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We Ditched the U.S. Rat Race for This Instead

3.5K views· 286 likes· 16:48· Jan 10, 2026

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How do you live on Social Security and still build long-term wealth? In this video, we tell the real story of how we retired, lived on Social Security, moved abroad, and ultimately built a $1,000,000 portfolio—without get-rich-quick schemes, without reckless risk, and without waiting until our 70s to start living. We didn’t retire early. We didn’t have a massive nest egg. And we didn’t want to trade our healthiest years for “one more year” of work. So we made a different choice. This video walks through: Why retirement in the U.S. didn’t work for us How healthcare nearly broke our plan Why we chose to live abroad instead of delaying life How we structured our finances so Social Security covered living expenses How our investment strategy focused on growth, reinvestment, and protection Why the portfolio was never used as lifestyle money And how we designed a system that supports life now while protecting the future This isn’t advice to copy our life. It’s an invitation to ask better questions, run honest numbers, and design a life that actually works for you. If you’re retired, close to retiring, or staring at the “one more year” problem — this video is for you. 👇 RESOURCES & SUPPORT • Currency transfers we personally use: Spartan FX (supports the channel at no extra cost to you) • Monthly community meetups & planning resources: https://www.itllbefunretirement.com 👍 If this video helped you think differently, please like, subscribe, and join us. We should have done this sooner. It’ll Be Fun. If you’re planning a move, already living here, or simply trying to understand your long-term options, this is one you’ll want to watch all the way through. 👍 Like the video if it helped 💬 Drop your questions or experience in the comments 🔔 Subscribe for real, lived-experience updates on moving abroad Join our community and monthly meetups at 👉 www.itllbefunretirement.com 🎯 How We Help You Move Abroad At It’ll Be Fun, we specialize in making international relocation easy! Whether you're: ✅ Planning a GAP Year ✈️ ✅ Moving to Portugal permanently 🏡 ✅ Exploring a digital nomad lifestyle 💻 We’ve got the resources, connections, and expert guidance to help you every step of the way! 🌐 Join Our Community 📧 FREE NEWSLETTER Get our latest tips, updates, and moving advice! Sign up on our website: ➡ www.itllbefunretirement.com 📅 MONTHLY ONLINE MEETUPS Join our live Q&A sessions and meet other expats! You can sign up via Patreon or on our website. Patreon: www.patreon.com/itllbefun Website: www.itllbefunretirement.com ✨ Our Trusted Partners & Relocation Resources A list of the services and people we trust to make your move smooth and stress-free. 🏠 Housing & Real Estate (Portugal) LCL Real Homes (Claudia Ribeiro) 📧 LCLRealHomes@gmail.com 📞 +351 967 440 896 🛂 Visa & Immigration Assistance Sandra Fernandes Consultancy (Save 10%) 📧 sandra.jfernandes@sjf.pt | contact@sjf.pt EI Migration Agency (Save 10%) 📧 gilda.pereira@eimigrante.pt | geral@eimigrante.pt 🌐 www.EImigrante.PT 💳 Taxes & Financial Planning Taxes for Expats (20+ Yrs Experience) ➡ www.taxesforexpats.com/ref/277 Bordr (Portuguese Tax Services) ➡ bordr.com/portugal/tax-filing?via=itllbefun Filomena Silva (Portuguese Tax Expert) - This is who we use in PT 📧 filomenasilva@zacariasdasilva.pt 📞 +351 965 013 674 💰 Money Transfers & Banking Wise (International Money Transfer) ➡ wise.prf.hn/click/camref:1100lqeJX Spartan FX (Best Exchange Rates) ➡ www.spartanfx.co.uk/fx-partner.php?sfxtrack=madeira 🚗 Transportation & Car Rentals Discover Cars ➡ www.discovercars.com/?a_aid=Itllbefun 📬 US Mail Services Traveling Mailbox (Virtual Mailbox) ➡ travelingmailbox.com/?ref=1351&campaign=It'llBeFun 🔐 VPN for Safe Browsing Abroad - Protect Your Financial Accounts Surfshark VPN (82% Off + 3 Free Months) ➡ https://get.surfshark.net/aff_c?offer_id=926&aff_id=17139 DISCLAIMER: The information provided on this channel is for entertainment and informational purposes only. We are not financial, legal, or immigration professionals. All information is based on our personal experiences and research. Please consult with qualified professionals (attorneys, tax advisors, etc.) for advice tailored to your unique situation. Some links are affiliates, which means we may earn a small commission at no extra cost to you. 00:00 – Welcome to It’ll Be Fun 00:08 – The Retirement Wall 02:05 – The Healthcare Problem 04:20 – Learning How Money Actually Works 06:55 – Looking Beyond the U.S. 09:10 – When Expected Income Disappeared 11:00 – Living Only on Social Security 12:55 – The Engine Behind the $1M Portfolio 14:45 – Building an It’ll Be Fun Life 16:20 – Final Thoughts

About This Video

In this video, we tell the real story behind why we ditched the U.S. “one more year” trap and built a life in Europe that actually works. I’m Allan, and Wolf’s the one who runs the investment side and designed the financial system behind our move. We didn’t retire early, we didn’t have a giant nest egg, and every time we ran the numbers in the U.S., everything looked “fine” until healthcare showed up and blew the plan apart—especially because Leslie is nine years younger than me and wasn’t anywhere near Medicare. Once we stopped treating it like a motivation problem and admitted it was structural, we started shopping outside the U.S.—Mexico, Costa Rica, Panama, Spain—and eventually Portugal. We sold our house, invested the proceeds, and moved, even after life punched us and Leslie’s remote job disappeared almost immediately. That forced us to commit: we lived on my Social Security, and the portfolio was never lifestyle money. The portfolio had one job—grow. Wolf used options trading to generate monthly income that we reinvested for compounding, while we built a calmer, bigger life with walkable cities, adventure, and affordable healthcare. This isn’t a blueprint to copy us. It’s an invitation to run honest numbers, protect healthcare, and build a system where life is lived now and the future is protected—because if it doesn’t feel alive, it doesn’t count.

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