I just wrote a check for $3,500.....Yes, folks.  You heard it.  I just wrote a check for 3,500 smackaroos…and it wasn’t for anything awesome like a vacation to Aruba or a hot tub for my back deck.  Unfortunately, the $3,500 check I just wrote was the June 15th installment of my personal income taxes.  What’s even worse is that the $3,500 I just paid in is ON TOP of the hundreds of dollars we’ve been withholding from Greg’s paychecks every month.  Have you ever heard the saying “mo’ money, mo’ problems?”  Although I’m only making a moderate salary as a freelancer, I’m still feeling slightly resentful about the money I just paid in.  When I think of how many freelance jobs I did to earn $3,500, my brain actually hurts. That’s a lot of freaking jobs, people!   Becoming self-employed made me feel like a rebel without a cause, but paying income taxes makes me feel like I’m not really the one in charge.  I no longer have a boss, but I’m still a slave to the man…..and I don’t like it at all.

However, I do think that it’s weird that I’ve never felt angry about paying taxes before.  After all, I’ve been paying income taxes for over fifteen years.  And honestly, I hadn’t thought much of it until now.  So, why does writing a check for my taxes feel so different?

Death by a Thousand Cuts

Greg is the one who estimated my tax payment, and he may have shouted some expletives when he figured out how much we had to pay.  Although it stressed us out, he was also able to explain why writing a check for our taxes feel so incredibly different than paying them via payroll deduction.  Greg thinks that paying taxes out of your paycheck is a lot like financing a car.  Since you’re only paying $300 or $400 per month, you don’t have to experience the awful feeling of handing over 20K of your hard-earned cashIt’s death by a thousand cuts, and it doesn’t hurt nearly as bad as paying for a big purchase in one  lump sum.  On the other hand, paying cash hurts.  I remember when we paid off the last $11,000 of Greg’s student loans in one lump sum.  I did it through our online bill pay, and I could barely bring myself hit “submit” even though I knew it was the right thing to do.  It was painful, and maybe that’s how it should be.  Always paying cash for things has taught me to feel the real impact of my spending.  It’s may also be the reason why I’m so incredibly cheap.

With all of that being said, I certainly don’t mind paying taxes.  After all, I enjoy the roads I drive on and the plethora of public services I have access to.  I love the fact that police and firefighters are available 24/7 to save people from peril or their own stupidity.  However, I feel like I’m paying a lot.  Too much, maybe. We’ll just have to see how it works out.

So, how about you?  Raise your hand if you love paying taxes!  How do you feel about paying taxes in a lump sum vs. paying weekly installments?