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Why Working in Italy is Difficult

Curious what it takes to move to Italy and get a job? Wondering if you have to speak Italian to live and work in Italy? Meet Amanda, the Canadian expat behind La Vita è Style, who after six years now feels at home in Milan, Italy.

Typically, I would ask Amanda to introduce herself; however, given her gift for stylish events, I asked if I could share her Lake Como destination wedding video instead.

Amanda & Michelangelo Lake Como Destination Wedding: Wedding Films by Marco La Boria

Working in Italy

Amanda and Michelangelo’s story began at the Parliament of Canada. Amanda was working as a tour guide. Michelangelo was on a family trip. Seeing what she thought was a group of lost Italians, Amanda went to help.

In a true Italian meet-cute, Amanda met Michelangelo and his entire family at the same time. Michelangelo was not Amanda’s first connection to Italy though. That story starts with her Grandparents, and this is where our interview begins!

Did You Speak Italian Before Moving to Italy?

Amanda: As a kid, my Grandparents forced me to go to Italian school every Saturday. They had to drag me crying. Like other kids, I wanted to stay home and watch cartoons. When I was about twelve I can remember thinking “This is a waste of time, when am I ever going to speak Italian. I live in Canada!”

My Grandparents were determined to share my Italian heritage with me. So I grew up speaking Italian with them. What I didn’t realize is that we were speaking a mix of Italian and the Molisano dialect. So, my first encounter with Michelangelo was a true lost-in-translation moment. I spoke broken Italian and he spoke broken English.

I was fortunate enough to speak broken or basic Italian before moving to Italy. ‘How was your day? What did you do?’ Basic. When I moved to Italy, I was able to do the basic things on my own. Speaking Italian at work however, was a different challenge. I didn’t have the vocabulary. I had to learn the jargon, terms you don’t learn in Saturday school when you’re 13 years old.

How Much Italian Do You Need to Speak for Work in Italy?

Amanda: Yes, I have to speak 100% Italian at work. For me, it was a sink or swim situation.

Brandy: Were your co-workers understanding?

Amanda: They were so understanding! Yes, they laugh, but it’s that my mistakes are endearing. They basically think it’s cute, we all laughed. Usually, it’s just making sure we’re on the same page on little difficulties like pronunciations. Especially around double letters.

Brandy: Any tips for someone hoping to learn to speak Italian after moving to Italy?

Amanda: Don’t get discouraged. I think if I hadn’t done the sink or swim, I wouldn’t have pushed through to the level I’m at today. Within the first year, I felt confident speaking Italian. I still struggle with verb conjugation. There are so many different tenses! It’s hard for me still, but I think just not being afraid to make a fool of yourself is important. Just know they will appreciate you trying. Also, push through. Some Italians switch to English as an olive branch to help but stick to Italian. I would even say “Listen, I’m really working on my Italian. Do you mind if we continue in Italian?”

When Deciding Where to Move in Italy, Why Milan?

Amanda: For me, the decision to move to Milan was twofold. First, school. I moved to Milan as a student to get a Master’s degree in International Arts Management from SDA Bocconi. Second, Michelangelo lived in Milan.

Once I had my Master’s degree I could have moved anywhere in Italy, but ultimately I wanted to stay in Milan. Of all Italy’s cities, it’s the most international. In 2015 when the World Expo happened, the city just felt like it grew and became more organized.

I remember feeling Milan opened up to international culture more then. Before the expo, metro announcements were only in Italian. Since the expo, they are also in English. In Milan, I don’t feel like a fish out of water. 

Plus, Milan is the fashion capital of Italy, so job opportunities are better here. Milan just seemed to fit, the way of life, the culture. Also, I love traveling. Rome is another option for an international airport in Italy. Milan is just so convenient for me to get back to Canada. It’s a direct flight. Since I travel a lot for work, the airport mattered.”

Stories of Moving to Italy, Amanda on Deciding to Live in Milan

Brandy: Speaking of, Let’s talk work!

How Did You Find Work in Italy?

Amanda: Before finishing my Master’s program in Milan, I had earned two undergrad degrees at the university in Canada. So in my head, I thought of myself as a pretty skilled person, a desirable candidate.

So, I started applying for jobs thinking ‘I got this, this should be a breeze.’ That summer I probably applied to over 70 jobs. I’m not talking boilerplate, copy-paste, I’m talking rewriting everything every time. All the resume keywords. All the things! I seriously only got two responses, both for internships.

I was so demoralized, I felt silly. I knew how to look for and get jobs in Canada. I knew what government jobs back home paid, and I knew I could get a good-paying salary and a job with a future, but I wanted Italy.

Thankfully, Michelangelo was there. He just said “Amanda do it for the experience” and I decided this would have to be my next step. So an internship was how I started my career in Italy. Six months in they hired me and it became a real job. In Italy, it’s standard to never get hired until after you have an internship.

Side Note: Amanda didn’t want to brag, but I happen to know she managed to become the marketing and events manager of a major fashion house!

Brandy: So your work experience before moving to Italy didn’t matter?

Amanda: It still shocks me. I had six years of work experience in Canada. Big jobs like working for the Canadian Parliament. In Canada, that meant a lot, but in Italy it meant nothing, it was viewed as a small bonus. In Italy, it’s what you do in Italy that counts.

I don’t want to be discouraging. Honestly, I just wish I would have known. I wouldn’t have wasted time applying for Sr. level positions that I believed I was eligible for had I known.

Brandy: Okay, let’s talk about the hard stuff, the reality of being an expat in Italy.

As an Expat, What are the Cons of Living in Italy?

Amanda: Adjusting to the way things work here. It’s not the culture by itself, it’s the way things are organized. Like getting a Permesso di Soggiorno (temporary residence permit). You’ll read the government website only to find out the instruction documents online are old. You’ll hear things like ‘Oh no, this law changed, now you need five photos instead of three. Since your appointment is now and you don’t have five photos, you’re going to need another appointment.’ Like I said all the tears, I cried, I wanted to pull my hair out.

Since the company that hired me sponsored my work visa, the day I went to get my permesso, my boss came with me to do the interview. We’d been talking with the police officer for a few minutes when he said ‘Next time, we sure to bring the immigrant with you.’ We looked at each other in shock. ‘I’m the immigrant’ I said and then the officer looked shocked. It was like because I’m white, clean, and speak Italian that I couldn’t be an immigrant.

These experiences haven’t hurt me so much as shocked me. Don’t get me wrong, Canada isn’t all roses and perfection, but I never saw things so transparently there. Not all experiences are like this though. I’ve had positive and I’ve had negative ones. There just seems to be a bit of cultural insensitivity towards anyone who isn’t Italian.

Brandy: If navigating Italian bureaucracy and the cultural insensitivity that comes with it is bad, let’s talk about the flip side. The reasons to stay.

What are the Pros of Living in Italy? The Rewards?

Amanda There’s really two things. It’s rewarding to be able to think, I did it! I survived. I was able to move my life to a new country, integrate, and not go insane. Mentally, my emotions are a roller coaster. There are highs and lows. Life in Italy is not perfect and it’s not a constant vacation. It’s not always great. I have days where I’m like, why did I do this?!

I could make three times as much in Canada, and I miss my family. Still, the fact that I know I did it, I left it all there and made it here, it just makes me very satisfied. No matter what happens with the rest of my life, this has been really rewarding.

The second thing is, it’s rewarding to live a culturally Italian life. It’s so rewarding to have a work-life balance. It’s not all a la dolce vita vacation, but it’s also not that far from it. It’s so gratifying on the weekend to pay 4€ to get to Lake Como.

Plus it’s happening, my dream. I always dreamed of living in Italy. I’ve embraced every part of Italian culture within my means. I say that because I live a simple life here. I’m not rich, there is no big inheritance, I’m making it work.

That’s the greatest part of life in Italy. With a basic income and modest means, you can eat well, have amazing wine, go to museums, embrace art and culture. You can travel and get to know other people who have integrated into the culture. It’s definitely rewarding.

Stories of Moving to Italy, Amanda on the Pros & Cons of Moving to Italy

Brandy: Do you feel at home here now?

Amanda: I do feel at home now. It took me six years because I always had doubts. I worried about fitting in. For a while, Michelangelo was my rock, he was my everything, but I had to segment and not force him to be everything. I had to push myself to make friends, make my own path, create my own routine. Once I really solidified my life here, I could see the long-term vision of life in Milan.

Brandy: Let’s talk about that long-term vision, what’s next for you?

Amanda: What’s next is taking this amazing Italian lifestyle, and integrating a little of my North American entrepreneurial spirit. Right now with La Vita è Style I offer planning for events and weddings. What I’ve found is that even if people don’t want a planner at the event the day of, sometimes they just need help with structure, organizing, or marketing the event. So I started offering digital-only experiences in addition to in-person coordination of events. It worked really well this year as I’ve been able to help people coordinate events even when they couldn’t travel.

Brandy: Dream client, who would it be?

Amanda: Another expat who dreams of getting married at Lake Como. It’s where I got married, and I would love to help someone realize that dream for themselves! For me, it would be 360. I was that person who always dreamed of it, I made it happen for myself, then to make it happen for someone else would be so cool.

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Amanda & Michelangelo’s Lake Como Wedding. Photography by Blue Rose Designs

Brandy: How can we follow your journey or get in touch if someone needs help planning an event in Italy?

Amanda: You can contact me and find out more about the digital event and in-person planning services I provide at La Vita è Events. I share my personal journey as an expat in Italy on Instagram. I post the good along with the things I’m going through here. I strive to be honest.

Side note, Amanda and I first connected through her Instagram. Her IGTV is adorable, fun, stylish, and yes, honest! You can find her @lavitaestyle

Amanda’s Italian journey might have been sparked by love, but it’s her stylish, tenacious spirit that has stoked her journey. From dreaming of a Lake Como wedding to getting married at Lake Como, to helping others organize their own weddings and events at Lake Como. I’m excited to see Amanda go full circle on her Italian dream. Amanda’s story is an inspiring reality check. Proof that a tenacious spirit and a little loving support can make the dream of living la vita dolce possible.

Stories of Moving to Italy is a series inspired by the beautiful complexity of living in Italy as an expat. Are you an expat in Italy? let me know! I’d love to connect and hear more about your story of moving to Italy. Share why you call your corner of Italy home in the comments below.

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