Doing My Own Taxes

I’ve been doing my own taxes since the ripe old age of 17. I started doing my taxes the first year after I got a paycheck because I heard about refunds. I wanted my $77 back so bad, and no one could tell me anything. In retrospect, I wish I waited a little longer before filing taxes because I could still be evading them now (kidding, kidding!). I’ve always filed through TurboTax because it was the one I saw the commercials for, and it was free (for my pathetic high school part time job income, free was of utmost importance). I’ve used them almost every year except for last year when they tried to CHARGE ME. I knew my income was below charging level so I switched to H&R Block. This year, I’m back with the OG, and my taxes got a whole lot more complicated.

Teacher Salary Income

This one is SO easy. Been there, done that, got the W-2, filled it out.

AmeriCorps Award Income

This is where it immediately got complicated. I had to enter extra income information because I received an AmeriCorps disbursement for doing TFA. Although the money does not go directly to me (it can only be used for Federal loans or directly disbursed to schools), I still have to report it as income. When I tried to report it as other income and clicked that I had a 1099, TurboTax said that I needed to pay $90 for TurboTax Self-Employed. At that point, I hadn’t even received my 1099 form, so I clicked out of that real quick to search for other options. Like I said earlier, if I’m filling my own taxes, it needs to be free*.

A couple of days later, my tax savior came in the form of a Lyft email. During the summer of 2018, I drove for Lyft for about a week. It was an interesting experience, but that’s a post for another time. Since I still get their emails, I saw that they were offering TurboTax Self-Employed for their drivers. FOR FREE!! I used it (or I will after I stop writing this to give me a break from y taxes) and now I’m able to file my 1099 FOR FREE!! I love you Lyft and will always support you over Uber.

Side Hustle Income

I have a side hustle(s) teaching English online. Right now, I work for three companies. I’ve been debating whether or not to report that income because I don’t think I need to. One company sends 1099 forms, but only over $600. I didn’t receive one from that company because I did not make that much. However, with my other company I did; they don’t send 1099s. I went back and forth on whether I should just file the non-1099 company, but if I filed that, I felt like I might as well file both. I’m terrified of getting audited, so I decided to file both.

This was so hard. There’s so much to add and keep track of. I looked up the square footage of my house. I called my mom to see how much my laptop that we got in 2014 cost. I went into Amazon and added up the cost of all my supplies. I calculated how much of my internet I use for my classes versus personal use. It was EXHAUSTING. I’m definitely keeping a spreadsheet of EVERYTHING this year. I know I’m going to open an individual retirement account, and I think it’s just going to make things even more complicated.

Deductions 

I STILL don’t understand deductions that much but one day I’ll read up on everything, and when I do, it’d over for you haters. All I know is that I get to tell them all the money I spent on my classroom and get a reduction of my tax burden for about 15% of it.

By the end of this process, I was feeling QUITE overwhelmed, but I survived. This was by far the hardest tax return I’ve done, and it’s mostly due to the fact that I vastly complicated my tax return by having a side hustle (especially ones that didn’t send 1099s.) When I started my returns, my plan was to try to minimize my tax refund because it seemed like I was getting quite a bit back. Although tax refunds have always felt like a bonus check, I know that it’s better to receive that money throughout the year through my paycheck; the value of a dollar now is more than that same dollar in six months. However, after actually filing my returns, I realized that withholding more than necessary throughout the year helped ease the burden of paying taxes for my side hustle money. This process has helped me realize what I need to do with my money throughout the year to prepare for next year’s taxes.