All Aboard the Tax Rollercoaster!

I am a glutton for punishment. That is, I do my taxes each year as soon as I can. The truth of the matter is that I do our taxes ASAP so I know whether we will owe money and to have more time to get the IRS payment together.

Doing my taxes can make me sick to my stomach, and this year was no exception!This year was no different. Unlike years past, I did not divert any of my freelance income to a savings account for taxes. Although I only made a few thousand dollars as “self employment” income, I was still concerned.

I was also unsure of how the whole mortgage interest deduction would work out for us. I had heard that some people see no difference in their taxes when they buy a house.

Lastly, I was worried that I screwed up our IRA withdrawals. Remember when we withdrew $40,000 from our Roth IRA’s to come up with the down payment for our house? I researched the hell out of that rule, but my mind was still not at ease. The rule requires the IRA to be open for 5 years and, depending on how it’s calculated, it could be argued that Mr. Stapler’s IRA was not open long enough for us to withdraw his contributions tax-free.

With the specter of Major Financial Screwup looming over me, I boarded the TurboTax rollercoaster.

You see, TurboTax has a little icon at the top of the screen, which shows you the amount you owe or the amount of your refund. With each step of the data-input process, the icon updates like a cash register. It’s thrilling and stressful at the same time. As an attorney, it’s a familiar feeling — I go into most hearings with a pit in the bottom of my stomach and by the end of it, my head is buzzing. I guess I really am a glutton for punishment!

In our case, our W2’s entitled us to a $10,000 refund. So, I was anchored at the “holy shit!” amount of an amazing refund. Then I entered my business income and the refund plummeted to $3,000. It’s still an awesome refund, but it’s not $10,000. Womp womp.

The beauty of being self-employed, however, are the business deductions. Home office. Server. Cell phone. Professional dues. Mileage. Oh, how I love the mileage deduction! After the business deductions came the daycare exemptions and charitable contributions.

We were back up to a $9,000 refund.

But the true moment that tested my mettle as a personal finance connoisseur was entering the 1099-R. That scary form arrived from Vanguard shortly after the new year. It detailed our IRA withdrawal and classified it as “Taxable amount not determined.” The distribution did not meet an exception. The refund plummeted to $50.

TurboTax followed up this heart attack moment with the magic questions: Did you buy your first home? When was the account opened? How much did we contribute in the past? After navigating that gauntlet, our refund shoots back up, to a thrilling $9,030 tax refund.

Why did TurboTax taunt me so?! 


Does that refund amount make you ill or does that make you thrill? If you’re a CPA, you’re likely scoffing at our amateur withholding choices — many financial professionals tailor their withholding so that they won’t get a refund. If you’re a spendthrift, you’re likely thinking of where to spend that huge chunk of change. I would like to think that money doesn’t burn a hole in our pockets, but this refund will probably get spent on something: Debt payoff, home improvement, or a car. Thankfully, we haven’t yet touched it — although it’s been sitting in our account, waiting for some company, for about a month.

And yes, dear readers, I will adjust our withholding on our W4’s, so we can use that money throughout the year instead of loaning Uncle Sam the money for free.

Have you braved the tax rollercoaster yet? Do you already have your refund? 

image from ponsulak, via

4 thoughts on “All Aboard the Tax Rollercoaster!

    • As soon as Mr. Stapler gets me his most recent paystub, I’m going to attempt to calculate a correct withholding for this year on the site. But in these days of Direct Deposit, receiving a paystub is more and more rare.

  1. I file my tax refund the day it becomes available! It’s exciting for me as well! I actually calculated my estimated taxes back in December of last year to see if my fiance and I should elope for tax purposes or wait until our official wedding this year. I’m a tax geek.

    • Well, it’s good to know your options! 😉 Before we were married, I calculated whether we should delay in order to qualify for the Public Service Loan Forgiveness program (back before it allowed for both people to have student debt and still qualify).

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