
Show Notes
Thinking about moving to Italy but not planning to retire? Then at some point, probably soon, you'll face the question: what am I actually going to do for work? In this episode of A New Life in Italy, Samantha Wilson sits down with Aisling, an Irish expat who moved to Italy, changed careers in her late 30s, and built a successful freelance business teaching English to corporate clients. If you’ve ever considered teaching English in Italy, freelancing, or starting over in a new country, this episode gives you a real, honest look at what it actually takes. Because the truth is… it’s not just about speaking English. It’s about qualifications, bureaucracy, relationships, and building something sustainable over time. Aisling shares her 10-year journey from working in the arts in Ireland to teaching business English in Milan, and eventually creating a flexible, location-independent career from her home in Tuscany. You’ll learn how she got started, what surprised her most about working in Italy, and why relationships matter more than resumes in the Italian business world. This episode is essential listening if you are planning your move to Italy and want to understand how to realistically support yourself once you arrive. What You’ll Learn in This Episode: How to teach English in Italy and what qualifications you actually need The difference between working for a language school and freelancing How to set up a freelance business in Italy, including Partita IVA Why you need a commercialista and how taxes work for freelancers How to find clients in Italy and why networking is everything The reality of Italian bureaucracy when starting a business How long it takes to build a stable income as an expat Why business English is one of the biggest opportunities in Italy How COVID changed remote work opportunities across the country What it really takes to build a sustainable career in Italy Who This Episode Is For: Anyone planning to move to Italy and needing to work Expats considering teaching English in Italy Freelancers and remote workers looking to relocate to Italy People changing careers later in life and starting over abroad Listeners who want a realistic view of working and living in Italy Resources Mentioned: Aisling’s book: Freelance English Teaching in Italy: How to Find High-Paying Clients and Build a Sustainable Career If you’re serious about moving to Italy and want expert guidance on visas, relocation, or building your life here, you’ll find everything you need at Smart Move Italy. And if this episode helped you, make sure to follow the podcast and share it with someone who’s dreaming about their own life in Italy. Because this move is possible… when you know how to do it right. Mentioned in this episode: Listen Vivace A life well lived is never finished. There is always another version of yourself waiting to emerge. Vivace exists for women who believe the most beautiful part of life is not what has already happened, but what comes next. https://vivacenetwork.com/ Vivace Media Network Listen Vivace A life well lived is never finished. There is always another version of yourself waiting to emerge. Vivace exists for women who believe the most beautiful part of life is not what has already happened, but what comes next. https://vivacenetwork.com/ Vivace Media Network
More from A New Life in Italy
For years, we've advised foreign buyers to be prepared to pay cash when buying property in Italy. Getting a mortgage as a non-resident has historically been difficult, and even buyers with substantial assets and strong incomes have struggled to meet Italian banks' requirements. But our advice is evolving. Through ongoing conversations with Italian banks and mortgage professionals, we're learning more about financing options worth exploring for foreign buyers, including those who don't live in Italy or earn their income in euros. In this episode of A New Life in Italy, Samantha Wilson explains what's changing, who may qualify for an Italian mortgage, how much you might be able to borrow, and what banks need to see before approving an application. Sam also explores why paying cash isn't automatically the best financial decision. Keeping some of your capital available could give you more flexibility to cover relocation costs, unexpected expenses, and the life you want to build in Italy. You'll also learn why property valuations and documentation matter, what additional mortgage costs to consider, and why it's essential to understand your financing options before making an offer. Plus, Sam answers three listener questions: Will you pay Italian property taxes if you own a home here but live abroad? How long does it take to get an Italian mortgage? Could selling your home and moving into a rental affect your elective residency permit renewal?
How do the values passed down through generations shape the way we think about quality, the products we use every day, and how we spend our time? And what can we learn from Italy’s approach to slowing down and enjoying life? In this episode of A New Life in Italy, Host Samantha Wilson speaks with Seth Spears, entrepreneur, product designer, father of six, and founder and Chief Visionary Officer of Wellnesse. Raised in a large Italian American family with Sicilian roots, Seth grew up appreciating quality and ingredients. A recent trip to Sicily with his mother brought him closer to his heritage, including a visit to the home where his great-grandfather lived before emigrating. Seth and Sam discuss how Italian culture has shaped his views on quality over quantity, slowing down, and making time for the people around us. They also explore Wellnesse, the oral care company Seth founded, and his approach to questioning the ingredients in everyday personal care products. In this conversation, they explore: Italian roots and family: Reconnecting with his Sicilian heritage and discovering his great-grandfather's home. Quality and everyday choices: From craftsmanship and product ingredients to why Seth founded Wellnesse. Slowing down: What spending two weeks in Cefalù taught Seth about letting go of productivity pressures and enjoying the moment.
Finding an apartment in Italy is only the beginning. For foreigners, especially those searching from abroad or needing a rental contract for a visa, getting from an online listing to actually signing a lease and getting the keys can be much more complicated than expected. In this episode of A New Life in Italy, Samantha Wilson explains why renting in Italy works differently from what many foreigners are used to. She discusses how landlords evaluate foreign tenants, why your savings or credit score may not tell the whole story, and how to present your financial situation in a way that makes sense to an Italian landlord. She even talks about the timing of your rental search, the possibility of paying rent before you arrive, and the importance of understanding contracts, deposits, fees and other details before you commit. Samantha also explains why your first Italian rental doesn't have to be your forever home. It can simply be your starting point while you get settled and discover what kind of home and lifestyle actually work for you in Italy. Plus, she answers listener questions about rental deposits and visas, cleaning when you move into a long-term rental, and who is responsible for repairs. Planning to rent in Italy? Smart Move Italy Property offers rental assistance to help you navigate the search and secure a home. Learn more about the service and submit your rental search criteria through the following link: www.smartmoveitalyproperty.com/rent/ 👈 Mentioned in this episode: Listen Vivace A life well lived is never finished. There is always another version of yourself waiting to emerge. Vivace exists for women who believe the most beautiful part of life is not what has already happened, but what comes next. https://vivacenetwork.com/ Vivace Media Network Listen Vivace A life well lived is never finished. There is always another version of yourself waiting to emerge. Vivace exists for women who believe the most beautiful part of life is not what has already happened, but what comes next. https://vivacenetwork.com/ Vivace Media Network
Learning Italian can feel like one of the biggest hurdles when you're planning a move to Italy. You can study for months or even years, understand quite a bit, and still find yourself stuck when someone asks you an unexpected question in Italian. In this episode, Samantha sits down with Clara and Martina, co-founders of My Italian Room, to talk about what learning Italian really looks like, especially as an adult. They discuss why mistakes are such an important part of learning, how small wins can build confidence, and why speaking shouldn't be something you leave until you feel "good enough." They also get practical about what you can accomplish with 15 or 20 minutes a day, active versus passive learning, apps like Duolingo, grammar, and how long it really takes to learn a language. If you've been putting off speaking Italian because you're waiting to feel ready, this conversation is a reminder that making mistakes isn't a sign that you're failing. It's part of the process. Guests: Clara and Martina are the co-founders of My Italian Room, an online Italian school helping learners move beyond studying Italian to speaking it with confidence. Through practical, conversation-focused programmes, they've built a global community where learners combine structured learning, authentic Italian, and regular opportunities to speak. Resources: As part of A New Life in Italy, Martina and Clara lead monthly live Italian lessons created specifically for members. These relaxed, practical sessions focus on the language you'll actually use in everyday life in Italy, from useful phrases and cultural context to building confidence when speaking with locals. Lessons are also recorded, so you can revisit them whenever you need. Learn more about A New Life in Italy. Join their Sunday newsletter Explore My Italian Room Follow My Italian Room on Instagram Smart Move Italy offers guidance on visas, Italian citizenship, residency, and building a life in Italy. Learn more and start planning your move to Italy today. www.smartmoveitaly.com Want to keep the conversation going? Join Vivace, a place for people who are curious about life, open to change, and haven't decided that the most interesting part of their story has already happened. www.vivacenetwork.com Ciao for now! Mentioned in this episode: Listen Vivace A life well lived is never finished. There is always another version of yourself waiting to emerge. Vivace exists for women who believe the most beautiful part of life is not what has already happened, but what comes next. https://vivacenetwork.com/ Vivace Media Network Listen Vivace A life well lived is never finished. There is always another version of yourself waiting to emerge. Vivace exists for women who believe the most beautiful part of life is not what has already happened, but what comes next. https://vivacenetwork.com/ Vivace Media Network
What happens when La Dolce Vita becomes real life? Samantha is joined by the hosts of Two Voices No Filter, Georgette Jupe and Valentina Dainelli, for a fun and candid conversation about the gap between the Italy we dream about and the Italy we actually live in. They talk about what happens when Italy becomes everyday life, the realities of building a life here, and why Italy doesn't have to be perfect to feel like home.