I had just gotten home from Positano.

We stayed near the Sirenuse Hotel – the most beautiful (and most expensive) hotel in town – and I took my son James for a drink overlooking the water as the sun went down. Every single person around us was a honeymooner. Twenty-somethings, bright shiny new rings, the whole thing.

I came home and told my wife: we’re taking a honeymoon every year for the rest of our lives. Starting next year, we travel like we’re on our honeymoon, and we spend money like it too. This photo ​above​ was taken this summer in Comporta, Portugal.

It got me thinking about something I’ve been wrestling with for two years now, ever since I started updating ​The Automatic Millionaire​: we spend our whole lives learning how to save and invest. Almost nobody teaches us how to spend and enjoy it once we get there.

So I sat down with my dear friend Jean Chatzky – a legend in personal finance, 30+ years in the business, founder of HerMoney.com – for the very first interview about her brand-new book, ​The Forever Paycheck​. It might be the most important conversation I’ve had on the show this year.

NEW EPISODE: THE FOREVER PAYCHECK, WITH JEAN CHATZKY

Jean opened the show with a story that stopped me cold. Her mom had $1.6 million in a retirement account when Jean’s dad passed away. She had Social Security, a small pension, everything she needed. Two years ago, Jean’s mom passed away too — and that account had grown to $1.7 million. She never touched it. Her kids told her constantly, “Mom, spend your money, we don’t need it,” and she still couldn’t do it.

There is data to back this up: 83% of retirees don’t take a dollar out of their retirement accounts until they’re legally forced to. There’s $45 trillion sitting in American retirement accounts right now, and almost none of it is coming out.

We get into why – it’s psychological. Jean calls it “precious cargo,” the same instinct that keeps a bottle of wine sitting in the cellar until it turns to vinegar. (I’ve got my own version of that story in here too – my dad’s wine collection, and the bottles of Silver Oak we waited too long to open.) We also talk about what a “forever paycheck” actually is, how annuities fit in without the baggage you’ve probably heard, and why your first decade of retirement — what Jean calls the “go-go years” – is the one you can’t afford to spend too cautiously.

If you’re retired, close to it, or have parents who are, watch this one. It might be the permission slip you need to actually enjoy what you’ve built.

WHERE TO GET THE BOOK

Jean’s new book, ​The Forever Paycheck​, is out on September 8th – pre-order it now.

LISTEN INSTEAD

Prefer audio? The full conversation is also wherever you get your podcasts, including ​Apple​ and ​Spotify​.

One last thing. My grandma used to keep a jar of “ice cream money” – a little set aside just for joy, no guilt attached. Jean’s book made me think about that jar differently. Maybe the whole point of the money we save isn’t the number in the account. Maybe it’s the ice cream.

Go enjoy some of yours this weekend.