My guest in this episode is Damien O’Farrell – Managing Director of Damien O’Farrell Mobility Services. His company is a boutique destination service provider specializing in bespoke relocation and immigration services, but also coaching programs aimed at expatriates who want to elevate their lives both personally and professionally.

I actually saw him in an article about Italy in digital nomad visas, and from that, I reached out to him. I’m really happy to have him on the podcast because he has a unique story. He’s been living in Italy for the last 34 years. What brought you to Italy?

Unlike a lot of other people, Italy was never on my radar. Circumstances brought me here in the spring/summer of 88, and I should have been here for two or three months. But I started working and things started happening and one year became two, two became three… And before I knew it, this was where I started to call home.

And then around 1990, I found myself in a situation where a lot of people were asking me how to do things: how to exchange a driver’s license, how to get a permit of stay. So I put together my first course, how to live and work successfully in Italy, and it’s still going today. We’ll be doing it next year in 2023. We stopped during the pandemic, but we will do it again next year. The reason why we stopped is because it’s a face-to-face meeting. I think a lot of people get a lot more out of events if they’re face-to-face. Then that led into my journey of global mobility.

You were about 30 years ahead of this global mobility curve. But what was it like when you moved to Italy 30 years ago? Can you also highlight the changes that took place between then and now?

I think if I had known how difficult the first two years would’ve been, I’m not sure I would’ve stayed. But when you’re young (maybe because you don’t know certain things), you have a higher bar for putting up with things and going through obstacles and difficulties.

It’s still challenging for people who move today. Certain things may have gotten easier as you can do certain things on your own. More information is available because of the internet which opened up the world for a lot of people at the same time. But it’s a double-edged sword because there’s a lot of misinformation, especially regarding the digital nomad visa. So, to answer your question, it’s still challenging to move. There’s a reason why it’s called a foreign country. I think if you move to a country where you don’t speak the language, you’re going to have a hundred times more problems. If you at least speak the language, it really helps. However, some of the most challenging relocations are from the United States to the UK and vice versa.

Did you speak Italian before moving to Italy?

Not a word.

What are some major issues that people overlook when moving abroad?

That it’s going to be a lot of hard work. Unless you’re independently wealthy and you’re coming with a lot of funds, you’re going to have to work and navigate the system without the language.

Some things are faster now. For example, bureaucracy, while still moving at a glacial pace, was even slower back then. It can take a long time to get things done. You don’t know if what you’re being told is really accurate. You could go down a rabbit hole for months and it leads to nothing.

Language is the other thing. If you don’t know it, you feel like a child because when you go into a bar, you have to point at what you want to eat. And also you lose your personality because even if you learn the language well, you are never really as funny in a second language as you are in your first. I would say the language is the most challenging thing and then getting work if you have to work.

Humor, of course, is a whole other discussion because each nationality finds things funny that maybe another doesn’t. I think Italians find me funny when don’t mean to be funny. They sometimes find my mindset funny which is interesting. But I don’t try to change anybody. You are never going to be happy if you try to change the local population. They are who they are, and you have to embrace that. And if you do that, that’s going to put you on a road to a more successful relocation.

But that brings in another point because you really have to ask yourself, is this a permanent move or is it a temporary one? What are you doing? Because if you are putting down roots, that’s a very different type of relocation.

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What are the benefits within your own mindset and you yourself – what good has come out of you being an ex-pat in another country?

I’m a foreigner in Italy. The thing about most of Europe is that no matter how long you live in a European country, you are always a foreigner. There are some countries, and once you gain your citizenship, they embrace you into the country. Europe doesn’t normally tend to be like that.

Expat in the true sense of the term in the world of global mobility is usually somebody who’s on an overseas assignment. And then they leave after a while. But if you come here permanently and you put down roots, you’re probably a foreigner like I am. You can use that to your advantage or you can use it to your disadvantage. So you can either blame it on everything that goes wrong, or you can look around and say, okay, I think I can do this better.

It sounds like a bit of a struggle. In your mind, how does being a foreigner and moving abroad benefit your mindset?

I was always very open to other cultures: even as a child I was listening to music in other languages, as they really attracted me. When I would hear someone on the street speaking another language, I was automatically attracted to that. Foreign for me was a good thing, so when I went abroad. I was really happy to be in a different culture despite the challenges. So my mindset was open to that.

To pick your mind on that entrepreneurial side of things…After living in a country for a long time, do you still find ways to innovate?

I do. I think Italy is a gold mine of opportunity with regard to the service industry, hospitality, and IT. However, you might have to tweak your approach and you have to be looking for the advantages. You also have to remember that what worked 10 years ago in Italy may not work now. So you’ve got to try to be a prognosticator in the sense that you’ve got to try to see what’s coming down the road.

With the onset of the internet era, much has been disrupted. Local people will not necessarily be getting work now because people are hiring others online. You have to look at that local market and see what it really needs.

I’m going to say something that’s a bit provocative, but if you didn’t have that get-up-and-go mentality in your own country, you’re probably not going to have it in a foreign country.

Again, if you’re thinking long-term, then you’ve got to get granular and ask yourself what the market needs. That’s what I did with Global Mobility. I knew that certain things in global mobility weren’t going to work forever, so I had to pivot or be unemployed.

You’ve relocated or been a part of 10,000+ individuals relocating to Italy. If we think about individuals who are electricians, for example, they can’t really very easily obtain a digital nomad visa specifically to Italy. So where and how do those people come over and what category do you find them a visa for?

An electrician would be a highly skilled job. You have to get certifications and licenses in most countries to go out and practice it. So then that would put you into a different category. You could start looking at a self-employment visa, or maybe a company will hire you and if the job description and your qualifications match what would be deemed a highly skilled position, that’s a pretty straightforward visa to get.

Is it possible for an electrician to move to Italy?

Nothing is impossible. I worked with a woman from the US. It took her five years to get here. We worked on her getting a job with a company in the States that had a presence in Italy, and that’s how she came over and started her life in Italy. But most people wouldn’t have the patience or the desire to do such a trick.

You mentioned going down a rabbit hole sometimes and yielding nothing. How can you prevent going down the wrong path for a visa application?

Well, one of the things that you have to make peace with is that when it comes to immigration and taxation, you’re going to have to spend some money. If you’re going to try to do it on your own, you could have problems further down the road. You have to remember that if you go into these ex-pat forms on the internet, you’re going to get a hundred different answers to your questions.

And if it’s a general question, that’s fine. If somebody’s asking, how do I get a tax code in Italy? That’s a general question. You go to the local tax office and you apply. But if people start saying, well, what are my taxes going to be in Italy? This is very case specific. So you need to make peace with the fact that you will have to spend money working with some professionals. And if you do that, you will save yourself a lot of time.

For example, right now, a lot of people are waiting for this elusive digital nomad visa in Italy. And to be perfectly honest with you, they’re just wasting valuable time. Instead of looking into alternative visas, they’re waiting for something that might never come.

How many other options would people who are waiting for a digital nomad visa have?

A digital nomad visa is a very specific visa. The one that Italy put together was not done with any type of test assessment or impact assessment, so it doesn’t make a lot of sense in many ways.

If you look at the Maltese digital nomad visa, it’s very clear. The criteria to meet to get the visa are very specific. You are supposed to stay one (maximum two years) and then you’ve got to go. That’s what a digital nomad visa is. It’s not supposed to be a visa that leads to citizenship or permanent residency or anything like that.

The next alternative for someone who would want to spend one to two years in Italy would be a self-employment visa. But that’s complex because it’s managed within the quota system, which is like the green card lottery in the US. There’s a certain number of visas and hundreds of thousands of people applying.

So there’s a possibility you would not get the visa. But then that would also entail that you would have to be tax compliant in Italy, which might not be favorable for you. So before you go down that route, you would have to talk to a tax expert. So really, if you’re looking at a short-term experience that would be in another country under the digital nomad visa, there really isn’t another alternative.

There is no digital nomad visa at present for Italy. Will it come by the end of the year? Possibly. Right now we have a government that is deluged with other problems. So I’m not sure that the digital nomad visa is high on their list of priorities.

Plus, I don’t think it was conceptualized correctly. I think there are a lot of missing pieces. First of all, it’s managed under Article 27 of the immigration process, which is for highly skilled workers, which in some cases can mean a master’s degree. In Malta that’s not required – what matters is that you have a job that can be done remotely. Italy’s going down a different route.

Having that master’s is something unheard of in these digital nomad visas. Do you think having a master’s degree is going to be required for the Italian digital nomad visa?

Well, they’ve already said that it’s going to be handled under Article 27, which is specifically for highly skilled individuals. You also have to be tax compliant, which means you have to have your taxation registered in Italy. While there are some taxation categories that are better than others, I don’t think that’s going to be attractive to a lot of genuine digital nomads.

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A lot of the people that are looking for this digital nomad visa are trying to use it as a backdoor into living in Italy permanently, and they’re just wasting their time doing that. They need to focus on another visa.
A lot of the people that are looking for this digital nomad visa are trying to use it as a backdoor into living in Italy permanently, and they’re just wasting their time doing that. They need to focus on another visa.

You were talking earlier about disrupting the space. Do you foresee these digital nomad visas, depending on how the regulation rolls out, disrupting the typical path that people pursue to obtain long-term visas?

I don’t think they’re really moving the needle because the people that come on a digital nomad visa are not really working locally, so they’re not bringing any know-how into the local market. They’re bringing money somewhat because they rent an apartment, they may go to restaurants and whatever. I don’t think that’s really the visa that’s going to disrupt any country. In fact, in Portugal and Spain, and Malta, the ones that are really moving the needle and making a difference are the ones up at the other end – the golden visas.

Does Italy have a golden visa?

No, but they have an investor’s visa which is different. Again, the internet is calling that the golden visa. It’s not. I see so much misinformation. It’s an investor’s visa. You can invest money in a company and you get an investor’s visa.

The golden visa in Spain, Portugal, Malta and Greece revolves around buying a property, renting a property, and so on and so forth. It’s very different.

You have hyper-focused on a niche. What were your reasons to do so? And also what are the pros and cons of niching down?

When I was doing what I call general relocation, which was working with multinationals. The reason why I wanted to get out of that is that I could see that everything was becoming about price. I just knew that if I continued on that road, I would have little to no margins.

Global mobility is very labor and time intensive. A work permit in Italy can take nine to 10 months – it goes on forever. I felt that it was time to work with clients that understood that if they wanted service up to a certain level, this was going to cost because otherwise, I was going to be in a deficit. You have to recognize when what you’re doing has reached the last stop. You can have many good years, and then that business model, for some reason or another, doesn’t work anymore.

For example, a lot of generation Z people are actually energized by a challenge. So companies recognized that, and they gave them less and less assistance, which meant that they were buying fewer services.

Do you see Italy being the most competitive digital nomad visa in Europe?

Based on what I know now, I would say it’d probably be the least competitive digital nomad visa, without a shadow of a doubt. I just think it’s too complex. And I think it’s targeting the wrong market.

Most people that are digital nomads are IT people or they’ve got some job they can do remotely. They do coding or they might do data entry. They may not have a master’s, or they may not have other documentation to prove that they’re so-called highly skilled individuals, even though they may be very skilled in what they do.

So I think Italy needs to re-look at that part. It’s like in business. The basis of business is you’ve got to market to the right audience. And if you’re not, you have a problem. You’re not going to have a business.

Some of the restrictions that they put, or requirements for obtaining a visa, like the digital nomad visa just make no sense. For Croatia, for example, you have to go with the homeowner to the consulate to actually apply. That makes it so difficult, especially if you’re renting an Airbnb. What do you think about the requirements for obtaining a digital nomad visa?

Whoever implemented the visa is not in touch with reality. There’s a disconnect. Yeah. It’s like an EU citizen. An EU citizen who stays in another EU member state is supposed to register at the town hall within 90 days if they’re going to be there for over 90 days.

But no town hall in Italy will register you for six months. They’ll just say it’s a waste of time. So in theory, this person is not compliant. And again, that all needs to be revamped, so there should be some type of short-term registration that takes into account Airbnb.

Also, in a lot of European cultures, people are cautious about anything that has to do with the authorities. So an owner might feel exposed in some way going to the town hall. It’s just too complicated.

Do you think that issues with visa implementation is a Schengen EU problem to address, or is that going too far?

I think the problem in Europe is similar to the US in a certain way, in that either you make things federal or European-wide, or you’re always going to have these problems. Because if you have a situation where you can do something in the Netherlands, but then if you go over the border into Belgium, you can’t. Or if you go from California to Nevada, you’ve got problems. I think that’s where a lot of the problems are.

I think that we need to harmonize certain things, and we’re getting there because in May of next year, the exit and entry system is going to come into place which means that every non-EU person entering who’s not a resident will be fingerprinted and photographed like in the United States. So they’re going to know when you’re coming and going. This is really going to limit people to the 90 days. They are beginning to harmonize the thing at a European level. But it would be nice if there was a European digital nomad visa for Europeans traveling that would cover you in all the countries. That would be wonderful. But that’s going to take a while.

Would the Schengen visa be the most ideal for non-EU citizens who want to relocate in the EU?

No, because you can’t work with a Schengen visa. The Schengen visa is essentially for non-EU people that need a visa because people coming from the US or Canada, can come in visa-free for up to 90 days, and then they have to go. So the Schengen visa is pretty useless if you want to work. You’ve got to have some type of national long-term visa.

Will the biometric scan system that is going to be implemented soon be EU-wide?

It will be implemented in all of Schengen, which means that it’s going to be exactly like how it is in the United States. In the 1980s, Europeans would go to the United States and they would overstay their visa, and many of them were able to get back out of the country without too many problems because there was no technology.

Then in the United States, they introduce a system whereby when you enter, they take your biometrics and when you exit, they do the same. So they know exactly when you come in and when you go out.

This system is supposed to be active in May of 2023, right across the Schengen area. So let’s say for example, you entered the Schengen area in Barcelona and Barcelona fingerprints you, they take the scan of your face and all of that and you hop over to Greece. So then Greece on the way out will do the same. It will come up on the screen. Oops, you went to Barcelona five months ago, so you’ve overstayed by two months. That’s a whole different ballgame.

When someone calls me and tells me they’ve overstayed in Italy, I’d say, well, don’t do a connecting flight in Zurich or Amsterdam because they are very stringent. But in Italy, it’s starting too.

To finish up, the question I ask all of my guests…if you could take all of your life experiences, turn around, and give someone one piece of advice from those experiences, what would it be?

Spend time abroad. It’s one of the best life experiences you will ever have because you end up appreciating your own country more.

If you travel abroad, you’re going to find out one of two things. You’re either going to realize how much you love your home country and never want to leave again, or how much you love other countries and want to continue traveling. So there’s really no downside to that.

The thing is that many ex-pats are kind of in two camps. Either they’re very negative about the adopted country or they’re the other extreme where everything is wonderful. I think there’s a lot of good stuff, but there’s some stuff that’s not so good also, and that’s why I’ve never understood when people say, well, I only want to make friends with Italians. I always thought, I just want to make friends with nice people. I don’t care where they’re from.

To wrap up, where can people find you? Where can they reach out to you? Where can they follow all the things that you’re involved with?

Well, they can reach out to me on my website, which is, and then I have a community-based Facebook group called Ultimate Italy. It has over 16,000 members and it’s a really good place for people to share information. When I have some time, I drop in myself and answer some questions, but it’s a good place to be to ask questions of the other members.

Damien, I appreciate your time so much and look forward to having you back.