Jean Chatzky Has Spent Decades Teaching Us How to Save for Retirement. Now She’s Given Us A Blueprint For Spending It

There are a few things in life that we practice for 40 years and then, almost overnight, need to start doing in reverse… but HerMoney CEO Jean Chatzky says that essentially describes our retirement system.

For most of our working lives, we’re told to save, save, save. We celebrate every big financial milestone, like when we save $10,000, when we invest our first $100,000, or maybe when we hit one of the all-important retirement benchmarks.

But then when we retire, we’re supposed to be excited to watch those numbers tick down. If that seems odd to you, welcome to the club. 

Now that I’m in my mid-40s, retirement seems here in a way that it never was before. 

And when I sat down recently with Jean Chatzky — my boss, my friend, and New York Times bestselling financial guru, among other things — to talk about her 15th book, The Forever Paycheck: The New Retirement Strategy to Spend More, Worry Less and Never Run Out of Money, I realized something: 

I’ve spent my entire adult life learning how to accumulate money… but I have absolutely no idea how I’m eventually going to convince myself to spend it.

Wait…We Forgot to Solve Half of Retirement?

One day, you retire, and the paychecks stop. And (newsflash!) there aren’t really classes out there teaching the finer points of decumulation — the term for turning the money you’ve accumulated into the money you can actually live on.

Ahem. It should come as no surprise that most of us aren’t handling the transition very well.

“We looked at the balances of people 20 years into retirement,” Jean told me when I interviewed her for The HerMoney Podcast. “They’re not digging into their resources, which means that they’re leaving an awful lot of life and an awful lot of joy on the table.”

That sentence stopped me in my tracks, because for years when I thought about the big “problems” one would encounter in retirement, running out of money was at the top of my list…but dying with far more money than you intended to leave behind because you were too frightened to enjoy it actually seems worse. 

A Million Dollars Doesn’t Feel Like a Paycheck

Jean pointed to a particular piece of research she encountered while writing the book:  Two groups of retirees with the same amount of wealth were compared. One group held its money in a retirement account, like a 401(k), while the other received its money as pension income.

The pension group spent twice as much. Not because they were richer, but simply because the money arrived differently. That distinction really gets at the entire psychological heart of The Forever Paycheck.

Imagine having $1 million sitting in an investment account. Every time you withdraw $5,000, you see the balance fall… Now imagine $5,000 simply arriving in your checking account every month. 

“Because you know that that money’s gonna arrive again the next month,” Jean says. “You get a do-over every single month.”

In other words, the paycheck gives you something a giant pile of money doesn’t necessarily provide: permission to spend it.

Jean Chatzky, Annuity Convert

One of the major tools Jean believes can help create that paycheck is a product that she spent a significant portion of her career viewing with enormous skepticism: Annuities.

“I used to be an annuity denier,” Jean says. Years ago, her mother’s financial adviser suggested buying an annuity for her mother. “I shut the guy down cold.”

For decades, annuities had a reputation for being expensive and complicated, and the prevailing wisdom in many personal finance circles was that people should simply invest their own money.

But things have changed. (How? Abridged version: Today’s annuity market includes simpler, lower-cost products with more flexibility, making it possible to use an annuity for just one piece of a retirement-income plan rather than locking up your entire nest egg.) 

Today, Jean estimates she’ll ultimately annuitize about 15% to 20% of her own portfolio. She also has a small pension from her years at The Today Show, so together those income sources will help her cover her fixed costs. The rest of her portfolio can remain invested, where it can continue growing and fund goals like charitable giving and leaving a legacy.

So…Is the 4% Rule Dead?

For decades, retirees have heard some version of the 4% rule: Withdraw roughly 4% of your portfolio per year during your retirement, and your money should last about 30 years.

Jean Chatzky says that in 2026, the rule is “dead-ish.” The problem isn’t that 4% is always wrong; it’s that things change. Markets crash, people live longer than expected — all kinds of “life” things happen. Not to mention that it’s difficult to base your retirement on a rule designed around money lasting 30 years when you don’t know whether you will last 25 years or 35! 

…which brings us back to the forever paycheck.

First, Figure Out What Your Life Actually Costs

Jean’s framework starts with asking a simple question: How much does it cost to be you?

Not some hypothetical 65-year-old in a retirement calculator — You! 

Will you downsize? How much do you want to travel? Are you going to have a mortgage? Do you have credit card debt? Are there hobbies or experiences you absolutely don’t want to give up? How much might you want to give your children? What about charity? 

If you’re unsure about most of those, Jean recommends paying particularly close attention to your spending during the decade leading up to retirement.

“A lot of people don’t know how much it’s gonna cost them to live in retirement because they don’t really know what it costs them to live today,” she says.

Once you understand what your life costs, you can look at how much of that number Social Security (and any pension income you might have) will cover. Then you determine the gap.

For some people, Jean Chatzy says, the best way to fill that gap will involve guaranteed income from insurance products such as annuities. Others may be comfortable creating an investment-based income strategy.

Essentially, she wants everyone to know that your retirement isn’t just your 401(k). It’s Social Security, pensions, investments, home equity, cash-value life insurance (if you have it), alongside potential part-time work, and potential annuities. They’re all pieces on the board that need to be considered. 

The Retirement Question We Haven’t Been Asking

For decades, we’ve been asking ourselves: Will I have enough? That’s still an incredibly important question. But it’s time we ask ourselves another one: Once I have enough, will I actually let myself use it?

That’s a question that’s particularly important for YOU — the HerMoney woman — who has spent years making responsible choices and watching your money grow. 

MORE ON HERMONEY:

• Use This Forever Paycheck Framework To Plan For The Retirement You Actually Want
• How To Navigate Retirement While Paying for College
• Meet The Newsletter That Makes Your Money Make Sense

The Forever Paycheck offers us a blueprint for actually enjoying it, and we hope you’ll pick up a copy and listen in as Jean unpacks some of her favorite parts of the book!