My money said no. Italy said go.

A birthday trip and a reminder to make room for living.

Margherita pizza at L’Antica Pizzeria da Michele in Naples. Only €6.50 ($7.25) for a taste of one of the city’s most famous pizzerias.

NAPLES, Italy — I was walking through O’Hare International Airport when I spotted a familiar face on the opposite moving walkway.

A coworker had just arrived in Chicago to cover the Knicks-Bulls game the following night. We exchanged greetings as the walkways carried us in opposite directions.

For 20 years, that could have been me.

I’d made that trip countless times during my career covering the NBA, including 17 years as a full-time beat writer. Another city. Another hotel. Another game. Another deadline.

But this time, I wasn’t traveling for work. I was headed to Italy to celebrate my birthday.

He was going to cover another basketball game. I was going to eat my way through Naples, explore the Amalfi Coast and see Rome.

For years, I had built my life around the NBA schedule. My birthday falls in early November, right as the season gets going. There was always another game to cover, another story to write, another flight to catch. Taking a birthday trip like this was never a priority — or even something I seriously considered.

I loved that career for a long time. It took me places I never imagined going and allowed me to do work I truly enjoyed.

But eventually, the life I’d worked so hard to build became one I no longer wanted. The routine grew stale. The perks lost their appeal.

Too many interviews produced the same rehearsed answers. Access to the people I covered became increasingly restricted. Even the games started to feel predictable. By the end of my tenure, I could practically tell you who would win just by looking at which team made more 3-pointers.

Worse, the job had consumed too much of my life.

I’d sacrificed sleep, health, weekends, holidays and time with people I loved. I missed moments with Parker. And even when I was home, I wasn’t always present. There was usually a deadline hanging over my head or another trip around the corner.

I had spent years pursuing a dream only to realize that achieving it didn’t mean I had to keep living it forever.

Walking through O’Hare that day, I felt the freedom of having made a different choice.

And I was about to celebrate that freedom with an obscene amount of pizza.

If you’ve followed Money Talks for a while, you might remember my 2023 confession that I’d spent $1,214 on pizza in a single year.

So visiting Naples, the birthplace of Neapolitan pizza, wasn’t just another stop on my itinerary. It was practically a pilgrimage.

I arrived with a list of pizzerias I’d researched for weeks. I intended to eat as much pizza as my stomach and schedule would allow.

Then I met Lucio.

My colorful bed-and-breakfast host was delighted that I’d come to Naples, but he had one request: Don’t spend the entire visit eating pizza.

Naples, he insisted, had too much wonderful food for that. I hadn’t traveled halfway around the world to be bullheaded and ignore a local’s advice.

I listened.

But pizza came first.

A collection of food and drink from my pilgrimage to Naples.

My introduction was pizza portafoglio, a folded pizza designed to be eaten on the go. I bought one for €2.50, or about $2.79, and wandered through Naples, eating and smiling as I walked.

The first few bites were mostly crust. Good crust, but crust nonetheless. Then I hit the cheese and tomato sauce and quickly understood the appeal.

I kept walking and kept biting until there was nothing left.

At Gino Sorbillo, I tried pizza fritta, a deep-fried pizza — that’s right, a deep-fried pizza — stuffed with ricotta, tomato sauce and a little oregano. It was like something you’d order at a state fair. Enormous. Delicious. Dangerous.

Then came L’Antica Pizzeria da Michele, the famous pizzeria featured in the Julia Roberts movie “Eat Pray Love.”

I arrived when it opened at 10:30 a.m. because even the to-go line at this place can get chaotic. By 10:33, though, I was seated. At 10:48, a margherita pizza was sitting in front of me.

The menu offered only four pizzas, all variations of the classics. Each cost €6.50, roughly $7.25. You can’t even get a medium pizza at Pizza Hut for that.

A friendly couple seated inches away offered me a slice of their marinara pizza. The woman was from France, the man from Spain, and they weren’t going to finish it, he told me. I happily accepted.

The oregano was a little overpowering for my taste, which confirmed I’d made the right choice ordering the margherita.

My pizza was excellent. But would I stand in line for hours to eat there? Absolutely not. Naples has too much good pizza, literally on every corner, for that.

My favorite came at 50 Kalò, a pizzeria I’d been eager to try.

I ordered another margherita and again devoured every bite. The crust was less charred, the flavor more intense, and each bite seemed better than the last. At €7.50, about $8.36, it was a steal. And worth every cent and calorie.

But Lucio’s advice kept ringing in my ears. So I ventured beyond pizza.

I tried pasta alla Genovese, with its rich, slow-cooked onion and meat sauce, and pasta patate e provola, a comforting combination of pasta, potatoes and smoked cheese.

I sampled babà, the rum-soaked Neapolitan pastry, and graffa, a fried doughnut.

And, of course, there was gelato.

One of my favorite meals turned into one of my favorite encounters.

At Tandem Ragù, a local restaurant known for its pasta, I struck up a conversation with a young man named Antso, an avid NBA fan.

Normally, I don’t make a habit of telling strangers about my old career. I’d traveled all this way, in part, to get some distance from that world. But there was something special about meeting someone halfway around the world who genuinely loved the sport.

So I decided to have a little fun.

I told him I was “the guy in the back” of that famous Russell Westbrook meme.

His reaction was priceless. Suddenly, we had even more to talk about.

We spent nearly two hours talking about basketball, Italy, America, food and life. Antso was the first person I met in Italy who connected with my American life and made me feel a little at home. I’d traveled nearly 5,000 miles to get away from that world, only to find an unexpected connection to it halfway across the globe.

During our conversation, Antso also mentioned that his father worked at a pizza restaurant on Capri, giving me one more reason to look forward to my visit to the island three days later.

Before I left, Antso offered me a shot of limoncello, the traditional lemon liqueur so closely associated with southern Italy.

It was my first taste.

And I loved it.

One of the sweetest surprises in Naples was meeting Antso. I’ll always remember his kindness and the conversation we enjoyed.

We took a quick selfie. He had already bragged to his friends in their group chat that he had met “the guy in the back” of Westbrook’s meme, circling my likeness in a bright green font.

I had come to Naples chasing pizza. Instead, some of my favorite memories came from the things I hadn’t planned.

A host who insisted I broaden my horizons. A conversation with a stranger who connected my old life to my new one. A shot of limoncello I never would have ordered on my own.

The best parts of the trip weren’t always the ones I’d planned.

I had also decided to travel differently.

For years, my standard luggage was a small rolling suitcase and a backpack. This time, I replaced the suitcase with a $168 Osprey travel backpack and carried a mini backpack alongside it.

Everything I needed for nine days fit inside those two bags. No checked luggage. No dragging a suitcase across cobblestones or wrestling wheels up staircases. I didn’t miss a thing.

It reinforced something I’ve come to appreciate: I can do a lot with a little.

Scenes from my walks around Naples.

But I didn’t hold back in spending on entertainment or enjoyment.

Traveling to Italy wasn’t financially convenient. Cancelling my trip could have saved me thousands at a critical time. I’d spent much of the year dealing with expenses I hadn’t anticipated, including substantial legal bills. I’d already put some financial goals on pause, and taking this trip meant accepting another tradeoff.

I put expenses on my credit card that I’m now working to pay off.

But I refused to let another year pass while I waited for every financial circumstance to become perfect.

I’ve spent much of my adult life working, saving, planning and preparing for the future. Those habits have served me well. I’m not abandoning them.

But what good is building a life if you never make time to enjoy living it?

I didn’t leave Italy with a new philosophy about money. I was reminded of something I already knew: money should give me options. It should make it possible to live the life I’m working so hard to build.

It should give me freedom.

Freedom to choose how I spend my time. Freedom to walk away from a career that no longer fulfills me. Freedom to get on a plane because there’s a place I want to see, not because there’s a job I have to do.

As I watched my coworker continue in one direction and me in the other, I knew exactly what that moment represented.

For so long, basketball had determined where I went.

This time, I got to decide.

And Naples was only the beginning.