Tune in to the podcast, where I discuss living and working abroad.

Below is a snapshot of what you’ll hear in my podcast with ACA.

The road to Milan

My fascination with life beyond the States began in high school, when I toured Scandinavia as a member of a regional soccer team. The experience sparked my curiosity about different cultures. Later, studying abroad in Florence and Milan deepened my appreciation for Italy and ultimately led me to pursue a career in international business, setting me on my expat journey.

While completing my MBA in the U.S.A. and Italy, I interned with Pirelli in Milan. Two years later, Pirelli offered me a job at their headquarters in Italy.

Upon my return to Milan, I encountered my first set of hurdles. Navigating Italy’s bureaucracy to obtain a work permit was an early challenge. Determination and adaptability made the process less painful.

Four lessons I learned on my expat journey

• Going with the flow – Italy can test your patience. Long waits at government offices, frequent transportation strikes, and bureaucratic hurdles taught me to stop sweating the small stuff and focus on adapting instead of resisting.

• The power of determination – Five years into my expat life, Pirelli sold my business unit, and I found myself without a job. Networking and persistence helped me secure a new role with a U.S. multinational in Italy, proving that resilience is a key trait to thriving in a foreign job market.

• Embracing cultural differences – Corporate culture in Italy differs from that in the U.S.A. One of my biggest adjustments was learning the importance of face time with colleagues. Some of my best career insights came from informal conversations over coffee, lunch, and social events, rather than being glued to my desk.

• Understanding hidden costs – I underestimated taxes and some other common expenses. For example, paying roughly 700 euros for my driver’s license caught me off guard. Later, I learned how to better manage my budget and anticipate expenses, resulting in fewer surprises.

The reality of living abroad

The fantasy of moving abroad often glosses over the complexities. An expat journey presents challenges such as feeling lonely, adapting to a new way of life that may not make sense at first, being labeled a foreigner, and dealing with skeptics. Despite that, creating a new life from scratch fosters resilience, resourcefulness, and cultural openness.

Advice for aspiring expats

Thinking of relocating? Do your research. Evaluate the job offer—salary, relocation assistance, health benefits, and long-term career impact. Understand the cost of living, essential documents needed, tax implications, and logistics. If you have a family, also factor in education.

For women seeking expat roles, assertiveness is crucial. Take initiative and communicate your interest in international assignments within your company. Opportunities can arise through company expansions, acquisitions, or rotational programs.

Reflections and final thoughts

Milan’s expat community is diverse—students, business professionals, artists, designers, and entrepreneurs make up the American community here. Milan is more than just a “working city.” It has beautifully manicured, hidden courtyards, notable art, rich culture, and opportunities to meet people from all over Italy and the world.

If I could advise my younger self, I’d say, “always step outside your comfort zone and take advantage of every opportunity–whether staying put, moving to another country, or returning home.”

My expat journey has enriched my life in ways I never expected. I received career opportunities across EMEA. Have friendships with people from all over the world. Lastly, I have experienced a deep cultural immersion that is not possible through travel alone. If you’re offered an opportunity to take an expat assignment, take it! It could be the most transformative experience of your life.

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When I landed in Italy 20 years ago, I was both excited and scared. I experienced mixed emotions. My thoughts ranged from this being a once-in-a-lifetime opportunity to what had I gotten myself into and everything in between. Was this the right move in my mid-30s? What if I fail or can’t hack it? Could I make it overseas without a safety net? These are just a few thoughts that raced through my mind until I got on the plane. Having doubts is normal. That’s when you must tell yourself that nothing significant happens in your comfort zone. I reminded myself that I wanted to live and work abroad. I had studied for it and made the preparations to go, so why not now?

A year from now, you will wish you had started today. — Karen Lamb

Spending time abroad can be a life-changing experience. Here’s how you can benefit and what you can expect from your time away from home.

Take a timeout from the political chaos in the States.

Has the outcome of the election got you down? Even though the future appears bleak, this is a perfect time to escape the stress and uncertainty of the Trump Administration. Depending on your chosen place, you could be looking at everything from a more welcoming and stable government to a lower cost of living, universal healthcare, and, of course, cheaper eggs! If you still believe in it, science has proven that extended exposure to political divisiveness negatively affects your well-being. Psychology Today explains how prolonged divisiveness fuels burnout.

I’m not one for running away from my problems. However, putting some distance between you and the 24-hour news cycle will do wonders for your mental well-being, even if it’s only temporary.

Lastly, you can still participate in the resistance from abroad by joining online movements like BuildTheResistance.org, donating money, participating in virtual protests and phone campaigns, and sharing news and information on social media.

When you go abroad, leave your comfort zone behind.

Every day, you will be put to the test. You’ll have many new experiences to conquer, from minor everyday nuisances to far more complex issues. This can include everything from ordering food, understanding the metro system, meeting new people, asking for help to read the 15-line items on your pay stub, going on vacation by yourself, renting an apartment, filing local taxes, to buying a home – all in a foreign language. A dose of vulnerability can help, along with resilience and the attitude to get up and try again.

Do one thing every day that scares you. — Eleanor Roosevelt

Access learning you won’t get in the classroom.

When you go abroad, you will likely take a language class or two where you will get the basics. There are language apps to support your learning along the way as well. I encourage you to take classes and try the available tech, but the real test will come when you wake up and step outside. I call it street learning. Start the morning at a café or coffee bar. Ordering and having coffee at the corner bar will be helpful in assimilating into your new home. Not only to observe how the locals do it but also to get a sense of what people are talking about and what’s on their minds. You can extend street learning to food and clothing shopping, dining out, and the office.

Experience a new culture firsthand when you live and work abroad.

In Italy, for example, there are more than 230 festivals and events every year related to historical events, food & wine, and local traditions.

Here are just a handful of events that I have experienced: the Epiphany, Jan 6, where the Befana (witch) leaves candy and sweets in the stockings of children; Venice’s Carnevale, the farewell party leading up to Lent, Feb 14-Mar 4; Vinitaly wine festival in Verona, Apr 6-9; The Infiorata di Noto, the Baroque Flower Festival, in Noto, Sicily, May 16-20; the Sagra del Limone, a festival dedicated to lemons, in Monterosso, Cinque Terre, May 17; The Festa della Repubblica, the birthday of the Italian Republic, Jun 2; and The Festa del Redentore which takes place in Venice and celebrates the end of the plague, Jul 19-20. When you live and work abroad, events and holidays can be great fun and provide an opportunity to learn more about a new culture.

Great people do things before they’re ready. They do things before they know they can do it. Doing what you’re afraid of, getting out of your comfort zone, taking risk like that – that is what life is. You might be really good. You might find out something about yourself that’s really special and if you’re not good, who cares? You tried something. Now you know something about yourself. — Amy Poehler

While overseas, open yourself up to new career opportunities.

After a few years of work experience abroad, I built up a resume that opened doors. I was exposed to opportunities that would never have been available to me in the States. A combination of experience and an extended network helped me advance my career and establish myself as an international marketing professional at home and overseas. Thanks to my success in Italy, I have been recruited and interviewed for jobs throughout EMEA.

Alternatively, being abroad can spark entrepreneurial pursuits. Many people I know have leveraged their experiences to start their own businesses in consulting, travel services, food and wine, and other opportunities related to their home overseas.

While a move of any type can be stressful, if you’ve done your research, then why not now? Today, there are more ways to go abroad than ever before. You can study, teach, volunteer, go with your current employer, get recruited internationally, or go on a digital nomad visa. You can do it yourself, or there are companies to help you find the right place and support you on your move.

An experience overseas will expand your horizons and open doors to a new you.

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Anyone who knows me, knows that working abroad is a dream come true.  I’ve constructed a full life in the country of my family’s roots – Italy.  If you have visited Italy, you can appreciate people who are full of passion, a rich culture, traditions that vary from town to town, and a history that spans ancient times to the present.  Living here has certainly influenced my thinking on how I should live my life.  Italians are passionate people who work hard and enjoy life.  With the best of food, wine, art, design, fashion, architecture, and a geographical position that appeals to cold- and warm-weather activity, it is easy to arrive in a place like Italy and fall into the trap that “la dolce vita” or “the good life” is something easily obtained.

The reality is that Italy can also be characterized as a country with a weak job market, corruption, high taxes, an inefficient government, public services that don’t work, and a lot of bureaucracy.  While your early months of expat life might feel like a scene from Netflix’s original series Emily in Paris, the reality is that to maintain a full and satisfying life abroad, you have to really work at it…all the time. 

“The way I see it, if you want the rainbow, you gotta put up with the rain.” – Dolly Parton

As I reflect on my time in Italy, there are some tough challenges to cope with while working abroad.

Trading places.

The first challenge of expat life is working, legally, in your new home country. A hard but useful lesson, one that everyone who is an expat will experience, is being an immigrant.  Even with the sponsorship of a globally-recognized Italian company, when I arrived in Italy from the USA there was no preferential treatment. 

I was labeled an “extracomunitario” or a “non-EU citizen” like many others arriving from outside the European Union.  Being called a “foreigner” or “outsider” is not exactly a warm and fuzzy feeling.  Having those words stamped on all your documents isn’t a badge of honor.  Going down to the immigration office to get my first “permesso di soggiorno” or “residence permit” is an experience that I will never forget.  The learning here is to standup tall and be proud of who you are.  Also, have compassion for those who are trying to create a better life somewhere else.

The bureaucracy.

I can’t speak for every country, but the paperwork that I needed to be admitted into the quota for my residence permit in Italy was insane, even when there was someone else doing the work for me. Once admitted, I had to return home to do more paperwork in my home country. Upon my return to Italy, it took even more time to have some of the basic services that one takes for granted at home – a form of identification, a checking account, access to healthcare, etc. Here, all I can say is that patience and determination will get you through this period.  Before you head off to your expat assignment, try to get first-hand feedback on the process from others from your home country who have gone through the work-permit process.

Finding your place far from home.

Once you are settled and start working abroad, you’ll need to create a life in your new country.  This isn’t spring break, so making meaningful connections may require more effort than usual.  On the job, you may be seen as a threat.   Integrating and finding your way will take time and will not happen overnight.  You’ll need to put yourself out there and try many experiences to find the right balance that works for you.  Join associations, volunteer and go out and meet people.

Maintain connections.

It is easy to lose touch.  Staying connected can be difficult due to time zone differences and any other excuses that come to mind.  Schedule time to connect with your family and friends.  Make the effort to see one another when you are at home or nearby.  Be sure to preserve the ties you created while you make new ones.  

Stay relevant on the job.

While expat life can open the doors to new opportunities, sometimes being too far from the corporate headquarters can be a disadvantage. Even when the experience you are undertaking makes you better at your job and more qualified for promotion, you may be passed over and even forgotten.  Here you’ll need to be assertive and vocal in order to keep yourself front and center.  And, even after proving yourself, you still might be excluded because you are not in the right location.  This is unfortunate. 

However, if there is anything the pandemic has taught us is that we can be productive even when we are not physically together in the same room.  Many companies are incorporating the learnings from the past year to create more flexible and dynamic work environments. However after all this, if you still feel that you are being put in the corner check out what you can do outside of your workday to advance your career.

Tax madness.

Something that many of us are dealing with in these days is the filing of our taxes.  If you’re an American, like me, you are required to file taxes in the USA.  Your worldwide income is subject to U.S. income tax no matter where you reside.  This means that every year you are living and working abroad, you’ll be filing taxes in two places, most likely requiring the service of an accountant.  Groups like American Citizens Abroad are advocating for tax reform.  If you want to keep your American citizenship, you must continue to file your taxes in the USA.  No matter where you’re from and where you’re going, you’ll want to understand your tax obligations.

Expat life is what you make it.

I went from the USA to Italy; you’ll probably be heading somewhere else. The point is that you’ll need to do your research on day-to-day expat life to understand the challenges of working abroad.  These are only a few but there could be other challenges to expat life. How you choose to manage the obstacles you encounter will affect your wellbeing while you are living and working abroad.  Like anything in life, you get what you put into it including “la dolce vita” or “the good life”.

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“I am who I am today because of the choices I made yesterday.”

Work overseas.

I often get asked the question, “when did you know that you wanted to work abroad and how did you do it”?  Growing up, I was always interested in travel and learning new things.  I studied abroad in college, and by the time I graduated, I knew I wanted a career that included an expat experience.  From there, I worked for large companies and organizations in roles that were international in scope. I returned to school for an international MBA, and that’s where I got my big break.

So, to answer the question, wanting to work abroad started as an interest that I steadily cultivated throughout my career.  In the beginning, I had no clue how I would go abroad professionally.  However, as I pursued my interests, I became more informed about the opportunities available to me, and what I needed to do to reach my goal.

So here are the steps I took to find work abroad.  I’ve also included some links to help you get started with your own journey. 

1. Study and travel abroad.

If you can manage it financially, I highly recommend you do it.  Studying or traveling to unfamiliar places will open your mind to so many things such as meeting people from all walks of life, learning a new language, experiencing a different culture, discovering new ways to approach age old problems, and, most importantly, stepping outside your comfort zone.  There is only an upside here that includes self-improvement, learning and career advancement.

Traveling abroad.

• Transitions Abroad: Transitions Abroad: Study Abroad and Educational Travel
• Go Abroad: GoAbroad
• EF: EF Education First

2. Work for an international company or organization.

More and more, I believe that working in a multinational or in an international organization not only prepares you for what is to come but also increases your chances of working overseas. Early in my career, I worked for one of the largest cruise companies which provided me with the opportunity to work with colleagues from diverse backgrounds and to travel extensively. Having this opportunity early on created the foundation for what would become a career filled with international experiences.  More importantly, I expanded my thinking on how vast the possibilities were when it came to career opportunities.

Find a corporate job.

• INSIDER: The 25 global companies with the best workplace cultures, according to employees
• Forbes: The World’s Best Employers
• LADDERS: These are the 50 best companies in the world to work for right now

3. Get your Master’s overseas.

At this point in my life, I was committed to getting an expat job.  I went back to school for an international MBA that included studying and interning abroad.  By this time, you have enough years of experience to have an idea what you want to do in life.  Today, there are more ways to get an advanced degree than ever before – online, part-time, executive, full-time, etc.  Regardless of what you choose, be sure to understand the commitment you are undertaking.  The outcome will depend 100 percent on you.  An advanced degree will not guarantee you get what you want.  What an advanced degree will do, is open doors. 

Get an advanced degree.

• U.S. News: Find the Best Grad Schools
• The Financial Times: FT Global MBA ranking 2021: Europe tops table but US dominate
• Forbes: The Latest Rankings Of The World’s Best Online MBA Programs

4. Stay in contact.

So, you studied abroad, traveled the world and worked in a global organization.  Now what?  Maintain and grow your network. My break came two years after finishing business school.  The company where I did my business school internship called me for a full-time job in Italy.

Network.

• Fast Company: How to feel less icky about networking
• Indeed career guide: 10 Tips To Help You Network Like a Pro
• LinkedIn: Four Tips to Network on Linked

5. When opportunity knocks, open the door.

Sounds obvious, doesn’t it? Well, it’s easy to come up with a list of excuses of why you can’t do something.  If I’m honest, after being offered the opportunity to return to Italy, I definitely had butterflies or doubts about going back.  But after the fluttering stopped, I knew that this opportunity was right for me.  And here I am today, in Italy.  No more explanation needed.

Take chances.

• Lifehack: Top 10 Fears That Hold Us Back In Life
• Inc.: 20 Great Courage-Inspiring Quotes
• Harvard Business Review: How to Overcome Your Fear of Making Mistakes

Everyone’s journey is different, but when I look back on my career, these steps were the actions and choices that helped me reach my goal. 

Photo by Ono Kosuki from Pexels.

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