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:

Sentire Media Website

APP Link

Sentire Media Website