Jennifer Pellerito was brought up in a culture of travel. Whether she was escaping to another world through books or hitting the road with her parents and sister, the practice nurtured her natural curiosity and passion for learning about history, culture and different ways of life. It was only natural that she’d end up founding a business that helps others explore the world. Today, Jen on the Run helps digital nomads build their businesses as they explore places as close as Pellerito’s long-time home of California, and as far as Spain.
There’s one place that has a special place in Pellerito’s heart, though. When she was a child, her parents took her on a tour of Italy, from Lake Como through Tuscany.
“It was a time before everyone had cell phones and before overtourism,” Pellerito reminisces. “I’m forever chasing the nostalgia of that first trip. There’s something that gives me so much wanderlust when I think about myself as a little girl, sitting on the steps of a water fountain in a piazza with a gelato melting in my hands. And then driving my parents crazy when I tried to run off and pet stray kittens. I was completely oblivious to the centuries-old history around me, but I was immersed in the moment and the simple pleasures of it all.
“To me, that’s Italy.”
While Pellerito is American, the little girl who sat on those steps with a melting gelato was also a descendant of Italian emigrants. Those familial ties allowed her to eventually relocate to the place of her childhood dreams and even secure citizenship in late summer of 2025.
It was many years before Pellerito returned to the country that stole her heart. Her next trip back was as an adult in 2018. She found herself in government offices in Sicily. The government worker pulled out a book from the 1890s, revealing Pellerito’s great-grandparents’ birth certificates. Handwritten in ink, they cemented a direct connection to the town around her.
“I could barely believe it,” she says. “I didn’t think I was going to pursue citizenship at that point. I was just excited to see their names as proof that my connection to the past was real, and that I was walking the same streets they once did.”
Three years later, she started getting serious about some big dreams. She researched what it would take to claim her citizenship by descent, quickly learning that using Italian government websites abroad was a frustrating process. Even when she could make it through the glitches, the Italian consulate in L.A. was always fully booked. The competition made it difficult to get an appointment. For a while, she gave up.
Then she started thinking, ‘What if I apply in Italy instead?’
She packed up her bags and booked a flight. She started the application process in Italy – which gave her a permesso di soggiorno, or permission to stay, as her citizenship paperwork was under review and processed.
She made it just in the nick of time. Immigration law is always evolving, and it’s evolving faster lately in countries around the world. As she got her citizenship papers in hand, Italy’s law changed. You can no longer claim citizenship by descent through your great-grandparents.
That’s not to say no one can claim citizenship by descent in Italy anymore. If your parents or grandparents were Italian citizens who never renounced their privileges, you likely still qualify. You just can’t go back three generations anymore like Pellerito did.
Aside from the costs of getting to Europe, securing citizenship itself wasn’t all that expensive for Pellerito. She paid:
Initially, Pellerito thought about hiring a lawyer to help her file her paperwork. This type of legal assistance can cost anywhere from $3,500 to $10,000 USD, though. When she found an error in their work early on, she decided the additional costs weren’t going to be worth it.
When Pellerito made her move, she was sitting on a bit of savings. Because she had that cushion, the costs weren’t a big deal for her personal finances.
But there were still the everyday costs we all have to worry about, like rent and food. Luckily for Pellerito, she didn’t have to worry about finding a job in her new locale in order to provide for herself.
“Working as a self-employed freelancer has been one of the greatest blessings I stumbled into,” she shares. “It’s allowed me to create my own work schedule, fund my travels, and live a location-independent lifestyle.”
For the most part, things like groceries and other everyday living expenses are a bit cheaper than they were in California, from Pellerito’s account. Rents can be high in bigger cities, but she initially settled in a medium-sized town where housing is more affordable.
The thing that does trip her up sometimes is currency conversion. She says it’s been especially tricky as she noticed the Euro further strengthened against the USD starting in January 2025.
“It’s easy to forget that a €15 pasta dinner actually costs a bit more than that, and even more so with more expensive items.”
TIP: Want help managing your money across multiple currencies? PocketSmith’s built for that.
The good thing about moving to a medium-sized town is that Pellerito saves on rent. But that also means her experience of culture shock has been a bit more full-on. She finds that she’s the only American, and often the only English speaker. When she tried to figure out how to sort the trash or how to properly order coffee at a cafe, that language gap left her sussing things out on her own.
“A bigger culture shock has been how it can be normal to be pushy here – you have to push back for what you want and learn how to speak up,” Pellerito says. “Kindness doesn’t always get you places, and sometimes you have to know when to be firm and not be intimidated. It can be normal to overhear two people seemingly arguing in Italian, only to find out later that that’s just the Italian way of having a discussion.”
As she learns a new language and navigates new cultural norms, she sometimes has homesick days. On those days, she wonders whether leaving her friends and family behind was worth the experience.
But despite the occasional hard day, the good outweighs the bad.
“I live in possibly the most beautiful country in the world with an endless coastline,” she says. “The food is incredible, and I generally feel so safe here. Public transit is great, and my cost of living is typically lower than where I was living in Los Angeles. I have the opportunity to learn Italian and meet so many incredible people. I’m way more social here than I was before, which has really helped my mental health a lot.”
Want to follow in Pellerito’s footsteps? She highly recommends estimating your costs before you hop on a plane. An easy way to get started is by checking the Global Spending Map for your destination country.
Remember to not just save the bare minimum you think you’ll need – life always has a way of throwing some extra expenses at us, so you’ll want some cushion in your savings. Especially if you’re trying to do something like claim citizenship in a new country.
If you are claiming citizenship by descent in Italy, Pellerito says you don’t have to be afraid of DIYing it. While you can enlist the help of a lawyer, lawyers are expensive. Doing it all yourself isn’t as intimidating as it initially appears.
While you do want to be prepared, if you have a dream, Pellerito encourages you to engage in that prep work sooner rather than later.
“Take the leap. If you move and decide it’s not for you, you can change course. My mentality is that everything is ‘un-doable.’ But more often than not, I usually don’t regret taking the chance.”
Brynne Conroy is an award-winning personal finance writer, creator of the popular women’s finance site, Femme Frugality, and author of The Feminist Financial Handbook, which was an Amazon #1 New Release across multiple categories including Poverty and LGBTQ Demographic Studies. Her work has been cited in academic texts, and she’s spoken at venues such as Vanderbilt University, the Financial Planning Association and the 529 Conference. Here at PocketSmith, Brynne covers personal finance within American financial systems.
