top of page


The 2032 Social Security Shockwave: Navigating the Politics and Taking Control of Your Retirement
The 2032 Social Security Shockwave: Navigating the Politics and Taking Control of Your Retirement
itllbefunretiremen
Jul 176 min read


Navigating the Politics of Paradise: Where Does Your US Political Mindset Fit in Southern Europe?
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
itllbefunretiremen
Jul 105 min read


Building Your It’ll Be Fun Life: Italy — La Dolce Vita vs. the 7% Solution
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
itllbefunretiremen
Jan 95 min read


The Long Game: Why We're Sticking with Portugal (Even with the 10-Year Rule)
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.
itllbefunretiremen
Dec 12, 20258 min read


Portugal's Citizenship Changes: What You Need to Know - UPDATED
Father and son in palermo Italy
itllbefunretiremen
Oct 26, 20255 min read


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 12, 20256 min read


YANKEE GO HOME
Portugal Doesn't Want Immigrants At Least Not Always
Leslie
Jul 31, 20244 min read
bottom of page