WEBVTT

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[ MUSIC ] 

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Hello. My name is Jacob Davidson. I'm a reporter with 

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Money. com, and believe it or not I have never done 

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my own taxes. I've had taxes filed for me in the past 

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but I think it's time that I become a real adult and do it 

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myself. So we're gonna see how it goes. I've obviously 

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heard doing your taxes is extremely difficult, but I 

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assume that since I'm just a normal individual, 

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unmarried, that can't possibly be that hard. Ok, so I'm 

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on the IRS website right now. I'm excited to file my tax 

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returns, as you can see by all these smiling people. 

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And so we're just gonna go to file your tax return. Go 

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to free file. Start 

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now, and then you'll see there's like a lot of options 

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here, and depending on your income bracket, you can 

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get different tax software for free. So, we've already 

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chosen one that didn't look to shady, Jackson Huett, so 

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we're just gonna, we're gonna go ahead and do it. So 

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I've hit my first screen of questions here, and they're 

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all pretty depressing. So I am 

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not blind, disabled, or deceased yet. Wow, easy 

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interview versus choosing income myself. So yeah, I 

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got no tips, no one tipped me even once. Oh wow, it's 

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like figuring all this out for me? Is this 

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like, supposed to be obvious? Enter your codes by 

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clicking [ LAUGH ] Look at all these things. I don't 

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know what these are. So 

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yeah, initially I didn't think this to be that 

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hard. I still don't think it's that hard, but I think what I 

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didn't expect was how vague the questions would be. I 

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mean, ultimately, on one hand, it's just filling boxes, 

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but on the other hand. There are some terms that, that 

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seems to mean certain things, but might mean others 

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and I'm not really sure. And this isn't the kinda thing I 

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wanna get wrong, so I'm gonna go ask my friend for 

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some help. [ MUSIC ] So, 

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I had some problems, so I brought in my friend Kara, 

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who knows a thing or two about taxes. So Kara, I have 

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a question here. If I put in $ 10, 000 here, then 

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that ends up showing $ 10, 000 in social 

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security wages. So, how is that true because I didn't 

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get any Social Security as a wage. Look, all you 

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have to do is put, in, is what is exactly on your W- 2. 

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They try to make this as fool proof as possible. 

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All you have to do is copy the information that you have 

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into here. You shouldn't have to 

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make any decisions on.. On your own. Right. It's just 

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copy, paste. Jake, 

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did you donate more than $ 6, 200 to charity? I did 

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not. Okay. So then it's not gonna be worth it to itemize 

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your charitable expenses because you'll just get more 

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back. With a standard deduction. Okay. All right, so I 

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thought it was gonna be easy. I think it turned out 

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to be a little bit harder than I though. Kara's right. 

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Ultimately if you just enter in what's in the boxes on 

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your form, it's not super difficult, but sometimes 

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depending on the software you're using, it's not clear 

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that certain things are in boxes or it's not clear a 

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certain language means certain things. So yeah, I think 

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this is definitely more of a, more of a hassle than I 

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expected. But I did think it was sort of interesting to go 

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through and just look at all the weird different things 

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you can get tax credits for. So, I guess what I learned is 

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you should pretty much document everything in your 

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entire life because one day there may be a tax 

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deduction that you need and you can get it.