Filing Your Taxes: The Ultimate DIY Project


Just a heads up, this post is sponsored by the folks at TurboTax. This should go without saying, but all content and opinions are our own and came straight from our own noggins.

When I was a freshman in college, I took one of those personality tests that would analyze your characteristics and spit out some careers that you might be well suited for. I had pretty lofty expectations for what they might suggest. A CEO? Maybe even a US Senator? Nope. Not even close. Ready for their top recommendation? A librarian. I was Dewey decima-ted. (I’m surprised they didn’t say comedian, am I right?) After analyzing the results, it actually wasn’t all that off-base. I like order, I like organization, and I like systems. And while I didn’t pursue the study of librarianship, it’s no wonder why I’m one of those weirdos who actually enjoys doing taxes.

But whether or not you’re part of the cool club of tax-filing enthusiasts, I’m going to share a likely unpopular opinion: everyone should be required to “do it yourself” and file your own taxes. No, not forever. But everyone should go through the process at least for a few years. Why? This shouldn’t come as a surprise, but we’re major proponents of being in the driver’s seat of one’s finances. If you’ve committed to starting a budget this year and you’re tracking your spending, one of the best ways to close out the year and reconcile all of your hard work is by doing your own taxes. You should know and understand what affects your taxes, where your money is going, and how to prevent more of your hard-earned money from leaving your pocket next year. And thanks to TurboTax, it’s totally possible to DIY your taxes this year without messing it up.


I’ve done our taxes all 9 years of our marriage except last year when we started our small business. Here’s how our tax filing usually goes. I’ll collect every scrap of financial paperwork that I’ve hoarded over the last 12 months, divide them into appropriate piles (W-2s, 1099s, business expense receipts, health insurance paperwork and bills, etc.), pull up TurboTax, and crank up some Rage Against the Machine (just because I like doing taxes doesn’t mean I like paying taxes). An hour or so later, we’re staring at our projected refund amount (because we don’t claim exemptions) and our taxes are on their electronic journey to the IRS.

A common misconception is that doing your own taxes means doing your taxes all by yourself. TurboTax lets you do your own taxes, while also offering step-by-step guides and on-demand help from actual, credentialed CPAs and enrolled agents. The software walks you through income, possible deductions, etc. in a super easy format while ensuring that you’re getting the maximum refund possible. A new feature we’re digging is the TurboTax ExplainWhy, which does exactly what you’d think — explains the “why” behind deductions, credits, and refunds as you go. For folks like us who like to know the nitty gritty of every little cent, this is an excellent “teach a man to fish” tool so that we’re all more informed taxpayers.


Early in our marriage, our taxes were pretty basic. (And psst, if you’re in that boat and file simple returns like a 1040A or 1040EZ, you can file completely free right here.) Admittedly, each year, our taxes have gotten more and more involved, especially now that we’re self-employed. With running a business, we’re now getting up close and personal with our taxes year-round. And TurboTax Self-Employed is a year-round tax prep and expense tracking solution for self-employed since it also includes a year of QuickBooks Self-Employed. So if you’ve got a side hustle or 2017 is the year you’re breaking out on your own (fist bump), make sure you’ve got your financial ducks in a row. Even better, right now TurboTax is offering OFB readers 10% off TurboTax Self Employed.

Here’s a final thought with taxes — you’re going to be doing them for a long time. The rest of your life in fact. So best to learn it sooner than later with software that will virtually hold your hand the entire way. Taxes might not be a DIY project you’d pin on Pinterest, but you’ll be more informed, self-sufficient, and prepared for your financial future.

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  • Reply Lee Chilvers February 16, 2017 at 5:40 am

    Ugh I used to hate having to file my own taxes. I’m so glad that we have people like you who actually enjoy it! (Even if perhaps not as much as being a librarian lol!)

  • Reply Katy February 16, 2017 at 1:42 pm

    We love TurboTax! Our taxes are slightly more complicated than most, we own a rental property, both have W-2 jobs and also contract jobs with 1099’s. It’s been a breeze every year with TurboTax.

    They also have great customer service over the phone for any questions you might have!. We used this more times than we’d like to admit the tax season after our son was born!

  • Reply Alexis @FITnancials February 24, 2017 at 4:59 pm

    I actually enjoy filing my taxes. I’ve been using Turbotax for a few years and they make it incredibly easy for the self-employeed!

  • Reply Jordan Packer March 1, 2017 at 1:29 am

    Taxes are mandatory and there is no escape to settling your own. With this system, the complexities of tax payment becomes simple. Good info on this post indeed.

  • Reply Adriana @MoneyJourney March 9, 2017 at 1:24 am

    I have never filed my own taxes. It’s not because I hate doing it, but because I’m a scaredy-cat . What if I make a mistake or forget to sign something important? Apparently we have Turbotax available in Italy too, I had no idea!

    By the way, I would have loved to be a librarian! Too bad I only discovered I love books later in life, as a kid I was more into anything else but reading 😀

  • Reply Mike@ninjabudgeter March 9, 2017 at 8:15 pm

    I have always done my own taxes. It’s embarrassing to admit how exciting it is to get a little bit of my own money back!

  • Reply Schambs Property Management April 1, 2017 at 7:11 pm

    This is a great article. Very informative for all eyes. Just the knowledge of the entire process of filing taxes yourself can save you hundred of dollars. Extra cash could easily be reinvested so this is perfect for getting started. Thanks again!

  • Reply Ms. Frugal Asian Finance April 2, 2017 at 2:19 pm

    We also used Turbo Tax to file our taxes. It saved us a ton of time and preempted many heated arguments 😉

  • Reply Christopher Steadman April 6, 2017 at 8:57 am

    Hello Joanna and Johnny,

    This is my first time here. You have such a cool blog. I have bookmarked it and going to read in my spare time.

    Keep up the good work!

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