Doing Your Taxes The Night Before

I have been gathering paperwork and sending things to my accountant for my 2013 taxes since early February, but a week or so ago I was chatting with Mike and declared I would do it myself for 2014. I won’t be making much money, I have ample savings to make the payments — how hard could it be? Then he reminded me that the first quarterly payment for freelancers is due at the same time as my 2013 taxes. Oh, great, okay. I opened this puppy up in a tab, left it open for a week, and then last night — April 13th — I decided now was the time. I got out a notebook and inhaled deeply. For the next four hours. Rather than write 3000 words about this experience I will fast forward to deciding at midnight last night I would do the ‘make an educated guess and throw some money at the government to cover my ass, rounded up to the nearest hundred’ method.

Cool. Okay I will just pay online, straight from my savings account. I had already transferred money to a checking account a few days before, to mail in checks for my 2013 taxes.

I did my state taxes first, which was easy. I gave them the routing number and account number and boom, done two days early. Then I went to and was faced with a lot of options.

I “enrolled” to do an electronic transfer. After entering in my SSN frankly an uncomfortable amount of times on a third party website, I was told they would be mailing me my PIN number within the next seven days. Oh great, perfect, since taxes are due in one day.

I could mail in a check the old-fashioned way but it was Sunday night and transferring money from savings to checking (two different banks, too) would mean the money wouldn’t be in there on the 15th and I KNOW the government somehow cashes those checks as soon as they arrive at the post office. My savings account says two business days is the transfer time but that doesn’t mean Bank of America would make those funds available right away. Knowing them they would have someone sitting there waiting for the IRS to cash my check, then charge me $35, then click some button to make funds available right after the overdraft fee goes through, at which point confetti would rain down from the dropped ceiling and all the employees would gather round the cubicle, lock arms, and do a little jig.

The third option is to use a third party site to pay with a debit or credit card. Okay! I just paid off my credit card and have enough credit available. Let’s see. The fee for using a debit card is $2.79. Okay, bullshit but not horrible. It’s my own fault that I am in this position anyway. Oh but wait, I don’t have enough money in my checking account to use a debit card. I just paid my state taxes with my debit card, if I hadn’t just literally done that maybe I could. I would have no money available for two days but would be fine. Oh well, it’s a moot point. Let’s see the credit card fees. The lowest fee is 1.88%. That SOUNDS like a small number but are you kidding me? In my case this would be about $30. A $30 credit card fee.

What if I underpaid a little, with my debit card, would the penalty be somewhere around $30? Would that somehow feel better than paying credit card fees? More legitimate somehow? More in my control?

Again: all of this is my fault.

I went to my savings account — RIP, ING Direct –, transferred the money to my checking account, and emailed the little payment voucher thing to Dustin so he could print it out at work because does anyone even own a printer? Looking back this is basically the #1 perk of working in an office. Besides you know, health insurance and STRAIGHTFORWARD TAXES. I think what I will do is look back into my checking history to see how fast the IRS typically cashes my checks, and sit refreshing my Bank of America checking account to see if my money goes through, and put a stamp on my voucher tonight, and scope out when pickup is in the various blue mailboxes in my neighborhood, see which one is the latest. And then if push comes to shove I will pay that $30 credit card fee. Then transfer that money from my checking account back to my credit card balance. Then close that checking account once and for all because I use Simple except there are no physical checks with Simple which is fine except when it comes to taxes, basically. It would be fine then, too, actually, if I didn’t wait until the night before to do this. I have had “close Bank of America account” on my to-do list for a year, especially since they charge me $12/month for “maintenance” when I go a month without depositing any money in it, which is insane, but then right when I am about to march in there and close it down once and for all, I have to send someone a physical check. And I promise myself this is the last time. But it isn’t. It never is.

Anyway I am doing my taxes myself this year.

Photo: Martha Soukop



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