Expat Stories – Jim Leo
Jim Leo is a Cigna Global customer. In this interview, he shares his expat story with us.

Jim Leo moved from the USA to Italy in 2002 and has been living there ever since.
Esta es su historia de expatriado.
Tell us about your expat move?
My grandparents were born in Italy and went to the USA. I came to Europe and met relatives and visited Italy many times. At age 39, I decided to leave my job, sell my home and move to Milan.
It was exciting but I also learned it is very different to live here compared with visiting.
¿Cuál cree que es la mejor manera de hacer amigos como expatriado?
When I first arrived, I studied Italian at a language school and met many other students.
I also liked meeting local people, but sometimes that was not easy with the language and to enter into groups that had been together for some time. But going out and meeting people was the best way to make friends.
To be honest, I do not have any fellow American friends here, it has not been easy to find, or maybe me not putting a lot into it. As I said, I met many before but they moved away and that was difficult.
¿Cuáles son los aspectos más destacables de su vida como expatriada hasta ahora?
It has been a wonderful experience and really glad I decided to move. At first, it was wonderful traveling and seeing different cities and countries. After starting work, that became more difficult.
Learning the language, but still not 100 percent fluent, has been a big highlight. Really living the experience and not just visiting has been amazing.
¿Cuáles han sido los mayores desafíos hasta ahora?
Some of the biggest challenges have been finding work in my area, it took 6 years to find my first job here in HR. The other challenge has been meeting people and having long term friendships. Many expat are here for a couple years and then gone.
I have had many friends over the years, but they have moved away, also some of my Italian friends. The other challenge, which ties into the next question, is that simple things we take for granted in the USA, are more complicated here, big bureaucracy.
¿Qué es lo que echa de menos de su país de origen?
The things I miss the most are family and friends, the conveniences in the USA, and the variety of food.
How much do you enjoy being an expat?
I really don't think of myself as an expat, I feel American when in the USA and Italian in Italy. I do feel more American though!
What advice would you give to those who are considering making an expat move?
I would say it is an amazing experience but it may not be for everyone. I can by myself, which was good because it only impacted myself, with a family it may not be easy for everyone to adjust.
Once you make to move, really try to experience the life in the country and not reflect too much on what you left in your home country. What I say to friends in the USA, I love it here, but coming on vacation in Italy is so much easier than trying to live here.
What would be the one piece of advice you wish you’d known before moving?
I wish I had known the language better and really have a good understanding of what it would be all about. Talking to someone that had gone through it would have been great.
Para terminar, ¿cómo describiría su viaje como expatriada en 10 palabras o menos?
It was not the easiest journey but so glad I did it!
Historias de los expatriados
Lisa Sellers is a Cigna Global customer. She moved from the UK to Bermuda in 1996. She currently lives in Antigua and Barbuda.
Karthik Manivasagam is the Head of Underwriting, Africa and NGO at Cigna.
@Cigna 2025
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