As I was surfing through LinkedIn, I came across this lovely message:

Sean,

The RUDE is awesome. TY. I'd love to learn more about your decision to renounce your US citizenship & the impact it has on your family. Have you shared that experience with your readers?

RO

I realize that it’s been nearly three years since I started writing the Rude. And maybe not all readers are up-to-speed on my “origin story.” I’m not sure I even wrote it in full. So here goes.

Joisey

I grew up very happily in Hasbrouck Heights, NJ, which was middle class at the time. I loved every second of it. I was a little nerd until about 6th grade when I started to play sports. Baseball was my best sport, but Heights was a football town.

So I switched to track to get fast for football. I played football for four years in high school and was the QB and one of the team captains my senior year.

From there, I attended Villanova, majoring in finance and minoring in political science.

But my dream was always to work at The Big Apple, and I finally got there in 1997.

New Yawk City

In the mid-to-late 90s, anyone could get a job anywhere. Thank heavens for that. I partied at Villanova.

After working in Weehawken, NJ, for about six months, I landed a job with Lehman Brothers (RIP) in the World Financial Center in March 1997.

But that job was boring, so I moved to Credit Suisse Financial Products in June 1998. CSFP was the derivatives boutique on Wall Street at the time. Even though I only worked in Operations, I knew I’d learn a lot.

Then, in June 1999, my boss called me into his office and told me I’d lost out on a job to become a trader’s assistant for one of the bigwigs.

I was pissed off, but he placated me by saying, “Hey, I was going to send the other guy to London for two weeks to learn about global operations. But since he’s leaving the team, I’ll send you instead.”

I was suddenly excited.

I landed in London and worked - and played - hard for two weeks. I knew London was the place for me. Honestly, I thought New York sucked to work in, even then. And London is Candyland for Alcoholics, and I loved the party scene.

I walked into my London manager’s office on the Monday after my weekend there. To this day, I can’t believe these words have come out of my mouth.

“Kevin, I know you hate Mike (my boss in NYC). And let’s face it, he hates you, too. If you really want to piss him off… hire me!”

At first, Kevin looked at me with that faux British “How dare you?” look. Then his eyes narrowed. Then he cracked a smile.

Then he pointed at me and shouted, “You’re hired!”

I couldn’t believe it then. I still can’t believe it now. But I was on a plane to start my new life in London four months later.

Ye Olde Londontown

Of course, I had no idea how damn expensive London is. The British love to pay taxes. It’s moronic.

But what was supposed to be a two-year deal turned into nine years and three months. I loved the city. I still do, though I haven’t returned in a long time.

It’s important to understand that another great reason to get “international experience” on your resumé is to strengthen an undistinguished academic record. I knew I’d never get into a top American b-school unless I moved abroad.

But that was taken care of, as my boss at Credit Suisse paid for me to attend London Business School at night. So, although it was two years of hell, I had no graduate loans at the end of it.

I got my British passport after six years of living in London, but I still had zero intention of giving up my American passport.

After tiring myself from being a punching bag for hedge fund managers, I decided to take a year off. After that, I got a job in financial training. It’s like Hogwarts for bankers. I loved that job.

I traveled the world teaching. Then, my boss decided to open up a Singapore office. Like an idiot, I volunteered to help out.

So, in January 2009, I headed to The Rock.

Asia

I hated Singapore from the first moment. It was too hot. I had no friends there. And my job started to suck badly.

After a year of misery, I started accumulating friends and met Pam. Eighteen months later, in July 2011, we married. I renounced my US citizenship the same week because I didn’t want our children born with a US passport wrapped around their necks.

You may think that’s strange, but two things happened in Singapore. The first was one of the best things I’ve ever seen.

In 2010, the Singapore government was so concerned about the economy after the crash that it lowered the maximum tax rate from 18% to 8%. That’s right—the SG government asked people to spend more in stores than on their government.

I loved it. However, since I was still a US citizen, I had to pay the difference (citizenship-based taxation) to the IRS, which wrecked my finances. I was furious.

The second was the IRS's overeagerness to prosecute “Accidental Americans.” These people were born in America, say, to Taiwanese parents who landed in Silicon Valley for two years. Some spoke no English and didn’t live in America after their parents took them back home. But the IRS would knock on their doors a quarter century later, demanding tax from them.

That did it for me. I needed to lose the US passport, and I did. And I could because I had my British passport to fall back on.

But truthfully, the overarching reason for getting rid of the passport was that I knew I was never returning to America. New Jersey had become a blue state shithole, and Texas, where my parents lived, is, well… boring as hell—apologies to Texans.

Since 2011, I haven’t filed a US tax return. Now that’s freedom.

In January 2015, we took a two-month break in Barcelona before relocating that March to Hong Kong, where Micah was finally born.

By the time we left Hong Kong in late 2018, I had realized that my family could get Italian passports. So Pam, Micah, and I retreated to the Philippines until we completed that process. Thanks to the government-mandated private sector shutdown of 2020-2021, we didn’t get to Italy until April 2022.

Northern Italy

With dual British and Italian citizenship, I landed in Northern Italy. Now, if you’re wondering what the taxes are here or anywhere else, I say there’s a deal almost everywhere.

When I arrived, there was a deal where new arrivals only paid taxes on 30% of their income in the north and 10% in the south.

For example, if you live in Asti (the north) and have an income of EUR 100,000, the Italian tax authorities make you pay 43% on EUR 30,000, which is about EUR 12,900, or an effective tax rate of 12.9%. And that’s before the deductions you can take.

In the south, you’d pay 43% on EUR 10,000, or EUR 4,300, for a 4.3% effective tax rate, before deductions.

Alas, that deal is no longer in effect.

But there are others, so hiring a good accountant is worth it.

The Costs

The main cost is leaving your family. I’m glad my parents are here now, but I haven’t seen them for a quarter of a century, and the rest of my cousins in Jersey are strangers. It’s no one’s fault. But when you’re away for a while, people move on. You move on.

Your hometown friends are the same. It’s great to reconnect when you can, but sometimes, that takes a full decade or more.

And moving around the world was a costly undertaking. But it’s really expensive now.

Finally, you will change permanently in ways you cannot anticipate. That’s the beautiful mystery of it all. But can you handle that? Your spouse? Your children? Spend time thinking about it. It’s worth it.

Wrap Up

Thanks, RO, for asking. I hope that did the trick.

Remember, you don’t have to leave now and forever. Dip your toe in, see places you’ve always wanted to see, and then jump in for a bit.

If it’s to your taste, then think about doing it as a permanent move.

You don’t have to force the issue. Let life unfold.