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Beat The IRS At Their Own Game

05 Feb
Closeup of US tax form 1040 and businessman hand calculating and filling report paper at the office.

Beat The IRS At Their Own Game

Whether you consider paying your taxes simply the price of living in a civilized society… or a pain in the proverbial… or downright theft… doesn’t really matter…

Tax season is upon us and Uncle Sam wants what’s due. No exceptions.

According to a new poll from the University of Chicago Harris School of Public Policy and The Associated Press-NORC Center for Public Affairs Research, two-thirds of U.S. taxpayers feel they pay “too much” in federal income taxes.

Sherlock Holmes can rest easy with those guys on the case.

Meanwhile, in Davos, Switzerland, the annual get-together of people with too much time on their hands and apparently too much money in their bank accounts once again saw the gathered “elites” clamor to pay more tax…

They write letters, they set up websites, they declare themselves “proud to pay more”… the one thing they don’t seem to do is put their hands in their pockets and actually pay what they say they want to.

Funny that.

Either way, my guess is whether they pay double in the morning or just continue to talk about it between now and deadline day, won’t make any difference to your bottom line or mine.

In this game you’ve got to look after yourself… arm yourself with the best intelligence you can and keep hold of as much of your hard-earned money as possible.

And the IRS don’t exactly make that easy or cheap…

According to the Treasury Department, individual U.S. taxpayers spent an average of $150 to prepare and file returns in 2023.

This year, the IRS are making free filing software, known as Direct File, available on a pilot program. This invitation-only service is initially being opened up to a group of government workers before being rolled out to qualifying taxpayers in 12 participating states later this year.

If you’re not numbered among that select group then you’d probably welcome some help. After all, the IRS tax code is one of the densest, most complex, most incomprehensible set of rules known to man.

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And the onus is on you to ensure that your every 1 and 0 is in the right place… mess up, and the IRS could come down on you like a ton of bricks.

You do not want to be audited and found wanting.

And the more money you make, the more likely you are to face an audit.

And let me be crystal clear… because, after all, you are reading a newsletter about going offshore… If you are an American, there is simply no way to escape the IRS.

No matter where you live in the world, U.S. citizens are required to file U.S. tax returns every year.

But here’s the thing: The IRS may be big, bad, and scary… But you don’t have to be afraid of them.

I don’t mind telling you, my tax affairs are complex. I’ve obtained multiple overseas residencies, I own property in several different countries, and I run a successful business incorporated outside the United States.

I could be an IRS target…

I may even get audited, but I’m not worried about it.

I know how to speak to the IRS. In fact, I was an Enrolled Agent for a brief period.

An Enrolled Agent isn’t an IRS auditor, but someone who passes a test given by the IRS that allows them to represent taxpayers in Tax Court. CPAs and attorneys are allowed as well.

So, I know how to talk to the IRS… especially about my personal taxes.

My message every tax-filing season is simple: You have to know how to beat the IRS at its own game.

That labyrinthine set of rules… All those different deductions and credits and form after form after form… If you know how to play the game, it’s a set of instructions for never paying a cent more than you have to.

That’s why I’m not worried about IRS audits…

Because I know the rules of the game, and I know how to use the IRS’s own tactics to ensure the IRS never gets more of my money than the minimum it is legally entitled to.

For me, this is not only fulfilling my legal obligation, but also my moral one.

The way I see it, I am morally bound to look after my family and the people and causes I care about… and I don’t owe the government one cent more than it’s entitled to.

Stay diversified,

Lief Simon

Lief Simon

Editor, Offshore Living Letter