Death and Taxes

It has been raining here for two days straight. We have had high winds. Power outages. It is damp and cold... and dreary. Before you jump to the go-to phrase: “But you live in Hawaiiii,” I just want to remind you that my house has no central heat, so when it’s cold outside, it is cold inside too. It even snowed at the top of our mountain yesterday. So yes, it sometimes gets cold in Hawaii too. 

But it’s not just the cold, dreary, weather that has me so crazy. It’s the mind-numbing challenges of being a small business owner and having to navigate certain things that I simply don’t understand. This time:  the dreaded 1099 tax form.

Last year, I had a consultant help me with some editing and computer-related marketing. The other day I got an email asking if I would be sending her a 1099? (A tax receipt for independent contractors.) It hadn't even occurred to me to do this. Why do we send 1099s to some people and not others? Should we 1099 our pool man, gardener, housekeeper? What about window cleaners? Hairdressers? Manicurists? Or do we only 1099 the people who work for our corporations? I called my accountant who said that it’s very easy to send out a 1099. Most of the forms are on-line and free. Except, of course, the ones that need to go to the IRS. Those I need to buy at Office Max. He said it would be easy, since I just had one consultant. 

What should have probably taken me only 15 minutes ended up taking hours and hours and probably cost me way more than it should have. It was a 40-minute drive roundtrip to the nearest Office Max only to learn that the one item I needed only came in packages of TEN. I explained to the nice man at Office Max that I only needed ONE form… not 10. He was very sympathetic when he gave me an “It is what it is” shoulder shrug. Desperate to ease my frustration, he was excited when he found a smaller package of forms that saved me a whopping three dollars. I went home and attempted to fill them out with the instructions on the tax website, but something seemed weird. The questions were not the same on the computer as they were in the hard copy form. 


Apparently, the really nice Office Max guy with the sympathetic shoulder shrug handed me the WRONG forms! I needed the 1099-misc NOT the 1099-Interest Income forms. But I had already opened the package and I was pretty sure that I threw away the receipt. Thankfully, I hadn’t printed any forms yet. So, I carefully gathered up my package of incorrect forms and attempted to re-tape the cellophane wrapping back over it. This did not work by the way… not even a little. I, then, went to hunt for my receipt in the kitchen garbage can, where I was concerned that the receipt might be buried under some wilted salad and discarded pasta with meat sauce that we ate for dinner the night before. But the gods were smiling down on me when I found the receipt, crumpled up underneath some inoffensive junk mail, and no smelly leftover food substances. 

I, then, got in the car and made my second 40-minute roundtrip back to Office Max. There I explained my mishap with the wrong package of 1099 forms to the cashier. She was very helpful and happily swapped them out, when I paid the difference and purchased another package of pens. G-d forbid you should ever walk into an office supply store and not need to buy just one more thing. 

When I returned home, I tried to find the file that I had spent too much time already filling out, but it was nowhere to be found. Not saved on my desktop. Not in my browser history. Not in my downloads. So I did another search for the forms, but somehow kept getting routed to commercial websites that make filling out tax forms “easier.” This led to a number of situations where for just $19.99/month I could filled out other forms on-line and save myself a lot of aggravation? But I don’t have other forms to fill out. I have one lousy form which has cost me $20 (for the package of 10), two 40-minute roundtrips to Office Max, and a brief phone conversation with my accountant which will probably cost me $100. So, I keep searching. Finally, I find a website that does not seem to require a lifetime membership, will allow me to fill these out on-line, and print them in my home office. But, they don’t line up with the forms I purchased. I don’t have the right software or something. I am truly ready to go postal. Finally, I texted a friend and she said I could fill these forms out by hand. Wait, what? This is music to my ears. Had I known that I would have saved myself hours of aggravation.

But wait. This one form actually requires three different versions (IRS, state, payee, payor). Then there are two other forms that have to be filled out too. I keep making mistakes, so I end up starting over. But finally, I get them all done. I make out the different envelopes to the IRS, the state, the contractor, and I think I am ready to head to the post office. (Which is now closed because this took hours longer than it should have.) But while talking to another friend, I learn that I cannot simply fold these forms and put them in regular envelopes. He claims they must be sent in special envelopes and that forms are folded in half. What? Where does it say that? 

So I spend several more hours searching the IRS and state tax websites to find out if that is true. I cannot find that rule anywhere. I am so frustrated with all of the time I have wasted on this “one” form. I don’t want to start over. I don’t want to drive 40-minutes roundtrip to Office Max to buy the “right” envelopes. I have had it. How do other small business owners do this? Why did my accountant say that it would only take me 15 minutes? Why didn’t my accountant offer to do this? 

I have done everything they have asked me. I have bought the stupid forms (twice). I have filled everything out in duplicate. I have separate envelopes. I cannot take it anymore. It’s pouring rain. My dog is barking incessantly because there are birds outside the window. My husband is still playing tennis… six hours later. How did HE not get rained out by the way? I decide to throw caution to the wind. I fold the forms like regular letters, stick them in a regular envelopes, and mail them the regular way. This devil may care, practicing the art of not giving a subtle f*ck, rebel without a cause, my way or the highway attitude is the only moment of joy I have felt since starting this ludicrous exercise in bureaucracy. 

Yes, I am living on the edge. Yes, I sent out my first 1099 AND I folded it in a regular envelope. It is my year of living dangerously… and I like it. They say that there are only two things for certain: Death and Taxes. I am certain that they are related. The paperwork that is required to do your taxes makes you want to kill someone. I took the high road. No one was injured during my complete meltdown, but I did go to dinner with my husband that night and broke down into a puddle of tears while sipping a much needed margarita and inhaling a basket of chips and salsa.