No, it’s not April 15th just yet. But I’m getting into that zone where I need to start sending relevant info to my accountant to get the ball rolling for my 2021 tax return.
I hate that I have to farm out my tax return preparation to a professional in order to get them done. I wish the US tax code wasn’t the way it was – who doesn’t?
But let me relate a little story to you that might get your mind right about whether or not to go it alone when doing your taxes…
I don’t remember the year, but it was somewhere around 2003-2004 when I first moved to Chicago. I had been using an accounting firm to prepare my tax returns since I began trading in 1998. But this year, I thought to myself:
“Sean, you’re smart. You’re college-educated. You almost minored in accounting, and you had straight A’s in all your accounting classes. You should be able to handle the filing of your own taxes!”
So I don’t remember if it was out of an act of curiosity, boredom, or just trying to pinch a penny, but I decided that year I’d prepare my own taxes.
I read all the official instruction manuals provided by the IRS. I gathered all my necessary trading documents. And I followed every procedure to a T. I left no i’s undotted, no t’s uncrossed.
After all the work was completed I had determined that I owed the IRS somewhere in the neighborhood of $4,000. Never happy about owing the IRS money, I nonetheless accepted it. It felt right. It felt fair. And I was prepared to send the return and my money off.
But before licking the stamps, on a lark, I decided maybe I should have an accountant ALSO prepare my taxes to compare notes. Let’s see how well I did? [Read more…]