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

I have a confession: I'm in my late 20s, and I had 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 to do that, and from 2014 to 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.

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

So this year I took the plunge and saw what every adult complains about this time of the year: doing their taxes.

A rundown of my financial situation

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

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

The TurboTax login experience: the first hurdle I faced

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

Did my parents create an account for me last year that I could log in to now? Was I supposed to log in to 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 that I'm ultimately glad I did.

I found out I did need to create an account. He ended up emailing me my tax return from last year on the spot, allowing me to upload it to my new TurboTax account.

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 each of these options affects your overall TurboTax experience, but I was honest and choose "not so good."

Because I uploaded my 2016 tax return, TurboTax then asked me whether anything changed in the past year, including whether I moved (I had) or got 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 W-2 on my computer, but this turned out to be an unnecessary step.

All I had to do was enter Business Insider's employer identification number, which I found on my W-2. TurboTax did the work for me, locating and uploading my W-2 on my behalf. This was a delightful surprise.

Between uploading last year's documents and this, my mood had turned from "not so good" to "good."

Figuring out my freelance income and expenses

Onto my "side job," as TurboTax called it: my photography freelance work.

Because both my freelance gigs last year paid under $600, I did not receive a 1099 tax form from either client. This made it relatively easy to file; I just manually entered the payment for each project.

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

Reporting everything else

After that, I entered information about my Charles Schwab savings account.

Usually, TurboTax can automatically import this information from major brokerages, 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 could skip over several the following questions about my 401K and IRAs. Because my W-2 had already done the job of telling TurboTax what I contributed last year, there was no need to manually enter information. (I have another 401K from a previous job, but I didn't contribute to it or take any money out, so there was nothing to report.)

Next up were questions about my rental property. Though I do rent my apartment, TurboTax wanted to know whether I owned a rental property. I don't, so I skipped these.

Finishing and paying up

The tail end of TurboTax — where I was asked several questions that didn't apply to me about 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 the tax-refund estimate at the top-left corner — a number larger than any refund I had ever received — kept me motivated.

One annoying thing about the TurboTax experience is that it's constantly trying to upgrade you to a different pricing tier. I had to click "no" on these prompts at least three 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 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 my largest refund ever. I finally understand those memes people post about being happy when their tax refund hits their bank account.

I also feel as if 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 is.

See you next year, TurboTax.

COMMON INSURANCE MISTAKES