How to Teach English in Italy and Build a Real Income

If moving to Italy is something you've been thinking about, dreaming about, or maybe even seriously planning, I want you to join me for something I do only once a year. It's my free move to Italy bootcamp happening September the 15th, 16th, and 17th. For one hour day over those three days, I'm going to help you cut through all of the noise and actually understand what it takes for you to move to Italy. We're talking visas, where to live, renting, buying taxes, timelines, bureaucracy, and most importantly, what you should be doing right now if you want to make this happen. I've helped hundreds of people make the move to Italy, and I can tell you that people have the easiest time or the ones who understand the process before they start. So come spend an hour day with me. It's completely free. It only happens once a year. And you can grab your seat at smartmoveitally.com/themoveitally bootcamp. We'll see you there. Well hello there, and welcome back to another episode of New Life in Italy. I'm your host Samantha Wilson, and today's episode is all about one thing. How you actually work and make money in Italy, because if you're not retiring, this question shows up very quick. What am I actually going to do for work when I move to Italy? And if you don't speak Italian, your options can feel very limited. So most people start looking at what they already know, and for many, that's English. Which is why so many people ask, "Can I move to Italy and teach English?" I mean, it sounds simple. It sounds accessible. It feels like something you can figure out once you arrive. But it's not just about speaking English, it's not just about finding a job. And it's definitely not as straightforward as people expect, because there's process, there's bureaucracy, and there's a learning curve. And there's a real timeline before this becomes something sustainable. So today I'm sitting down with a woman who has actually done this. She moved to Italy, changed careers in her late 30s, built a freelance business teaching English, and now lives in a small village in Tuscany while working with clients across the country. We're going to talk about what it really takes, how long it actually takes to make money where the real opportunities are, and what you need to know before you even consider this path. So whether you're just thinking about your move or you're already planning and trying to figure out how this is all going to work, this episode is for you. I'm Samantha Wilson, and this is a new life in Italy. I show for people who love Italy and are quietly trying to figure out what it would really take to build a life here. We talk honestly about the practical choices, the emotional shifts, and the parts of this journey that don't always get talked about, so that you can move forward feeling informed, grounded, and more confident. If you're somewhere between dreaming and doing you are in exactly the right place, now let's get into today's show. So today's episode is an interview, and I want to set this up properly because I think that this story is incredibly relatable for so many of you listening. I sat down with Ashling, who is originally from Ireland, and has not been living in Italy for about 10 years. And her story is not the usual, I moved to Italy, and everything just magically worked out. She had a full career in Ireland. She was working in the arts and cultural management, including with a bunch of different opera companies, and then she made the decision to move to Italy for love. And like so many of you will face, she had to start over, a new country, a new system, no network at all, and a career that didn't translate here in Italy. So she asked herself the same question that so many of you are asking right now. What can I actually do when I move? And like many expats, she turned to teaching English. But what I love about her story is that she didn't just treat this like a, like a temporary solution. She actually built it into a real career. She got her Tefal certification before moving to Italy. She landed a job within, I think, a month being in Milan. She was teaching business English to corporate clients. And then she made a decision that most people in Italy would never, ever make. She walked away from a permanent contract. Which if you know anything about Italy, this is a work contract that is considered one of the most secure and desirable positions that you can have. In fact, a lot of Italians will have, you know, parties if they get this permanent contract. But she gave it up and she chose to go freelance. And this is where the conversation can get really interesting because we talk about what it actually takes to build a freelance business in Italy, teaching English. But we also talk about something even more important. And that is how it all actually works in Italy because it's not about sending emails or about submitting resumes that you might be used to in Italy. It's about relationships, Ashling literally built her business by walking around Milan, meeting people face-to-face, knocking on doors, old school stuff, you know, having conversations and building trust. And that is such a key takeaway because if you don't understand that one piece about Italy, nothing else will work the way you expect it to. And this goes for everything that you want to do from building a business to building your friendship circle to even finding a plumber. I mean, it's about relationships here. It is so important to understand that. Now we also talk about income and how long it realistically takes to build something that's stable. And she says it's about two years, not two months, not six months, but two years of building these relationships, delivering quality and growing your network because it takes time for people to talk about you, to get to know you, and trust you, and then tell their friends about you. And she's taken all of this experience and turned it into a book that actually walks people step by step through how to build a freelance English teaching business in Italy. So if this is something that you've been thinking about, this conversation is going to give you a very real look at what that path actually looks like. Well, hello, Ashling. Welcome to the show. Thank you. It's a pleasure. I am really quite excited to talk about this because a lot of people that I speak to, their idea of moving to Italy, of course, isn't always just to retire and drink wine all day, although, you know, a lot of people do dream of that too. But really a lot of people think about, what am I going to do? What is my job going to be or, you know, what can I do if I can work? And a lot of people lean into language because I think this is a common thread for expats all over the world is to teach English in the new country that they're in. Yes, absolutely. I think it's really, I suppose, if you're thinking also of having to change your career and then moving to a country where English is not the main language, English teaching really comes up as the number one thing to do to be able to at least start working in that country. So I think it's a popular choice for a lot of people who come to Italy and are, let's say, still of working age who don't have the luxury to come and retire, as you say, and then sit behind all day, right? So again, and obviously people think while I speak English, you know, it should be an easy thing to do for a living, but it isn't. It's not just, I think, an easy thing to do as a job. But when we're in Italy, we're talking about a lot of bureaucracy that surrounds everything that we do here. And I do want to talk about that. But first, I want everybody to understand a little bit more about who you are and where you live now and you did talk a little bit there about changing your career. So maybe you can just let everybody know a little bit more about yourself. Sure. Well, I'm from Ireland and I've been living initially for 10 years now. And I guess the reason I'm here is because I'm married to an Italian, so I met my husband in, actually, in Dublin, and then after a year or so of the long distance relationship, I decided to move to Milan where we were at the time. My husband was living there at the time. And in order to do that, to make that move, I had to change careers because in Ireland, I was working in arts and cultural management, so in a very different career. So I was also a creative director of a theater and I worked on the project bases with different arts organizations and opera companies also for an orchestra. So this was my kind of work. But moving to Italy, I knew that that would be quite difficult to make that transfer from working in that area. industry in Ireland to Italy, also without any contacts, you know, that industry also is very much based on your contacts, the relationships you've built up. And I had no relationships in that sense with Italy. So thinking about making the move, I thought, okay, well, what can I do? You know, I was 38 at the time, and you know, so still, you know, mid-career to work. And so I thought, okay, I'll look at teaching English. And so before I made the move while I was still in Dublin, I completed a Tefl certificate, which is for certificate for teaching English as a foreign language. So that then prepared me for when I made the move to Italy. And I actually, within a month after moving to Italy, moving to Milan, I got a full-time job teaching. So I was actually working with one of the big five consultancy companies. And teaching business English, helping the senior managers and partners to improve their communication skills in the English language. Right. Well, do you find there's a lot of work for that, you know, in business English? I know there's a lot of tutors and language schools for, you know, just everyday life. But what about, you know, this area getting into the business world? Well, I absolutely, in Italy, unfortunately, still ranks quite low in terms of the English language skill on an international business level. Actually, business English is a very, there's a lot of opportunity initially for this kind of work, because also now, you know, with global business, it's so vital for Italian companies to be able to communicate well in English. And this actually was the area that I chose to particularly go into. So working in corporate environments and working with business professionals. Right. And so you work, I think you had said that you got a job in Milan with one of the major companies, I guess, at Teach Business English. And did you continue there or did you change? Yeah, so I am in my first year, I had a contractual tempo in determinato, which is, let's say, one of the most sought after contracts, initially, in terms of work, because it's a very stable and secure contract. Yes, you have parties, you have house parties when you get one of those, initially. Yes, and so, and so then after a year, when I decided I was going to give that up to go freelancing, everybody thought I was crazy. Crazy, yeah. What, what are you doing? I go trying to go freelance when you have this contract, which is no so protected. But really after the year, I learned a lot in that first year. But for me, I just realized it, working under this kind of contract and working for another company didn't, didn't release suit me, also because I had come from being freelance in Ireland at that point. And I missed that, and I was very used to managing my own my own work, my own business, and I just thought, no, I really want to give that a go here too. And also just to give myself that more control over my time and freedom. And also the freedom to really enjoy life in Italy, because that was something that under the original contract was more challenging because I found it more restrictive, you know, because I was told when I could take my holidays. Exactly. And yeah, and you're working in Milan, which is an entirely different world in Italy anyway, for the work world, right? This is a lot more intense. Absolutely, it's very intense. And then, you know, you're obliged to take your holidays around Faragosto, you know, always in August when everyone else is on holidays and maybe the more expensive time to go on holidays. And I was just really looking for a bit more freedom, also freedom in terms of my time, but also freedom in terms of choosing my, choosing my clients who, who I wanted to work with, who I resonated more with in terms of, you know, investing my, my own time and my own business. So, yes, I, I made that decision. I even though everyone thought I was a bit. Yeah, started, started going freelance. So, tell me what it actually takes, you know, to set yourself up as a freelance or freelance English teacher, especially in this category of business English. What did you have to do for that? So, setting up here is very different to my previous experience of setting up in Ireland, because in Ireland, it's quite simple to go freelance. There isn't a huge amount of bureaucracy around that. Whereas here in Italy, it's quite structured. So, the first thing you need to do is open Partita Iva, which is basically your, your tax code that defines you as self-employed in Italy. And it's, this is really important for everything that you, the business that you do going forward in terms of your taxes, your tax declarations. And you're invoicing in terms of the, of the, the tax and taxes and reporting, et cetera. That is something that it was very different. The whole new world, right? Yeah, yeah, because in, in Ireland, I could do it myself, you know, I, you know, it was a small business and, and I could do my tax return myself, all my accounting. It was very straightforward. Here, it's not so straightforward. And you really need to have a very good commercialista or a tributarista. So these are the, the, the, the two principal figures who would help you with your, your accounting and, and tax. Here, as, as I'm sure, this has come up in a lot of your other podcasts, it's, it's not simple to, um, to manage the, the tax system initially. And you really have to rely on a professional who's going to really guide you through it and, and, and make sure everything is, is, is all correct. That's right. Because the penalties are enormous if they're, if it's not correct. But also, you know, I think that when you're working, especially, I, what you're talking about is working with businesses to help them with their English, they're going to want to be sure that you can invoice them correctly because they want to write it off as an expense. So all of this needs to be done not just for the professionalism, but also for the tax reasons. Oh, absolutely. Yes. And, and even in the 10 years I've been doing this, things have changed because when I started out, you know, the invoices were paper. And I would send paper invoices. And then you had to buy Marco da Bolo, which is like a little tax stamp that, and that was a physical stamp that I have to stick onto the paper invoices. And, but recently in the last few years, the legislation has changed. And now it's necessary to send electronic invoices. So, um, in the one, and the one hand, it makes things easier from a reporting point of view. But then it does add that extra level of work where you need a platform to be able to issue these electronic invoices. And then the, the, the stamp is no longer a physical stamp. You also, I'm add that into your electronic invoices. Right. So tell me about besides the, you know, bureaucracy, which is a very, very deep rabbit hole, especially in business side of, I always say to people with, with the business in Italy that honestly, this country has so much to offer. It really, in my opinion, has the best of everything. If it would just fix the way business is done and the bureaucracy, this country would be unstoppable. And I talk about it all the time. And even from the point of, you know, a large business to even a smaller freelance business, the same problems run through both way, you know, both versions. And it's one of those things that need to be fixed. But in order for that to even be a problem, you have to have the business in the first place. So, can we talk a little bit about, you know, how did you find your clients? How did you even get started? Sure. Well, when I started originally, I did a lot of walking around Milan and meeting, just, just going to meet lots of different organizations. I really just got a out there and when spend, I invested quite a lot of time in going in person to meet people and really that's how things work initially. It's building relationships, getting to know people, you know, people are curious, they want to get to know you, you know, they will really decide to work with you based in my experience, based more on an initial meeting, rather than necessarily all your qualifications and experience, you know. Right, it's not about email here, you don't email to picture services, it really is about relationship building. Absolutely. Absolutely. And what I found also, you know, with going to meet people in lots of different, lots of different businesses and types of companies, that a lot of the relationships, they really come from that initial conversation that chat of telling them your background and then they're curious about where you come from, what you might bring to them. For more than what your qualification is, I mean, I rarely talked about my tiffle certification or even my primary degree, very much in these conversations, they always kind of went somewhere else. And then these, yeah, the relationships came, came from that, from being given a chance from being, yeah, building up these relationships. Right. Right. So you brought on your clients and you work remotely, you work from home? I do. Now I do. So I'm living in rural Tuscany now. So five years ago, we made them move from Milan. So it all coincided with COVID. So it's a kind of a long story, but COVID hit. And we were in Milan in the, like, the epicenter. Yes, for sure. I also had discovered I was pregnant just before COVID broke out. And we already had bought a house here in Tuscany, which we were using really as a holiday home, but also we were renting it out. So we had done that for a year. And then it was going well. But then when COVID hit, all our, you know, the cancellations came in and we had a new baby and we said, okay, let's just move there ourselves, because we were in a, we were in a nice apartment in the, more or less the center of Milan, but it was, you know, on the top floor, the lift didn't go all the way up. It wasn't really conducive to having a baby and a roller. And we said, okay, at that point, all the work had already gone online. And so I, you know, life in Milan for me was hopping around the city between the Metro and the trams going from, you know, company to company from the university where I, where I teach and to different, different companies. And then all of a sudden with COVID, everything then went online. And it stayed online. So, so when we made the move here to Tuscany, I, I've kept all my clients. So most of my clients now are, are still in Milan. I had some in Rome also, but it's, it's just all gone online. So life has changed a lot. I know, I think it's one of the, one of the major shifts I know here in Italy through COVID was pulling Italy forward into this a little bit closer into the digital way of doing business and communicating. And, you know, I guess in a sense, that's one of the pros that came out of such a horrible time. But, you know, I know that during, not well recently, you have also written a book on freelancing English. It's called, I think freelance English teaching in Italy had to find high paying clients and build a sustainable career. And I think it is such a great, really a great resource for people because as I said earlier, a lot of people think about this, but I do want to quickly just note that you are Irish and you are married to an Italian. So the work visa wasn't something that you had to consider. Obviously, if people want to move to Italy to teach English in any capacity, they either need to be European citizen, marry to or of course, a visa. So let's just talk about perhaps from the level of somebody can move and live and work in Italy. They're already beyond that visa piece or that immigration piece. Tell me what you think they should do. Like, what are the first concrete steps that someone should take in order to replicate in a sense, which you've done? Sure. Well, I mean, the first thing is to complete a tackle certificate. So one of the certificates to be able to teach English as a foreign language and generally speaking, you would also need a bachelor's degree. So these are, let's say, the minimum requirements for teaching English in Italy. So my book focuses on the path as a freelance English teacher. A lot of people when they first arrive and work for language school, which can be, you know, really great experience also for people who've had to change career and come here and maybe they don't have a lot of teaching experience, prior teaching experience. So working for language schools has a really great place for people starting out. In terms of freelancing English teaching, this is where you can really have the opportunity to increase your income because with the school, there will always be a limit on your hourly rate because naturally, the school has lots of overheads, et cetera. So in terms of setting up on a freelance basis, the benefit is you can go after contracts that then you're getting to keep 100% of those. Exactly. Okay. So going back to the business English, the great thing about this business English courses is that Italy actually invests a lot of money in this. So for a lot of companies, there is special funding allocated for this for professional development and especially for English. So you have a lot of opportunity to win these kinds of contracts that are basically for government funded programs. Right. That's very important for people to know because if you're trying to sell your service, you can always explain to the business that might not know about it, that they could get a, is it a subsidized? Yes, it is. It is exactly. And then also, for example, there are a lot of consultancy companies in Italy that actually work to obtain this funding for their clients. So for example, some of my clients are consultancy companies who then hire me because they've already maybe successfully obtained the funding on behalf of their client. And then I work with them to actually provide the course for the service. For the service. Well, that's smart. Yeah. That's a great way in. Exactly. Yeah. So how realistically, how long does it take for someone to build a stable income as a freelancer here, as a freelance English teacher here? I know this could be, I guess, how long is a piece of string? But generally speaking, what should people expect? Because it's different in Italy. Things aren't quite as usually as quick. Sure. I mean, I think within two years, I think you can. A lot of it goes back to that relationship building. And just being able to, you know, deliver quality courses because it's all based on, you know, the quality of your work at the end of the day. And if a company is happy with that, you know, and so in terms of the big business English courses, a lot of the work also, it's not just when you're freelance, it's not just preparing the courses and the teaching. It's all the other activities of looking after those relationships with your clients, with the HR department. And once you really manage those relationships well and work well with those people, you will, your work will keep coming back to you, you know, you'll have more courses and more courses. And also be recommended, which is what's happened to me, but from company to company, or you might have a contact in one company who then moves to a different company. And they take you with them, you know, and that's also happened to me, which is wonderful, because then, you know, you're working for two companies, but from the same source. Yes, that's really good. So culturally, maybe this is a little bit different, or do you think it's the same as in Ireland? It can happen also in Ireland in terms of the, yeah, the relationships, but But here, I think some of the differences are, you know, I think over here, they don't, in my experience, haven't, you know, checked a lot of references, for example, maybe in Ireland, they ask more for references from other employers and written references, and it might be a bit more formalized. And so here, it's something that surprised me because knowing how much Italians love their bureaucracy and paperwork, I did find it strange at the beginning that they, I wasn't asked for written references from previous employers, really, they really, you know, accepted what I said and didn't always look for proof or even proof of a qualification. I was actually rarely asked to provide the certificate or a copy of my degree. So in terms, in terms of that, you know, it was a bit, yeah, surprising to me. Well, I think that speaks again, you know, what we said at the beginning, this country is built on relationships, and even when it comes to starting your own business, a freelance business, then it's those relationships that will not just get you through the door, but that will carry you all the way down the road, right, that will continue your business. Oh, absolutely, 100%, it's about the relationships. Well, Ashling, this has been such a great conversation, and your book, I'm going to put in a link in the show notes. So everybody who is interested in thinking about teaching and moving to Italy to teach English, I highly recommend that you get to the show notes and you find it and use it as a resource because it's really very helpful. Is there anywhere else that people can find you online? Well, I've on LinkedIn under Ashling Sullivan. Yeah. I'll put that on the show notes as well, so if you need to get a hold of Ashling, that's where you can find her and also find her book in the show notes. Ashling, again, a real pleasure to meet you and good luck, and I'm sure we'll chat again soon. Thank you. Thank you so much, Samantha. So here's what I want you to really take away from this episode. And that's the first reality check. And that is if you are not an Italian dual citizen or the spouse of a visa holder or a visa holder yourself, then you cannot work in Italy, also not teach English in Italy. So before you dive down that Google rabbit hole, make sure that you have the immigration piece squared away. Now, second, working in Italy will mean that you will have to change how you work. It's different here, and I can feel a little bit uncomfortable for some people. It can feel uncertain, and at times it can feel like you are starting from zero, and in reality you are. But what Ashling's story shows us is that starting over doesn't mean starting from nothing because you are still bringing your experience, you're still bringing your skills, and you're able to adapt. And then once you're here, you can build something new in a way that actually fits the life that you want here. And practically speaking, if you're thinking about this path, here's what I want you to focus on. Number one, make sure again that you can legally work in Italy. Take care of immigration first. Get qualified before you come, understand the legal and tax setup very early. Be prepared to build relationships, this stuff takes time, my friends. Don't just send in applications and do not just email people. You'll need to speak to them. And give yourself time real time to build something sustainable. Because Italy rewards patience. It rewards consistency, and it rewards people who show up and stay. And if you can do that, there's absolutely a path for you here. Now, if you want to learn more about Ashling and her book, I have linked it to the show notes, and I highly recommend it if it's something that you're seriously considering. And if you're at the stage where you're trying to figure it all out, and your move and your visas, and your planning, well, of course, that's exactly what we can help you with. All of the links are in the show notes. It's time for listener questions. My team has picked three listener questions all left on our voicemail. I have no idea what these questions are, but I haven't been stumped yet. Are you ready? Let's get started. All right, my friends, it's time for question time. Question number one, can I legally freelance in Italy on a visa? And which visa actually allows this? All right. Big question. So we talked about in this episode about becoming an English teacher or teaching English in Italy, but the reality is you have to get your immigration settled. So the kinds of visas that you can work as an English teacher in Italy are your self-employment visa. Investor visa, if you are a spouse of a visa holder, like you're the spouse of a digital nomad visa holder, the spouse of an investor visa, the spouse of a student visa, all of these things can help you or allow you to work in Italy, or you're the spouse of an Italian resident or the spouse of a European resident. All of these reasons can allow you to work in Italy. Now, a little bit of a note, the self-employment visa in Italy is excruciatingly hard to get. If you can qualify for any of those other visas, it is always better to do. Now, also remember that you cannot start a business and move to Italy as the business owner. So if you're thinking, well, I'm going to start a business teaching English to business people in Italy, and therefore I will move to Italy and work in this business. This is not possible. You need to have another visa in order to come to Italy first and work. Now, if you need more visa help, there is a free guidebook and I've put the link in the show notes so you can read more about each of those because it's really quite detailed, almost a podcast itself. Question number two, how much does it really cost to set up a partita Eva and run a freelance business in Italy? So as a reminder, a partita Eva is like a little business, think of it like an LLC or an incorporated a little business in Italy, and you'll need to have one of these when you are running a business when you're making more than actually 5,000 euros a year in Italy. So to set one up, you will need a commercialista, which is like a CPA or a tax accountant here in Italy. And the cost to set that up is about five to 700 euros, really depending on the structure that you're building. Of course, if you're setting up a big SRL, which is a much larger type of a company, which you won't be doing in this case, but if you were, there's different ranges. But just for a small, simple partita Eva for teaching English, about five, 700 euros. And the taxes you'll have to talk to your commercialista because it depends on the regime, the tax regime that you have elected. If you are new to Italy, there's lots of great tax incentives from a flat 5% tax to impatriate, which is 50/50, 50% of your income is taxed free and 50% is taxed at regular Italian rights. Now, I do have an episode talking about different tax structures in Italy that you can have a listen to while linking in this episode. But those are the two things you need. The best takeaway here is you need to contact a commercialista in Italy. And we also have a couple of those, too. You can head over to our website to learn a little bit more. Question number three, can I come on a digital nomad visa and teach English? Now, this is a very interesting question because there's a couple of ways I can attack this question. Number one is if you are the spouse of a digital nomad visa holder, then yes, you can come here with the spouse and you can teach English. You can actually do anything you want. The digital nomad, however, is restricted to the activity or the work that they've claimed that they do to get the visa. So the question is, if your existing business with existing clients and you have a degree in teaching or something related and your business is teaching English, then technically yes. You can come as a digital nomad and come to Italy and continue to do your English teaching online as a remote worker. But keep in mind, you cannot be working for Italian businesses on the digital nomad visa. So this is where your restriction is going to be. So if you're thinking of moving to Italy to start a business in Italy and teach Italians, say business English like Ashling did, the digital nomad visa is probably not the way to go because it'll be with an Italian company. But if you're this spouse of a digital nomad visa holder or even a student visa holder or investment visa holder and absolutely anything you like. Before we wrap up, I want to remind you of something. You don't need all of the answers right now. You just need the right questions and the space to think clearly. If this episode helped you feel more grounded or less alone, that's exactly why the show exists. You can find all of the links and the resources that I mentioned in today's episode in the show notes. And if you want to go deeper, head over to smartmoveitily.com for more ways that we can help you make your move to Italy a whole lot easier. And if you're enjoying the show, subscribing, leaving a review, or sharing it with someone that is also dreaming about Italy, helps more than you know. Thanks again for spending time with me. I will see you next week. Ciao for now. now. It's my free, moved to Italy bootcamp happening September 15th, 16th, and 17th. For one hour day, over those three days, I'm going to help you cut through all of the noise and actually understand what it takes for you to move to Italy. I've helped hundreds of people make the move to Italy and I can tell you that people have the easiest time are the ones who understand the process before they start. It's completely free, it only happens once a year. We'll see you there.