Let's put this in perspective - I have an advanced degree in accounting. I should be able to file a tax form with 100% confidence that I did everything right. But every year I have some strange question that I need to get answered. One year I tried reading all the instructions on the IRS website - won't make that mistake again. The next I tried calling that toll free IRS helpline - but they've obviously been told not to give yes or no answers. I hung up more confused than ever. I've purchased tax books, watched videos on how to do taxes, and called up my CPA friends who specialize in income taxes. Still, every year, I wonder if I'm doing this right.
And every year when I hit that 'send' button on TurboTax, I pause to say a brief prayer. "God, please let my form 1040 sail through the system, let my Schedules A, B, and C be correctly alphabetized, and let form 88-whatever be accurately reporting whatever the heck it is that I have to file it for."
I'm so concerned about accuracy that I pulled out a $150 deduction this year because the receipt I had lacked a taxpayer ID#. I don't think most people are as paranoid as I, because TurboTax has this lovely feature that allows you to compare your return with national averages. And every year, I discover that we pay far more than the national average in taxes. This does not comfort me. It makes me wonder what I'm doing wrong?
Ultimately, it isn't paying my taxes that bothers me. I think I get a decent return (it could be better, but still it is decent) in terms of access to education, interstate transportation, and national defense. I don't think I'll ever get any return from my contributions to healthcare or retirement. But what really bothers me is this: trying to do the right thing shouldn't be this difficult.