18: Still Going: Our Messy, Complicated, Absolutely Worth-It Road to Portugal

March 2026

Nobody tells you that chasing a dream feels a lot like a second job.

When my wife and I decided we were going to move to Portugal, I pictured it like this: sell the houses, get the paperwork together, pack our bags, and go. Well, maybe not THAT simple but in essence, a clean break. A new chapter.

What I didn't picture was rebuilding a chimney, filling out and mailing complicated paperwork for a foreign bank account, calling a federal government agency nearly every day for six months only to be told — essentially — we'll get back to you in another 60 days.

And yet. Here we are. Still going.

The Checklist That Never Gets Shorter

Moving internationally isn't just a logistical challenge. It's a gauntlet. At any given moment, we're tracking a list of tasks that would make a project manager flinch:

Selling not one, but two properties. Obtaining FBI background checks and Portuguese criminal record clearances. Setting up a foreign bank account. Securing Schengen health insurance. Gathering reference information. Getting our NIF (tax identification number) in Portugal. Applying for a D7 Visa. Finding a rental — with a contract in both of our names.

Each one of those bullets sounds simple. Each one has surprised us.

The Rental House Chronicles

We finally sold our rental house. That's the good news.

The less good news is that selling it felt less like a transaction and more like an archaeological excavation of everything that could possibly be wrong with a property. The chimney needed to be rebuilt. The buyer wanted the sewer line scoped and cleaned. A vapor barrier had to be installed under the house. Mold abatement had to be done on a small section of the attic. Sheetrock repairs in the garage. One thing after another, each discovered only after we thought we were through.

We got it done. But "more difficult than anticipated" is putting it gently.

Living in a Showroom

Our primary residence is currently on the market, which means we're living in a home that has to be perpetually guest-ready. A realtor could call at any moment and bring potential buyers through. Fortunately, we’ve sold off all the potential clutter. What remains is a few articles of furniture and kitchen stuff (so we can still live somewhat normally).

So far: no offers. The house is beautiful. The market is what it is.

We wait.

Bureaucracy as an Olympic Sport

The FBI background check — something I assumed would be a routine expense — turned out to cost roughly ten times what I had budgeted for. And even though we filed electronically, we're looking at a two-month turnaround. I'm still figuring out exactly how to obtain the Portuguese criminal background check.

The bank account setup in Portugal has been its own adventure. Forty pages of documents. A dozen signatures between the two of us. More than $140 in shipping costs. And even after all of that, it's still not fully verified. We're waiting on that too.

We still need to secure Schengen health insurance for both of us.

The One That Keeps Me Up at Night

Here's the situation I genuinely didn't see coming.

I retired from the Federal Government last September. It is now mid-March 2026 — more than six months later — and I have not received a single retirement payment.

I call the Office of Personnel Management almost every day. I get almost nothing back. I've escalated to my state representative and senator. Their offices reached out on my behalf, and the response from OPM was, essentially: we'll review the senator's request within the next 60 days.

Sixty days. Which pushes us from six months without pay to potentially eight months without pay, with no guarantee of resolution even then.

To show income for the D7 Visa — the visa that gets us into Portugal — we need to demonstrate consistent retirement earnings. Without that documentation, our whole timeline is at risk.

I'm pressing my senator's office to lean harder. I'm keeping every record. I'm not giving up on this piece.

Keep your fingers crossed for us. Genuinely.

What's Actually Working

I don't want this to read like a litany of complaints, because the full picture includes some things that are going remarkably well.

We've been working with a company called Portugal the Place, and they have been worth every penny. They're helping us zero in on Braga as our landing spot — a city in northern Portugal with deep history, a thriving university culture, and a pace of life that sounds deeply appealing. They do virtual walkthroughs of rentals, handle coordination with landlords on our behalf, and have connected us with trusted partners for banking, taxes, and insurance. When it comes time for our visa appointment, they'll help us pull the final package together.

And then there are our friends — already living in Portugal, already in Braga — who, not three minutes before I sat down to write this, offered to serve as a mailing address for us during the transition. Because sometimes you want to order linens before you arrive. Their words: "We help one another here, and that's especially true for us, for you two."

That kind of generosity doesn't have a line item. But it means everything.

Why We're Still Doing This

I'd be lying if I said this process was easy. It's not. It's a lot of work, a lot of things to track, and a lot of uncertainty — often all at once. There are days when the stack of tasks feels genuinely unmanageable.

But here's what I know: the deeper we get into this, the more certain I am that it's exactly what we want.

I want to stand in front of the Almendres Cromlech — a megalithic stone circle older than Stonehenge, sitting quietly in the cork forests outside Évora — and feel the weight of that kind of time.

I want to walk the Passadiços do Paiva, the wooden walkways that hug the cliffs above a wild river gorge in ways that make you catch your breath.

I want to see Monsanto, the village where houses were built between giant boulders on a mountain. I want to swim in the natural pools of Foz d'Égua, find the hidden lagoons of the remote mountain village connected by stone bridges. I want to look out from the walls of Castelo de Marvão, a sky castle perched above the Spanish plains. I want to walk the ancient Roman city of Conímbriga and see those remarkably preserved mosaics with my own eyes.

And yes — I want all the things off the beaten path too. The foods I haven't tasted, the roads I haven't driven or bicycled, the people I haven't met yet. I’m also no prude to the touristy spots.  I’ll see those too.  They’re popular for a reason.

One Chapter Closing, Another Opening

When I was working full time, life was busy in a particular way. Job demands. Raising kids. Managing two houses. There was always something pulling at you.

Retirement was supposed to be different. And in many ways it is — but right now, getting ready to go is practically a job in itself. I feel nearly as occupied as I did during my working years, just with a different set of tasks.

The difference is this: I can see the other side.

I can see a version of our life where the majority of decisions are the enriching ones. The exciting ones. Where the hard work of today gives way to the joy of what's next.

We're not there yet. But we're going.

Follow along as we navigate the road to Portugal — one bureaucratic hurdle, one house showing, and one breathtaking destination at a time.

Is there a place in the world that's been calling your name? We'd love to hear where your dream destination is — and what's standing between you and it. Let us know in the comments below!