A Quick Guide to Tax Season 2019

It’s that joyous time of year again, tax season!

Hey, don’t cry, it’s not that bad!

We know tax season sucks, so we crafted together this quick guide to help you through the pain. We’re here to answer the most popular questions, keep you up to speed and make sure you’re aware of any major changes in this 2019 tax season.

First time filing taxes? Then you should read this first.

When can I file my tax return?

The IRS has confirmed they’ll begin processing tax returns for the 2019 tax season starting January 28th.

But that doesn’t mean you have to wait, you can file your taxes online whenever you want!

It’s important to mention that if you’re filing a tax return online, you can start whenever you like. Just be aware that even if you send your forms in early, the IRS won’t start processing it until tax season begins on January 28th.

How long do I have?

illustration of a calendar showing april 15th

You have until April 15th to file your tax return this year.

What if I can’t file taxes by April 15th?

Can’t file your tax return by then? Don’t worry! The IRS has a few different extension plans to chose from. Be aware that even if you get an extension, that still doesn’t mean you get off scott-free.

On the contrary, requesting an extension can get quite pricey. Let’s take a look.

  • 2 Month Extension – This is the most common of the two, and gives you a 2-month extension starting April 15th. You won’t be hit with a penalty, but you do have to pay interest on it. Currently, the annual interest rate is around 3.81%.
  • 6 Month Extension – This is where things start to get pricey. If you request a 6-month extension, you’ll have to pay both interest and a monthly penalty on the taxes you owe. Currently, the penalty is 0.5% on your total taxes, stacking up to a maximum of 25%

As you can see, it’s probably in your best interest (ha, puns) to file your tax return by the end of the tax season. If not, you could be paying quite a bit in extra fees!

Does the government shutdown affect my tax return?

Nope! Thankfully, filing your taxes won’t be affected by the government shut down.

That being said, whether or not the shutdown will affect how long your refund takes to get filed remains to be seen.

File your tax return online for FREE

Oh internet, how easy you make things! Doing taxes has never been easier (or cheaper) and it just keeps getting better every year.

Most (though not all) online tax companies will file both state and federal taxes for free. As such, be sure to read the fine print before you commit to filing with anyone!

Here are 3 popular sites that you can file your taxes with, for free!

H&R Block

H&R Block is a great one to pick if you just want to get tax season over with quick and easy. They explain things relatively well and will walk you through the process of finding exemptions and credits for you.

The biggest downside we saw was that our tax return was just slightly smaller going through H&R Block. It was only $20, but still, more money is more money when filing for free.


  • Simple and easy to use
  • Takes the least time
  • Clean UI


  • Can be a bit too simple sometimes
  • Isn’t as informative about certain things
  • We saw a very slightly smaller return

Tax Slayer

illustration of a cartoon reaper

Next up is TaxSlayer. While their name may be cringe-worthy, they have a pretty good web app for filing taxes online. The UI is slick, responsive, and user-friendly. On top of that, they file both state and federal taxes for free.

However, they do try to bury the fact that you can file state taxes with them for free – but only once. Keep this in mind if you’ve filed with TaxSlayer before!


  • Nice UI
  • Takes a bit longer, but you get more information


  • They push unnecessary fees
  • Customer support is limited


Last but not least, we have TurboTax. Their slick filing system will guide you through the entire process one step at a time. Not only do they make your taxes easy, but they’ll also help find any credits you qualify for to maximize your tax refund.

The downside is that, while still 100% free to file federal and state taxes, things get ugly when applying for credits. Some (but not all) exemptions and credits require that you pay for their “premium” service to be able to use them. Note that it doesn’t tell you this until after you’ve gone through the process of figuring what you qualify for. It feels a little scummy.


  • Well known and trusted brand
  • Relatively easy to use
  • Heaping amounts of information


  • While they used to be 100% free, TurboTax now tries to force you to pay for their service depending on how complicated your taxes are.
  • Scummy money-grabbing tactics
  • Sometimes they have a little bit too much information

IRS FreeFile Alliance

If you prefer to stick with the IRS, you may be able to qualify for their Free File Alliance program. To make a long story short, if you make under $66,000 you don’t have to pay any fees to file with these certified IRS partners.

You can read more about the Free File Alliance program over here.

Get the most out of your tax return

illustration of a hand holding cash

Did you know you can get a tax credit for having a low income? Or that you can get $500 back for claiming that screaming child in the background as a dependent?

Exemptions, credits, and deductions are the crown jewel of tax season, so make sure you stay up to date on what you qualify for!

Tax exemptions for 2019

While online filing does a great job of finding all the exemptions you can get, they’re certainly not bulletproof. You don’t want to miss out on paying fewer taxes! Get up to date on all the major exemptions you may qualify for, right here.

Big changes to deductions this tax season

Did you know that the standard deduction doubled in 2019? That’s right! Here’s what deductions look like now:

illustration of tax deduction income limits

You can read more about what the Tax Cuts and Jobs Act (TCJA) changed for our 2019 tax season over here.

Get all the tax credits you can!

Tax credits are awesome! Why? Because they’re a direct reduction/refund back to you, without any IRS shenanigans involved.

There’s almost certainly 1 or 2 tax credits that you qualify for, so make sure you brush up on tax credits before filing this tax season!

How dependents work this tax season

Got kids? Get money back! I know, kids don’t usually mean more money, but you can get some sweet exemptions and credits by filing your kids as a dependent. Learn more about dependents and how you can profit from your children over here.

Maybe for once, they’ll owe you for a change!

When will I see my refund?

The IRS says it will take around 22 days to see your refund in the mail. That being said, if you filed your tax return online and used direct deposit, you’ll likely see it much sooner.

As an example, last year I filed my taxes online and had the refund within 7 days. Impressive!

What to do after filing your taxes

Yay, taxes are finished! That means you’re done right? Hold your horses’ cowboy, there are a few remaining things left to do.

Did you get a sizable refund on your tax return? Then now’s the perfect time to make some changes to your W4, or rather, your tax withholding allowances.

Learn how you can increase your paycheck right now by adjusting your tax withholding allowances. I know, it sounds boring, but trust me, it’s super easy!


OK, now taxes are done, yay!

If you’re just filing online, taxes are super easy. This is especially true in 2019, as the TCJA has encouraged most people to simply take the standard deduction.

It’s estimated that over 92% of tax payers will chose the standard deduction this year, up from 78% in 2018.

We hope this guide to the tax season of 2019 was helpful! Let us know how your tax return went on social media.

Want more helpful guides, tips, and finance info? Then sign up for our weekly newsletter, it’s super awesome!

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Puppy Tax

Picture of Mika in the mountains.

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