Quitting My Job, Selling My House, and Moving to Italy

Me in Florence

The Background

“You know, we could all get Italian citizenship.”

When my uncle first told me this at a family wedding in 2019, I took it as more of an interesting conversation topic rather than something that we or anyone else of Italian descent would actually do. He followed with some ideas about what would be required – documents, hoops to jump through, etc. It sounded interesting but complicated, and I pretty soon forgot about it.

Fast forward to 4th of July 2021, and I’m visiting family in New England. Over dinner, as is usually the case, we got to talking about the family, and as expected the idea of us getting Italian citizenship came up. I asked what we would need to do, and my cousin and aunt (who had done some research) said we would need to get our hands on the original birth and marriage records for our great grandparents. I mentioned to my cousin that we should go to Italy (partially for fun – as I had never been), and especially go to the town that our great grandparents came from. He was interested, and that was the end of that conversation.

Three weeks later we booked flights, and in August we were on our way to Rome for a 2 week vacation consisting of Rome, the Amalfi coast, and a day trip to our ancestral town just outside of Salerno. Needless to say I was quickly enamored with Italy. From the language, to the food, to the warmth and hospitality of the people – I loved it all. Yeah, I saw some problems. Rome was very dirty. People drove like they were the only ones on the road. Locals told me that it was a difficult place to live and there were lots of problems with the government. For better or worse, I was fascinated. Additionally, the trip to our ancestral town could not have been more of a success. Our expectation was just to show up, drive around the town, go to the town hall and collect some papers, then leave. Instead, we met some great people in town, including the Mayor. They fed us, gave us a tour of the town, showed us where our great grandfather lived over 100 years ago, and presented us with the documents we needed. It was a bizarre, undeserved, yet beautiful day.

If you are traveling to Italy soon, check out some of my recommendations for Rome, Florence, Amalfi Coast, and more.

Research, Research, and More Research

After the trip, I began to research more in-depth the process for Italian citizenship through descent (called jure sanguinis) pretty heavily. The way most Americans do it is by applying through an Italian consulates in the US, and because of the amount of applicants relative to the number of consulates, it can take up to 4-5 years. That was pretty unexciting. What’s the alternative? Turns out you can do the process by establishing residency in Italy and submitting the paperwork there, and it could be done in less than a year. Ok…that’s an idea.

Obsessive research and deliberation ensued.

(If you’re interested in learning more about the Italian citizenship process, feel free to contact me through the Contact form on this website. It’s a lot of details that would bore most readers of this article.)

Was I in a rush to get citizenship? I had no reason to rush. As a U.S. citizen, there’s not much to gain in terms of employment opportunities or standard of living. Other people with Italian ancestry (such as in Argentina or especially Brazil, which has the largest population of Italian descendants) may have more to gain by having unrestricted access to the EU. That said, I did have a fear that this weird law (let’s be honest here) had a shelf life.

Just picture it:

“Ok sir, let’s take a look at your application. You’ve never been to Italy, you don’t speak any Italian, and your most Italian qualities are a funny last name and that you’ve seen The Godfather nine – sorry – ten times. Ok – here’s your Italian ID, passport, and access to the Italian healthcare and education systems.”

That’s a grotesque caricature of the process – but you get my point.

More Than Just a Passport

In reality, it wasn’t just about the citizenship. My interest in a new experience – one abroad, and long term, was just as great. Until that point, I had always lived a pretty modest lifestyle, and since 2017 (when I became aware of the concept of early retirement, at an age when it actually sunk in), I became moderately aggressive with saving and investing, with the idea that maybe I could retire at 40 and 45 and live a life of adventure and exploration.

However, I was 29 years old and had always lived within 20 minutes of the house I grew up in. So I was learning that despite the benefits of steadfast work and saving to pay my future self, there could be value in taking a sabbatical or gap year. Whether it’s having time to explore a new culture, learn a language, or see what life would be like without the constraint of an 8-5 job.

Going to Italy to take residency and apply for citizenship seemed like a great way to give a sabbatical a dual-purpose. Experience, and EU citizenship.

So there were these two pieces – the increasing desire for a new experience, and the citizenship opportunity to make a joint-purpose out of it. The third piece (which had actually come a couple months prior) was some serious medical news about a good friend (the details of which I’ll omit out of respect for their privacy). The concept of “don’t take your health for granted” was not new to me, but it just took too long to appreciate. My mother, having suffered a rare spinal condition resulting in over 20 surgeries, always told me as such. If she could do even as little as go for a mile walk in the neighborhood, she would be doing it every day. The thought of these people close to me with serious health challenges – alongside the image of myself spending my most physically able years working a desk job – was wearing on me more and more. I had read enough Tim Ferriss (4-Hour Workweek) and Rolf Potts (Vagabonding) to be convinced that if I really wanted to do something, I should plan on it sooner rather than later, and the word “someday” was Latin for “never”.

So putting all these pieces together in my head – I decided that I would do whatever I could to make Italy happen. But how?

The Job

Would I try to negotiate a sabbatical from work? What about, “I’m going to go do this Italy thing for six months and be back on date XYZ”. Here’s the problem with that – the timeline for the citizenship process is very open ended. It can take from three months to up to a year in some cases. I knew I couldn’t give an indefinite timeline to my employer and expect them to take me back at my convenience. I had a great job as an engineer at a company with lots of opportunity – was I really ready to give that up if it was my only option to make Italy happen? What if I request to work remotely and stay on, part time? That way I could maintain continuity.

So my plan was to give three months’ notice and propose to work part-time remotely, but state clearly that regardless of the outcome, I was going to Italy. This would allow time for: a) remote work approval and development of a work plan, or b) hiring my replacement, which I was happy to help with. I very much wanted to leave the company on the highest note possible, if it came to that. Three months would also give me time to get all my citizenship paperwork in order before departing – which is critical to the process. I viewed either outcome as a win. Remote work approval, and I could have some income, be involved with some interesting projects, and maintain continuity with the company. No approval, and I would have more time to immerse, explore, and see what life would look like without an 8-5 job.

As it turns out, getting approval for working in another country when you work for a large corporation is easier said than done. Between work visa requirements (for Italy) and business case requirements (for my employer), it wasn’t so simple. If you work for a small company, you can (and people often do) work in the grey, taking advantage of the fact that Italian law has not caught up to the concept of remote work. But neither my employer nor I wanted to risk getting either party into trouble. In the end, the remote arrangement wasn’t approved. 

I gave them my last day. It was definitely bitter-sweet for me, my boss (who was fighting for it to work out), and the team. I really didn’t intend to leave after only 2 years. But that was that, and we quickly moved to interview and hire my replacement (which we ultimately did, and from what I’ve heard they’ve worked out very well).

The House

Next I needed to figure out what to do with my house. Rent or sell. According to nearly everyone, the smart thing to do was to rent it out. Yes – having a home to come back to would be great, but being a landlord is more than just collecting rent. I wasn’t thrilled with the idea of going from first time homebuyer to first time landlord while overseas. Never mind my distaste for the American fetishization of homeownership, where somehow we’ve all been convinced that you’ll never be happy and complete until you own a house. And once it’s paid-off, you reach a state of transcendence, otherwise experienced only by the most enlightened of Buddhist monks.

Resentful rants aside – selling my charming (i.e. small) house wouldn’t allow me to retire. But given that it was 2021, a sale could give me a cushion and peace of mind while abroad without, constant stress of running out of money in case my citizenship process ran long. This would not be the case with a rental property, after subtracting from the rent the property management fees, rental income tax, up front repairs, mortgage, property tax, HOA dues, and insurance.

As with many financial decisions, after running the numbers and analyzing it to a pulp, the end decision for me often comes down to a gut feeling or “follow your heart”, if you prefer. If I kept my house and rented it out, it would not be for the purpose of making money but to have a house to come back to when I returned – and nothing else. Being always drawn to simplicity, my post-analysis gut said, “sell”. So I sold.

Then I bought a one-way ticket to Florence.


I’ve been in Italy for 7 months, and the experience has been nothing short of amazing.

Many people think I’m living the dream. And there’s no doubt that I am (though if this were truly “the dream” I would have enough money to continue it forever, but I digress). It’s a combination of discipline, risk-taking, and luck that have allowed me to do this. Risk-taking, and admittedly slight recklessness, because I gave up a great job and home to move to another continent after having never really left my hometown my whole life. Discipline, because I worked and saved enough money over time to be able to do what I’m doing. And luck, not only because of selling a house at a good time, but because I was born into a great family with parents who instilled in me the value of hard work and discipline, and who supported me when I wanted to try something new (even if they needed time to warm up to the idea). In the end, I knew that if I didn’t do it, it would have always been the thing that I “wanted to do”. So I went for it.

As far as what’s been going on since then, that’s what I created this blog for. As of this writing, I have been recognized as an Italian citizen, and I have traveled to most major parts of Italy (but I’m not done). Future posts will shed more light on my experiences. If you’re interested in hearing more about my experience, check out the conversation I had with Chase Warrington on his podcast, About Abroad (update – podcast round 2 here!)

Thanks for reading.

10 thoughts on “Quitting My Job, Selling My House, and Moving to Italy”

  1. Anthony, I know your entire family is so proud of you and the courage you showed to take this adventure. I know it wasn’t easy but the trade off is well worth it. I am so proud of you too and wish you a beautiful adventure every day you are there. What you are experiencing is a once in a lifetime (for most people) opportunity! So proud of you and the amazing young man you are! Take care, Helen

  2. Auguri on the citizenship. I just found your blog because of the interactive map you created. I live in Umbria and have for 8 years but I retired at 62 so not an “early” retirement. I really enjoyed this post.

  3. I love everything about this article! You have a real talent for writing and an interesting story to tell. Not to mention how lovely it was to meet happy-go-lucky, fresh-off-the-boat Anthony in Florence! I hope your Italian dream never comes to an end ❤️

  4. Great story! It was a pleasure to meet you and I hope you keep living your dream in Italy. We need people like you. See you!

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