Doing Your Own Taxes Isn’t As Scary As You Think


Before graduating to full adulthood, I was terrified to do my own taxes. I wouldn’t even consider the idea. In fact, I felt like there was no way I could understand the process and no way I could get it right. Essentially, I thought I would end up being audited and thrown in jail if I tried to do any such thing. Do not pass Go, do not collect $200. You screwed up your taxes and we’re throwing away the key. False. This was my thought process throughout my entire 20s. Then I hit 30, split up with my fiance, and was starting my life over in an empty apartment with 4 lawn chairs. That’s a story for another time. You can actually listen to it here. The point is that when I re-booted my life, I had to start from scratch and I didn’t have extra money to go pay someone else to do my taxes for me, like I had done in the past without a second thought. I had 4 lawn chairs to my name for god’s sake. I had to figure everything out on my own for the first time in my life. I did. And it was totally fine.

NOTE: I am not being paid a dime to plug TurboTax. It’s just the program I used. And, it worked great for me. 

I Had An Idea

As I sat there alone in my dank apartment with my W-2, I got an idea.The idea was to attempt do my own taxes. Or, at least plug in the numbers and see what happened. Ever since I started earning an income at the retirement home, followed by McDonald’s, and so on, I had been going to a place like H&R Block and paying them to do my taxes. Looking back, it seems silly that I paid hard-earned money to people who were just, in essence, typing my numbers into an automated program like TurboTax. Granted, this was before TurboTax and similar programs were common amongst DIY tax people. That makes me feel a little less embarrassed. But as the years went by and I earned more and more money with fewer and fewer deductions, the cost of having someone do my taxes for me was starting to irritate me. The cost was easy to overlook when I was still with my fiance, but now that all living expenses were on me, I had to do something. I didn’t want to pay someone >$100 to plug in some numbers. I was a smart person. I could do it. And so I did.

Related: Saving Millions By Rejecting That New Car Smell

Online Tools

peer_pressure(1)So, one night in February I had all of my tax documents in front of me at my corner desk in the apartment – I had bought myself some furniture at that point. I started to search the wonderful World Wide Web for tax laws. I read forums about doing your own taxes. I took notes. I looked at the breadth of my taxes. In retrospect, it was silly of me to be so intimidated. After all, I was single with a W-2 income and some student loan interest to deduct. The one thing I did have that was scaring me was my rental property. How could I possibly know what to do with that?   No matter, I went for it. My thought was that I didn’t need to actually submit anything. I was just going to plug in the numbers – like they did at H&R Block and see what comes back. Then I can go to H&R Block and have it done by a professional. At least it would give me a good idea as to what my refund was going to be.

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I finally decided to go for it. I logged onto and made a profile. I followed the prompts and started plugging in numbers. Then it came to the rental property. I pulled out my little ledger that I had been using all year to record my expenses. I plugged in all the numbers the program required, including PMI, mortgage interest, and property tax information. I also entered the annual amount I had spent on upkeep and maintenance. I was prompted for Every. Single. Line. Item. Easy peasy.

At the time, I was having extra taken out of each paycheck to make sure I wouldn’t actually owe the government anything when tax season rolled around. I know that might sound absurd to some folks, but you have to remember I was single and didn’t have anyone else to back me up. Not only was I supporting myself, I was also subsidizing my mother’s living expenses at the time (to the tune of $800/mo). I didn’t have any room for financial error. Per my perspective, a lot was riding on my shoulders. Hence, the need to try to save a dime by doing my own taxes.

Related: My Single Biggest Financial Mistake: A Decade-Long Disaster

Finally, everything had been entered and TurboTax had an enticing return staring me in the face. If I just submitted it, I could have it electronically deposited into my account in about a week. But no, I didn’t trust myself. I just did it to see what my refund was going to be. The plan was to exit out and still go pay to have it done by the professionals. But why would I do that when I could just submit the information and get my refund without paying anyone a single dollar? Because, again, I didn’t know what I was doing. Did I? No. The answer was no and I was going to cancel it. But wait, I was a smart person. My taxes were pretty vanilla, with the exception of ONE rental property. And TurboTax made me feel like I had entered that correctly, too. It was truly a moment when I had tiny, opposing, invisible versions of myself sitting on each shoulder pushing me to make a decision. Decision made. SUBMITTED. 

I did it. I did my own taxes. And I felt powerful. I conquered something I never thought I could ever do on my own. I also thought I could never live on my own or start my life over at 30, but I was doing that, too. It’s funny how much you can accomplish if you’re forced into a situation or you start expecting more of yourself. My driver was saving money. I saved money that year. But, more importantly, I also grew as a person. I defeated a fear I had my entire adult life. I continued doing my own taxes using that same online program for years after that. It served me well and saw me through a daughter and a second home purchase.

Related: Why We Include Our Home’s Value In Our Net Worth

DIY Taxes

This year will be the first year that I will not be doing my own taxes. The reasons are many. Mainly because I’m now married to someone with a somewhat complicated business. Although I feel extremely comfortable with online DIY tax programs for “normal life stuff”, I don’t feel so confident about getting everything right with his multi-faceted business. This year, we will be paying a professional.

But, if you’re a Millennial or a Gen-Xer who has nothing out of the ordinary and has never done your own taxes, I say shake off those fears and go for it.

Note: Houses, spouses, and kids (oh my!) are not out of the ordinary.  

Believe me, you are probably smarter than you’re giving yourself credit for; it’s likely a lack of confidence that’s holding you back. Make up your mind and believe you are smart enough to navigate an online DIY tax program. You can tackle it the way I did – just try it. If you feel you didn’t do it right or the refund amount is grossly out-of-whack, cancel it and go to a professional. What have you got to lose?

What are your thoughts on DIY taxes? Are you considering it?


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17 thoughts on “Doing Your Own Taxes Isn’t As Scary As You Think

  1. I’ve done my own taxes for the past two years. I have a rental property as well, and that makes me a little nervous, but it’s been good I’d say. Rental properties are an awesome way to build wealth. I brought in about $17k in rental income and only increased my tax bill about $1k due to depreciation, interest, PMI, expenses, etc. The government wants people to own houses!

    Liked by 1 person

  2. I’ve always done my own taxes. We don’t have multiple business interests or anything complicated that would require hiring an expert. I’ve used H&R Block in the past put am switching to Turbo Tax this year as I can directly upload tax statements from my investment accounts.

    Unless you have a really complicated situation, DIY is the way to go. Buy a software program, answer a few questions, and submit. It really is pretty easy. And in the off chance that you get audited (1% chance for the general public) they will offer audit support.

    Liked by 1 person

  3. I’ve never paid anyone to do my taxes, but they’ve always been pretty straightforward. My parents use TurboTax and cd version lets you file multiple returns without additional cost. Once I got older, I started using the online version of TaxAct, which I still use, although I’m debating if I should use TurboTax instead. A little more expensive but I think it’s more user-friendly.

    Liked by 1 person

  4. I’ve never hired someone to do our taxes. I have one or two complicated investments (0 coupon bonds and foreign stocks to name two), but for the most part my tax situation has been straight forward. I do plan on hiring one next year to do my wife’s freelance taxes but even hat I expect to be a one year thing. Laws change from year to year but once you get the hang of it it’s mostly the same every year except a few key rules. For those you use the program and the IRS website. So we will use someone next year and side by side do a non filled online example via tax act. Once I can replicate what they’ve done I don’t expect to need an accountant for taxes again unless my situation majorly changes.

    Liked by 1 person

  5. One of my fist jobs after having the Princessa (our second and final child) was with Intuit. I was Tech Support for the CPA’s software side of TurboTax!
    For the past 23 years, I have been doing my own and everybody else’s taxes that I can confidently handle! The software makes it so easy to do – once you get over that initial terror!

    I have spread the word for the past two decades!

    Also, their (QuickBooks and) Quicken have been stellar products that helped me micromanage my budgeting for those same decades!

    I was heartbroken this year when I discovered that my beloved Quicken wouldn’t work (even with all their voodoo patches) on my Windows10 computer… :-/
    They couldn’t get it to work, and refunded my purchase. I’ll try them again as soon as they issue the next version.

    Liked by 1 person

  6. Your first-time tax DIY sounds a bit less stressful than mine. I was 19 and had most of my info entered into the software (very simple, just a W-2 and maybe some investment interest) and decided to play around one night seeing what my refund would be if I maxed out an IRA. The next day, when I submitted the return I forgot to put the IRA numbers back to reality! $40 expense to file an amended return was a fairly cheap lesson in comparison to the accounting degree and CPA license I have now.

    Now I get paid to do taxes and occasionally fix people’s returns that were botched by big-box tax shops. People don’t realize that those paid preparers don’t get much training and don’t generally need/have any kind of license, and if they screw up your return, YOU are probably the one liable for the IRS penalties/interest. /rant

    Liked by 1 person

  7. So, I’ve always done my own taxes. In fact, the first two years, I did them the old school way on the actual tax forms the IRS provides (gasp), with no software assist or anything. Actually, it was a good eye opener into what really affects how much tax you end up paying.

    Having said that, I’m not perfect. One year, I forgot to report a retirement contribution and my return was 300 short. I ended up getting it after I filed an amended return. This year, I forgot to report state tax withheld. Return was 800 short. Again, I will have to wait until the amended return goes through to get that money. I suppose I should probably be a little more thorough I file :).

    Liked by 1 person

  8. I’ve done my own taxes ever since I started working on Wall Street. I started with TurboTax, but now use H&R block because it is cheaper. It’s great to do your own taxes because you understand them better and can take steps to legally reduce your tax burden.

    Liked by 1 person

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