Don't Wait Until Retirement to Start Living: A Lesson From My Trip to Italy

I recently returned from two weeks in Italy, a trip that had been on my bucket list for quite some time.

And I have to tell you, it was everything I hoped it would be.

We traveled through some beautiful parts of Italy, visiting Modena, Parma, Bologna, Assisi, Alberobello, and several towns throughout Puglia and Tuscany.

Every place had its own personality, scenery, traditions, and, of course, incredible food.

But if I had to pick a favorite, it would probably be San Gimignano and the Tuscan countryside.

There's just something about those rolling hills, vineyards, and old farmhouses scattered across the landscape. The scenery almost looks like a painting.

I loved taking in those views and experiencing a slower pace of life. Sitting at a café, watching people go about their day, and enjoying the simple pleasure of being somewhere different.

For someone who's spent much of his life working, building a business, and juggling responsibilities, it felt pretty good to slow down.

And it got me thinking.

We spend so much time preparing for the future that sometimes we forget to enjoy the life we're living right now.

A Little More Living, a Little Less Working

One of my favorite things about Italy was experiencing the food and culture.

And we did plenty of both!

We took several cooking classes, learning to make different types of pasta, pizza, focaccia, and even gelato.

We visited local cheesemakers and balsamic vinegar producers, learning about the traditions and craftsmanship behind foods the Italians have been making for generations.

And the food tours were fantastic. Each city had its own specialties, and we had the opportunity to taste foods that were unique to the area.

I love cooking, so getting to learn new techniques and experience authentic Italian food was especially enjoyable.

But it wasn't just about the food.

It was about trying something new, learning from people who live differently than we do, and enjoying experiences that you simply can't get from your everyday routine.

Our trip ended with dinner at Grotta Palazzese in Polignano a Mare.

What an incredible way to finish the trip.

The restaurant sits inside a beautiful seaside grotto, with stunning views of the surrounding cliffs and ocean. At night, the setting was spectacular, and the food was just as memorable.

It was one of those experiences that makes you appreciate the opportunity to travel and see the world.

The Trip Reminded Me of Something Important

During those two weeks, I had plenty of time to reflect.

I thought about how grateful I was to be able to take this trip, enjoy new experiences, and explore another part of the world while I'm still healthy and active.

I also came home feeling rejuvenated.

And it reminded me of conversations I have with clients preparing for retirement.

Many of the professionals I work with have spent decades building successful careers, raising families, and saving diligently for the future.

They're very good at working hard and putting money away.

But sometimes, they're not nearly as comfortable spending that money on themselves.

There's always another reason to wait.

Another year of work. Another savings goal. Another responsibility that needs attention.

And before you know it, years have passed.

I certainly believe in being financially responsible and preparing for retirement. It's what I help people do every day.

But I also believe there needs to be a balance between saving for tomorrow and enjoying today.

After all, we don't know what our health, energy, or circumstances will look like ten or twenty years from now.

Some of those bucket-list experiences may be more enjoyable while we're younger and more active.

That doesn't mean throwing caution to the wind or spending money you can't afford.

It means making the things you want to experience in life part of your financial plan, instead of treating them as something you'll get around to someday.

Designing a Life Worth Enjoying

One thing I've always believed is that financial planning should be about more than investment returns and retirement account balances.

It's about what your money allows you to do.

Maybe that's traveling through Italy, spending more time with grandchildren, learning a new hobby, or simply having the freedom to take a few weeks away from work.

Those experiences are different for everyone.

And that's exactly why retirement planning should be personal.

At Designing Wealth, I help busy professionals prepare for retirement by bringing together retirement income planning, tax-smart strategies, and the lifestyle goals that matter most to them.

Part of that conversation is understanding not just how much money they'll need in retirement, but how they want to enjoy their lives along the way.

My trip to Italy reminded me how important that balance really is.

I came home with some wonderful memories, a greater appreciation for Italian culture, a few new cooking skills, and a renewed appreciation for taking time away.

And maybe that's the biggest lesson I brought home.

Don't become so focused on saving for the life you want someday that you forget to enjoy some of it today.

Sometimes, it's worth taking the trip.

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