For the past couple of years (couple, three, four …) completing the required annual federal income tax return by the due date has been too much of a burden for me to accomplish.

So, on or around April 14 each year, I request an “extension to file,” which automatically gives the taxpayer an extra six months to file a return. The IRS is very clear that having permission to file late does not grant permission to pay late. Thus, if you owe the Feds money, you must pay when you request an extension. Now this begs the question: If you need another six months to file, how do you know how much you’re going to owe?

Glad you asked. You must “do” your tax return in some type of rough draft form to figure out which pound of flesh you’ll need to amputate to keep Uncle Sam quiet for half a year while you look for loopholes.

My first result was ugly. (“Really? You’re telling me that I took in so much money that you want more? My bank account disagrees with you!) But, I submitted two-thirds of the amount due (It’s legal.) with my extension request. I swear, the payment was processed and withdrawn from my account before I could enter the transaction in my checkbook.

I had a little talk with myself about this procrastination problem. “Don’t ever do this again! You’re all worked up and stressing over this. Another hour or so and you could have it finished! Now, you’ll have to face the torture again!”

Then I promptly forgot about the IRS for about five months.

In September, in one of those heart-stopping, on the verge of catastrophe moments of panic, I realized that my six-month extension was about to expire and I never got around to looking for those loopholes, mainly in the form of charitable donations and “taxes paid.” To my dismay, there were few to find.

Sadly, on Oct. 12, after a couple of hours scouring receipts, little scraps of paper, and official documents, I faced the fact that my initial, pencil-scrawled paper Form 1040 and my accompanying Schedule A, roughed out on April 14, was within a couple of dollars of the final tally. There was no possible way to spin it: I owed an additional, hefty sum.

Painful as that may be, it didn’t come close to the fresh Hades I was about to enter when I tried to e-file my return.


To be continued ...


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