Mini-Retirement 2025 (Week 2)

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Expectations are a tricky thing.

Before traveling to Italy, I had a few floating around in my mind.

Some based on what I'd read, some from what others had told me, and some from what I assumed based on travel forums and YouTube videos.

Here's a snapshot of a few:

• Milan is meh

• Como is packed shoulder-to-shoulder with tourists

• Bologna is one of Italy's best-kept secrets

Now that I've been in Italy for a little over two weeks, here's what I've actually found:

Milan? 

I loved it.

The people were kind, the energy was vibrant, and every bar and café offered snacks with drinks (a small but welcome detail).

While I was only there for a few days, I left wanting more time to explore.

So much for "meh."

Como?

Tourist-heavy, yes, but not unbearable.

While the main drag had its share of visitors, I was pleasantly surprised at how easily I could escape the crowds.

One of my favorite life experiences occurred during our brief stay: we took the funicular to the top of the mountain, bypassed the tourist-heavy cafés, wandered for a bit, and stumbled upon one of the best meals I've ever had, complete with breathtaking views and not a single rushed moment.

A reminder that the best travel memories often come from moments you don't plan.

Bologna? 

A slower start than expected.

We're currently here and to be honest, I was initially waiting to be blown away.

I wasn't.

At least, not right away.

Don't get me wrong, Bologna is a very cool city with a lot to offer, but, like many things in life, it didn't instantly live up to the hype.

The city center has been more crowded with tourists than I anticipated.

And while I knew I'd be surrounded by pasta and pizza, I didn't realize how limited the variety would feel after a few days, especially since I don't eat much dairy (cheese and cream-based sauces).

Still, the more I explore the more I'm finding little corners and experiences that are beginning to shift my first impression.

We found a German restaurant that broke up the carb cycle and a burger joint that served us an incredible pulled-pork tortelloni.

And I mapped out a few more local spots that seem promising.

Which brings me to the real surprise of week two: not just the cities, but the pace.

Going from "vacation mode" to "mini-retirement mode" is a bit more jarring than I expected.

In Milan and Como, we were only there for a few days, so the urge to do and see as much as possible came naturally.

But when you're in a place for four to five weeks, there's no need to rush.

And yet, slowing down (truly slowing down) is more challenging than it sounds.

Even though I know I have time, it's still a challenge to sit still, be present, and let the day unfold on its own terms.

And, there is the Sanctuary of San Luca…

Yesterday, we decided to make the trek to the Sanctuary.

It was one of my favorite experiences in Bologna so far.

It's perched high above the city and the trek to it is under two miles of porticos, which is nice for blocking the sun on a warm day and offering some lovely views.

I loved the experience.

In fact, I plan to walk up to the Sanctuary every morning from now on.

Not only is it an incredible start to the day, but the entrance to the walk is literally right outside our Airbnb.

What's the point of all this?

The point is that expectations can quietly shape your experience.

Whether it's a city you're visiting for the first time or a dream trip you've built up for years, it's easy to fall into the trap of assuming you'll feel a certain way the moment you arrive.

But some places don't instantly wow you.

They grow on you slowly.

They ask you to pay closer attention, to drop your assumptions, and to let the experience unfold instead of trying to control it.

If we're not careful, expectations can rob us of the joy that's right in front of us.

They build invisible checklists in our minds about how we should feel, what we should see, and what the highlight should be.

But the magic of travel (and life) isn't always about the big, bold moments.

Sometimes it's the quiet mornings on a hilltop.

Sometimes it's discovering that your Airbnb is around the corner from an incredible experience.

Sometimes it's the moment your opinion shifts (just a little) because you were willing to give something a second chance.

Final Thought

Expectations aren't always wrong.

But they're rarely the whole story.

Let them guide you, not govern you.

Because the real adventure often starts the moment you stop chasing what you thought would happen and begin enjoying what actually is.

Quotes that caught my attention:

“For fast-acting relief, try slowing down.”

​—Jane Wagner​

“The time to relax is when you don’t have time for it.”

​—Sydney J. Harris

Article that caught my attention:

I'm not alone when it comes to mini-retirements!

This "42-year-old has ‘mini-retired’ 12 times and counting!"

"It’s a great way to ‘disconnect and relax more deeply’ without leaving work"

Click here to read the article.

You can find the collection of financial tools & resources that helped me grow from a 6-figure debt to a 6-figure net worth by clicking here.

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