“The Tax Man Cometh”

Call me crazy, strange, goody two-shoes, whatever you need to call me to fully explain my desire to be the ideal taxpayer. Since I was 15 and got my first W-2, I’ve been on a personal journey to be the first in line to file my taxes every year and to learn as much as possible about the scariest governmental office known to man, the IRS. Maybe it’s a throw back to my brown nosing days in high school when I could care less about trying to be the head cheerleader’s BFF and was more focused on figuring out what snacks might win my geometry teacher over on any given day. In fact, I think my affinity for quickly winning over my teachers’ affections might have been the start of my career in public relations, or politics, or any other brown nosing profession that I would probably be really good at.

So a few weeks ago when my business partner Melissa suggested attending a tax course at a nearby university, knowing full well such offer would bring me the kind of giddy only a closet nerd would understand, I was pretty stoked at what I referred to as an “amazing educational opportunity for our business.” Forgive me for the tangent I am about to go on… I’m convinced that even if you have a PhD in Business, navigating the small business world is much like a game of Sudoku…eventually the equations will make sense, but getting there is the problem. I consider myself a pretty smart person, and when I lack, I lean on a lifeline and phone a friend. In my world of checklists and charts, I’m not as comfortable as I should be with learning as I go. If you need a details girl, call me. If you need someone who will play Sudoku with you for a little while, well, call your own lifeline on that one. I’m off topic now, I can own that.

Back to the tax class. I’ll admit it, I was a tiny bit excited about my tax class for a couple of reasons; 1) for some reason even though I loathe math like I loathe southern style cockroaches, I get a kick out of doing my own taxes and 2) this would be another topic for which I could create a mental checklist and in turn keep us in business, and more importantly out of jail.

I’ve often wondered how the writers for Saturday Night Live come up with the most comedic, ironically true to form characters for their show, which to me is nothing short of genius. Five minutes into the tax class and I knew exactly where they come up with their off the wall ideas, the next SNL character was standing right in front of me in all his high water, ten shades of blue glory. As I was trying to absorb all that the state revenue office had to offer up-and-coming small businesses, I found my upper lip perpetually underneath my two front teeth. In a classroom of only seven people, my business partner and I found ourselves in constant eye contact with an IRS employee fit for a full SNL spinoff movie. Twenty minutes of awkward pauses during his presentation was all I could take before I just had to look down for the rest of the presentation. It was also when my mind started daydreaming about getting rich off my mini novella about a proud IRS rep who gets his kicks from auditing unsuspecting new business owners and wearing the shortest tie he can find. Oh and from making constant eye contact during training sessions with women who laugh at inappropriate times. At some point into my daydream, Melissa kicked me under the table and asked if I was okay. I responded as maturely as possible with a note I slid across the table letting her know I might literally burst out with an LOL and embarrass her and everyone in the class, so it was just safer for me to keep my eyes in a downward position. I also added something about our next business venture, which included a phone call to SNL.

Okay, I know I shouldn’t judge. I should practice what I preach and throw all judgment to the wind despite the length of someone’s tie or their particular enjoyment of the color blue in its most faded, lifeless form. But in the cloud of serious I tend to get caught up in, especially when it comes to making sure I pay Uncle Sam what he is owed, Mr. Tax Man who spent half an hour informing us that he really does enjoy auditing people was just what I needed to put a smile on my face.

I didn’t exactly get the education I was hoping for during the “amazing educational opportunity” the Department of Revenue was kind enough to host. But during my exit strategy, aimed solely at avoiding the king of eye contact, I managed to scoop up an armful of print materials I’ve been using for reading material over a glass of wine for a few nights now.

I may not have everything checked off my small business ownership for dummies list yet, but you can rest assured that when the taxman comes, I’m pretty sure I’ll be ready. If nothing else, I’ll have a pretty good sketch for SNL’s next awkwardly inappropriate character.

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