The Procrastinator's Guide To Filing Taxes

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Long before we are functioning, earning members of society, April 15 is drilled into our heads. This would make any reasonable person think that Tax Day is THE most important day of the year, with the only other days typically ingrained into our childhood memories being Christmas, New Years, and our birthdays. Tax season is the joyous time of the year when we gather our W-2s, our 1099s, and our 1098Es and plug those excitement eliciting forms into other forms so we can fulfill our civic duty and pay the Tax Man.

Taxes aren’t always easy, though – they’re a major source of anxiety and stress for some, especially those who haven’t been doing them all that long. This stress and anxiety leads to procrastination, which then leads to us to ignore Tax Day until April - and we all know what happens when we’ve waited to the last minute to file. We get that familiar pit in our chest, our heartrate increases, and we get nervous, which only leads to more anxiety and procrastination.

Sound familiar? Behold fellow procrastinators: tips for your last-minute, tax-filing needs!


It’s super easy to overthink something and psych ourselves out. We do it all the time. Let’s not do that here.

Taxes are intimidating, and frustrating, and tedious, but they’re necessary for a functioning society and, whether we like it or not, it’s the law. Lucky for most of us, all they entail is getting the proper forms in order and filling in the requisite boxes. It’s a pain in the tush, but I swear, it sounds harder than it actually is.

For those new to this tax game, don’t be afraid to ask for help. Parents are a great resource, as are older siblings and other family members. Friends are also reliable resources because they may be more comfortable with filing and may be able to walk us through it.


TurboTax. That’s it.

I don’t know how they did it, but the people over at Intuit and TurboTax made filing taxes incredibly easy. For returning users, all it takes is an upload of 2017’s W-2 and then some requisite document reviews, and that’s it. For first time users, there is some data entry required, but they’ll breakdown every step and explain why it’s needed – all without patronizing, which is a huge plus.

It won’t make any of us experts on the tax code, not by a long shot, but it will help us understand a bit why we need to submit certain information, and it’ll do the heavy lifting for us.

The very basic level is free, and there are different payment options for different tiers of service, but 1) the payment can be made with our tax return, and 2) it’s a small price to pay for peace of mind.

I’ve been told HR Block has a similar service. I’ve not used it, but I’m sure it works in much the same way, and for anyone looking to file taxes in a hurry, these seem like the best options available.


Paying taxes is our civic duty. Do we like it? Not particularly, but we enjoy driving on paved roads, and lounging in publicly funded parks. The fact of the matter is, as painful as taxes are, they are a necessary evil. Plus, if we don’t pay them, the tax man cometh, and no one wants to be on the wrong side of that squabble.

Plus, once they’re done, they’re done. No more taxes to worry about until April of 2019, which is basically a lifetime away!

Until next time – Have you seen my W-2?

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When Arye isn't helping optimize your time, he is doing his part to ensure life is full of shenanigans.