Readers Blog: Dobie Maxwell's 'Dented Can' Diary

Old Home Weak

Tuesday August 10th, 2010 - Chicago, IL

   I have a new show business goal. I would like to be the first entertainer in history to get a reputation for having his income tax situation not only clean, but immaculate. For every Wesley Snipes, Willie Nelson, Redd Foxx, Joe Louis and so many others, I’ve personally never heard of anyone who’s on top of it year after year. I’m sure there must be, but who?

   For me, it’s been a life long pain in the I.R.- ass. A flair for math has never been one of my talents and my organizational skills are even worse. Saving fifty cent toll road receipts for months in an envelope to add up in April has never crossed my mind as a fun activity.

   I know it’s a necessity in life and especially in my own business as an entertainer so it’s to the point now there’s really no excuse at all. I’ve had a lifetime to master this but I feel no closer to having it aced now than I ever have. I was maybe halfway decent for a couple of years, and they weren’t even in a row. Depending on how goes my mood, so do taxes.

   This year, I’ve really let it hit the skids. I thought I was ahead of the game and had a big head start, but now I can’t even find my files at all. I’m talking about for 2009, as the IRS is sending me multiple letters telling me they haven’t received my 2008 return, which is a mystery because I paid my accountant to do it as I do every year. Somehow, it’s been lost.
 
   I really didn’t need another stop to make before heading out to sea, but I went to see my accountant to hopefully clear this all up. He showed me my return from 2008, and I don’t owe the government any money. He made a copy, I signed it, and he said he’d send it out.

   He’s a very laid back soft spoken guy, and pretty typical of what one would think to be an accountant type. He’s very Jewish, but that’s a good thing. I don’t want an accountant who’s half Swedish and half Jamaican. Give me a Jewish guy to handle my tax situation. I’ve trusted him now for probably ten years or more, and he knows how flighty I can be.

   He pointed his finger at me and said “NO false promises this year, Mr. Comedian. Get yourself a better system of keeping records. You know what you have to do - now DO it.” He’s so right. I just wish it was that easy. For some reason I seem to have a mental block. I always say I’m never going to let this happen again, and then it does. I’m embarrassed.

   I fly out at 6:20am tomorrow, and I come back next Sunday for two days before doing it all over again. He told me to bring my paperwork in Monday or Tuesday and said it’s not doing anyone any good to keep filing extensions every year. He’s right, but I guess I feel I get a little reprieve from the government or something by doing it, so I do. It‘s a crutch.

   Little does he know, when I got home I wasn’t able to find my paperwork for the life of me. I’ve moved everything around countless times recently as I’ve been clearing out all of my sports cards, sorting laundry, whatever. I obviously had to have put them somewhere, but I sure couldn’t find them today, no matter how hard I looked. I’ll find them when I get back, and take them in and get it done like I always do. But I really need a better system.

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