History of Taxes: A Personal Story (Part 1)

According to one statistic from my state, 92% of income tax returns are filed electronically. However, this year - for the first time in my life - I did our taxes with paper and pen, mailed them in, and became one of the 8%. 

Time it'll take to get my return back? 6-8 weeks. 

It’s an awkward story full of small personal mistakes. But it led me to wonder - How did the American tax system become the most complicated tax system in the world?

Why does it take the average American 13 hours of their life to prepare for settling up with Uncle Sam before April 15th?

Mistakes, Mistakes, Mistakes!

This year, one form accounting for $6 in dividends being taxed at 10%  (because I accidentally went over on my Roth) caused our entire tax return to be “out of scope” for the person I regularly complete my taxes with. 

As a result, I had to spend hours finding the forms online, printing them, manually writing on them, and then mailing the whole beast in. I could have e-filed, but all of the information  was completed. It seems counter-intuitive, but manually filing was honestly the quickest solution.

(I’m crossing my fingers it works because we are getting a lot back. I gave a big loan to the government throughout the year because I’m part imbecile - ha.)

But with good reasoning. My husband and I have always filed “zero” at work because we never know how much our music is going to make as a side-hustle.

In certain years, we’ve ended up still paying in a large chunk, even after filing zero at our full-time jobs. (Owe more than a thousand? It’s your fault. You might get fined. The government has thousands upon thousands of your dollars on April 15th? No biggie.)

Since we’ve scaled back on our side-hustles, we’re starting to get a lot back.

 A lot.

That I want - right now.

Back to the Helpful Man Who Said I Was “Out of Scope”

I stared at him blankly. 

“What does out of scope mean?”

“It means I can’t file your taxes or be associated with this.”

“But they're done. We just spent 2 hours figuring out every last number!”

“You will have to redo them yourself.”

He could see my disappointment. The whole situation was starting to make me think abstractly....uh-oh. 

“These are small details that waste people’s lives!”

He nodded.

Then he went all growth mindset on me and said it would be an interesting chance to learn something new. 

So I did. 

I learned about the history of the tax system itself (stay tuned for Part 2) so I could be less upset about my own piddly situation.

Next week we’ll talk about Lincoln, Taft, Wilson and how a document of 11,400 words became a code of 4 million.

Have you ever made a mistake with your taxes? Have you ever thought you were done only to find out you had to start over?


7 Replies to “History of Taxes: A Personal Story (Part 1)”

    1. I wrote this post a few weeks ago before everything went haywire (good thing, because getting ahead on the blog awhile back is the only reason posts keep coming out – I haven’t made time to write at all for weeks)! Anyhow, we did get our refund about a week ago. I was glad to see the government was still at work and getting people their refunds.

      Hope you enjoy next week’s post too! Thanks for stopping by!

  1. oh, i helped my young protege, malevolent missy with her taxes last year. she waited until the very last day so we went through to e-file for free but she didn’t have the necessary info from ’18 so i just printed up the state and federal forms and we filled them in and she mailed them from the post office on april 15. this year she learned the lesson and got them done early. i wrote a thing this past year about a mid-year checkup where i took a gauge of estimated income and a close look at the brackets manually. it’s worth knowing where you might want to capture capital gains or losses at the end of a year.

    i also had a starter marriage where she didn’t file taxes for years before we met and refused to file jointly. after the best day ever and the split i had to refile about 3 years worth and set up a payment plan with the i.r.s. surprisingly it wasn’t that hard.

  2. I agree! I feel like I have far more of an understanding now.

    Otherwise, it seemed like a “random” number came up at the end and I was happy to pay (or refund it) just to get the whole process over with!

  3. I’ve always filed “in writing” and I’ve always paid a certified “Tax Superstar” who is versed with both corporate & entertainment law to do it, but that’s just me. It ain’t cheap, but it has had an ROI over the years.

    Primarily because said “Superstar” was always able to deftly keep my exec W2 income completely separate from my music income. There are very legal ways to do so. So even when I was earning “huge” on both fronts, I never paid on the music side.

    Now that I’m retired and a “low earner” on both sides, I still am tax free on the creative side. In my opinion, there is a great deal of ambiguity baked into the tax code which is why I am certain that writing about my music adventures on my blog will somehow translate into funding my next music project.

    General advice: Always file in writing.

    1. Thanks for sharing your tax story. Sounds interesting and quite a bit more complicated than mine.

      I don’t think I will file in writing going forward, but I also find my situation to be pretty simple. Good luck with funding your next music project with the blog. Sounds like a good way to do it at this time of little touring, little live performance, and general uncertainty.

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