Hoping for better luck next year with DIY tax preparation

It was going on late afternoon, and I was still in my pajamas. Not that I’d been lazy — on the contrary, I’d been very occupied. I was filling out the 1040 using software from the IRS website. And everything had gone badly.

“Let Free File do the hard work for you” the IRS site says. Indeed, the software program did seem simple. Pop-up boxes guided every step.

But then, the 1040 finished, I tried to file. A message said that my income exceeded the limit to use that software program. I had chosen the program without thinking that the conversion of a traditional IRA to a Roth IRA would push me over the limit. An on-screen box said return to the IRS, and in frustration I impulsively clicked it and lost everything. If I’d paused to think first, I could have tried to backtrack through the steps to copy the numbers.

Okay, I reassured myself, if I redo immediately, I’ll remember most of what I did.

Another Free File software program for which my income qualified would allow working online but not filing electronically. That was acceptable; the finished form could be printed out.

Just before breaking to prepare lunch, I decided to print out a worksheet from the 1040 instruction book. I returned to the computer to find the entire 1040 instruction booklet was printing instead of a single page.

Meanwhile, Lizzy, my cat, maybe feeling neglected, asked for attention the way she knows best: She pooped twice under the dining table.

When I finished the second go-around and went to print the 1040 form, I couldn’t get it to fit an 8½ x 11 page. The pages kept printing at about double size. The right side, with the critical numbers, was cut off. If the right side had printed instead, I might have been tempted to send the return to the IRS with the left side missing.

The last resort was to print out a blank form and copy everything in by hand. Only when putting the pages into an envelope did I realize the sheets were from my recycling pile. The reverse sides contained condominium news. The obvious solution was to photocopy, but by that point I felt too much 1040 aversion to care. If it looked sloppy to the IRS, so what? It wasn’t likely they’d reject the return. In fact, I even felt some satisfaction in drawing X’s through the back sides.

The good thing — besides being done — was that I didn’t owe money.

I hear other people talk about getting records together for their tax preparers. Few mention doing their own taxes. I suspect I’m in a minority. I hate doing taxes, so why not turn the chore over to someone else? I suppose it’s partly stubbornness and partly penny-pinching. But I also have had bad experiences the two times I had someone else prepare my taxes.

Once was the year I bought my first condo. I had withdrawn the down payment from mutual funds. That was back before investment companies provided the cost basis on the sale of mutual fund shares. The preparer calculated my capital gains using the cost basis least advantageous to me. Suspicious about how much I owed, I refigured the taxes and saved hundreds of dollars.

The other time, an accountant relative made a mistake on my 1040 for which the IRS issued a fine.

Besides, the problem this year wasn’t with the the actual tax preparation but the software. If things hadn’t gone wrong with the software, I might have finished in, say, about three hours. (I take the standard deduction.)

Lesson for next year: take more care with the choice of software. Maybe use a program from somewhere other than the IRS site.

The online state return, in contrast, presented no problems in preparing or filing. It was finished in lickety-split time. With all the bad press the state of Illinois is getting, I’m happy to report something it’s done right.



"You can be a shameless toady, or you can try not to let the door hit you on the way out."

Chicago Tribune columnist Steve Chapman


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  • I recommend TurboTax online. It is not very expensive, and it walks you through all the steps and then handles the e-filing.

    And I enjoy your posts!

  • In reply to Architecture fan:

    Thanks for the compliment and the tip.

  • We use H&R Block. It's okay. I think the first year, it was free. This year, we paid $34 and some change. They forgot to ask us about our quarterly tax payments. It took awhile to find where to go so we could input that info. We've used Turbo Tax but it seemed too expensive for a simple return, no itemizing, standard deduction. However, we did like Turbo Tax.

  • It wasn't H&R Block, but one of its competitors, that took the easy way out on my taxes, which would have resulted in a big bill if I hadn't redone them. I think I am going to continue to do them myself but take more care looking for a good software program.

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