Let’s talk money this week. What is "enough"? Do you have enough? And when you make the leap to move abroad, what are the truly scary financial realities you might face? According to a survey by Schroders, only 5% of retirees say they are "Living the Dream," while nearly 20% say they are actively struggling. These are the kind of terrifying numbers we hear tossed around throughout our working lives. But then, almost overnight, we wake up and realize we’re finally old enough f

The 2032 Social Security Shockwave: Navigating the Politics and Taking Control of Your Retirement

Alan enjoying life The dream of packing up a life in the US to retire or build a digital nomad career under the suns of Southern Europe is a powerful one. Whether it’s the rugged Atlantic coastline of Portugal, the historic hills of Rome, or an island sanctuary in Greece, the aesthetic appeal is undeniable. But when Americans make the move, they often bring along a mental map of politics shaped by a strict Democratic-versus-Republican, red-and-blue landscape. Applying that bi

A Global Competition Most Americans Don't Realize Exists For over a century, America was the country attracting the world's immigrants. People came to the United States looking for opportunity, freedom, jobs, and a better future for their families. Today, something remarkable is happening. Countries around the world are increasingly competing for Americans. Not because they need factory workers. Not because they want tourists. They want retirees with Social Security checks. T

Chateau de Chantilly France

Why the Portugal property market is still strong and growing.

If you’ve ever planned a road trip through Italy , you know the dream: cruising past Tuscan vineyards, navigating the rugged coast of Sicily, and finding those hidden trattorias that aren't on any bus route. But you also know the potential nightmare: the confusing world of Italian car rentals, hidden fees, and the dreaded "insurance talk" at the rental desk. On our last big trip, we tackled both the Italian mainland and Sicily by car. To keep things simple (and affordable),

We Should Have Done This Sooner - It'll Be Fun! Welcome back to "Building Your It'll Be Fun Life!" We have looked at France (colder, more expensive), and we have looked at Italy (chaotic, interesting). Now, we have to talk about the one that got away. The original dream. Spain . If you have been following our journey, you know we live in Northern Portugal (Caminha) . We love it here. But recently, we took a trip across the border just north of us, up to Vigo and the charmin

Italy has a rare ability to work for both retirees and young entrepreneurs — but for very different reasons. Retirees are drawn to the slower pace, rich culture, affordable housing in smaller towns, and powerful tax incentives like the 7% flat tax on foreign income. Younger entrepreneurs, on the other hand, benefit from new digital nomad visas, startup incentives, and global connectivity. Add world-class food, walkable towns, and deep community roots, and Italy becomes more t

Wolf & Lessa Paris, France By Leslie – It’ll Be Fun France vs. Portugal: The Adventure, the Dream, and the Math That Keeps Us Grounded One of the great myths of moving abroad is that once you choose a country, the other options fade quietly into the background. That you “decide,” settle in, and never look back. That hasn’t been our experience at all. As we begin a new year and continue our Building Your It’ll Be Fun Life series, we want to be honest about something most expa

Alan & Wolf By Leslie – It’ll Be Fun Lately, it feels like every conversation about Portugal starts the same way: “Are you still staying?” “Is Portugal still worth it?” “Didn’t they change everything?” And honestly — We get the anxiety. First, the real estate Golden Visa ended. Then the Non-Habitual Resident tax program closed to new people. And in late 2025, the headline that really rattled nerves: citizenship timelines potentially stretching from five years to ten for immi

Why Living In Portugal Is Worth It. Even with all the political issues, policy changes and high taxes. There is something to be siad for this country. Come join us to see how we have built our It'll Be Fun Life.

Discover how to retire in the USA and still travel the world—without needing millions. The team at It'll Be Fun, share their strategy for building a comfortable, travel-rich life with a paid-off home, smart budgeting, and flexible investing. Explore nine affordable U.S. states perfect for creating a stable base while enjoying months of slow travel abroad each year.

Father and son in palermo Italy

How Much Is too Much to Pay In Taxes? For the millions of Americans retired or retiring across Europe, financial planning has long been a balancing act between local tax laws and the unique demands of the U.S. tax system. Favorable regimes, like Portugal's recently ended Non-Habitual Resident (NHR) program, have offered years of stability and significant savings.

Portugal with Wolf Relocating abroad is an exciting adventure filled with new opportunities and experiences. However, it also requires...

We thought Portugal's new housing laws protected our condo from short-term rentals. We were wrong. We understood the rules but missed the math. A legal loophole allowed wealthy investors to gain a majority in our small building, legally turning our home into a hotel. This is our cautionary tale so you can avoid our costly mistake and understand the risks before you buy.

Your Social Security Abroad: The Rules, The Rumors, and What You Can Actually Control. Let's talk about the single biggest financial question that lands in our inbox. It’s a one-two punch of worry that can stop a beautiful dream in its tracks. This is a huge deal. Your benefits are the financial bedrock of your retirement, and uncertainty around them is paralyzing. So, let’s tackle both parts of this fear head-on, and then talk about the only mindset that will actually get yo

Madeira, Portugal Bom dia!!!! If you've been following our "It'll be fun" channel, you know we're all about making the dream of moving...

Moving to a new country can be an exciting yet daunting experience. You might be dreaming of beautiful landscapes, unique cultures, and...