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U.S. Expat Retirement in Europe: A Looming Tax Storm?
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.
itllbefunretiremen
Sep 126 min read


Essential Steps to Take Before Relocating to Another Country
Portugal with Wolf Relocating abroad is an exciting adventure filled with new opportunities and experiences. However, it also requires...
itllbefunretiremen
Sep 84 min read


Our Portuguese Dream Condo Became a Full-Time Airbnb: The Legal Loophole We Never Saw Coming
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.
itllbefunretiremen
Aug 156 min read


Social Security for US Expats: Will the Rules Change? (2025)
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
itllbefunretiremen
Aug 34 min read


The 2025 Definitive Guide to Retirement in Portugal: Navigating a New Landscape of Opportunity
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...
itllbefunretiremen
Jul 136 min read


What to Expect When Starting a New Life in a Foreign Country
Moving to a new country can be an exciting yet daunting experience. You might be dreaming of beautiful landscapes, unique cultures, and...
itllbefunretiremen
Jul 103 min read


Buying a House in Portugal with a Mortgage? Our Unfiltered Guide
Dreaming of buying a home in Portugal but need a mortgage? It's a minefield. Sellers want cash and won't wait for bank approvals. We're Alan & Leslie from It'll Be Fun, and we've cracked the code. Our guide gives you the real scoop on how to navigate Portugal's hot market, beat cash buyers, and secure your dream home without losing your mind (or your deposit!). Learn our strategy and get the expert team you need.
itllbefunretiremen
Jul 96 min read


🌍 How to Outsmart the Exchange Rate
Struggling with today’s exchange rates? Learn how to manage international money transfers smartly—even when the USD is down. This guide covers timing your exchange, protecting large transfers, and using tools to avoid losing thousands. Perfect for anyone moving abroad or funding overseas accounts.
itllbefunretiremen
Jun 155 min read


The Shocking TRUTH About Living in Portugal: What No One Tells You
The Shocking TRUTH About Retiring in Portugal: What No One Tells You Let Us Guide You
itllbefunretiremen
May 276 min read


Moving Overseas - Takes More Than You Think
Thinking of moving to Portugal from the U.S.? Don’t wing it. From visa types (like the D7 or Digital Nomad visa) to real income requirements and unexpected costs, we break down what it really takes to start a new life abroad. This isn’t a vacation—it’s a life reset. Get clear, get organized, and do it right the first time. Bonus: use our 30% off code for the Ultimate Moving Abroad Program!
itllbefunretiremen
May 104 min read


What to Expect When Starting a New Life Overseas
Thinking of starting a new life overseas? Discover essential tips on housing, cultural adaptation, finances, work, and building a support network abroad. Whether you're moving to Lisbon, Paris, or Tokyo, this guide helps you navigate challenges, embrace local culture, and thrive in your new environment. Perfect for expats and digital nomads seeking a smooth transition and personal growth.
itllbefunretiremen
Apr 305 min read


America’s Man-Made Crisis:
How Tariff Wars Are Threatening Your Future —
and What You Can Do About It
itllbefunretiremen
Apr 295 min read


Renting in Portugal in 2025: What Americans Really Need to Know (That No One Tells You)
Renting in Portugal in 2025 can be challenging, especially for Americans unfamiliar with the local process. From understanding legal lease requirements to dealing with limited inventory and landlord preferences, this guide explains what to expect, what’s changed, and how to successfully secure a rental for your move abroad. Learn the key differences and how to avoid common mistakes.
itllbefunretiremen
Apr 255 min read


Living Off One Social Security Check: A Smart Approach to Financial Freedom
Facing a Chaotic World Together Let’s be honest: the world feels a little upside-down right now. Tariffs are soaring, countries are...
itllbefunretiremen
Apr 105 min read


Moving Abroad – The Best Adventure Yet!
Moving Abroad - Do you have enough money? Worried. Well we have you covered. Retire on a very small budget.
itllbefunretiremen
Mar 145 min read


Portugal Taxes, NHR 2.0- Everything You Wanted to Know It'll Be Fun
Portugal Taxes - Here's the basics on the new NHR 2.0. See if you qualify for tax savings.
itllbefunretiremen
Feb 74 min read


Americans Are Embracing Life Abroad: How to Move with Purpose
Many Americans Are Moving Abroad, It's important that we choose well and make a positive impact.
Leslie
Jan 243 min read


"Estate Planning in Portugal: Who Will Get Your Money?"
Let us guide you through Estate Planning, Wills, Moving Abroad
Leslie
Jan 165 min read


Living Rich Without Millions—Your Path to Financial Freedom
We've helped 100's of people move abroad and build financial independence. Stop waiting. We should have done this sooner.
itllbefunretiremen
Dec 31, 20245 min read


It' Time To Set Goals for 2025 and Bring Them to Life
How to Set Goals for 2025 that will actually happen.
itllbefunretiremen
Dec 23, 20245 min read
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