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Category: Taxes

16 Sep
A man filing taxes

The Challenges Of Tax Filing While Being Abroad

Oct. 15 Looms—Here's What You Need To Know To Stay Compliant That is, any American who filed for an extension is now buckling down to prepare his 2018 tax return... myself included. One related topic that has been generating lots of questions for me, both during last week's Retire Overseas Conference in Houston and in my inbox [...]
08 Apr
Blackboard with April 15 Tax Day written in big letters

Admitting Defeat On Tax Form 5471… For This Year Anyway

How The IRS Finally Got Me To Cry Uncle OK. I give up. I started working on my U.S. tax returns last week. Ordinarily, that'd have allowed me plenty of time to finalize everything in time to file on the 15th. But these are not ordinary times, dear fellow offshore American. The changes as represented [...]
07 Mar
tax return being filled out

An Update On Tax Changes And Qualified Opportunity Zones

Qualified Opportunity Zone Tax Breaks—Setting The Record Straight The U.S. tax code is nearly 75,000 pages long. That is to say… U.S. taxes are the most complicated in the world. Tax bills are passed based on political whim and agenda and then the IRS is tasked with drafting detailed regulations to connect the new laws [...]
14 Feb
man calculating taxes with a calculator

How To Stay Compliant With Offshore Taxes

Everything The American (And Canadian) Needs To Know About Offshore Taxes This month’s issue of my Simon Letter service features my annual review, overview, and update on taxes for the American abroad. The big change affecting us Americans overseas since my report this time last year is the 2017 tax law that now forces U.S.-controlled [...]
03 Dec
portimao, portugal beach

Five Flags: Comparing Panama And Portugal’s Citizenship, Residency, Real Estate, And Taxes

#1 Choice For Going Offshore In 2019 We Americans tend to dismiss Europe for overseas lifestyle and investment options, thinking this part of the world is too complicated or too expensive. The truth is that some European countries can be cheaper than destinations that might much sooner come to mind as top live and invest [...]
12 Nov
couple tax return

Considering Your Tax Options? Remember To Put Profits First

Why I'm Sometimes OK Paying More Taxes A few years ago, after reading an article I'd written detailing an American's ongoing obligation to file a tax return with the IRS each year even after he's moved overseas, a reader wrote in to correct me. The reader proudly pointed out that an American does not need [...]
04 Oct
A view of downtown Panama City at sunset

Take Your Business Offshore To Operate Tax-Free

How To Operate Your Business Tax-Free By Going Offshore The key advantage of going offshore is diversification. The good news is that you have the opportunity to diversify not only your investments in this way, but your life, too—both your personal life and your professional one. That is, in today's world, you can realize many [...]
09 Aug
A desk with laptop, glasses, calculator, and euros

Tax Rules: How To Minimize By Keeping A Global Mindset

How To Reduce Your Tax Burden… Maybe To Zero I’ve been reviewing tax regimes of a couple dozen countries over the last few weeks, trying to help out with the Overseas Retirement Index that sister publication Overseas Living Letter puts out each year. The research has reminded me of two things. First, the United States has the [...]
23 Apr
hand holding a pencil which has written the word tax in capital letters on a piece of paper

There Are Many Reasons For Going Offshore, Taxes Aren’t One

Last week was the end of the official tax season for Americans. We all got an extra day this year because the IRS’s online system crashed in the 11th hour. Too much traffic in the final hours leading up to the midnight deadline. Seems more and more people wait until the last minute to file.