Freelance Writers: 3 Perfectly Legitimate Reasons to File a Tax Extension

Traditionally, today is tax day for Americans. And if you’re a freelance writer, you’re either:

(I) Done with your taxes: An early bird — and the rest of us are scowling at you;

(II) Doing your taxes: A last-minute, get-it-done type of person that most of us relate to; or

(III) The consummate procrastinator: Hey, filing an extension is the only way out of this mess! The are plenty of us who feel your pain.

If you fall in the last two categories – good news – you have until Monday to get your taxes done. The reason is because of Emancipation Day, a D.C. state holiday which marks the anniversary of the abolition of slavery in the nation’s capital.

Emancipation Day aka Tax Day

The Portland Press Herald gives a bit more insight into this holiday, explaining that …

Tax Deadline 2016The holiday, which shuts down city government, will be celebrated April 15, also known as Tax Day. That means the entire country gets a three-day reprieve on filing its 2015 taxes, making the official tax filing deadline Monday, April 18.

Emancipation Day typically is celebrated April 16, the day in 1862 when President Abraham Lincoln signed the Compensated Emancipation Act, which freed about 3,100 slaves living in the District.

Maine & Massachusetts Residents – You Get Even Longer to File This Year

Yep, if you’re lucky enough to live in one of these states, you get another day – your taxes aren’t due until April 19th on April 18th, those states are celebrating Patriots’ Day – a holiday commemorating the 1775 battles of Lexington and Concord.

So you have a few more days to ugh ahm, procrastinate, ahm, put off doing – oh forget it … just file your extension and enjoy the weekend. Seriously though, following are three good reasons to do so.

How Much Longer Do I Get to File When If I File a Tax Extension?

You get six more months. So for this year, you have until October 17th to file. Sweet, no?

1. Travel

Whether it’s a simple vacation, or you’re a snowbird who migrates from snowy peaks to sunny beaches – or you live abroad (like I do), travel is a perfectly legitimate reason to file a tax extension. I’m doing so this year because my paperwork still comes to a PO Box in the states.

Now as a freelance writer, I can access 99% of my documentation online, but I still feel comfortable having the paper versions of my 1099s in my hand. One reason is, I don’t want to be off by once s-cent-tilla.

So if I haven’t dropped into the states to gather all my mail, I usually file an extension.

2. Life

Sometimes life just gets in the way – a death, a marriage, a graduation, an illness, work, the kids, your spouse – you name it. So instead of stressing about taxes, file an extension. Take care of “life” first. Worry about taxes later.

3. Procrastination

Unfortunately, I’m too cozy with this excuse this year. I happen to be back in the states (have been since mid-February). So I have all of my documents and could easily file on time. But to be honest, I’m just not ready to deal. I’ve been working and enjoying my friends and family, so I’m filing an extension.

Filing Taxes as a Self-Employed U.S. Citizen Living Abroad

This is the first year I’ll be filing taxes as a freelancer who lives and works abroad (my writing business is registered in Jamaica). So to be honest, I’m not quite sure how it’s all going to shake out. I have an idea, but will be paying an accountant to do my taxes this year instead of doing them myself, which I usually use TurboTax to do.

I want to make sure all of my I’s are dotted and T’s are crossed. FYI, here’s some helpful information on your tax responsibilities as a U.S. citizen living and working abroad.

Filing an extension does NOT give you more time to pay up if you owe. It just gives you time to get all of your paperwork together. So in a sense, you still have some work to do if you’re filing an extension but have no idea of your earnings because you must send in what you owe by the tax filing deadline.

And get this, if you underestimate, you will be penalized. Learn more about this, and get more last-minute tax tips.

Oy vey … there’s still no escaping Uncle Sam. That old idiomatic expression is true … the only two certain things in life are taxes and death!

File Your Tax Extension in Seconds

Here’s the link on the Internal Revenue Service’s (IRS) site. It’s free and only takes seconds — really.

CAUTION: Tax Scams

There are a lot of tax scams out there, especially on the web. Scammers know that people are filing and doing so online, so lots of spoof sites are set up to steal your information. Consequently, you need to be careful about sites that let you “sign up and file for free.” That’s why I put the link from the IRS’s site for filing an extension.

There are many legitimate ones on the web that allow yo to do so (eg, TurboTax), but be leery of going to just any site.

And one more thing, the IRS website extension is irs.GOV (not.com); not that that’s a scam site, just wanted you to be aware that because it’s a government agency, it has the dot gov extension.

Here’s some helfpul informaton fromt eh IRS about how to avoid tax scams — and stay safe online, ok?

Now that that’s done … on the bright side, it’s Friday. Go have a drinkie pooh – or two, or three – and forget your tax troubles until Monday (or Tuesday if you’re in Massachusetts or Maine).

Which Tax Camp Do You Fall In?

Are you finished; diggig in and getting them done at the last minute; or a true procrastinator and putting it of by filing an extension? Sound off in the comments section below. As I already said, this year, I’m a “true procrastinator.” Meh … sue me.

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