A Tale of Cowardice

This is the very first year that I will file tax forms in relation to my investments. The very first time in my life that I’ve actually had real, Big Dog investment income to report.

I’m having to fight the urge to turn tail and run.

The other day I received the small package with the necessary tax forms to file on one of my tiny little investments. I turned the envelope in my hands, shaking at the fact that it was my name, and my address on the envelope. It just didn’t seem real.

I went to open it and stopped. Surely something as important as this needed to be commemorated? I pulled out my camera and snapped a photo.

And then, like the big fat coward I am, I set the envelope aside. I just couldn’t bear to open it. Opening it would make it real.

I have sat at my desk, turning that envelope over in my hands for days now. I’ve debated upon the best way to open it. Should I open it at the top, or tear off the side like my dad did his letters when I was little? Should I use a knife, or invest in one of those fancy little letter openers that I imagine rich people use?

I’d debate for a time then set the letter aside once again.

Did my dad feel this way when he bought his first apartment building in Chicago? Did he feel this way when he made his lone investment in the stock market?

I wish he was alive so I could ask. All I can remember is that he stored his important papers in a combination of cigar and shoeboxes. He preferred Choice-branded pencils (new) whenever he worked up his taxes. I can still see his papers spread out upon the table as he scratched out his calculations, cussed a bit, and made some erasures before starting again. The sweat would bead upon his brow as he leaned over his work, laser-focused on Getting It Right.

This really shouldn’t phase me. I’ve been filing taxes on my book royalties for ages now. But this is different and new. This marks my first Baby Steps into the Big Leagues.

The forms from my broker sent me were easy to open. They were digital so I downloaded them to my computer and plugged them into my online income tax preparation software without a thought.

But these? These forms are old school. These forms are real, right here in my hands. These papers are concrete proof that I’m either completely insane or in the early stages of something brilliant.

Before I went to bed last night I picked the envelope up once more and turned it over in my hands.

“Screw it!” I tore a small strip off the side of the envelope, just like Dad used to do and slid the papers into my hands.

I grinned. A tear slipped down my face as I quickly scanned through the document. It came with an instruction booklet, which is good since I’m still learning this stuff.

I’ve got three days off this week. My goal is to enter in the information from this form and figure out how to handle the info related to the stocks I sold over the past year while I experimented. I’ve already entered my W-2 from work and the 1099s related to my writing business. I’ve got to double-check, verify that I’m doing this right before I screw up my courage, close my eyes, and file this sucker with the state and federal government.

Wish me luck.