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I filed my own taxes for the first time ever using TurboTax - and got the biggest refund I've ever received

Sarah Jacobs   

I filed my own taxes for the first time ever using TurboTax - and got the biggest refund I've ever received
Finance5 min read

Sarah Jacobs doing taxes

Business Insider

Actual footage of me doing my taxes for the first time on TurboTax.

  • TurboTax is one of the most popular online services for filing your tax return.
  • I decided to file my own taxes this year for the first time ever, and it was easier than I thought it would be.
  • TurboTax displays a tax refund estimate in the top left corner that kept me motivated when the process got a bit tedious.


I have a confession: I'm in my late 20s and I have never done the work of filing my own taxes until this February.

For years I was fortunate enough to rely on my parents who so kindly offered, and in 2014 through 2016, I paid a trusty client service representative at H&R Block. Last year, my parents offered the favor again and like any sensible person, I didn't refuse.

However this year, I felt it was finally time to become a fully realized adult and do my own taxes. I was tired of shelling out my money to an H&R Block employee who - although friendly and knowledgeable - seemed to be inputting data that I was pretty sure I could be typing myself.

So this year I decided to take the plunge and see what every adult complains about this time of the year: doing their taxes.

A rundown of my financial situation

My finances are pretty straight forward - I had the same, full time job throughout 2017, two paying freelance gigs, and one major freelance expense that I was hoping I could write off. I also have a savings account with Charles Schwab that I knew I needed to include. I don't have any dependents, nor do I own property, and I currently don't have student loans.

Because of my freelance work, I heard TurboTax was probably the best option for me - plus, my parents had used TurboTax to file my taxes last year. Having last year's documents helped speed up my process by a little.

The TurboTax login experience: the first hurdle I faced

TurboTax 5

TurboTax

The dreaded login screen.

The first thing TurboTax asks you is if you'd like to sign in to your account. I was already unsure what to do.

Had my parents created an account for me last year that I could log into now? Was I suppose to log into their account? How did this work?

This prompted me to call my father within zero minutes of starting my taxes, a move I am not proud of - but ultimately I'm glad I did it. I found out that I did need to create my own account, and he ended up emailing me my tax return from last year on the spot. This allowed me to upload it into my newly created TurboTax account.

TurboTax

Turbo Tax

Why, thanks for asking!

TurboTax then asked me how I was feeling about doing my taxes ("Good," "Not so good," or "Don't ask") - I'm not sure how choosing one of these options over the other affects your overall TurboTax experience - but I decided to be honest and choose "Not so good."

Because I was able to upload my 2016 tax return, TurboTax then asked me if anything had changed in the last year, including: if I had moved (I had) and gotten married (I hadn't).

TurboTax automatically pulled in my salary from my full-time job

Then came the actual filing part for my full time job. I had prepped for this moment by downloading a PDF version of my W2 onto my computer. However, this turned out to be an unnecessary step.

All I actually had to do was enter Business Insider's employer identification number (which I found on my W2). TurboTax did the work for me, locating and uploading my W2 on my behalf. This was a delightful surprise.

Between this, and having uploaded last year's documents, my mood had turned around from "Not so good" to "Good."

Figuring out my freelance income and expenses

Turbo Tax, freelance

Turbo Tax

Nice pun, TurboTax.

On to my "side job" as TurboTax would call it: my photography freelance work. Because both of my freelance gigs in 2017 paid below $600, I did not received a 1099 tax form from either client. This made it relatively easy to file - I just manually entered the payment amount for each project.

I was also able to expense the photography studio rent I paid last year - which was more than double the amount that I made. To my delight, this expense greatly increased my federal tax refund.

Reporting everything else

After that, I entered information regarding my Charles Schwab savings account. Usually, TurboTax can automatically import this information from major brokerages, such as Charles Schwab, but the documents weren't ready yet, meaning I had to manually enter my capital gains and dividends. This didn't take too long, but identifying the correct numbers on the documents I had downloaded (apparently called a 1099-INT and 1099-DIV) was a little tricky.

I was able to skip over a number of the following questions regarding my 401K and IRA's. Because my W2 had already done the job of telling TurboTax what I contributed last year, there was no need to manually enter information - and, although I have another 401K from a previous job, I did not contribute to that account or take any money out so there was nothing to report.

Next up was questions regarding my rental property - and although I do rent my apartment, TurboTax wanted to know if I own a rental property. I don't, so I skipped this question.

Finishing and paying up

The tail end of TurboTax - where I was asked a number of questions that didn't apply to me regarding small business ownership, gambling, jury duty, health insurance, and other life-events - began to feel tedious.

I was very ready for it to be over, but I kept looking at that tax refund estimate on the top left corner - a number larger than any previous refund I had ever received - and it kept me motivated.

One annoying thing about the TurboTax experience is they're constantly trying to upgrade you into a different pricing tier. I had to click "No" to these prompts about 3 different times.

After about an hour and a half of filling out questions, it was time to pay up. I ended up shelling out $138.25 for using TurboTax. A number that I wasn't mad about after seeing my refund.

I would do it again

Assuming I didn't do this entirely wrong - which, only time will tell - I received the largest refund I have ever gotten. I finally understand those memes people post about being happy when their tax refund hits their bank account.

I also feel like I have a much better grasp on what types of income need to be reported, where to find numbers on long financial forms, and just how annoying - but ultimately simple - filing your taxes really is.

See you next year, TurboTax.

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