes them take some out every year, whether they need it or not.

Pile three is the Roth. The mirror image. Tax was paid going in, so nothing is owed coming out. And no one forces them to touch it. Ever, in their lifetimes.

Three piles. Three completely different rulebooks.

So which one do you spend first?

The standard advice goes like this. Spend the ordinary account first. Then the traditional I-R-A. And save the Roth for absolute last.

And honestly? The logic is good. It lets the two tax-sheltered piles keep growing. It spends the gentlest-taxed dollars first. It protects the Roth, the most flexible pile, for as long as possible.

As a starting point, it's hard to argue with.

But here's where it can quietly backfire.

Think about what "save the traditional I-R-A for later" actually does. That pile doesn't sit still and wait politely. It keeps growing. Year after year. Untouched.

Then Margaret and Tom hit seventy-three.

For anyone born in nineteen sixty or later, that age climbs to seventy-five.

And the law says, now you have to start pulling money out. On a schedule you don't control. Taxed like income. And if you simply forget? The penalty is stiff. Twenty-five percent of what you should have taken, though it can drop to ten percent if you correct it within the allowed window.

Here's the piece people miss.

Your income is taxed in layers. The more you pull out in one year, the higher the layer you reach, and the steeper the rate on that top slice.

A traditional I-R-A left alone for a decade can grow so large that the forced withdrawals push you into a higher bracket than you ever paid while you were working.

That's worth pausing on. You could pay a higher rate in retirement than you did in your peak earning years.

And it doesn't stop there. That same jump can drag more of your Social Security into the taxable column. It can raise your Medicare premiums, through a surcharge people call Irma, spelled I-R-M-A-A.

So you didn't dodge the tax. You mailed it forward. To your seventy-five-year-old self. In a bigger envelope.

Here's the picture I keep coming back to.

Think of the traditional I-R-A as a tank filling up behind a valve. If you leave the valve shut for years, the pressure just builds. Then at seventy-three, the law opens it wide, all at once, on its terms — and the flood is bigger than anything you'd have chosen.

But if you crack that valve open a little in the calm years, letting a measured amount through when the pressure is low, you control the flow yourself.

And the calm years? Those are the ones right after you stop working.

That's the takeaway. Leaving the never-taxed pile alone may make the later tax problem larger, not smaller.

So let's go back to Margaret and Tom, because the calm years are where their real story lives.

They're sixty-three. Work has ended. Neither has turned on Social Security yet. Nothing is being forced out of any account.

Which means their income, right now, is about as low as it will ever be for the rest of their adult lives.

This quiet stretch — from the day the paychecks stop to the day the forced withdrawals begin — is the widest planning window most people ever get. And it's easy to sail right through it without noticing.

Now, here's what's actually underneath the money for these two.

Tom has a private worry he hasn't fully said out loud. He does the math sometimes, late at night. What happens when one of us is gone?

Because there's a hard truth here. When one spouse dies, the survivor usually files taxes alone. The survivor may have much of the same money, but less room in the tax brackets. So the tax bill can feel larger, even when income is lower. It's a real enough pattern that it has its own name — the widow's penalty.

So when Tom thinks about spreading the tax out now, during the calm years, he's not chasing a clever trick. He's trying to make sure that whichever one of them is left behind isn't handed a mess on the hardest morning of their life.

That's what this decision is really about. Not the spreadsheet. The person still at the kitchen table years from now.

So what do Margaret and Tom actually do with that window? Let's talk options — not instructions, just what's worth weighing.

The core idea is to use those low-income years on purpose. Not to pay the least tax this year — in fact, most of these years, they'll choose to pay a little more. It's about paying at their lowest rate now instead of their highest rate later, measured across a whole retirement, not one single April.

There are three tools to notice here.

First, the traditional account. One move is to take money out of it, or shift part of it into a Roth — a Roth conversion — but only up to the top of a low bracket, and no further. In twenty twenty-six, for a married couple, the twelve percent bracket runs to roughly one hundred thousand dollars of taxable income. That's the space Margaret and Tom might choose to fill, and then stop. A conversion taxed at twelve percent now, instead of twenty-four percent or more down the road.

Second, the ordinary account. In twenty twenty-six, a married couple with taxable income under about ninety-eight thousand nine hundred dollars may pay zero federal tax on long-held investment gains. So they might be able to sell something that has grown for years and owe no federal tax on that gain. That doesn't mean the move is right. It means the window is worth noticing.

Third, the Roth. And here's a twist on the old rule about saving it for last.

Because a Roth withdrawal adds nothing to your taxable income, it's the one pile you can dip into in a high-income year without setting off any of those tripwires. A big unexpected expense that would otherwise push you over a Medicare line, or into the next bracket? The Roth can keep you under it.

So the Roth isn't really a last resort. It's more like a valve you open in exactly the years it helps.

Now, one honest caveat. None of this means the simple order is wrong for everyone. If your pre-tax pile is modest, if guaranteed income already covers your needs, if your bracket is low and likely to stay low — then spend-the-ordinary-account-first and save-the-Roth-for-last may be all you ever need.

There's no single sequence that's right for everybody. It depends on the size of each pile, your bracket now versus later, your health, and what you hope to leave behind.

And because the big moves — Roth conversions especially — are very hard to undo once made, this is exactly the kind of thing to map with a tax professional, a C-P-A, before you touch anything.

The takeaway here? The window is real, it's brief, and it rewards the people who notice it's open.

So here's your Considerate Step this week.

Find your three piles, and write down one number for each. What's in your ordinary account. What's in your traditional, pre-tax accounts. What's in your Roth.

Three numbers, on one piece of paper, in three columns. Don't optimize anything. Don't move a dollar. Just see the shape of what you've built, sorted by how it'll be taxed.

Most people have never once looked at their savings that way. And you can't choose the order you draw from three piles until you can see all three at the same time.

Let me leave you with Margaret and Tom.

Picture them a few years on, in the version where they noticed the calm years and used them. It's a quiet January. Tom's got the coffee going. They're opening the valve just a little — moving a measured slice from the traditional pile, filling the low bracket, and stopping there.

It's not dramatic. It's not clever. It's just a small choice, made on purpose, that they'll make again next year, and the year after.

And that's the whole idea today. The order you draw from your accounts almost never feels like a big decision in any single year. It's a small choice, made over and over. And small choices compound.

If Tom's late-night question stayed with you — what happens to the one left filing alone — you'll find a sibling episode at a considerate retirement dot com called The Widow's Penalty, about what the two of you can do while you're both still here.

And if you'd like to lay your own three piles on the table and pencil out an order your future self could live with, we're glad to sit with that page with you, and bring in a C-P-A for the tax side, where it belongs. There's a time to talk there whenever you're ready.

One quick, important note.

I'm the founder of Considerate Capital, a registered investment adviser, and this show is educational and general — not personal financial, tax, or legal advice, and not a recommendation for your situation.

Anyone I describe, Margaret and Tom included, is a hypothetical composite, not a real client.

And nothing here is a promise of results.

For advice about your own life, talk with a professional who knows the details.

I'm Josh Mangoubi.

Until next time — go find your three piles, and write down one number for each. That's where every good decision here begins.