Your 2025 tax questions, answered

Tax attorneys Hana Boruchov and Leo Gabovich answer questions from our audience about the 2025 tax season. They explain whether or not to get an accountant, what to do if you can't pay your tax bill, and how to handle taxes when you work remotely. Learn more about sponsor message choices: podcastchoices.com/adchoicesNPR Privacy Policy

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

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• 0:16Marielle Segarra?

  You're listening to Life Kit from NPR.

• 0:24Marielle Segarra?

  Hey, everybody. It's Marielle. So it's that time again, time to file your taxes. If you're getting a refund, maybe you've already done that. If not, maybe you're waiting until the very last minute. Either way, the deadline to file and pay what you owe is April 15. I will say, pretty much everybody I know dreads the filing part because it involves paperwork and numbers, but also because it's scary. Most of us didn't learn how to do our taxes in school. And so you may worry you're not doing it right and that you're going to get hauled off in handcuffs because you forgot to report one of your 1099s. That isn't going to happen, by the way. So let's all take a big, deep breath together. For this episode of Life Kit, we collected tax questions from listeners and I posed

• 1:08Marielle Segarra?

  them to two tax attorneys, Hannah Borakov and Leo Gabovic, partners at the firm Borakov-Gabovic and Associates PC. I asked them your questions and added in some more in the hopes that we could make tax time a little easier for all of us.

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• 2:54Marielle Segarra?

  All right, so let's start here. When do y'all recommend that people have an accountant file their taxes versus just doing TurboTax or FreeTaxUSA or one of the online softwares?

• 3:05Speaker 07

  In my opinion, if you've just got a W-2, even if you have a W-2, and let's say you have a few like, common kind of deductions where you've got kids, you've got real estate property taxes, things like that. Even in those cases, the software today is so intelligent and easy to use. I tell people all the time, hey, just use that for yourself. There's no reason to pay an accountant hundreds of dollars when you could really just spend half an hour and just get it done for yourself. Where I highly recommend it is if you have your own business or even if you're a freelancer, you're on a 1099 basis, something like that, you want an accountant involved. Even if, you know, you're not breaking the bank,

• 3:50Speaker 07

  you want to have somebody who's knowledgeable, who'll guide you and set you up for success.

• 3:55Marielle Segarra?

  Since we're talking about freelance, another question that came up. If you have freelance income, maybe it's a small amount, like $150 or something. And you didn't get a 1099 form for it in the mail. Do you still have to report it when you file your taxes? And just explain, what is a 1099?

• 4:13Speaker 08

  In this case, when you're talking about a freelancer, it would be like an independent contractor. Instead of getting a W-2, so you're not on a salary, you're not an employee, you're an independent contractor, you get what's called a 1099. It is a form that will get sent to you in the mail if it's over a certain amount that was paid over to you over the course of the year. And you're supposed to use that to report on your, when you file your taxes.

• 4:35Marielle Segarra?

  And it comes from the company that paid you that $150 or whatever?

• 4:39Speaker 08

  Correct. Yes, yes.

• 4:40Marielle Segarra?

  But they're, they don't have to send you a 1099 if it was under a certain threshold, right? If it was under a certain amount of money?

• 4:47Speaker 07

  Right. They don't have to give you a 1099 if it's under a certain threshold. But if you're above the minimum filing threshold that you have to file a tax return, even if you didn't get a 1099, you're supposed to report all income that you receive. So yeah, even if you didn't get a 1099 for that $150, legally, you're supposed to report it. From a practical perspective, I wouldn't recommend people do this. But I have to say that, yeah, without a 1099 present, the IRS is not made aware of that transaction. If you want to take the risk of not reporting it, you can take that risk. But if you get audited, you would still have had to pay the tax on that $150.

• 5:25Marielle Segarra?

  What happens if you don't report something like that? Like 100, like I'm talking about small amounts, you know? But like if, let's say you got audited and, and then the IRS was like somehow found out that you made $150 at this job and like, what is the, what is the penalty?

• 5:43Speaker 08

  So in that case, I mean, the likelihood of an auditor scrutinizing $150 is extremely low because they're limited in manpower and they're, they're not looking for 150 bucks. They're looking for much larger sums of unreported income.

• 5:58Speaker 07

  I will say that not necessarily the $150, but I've absolutely seen taxpayers who might have missed, you know, $1,500, 1099, getting a letter in the mail saying, hey, you missed this and we've adjusted your return. So now you owe us, you know, another $300 or $400 in tax. And interest and usually a co-equal almost amount of penalties by that point, where it'll probably be another $400 in penalties, you know. The good thing is cases that you mentioned before, if someone didn't get a 1099, they legitimately forgot about it. They tell the IRS when they get that letter, hey, whoops, I didn't realize I had that 1099.

• 6:39Speaker 07

  I'm a W2 or I've got so many 1099s, you know, something that's legitimate. The IRS is going to waive the penalty, but you still have to pay the tax. So that's kind of what it boils down to.

• 6:51Marielle Segarra?

  I've seen a lot of memes around tax time that are like, the IRS is like, tell us how much you owe and pay us. And then you're like, well, you know how much I owe? How much? And they're like, not telling. You guess first and then you pay. And then they're like, wrong. You know, like, that's always, that always has felt really strange to me. And I think to a lot of people, like, why doesn't the IRS just send you a bill?

• 7:19Speaker 07

  Right. Other governments, you know, other countries, some of them do do it that way, which sure seems intelligent to me. I think there are some benefits to the system that we have, especially for, you know, a lot of the, not the typical W2, you know, standard deduction filers. I think a big reason for why it is the way it is, is because of lobbying. I mean, there's a lot of money in tax preparing. Honestly, I think the lobbyists don't want to push the IRS away from that. And on that note, I mean, technically, if you don't file your return, in a lot of cases, especially if they have a 1099 and W2 on file, they'll file what's known as a substitute return, which is just going to have exactly whatever they have on file.

• 8:01Speaker 07

  So if they've got a W2, they'll assume that's the amount of income you made and they'll give you the standard deduction because obviously they're not going to go rooting around and deciding what deductions you'd be entitled to. And that's that. But of course, the catch is that when you non-file, you get hit with all sorts of non-filing and late payment penalties and all of that. And the IRS really wants to encourage people to file to the point that the failure to file penalties are harsher than the failure to pay penalties.

• 8:29Marielle Segarra?

  So it sounds like the piece of advice for people around tax time also is, you should file your taxes. Or you can also get an extension, right? You can file for an extension and you have until October of that year to file your tax return, but you still have to pay now, right? Which means you kind of have to do the work of estimating how much you owe.

• 8:53Speaker 08

  Right, but also you can amend your returns, right? So if there's any sort of errors that you catch later on, do that.

• 8:59Marielle Segarra?

  Okay, got you. So if you filed and then you realized you forgot to include some investment, this happened to me, actually. I filed my taxes and then I had a certain kind of investment account for the first time and I forgot that you're supposed to report the income from that. And then I went back and amended my return and I sent the IRS more money. And then they sent me back the money and they said, no, no, you got it right the first time. And I was like, no, I think you're wrong. And this is actually something that like someone emailed us about as well. They got money back from the IRS, but they're like, I don't get it. Why did you send me this money back? If that happens, if you file your taxes and the IRS or your state is actually like, no,

• 9:43Marielle Segarra?

  you overpaid, here's your money back, that's the end of it, right? It's legally yours to keep, even if you think that they're wrong?

• 9:50Speaker 08

  Well, they make mistakes too. So you can cash that check and put it in your bank account. And there could be a situation where they come back again, months later or years later and say, we made a mistake, we're going to make an adjustment. They can make changes and then you might owe again.

• 10:06Speaker 07

  And what I will say about that is that, you know, depending on the amount, you may want to get an attorney involved if it gets to that point.

• 10:14Marielle Segarra?

  All right, so another question. A lot of people are working remotely these days and they might live in a state that doesn't have an income tax, like Texas or Florida, right? But their company is located in a state that does have an income tax, like New Jersey or New York. And they're wondering, do I have to pay income taxes because my company is located in a state that has them?

• 10:38Speaker 07

  Yeah, so with COVID, there have been a lot of different regulations amongst the states. New York is particularly aggressive about it. So there's something known as the, at least in New York, as the convenience of the employer rule. And this kind of rule, from what I've seen, what it effectively means is if you're working out of the state for a New York employer purely for your benefit.

• 11:05Speaker 07

  You still have to pay those New York state income taxes. So, somebody living in New Jersey remotely, working for a New York employer, New York's position is going to be that, hey, you need to be paying taxes on this New York source income as they see it.

• 11:19Marielle Segarra?

  Is that what's referred to as a non-resident income tax?

• 11:23Speaker 07

  Non-resident income tax return, yeah.

• 11:24Marielle Segarra?

  Yeah, okay. So if you are being taxed by a state where you don't live, do you also need to pay income taxes in your home state?

• 11:33Speaker 07

  It depends on the state. What it really boils down to is, right, hey, should this income be taxable by our state? Is it being sourced from our state? And I guess that's the best way that I can kind of explain it is, if you're trying to separate yourself from being taxed by a certain state that you might work in, if at all possible, you'd have to kind of show why your income is not necessarily sourced from business in that state.

• 11:57Marielle Segarra?

  Okay. And I should say here, you can often get a tax credit in your state to offset whatever you paid in income taxes to another state. This stuff just gets kind of complicated. So another question for you, let's say you file your taxes and you realize, oh, I am not getting money back, I am not striking even, I owe money. What can people do if they can't afford their tax bill?

• 12:21Speaker 08

  Yes, so if you can't afford to pay in full, which is a lot of people, there are options. So there's an installment agreement you can apply for. And there are different types of installment agreements, but with an installment agreement, typically it's, what, 72 months, it's like max term. You divide how much you owe by that term. So that's just a straight payment plan. There are also options, if you can't afford to pay on a payment plan, divide it over the certain number of months, you can do what's called a partial pay installment agreement, which is not what you actually owe, but what you can afford to pay. Another option is what's called an offer and compromise. So, an offer and compromise is a deal with the government where you say, okay, I owe $50,000.

• 13:06Speaker 08

  There's no way I can pay $50,000. You actually compromise not just the tax, but the interest and the penalty. So the total dollar amount. And then there's also another option called currently non-collectible status. So if you have really, really zero dollars, you might have health issues. You know, let's say you're ill, or let's say you're retired. You don't have income coming in. The amount is still owed. However, you're not making payments on it. They're not collecting against you.

• 13:30Marielle Segarra?

  I'm wondering, what is the first step for somebody who realizes that they're in this situation? I mean, they might not have an accountant or a tax lawyer. They might just have like filed their taxes through an online software. Should they get professional help?

• 13:45Speaker 08

  Well, yeah, so it depends on how much that's owed and how much they have the ability to pay. If it's an amount that they think is manageable, they could set up their own payment plan online. They can always call. There is a phone number for the IRS. The wait times can be a bit long and, you know. In terms of getting a tax professional involved, really depends on the complexity of the issue. So you got to think, how much is it going to cost to hire an accountant? How much is it going to cost to hire an attorney versus doing it myself? And how much that's owed? So you have to balance that.

• 14:19Speaker 07

  I just wanted to add that there's a wonderful resource, both on the IRS and the state level, known as Taxpayer Advocate. They kind of oversee, you know, some of the functions of the IRS and the State Tax Department. And at least on the IRS level, they can even issue taxpayer advocate orders to basically say, hey, IRS, you need to help out a taxpayer. And the reason why I like Taxpayer Advocate is they're super straightforward. One-page forms generally, hey, describe what your issue is and what do you want us to do about it? And, you know, aside from the fact that they're super helpful. People think of the IRS as like this scary place, but Taxpayer Advocate, they're your friends. You'll get an advocate assigned. They will call you. They will send you a letter, let you know what's going on.

• 15:02Marielle Segarra?

  They're like the social workers of the IRS.

• 15:04Speaker 07

  Yeah, essentially. And the reason why I'm such a huge fan of them too is, you know, when I used to work at the State Tax Department, Office of Counsel was in this building. We were on one floor. And taxpayer advocates' office was literally just hallway right across from us. And I can't tell you how many times I had advocates literally walk up to me at my desk, "Hey, you're working on this case," or "You've got this case coming down the pipeline," before I even knew about it. "And I'm helping this taxpayer, and here's the issue, and this is what we want you to do about it." And to have that kind of advocacy for $0 is phenomenal.

• 15:35Marielle Segarra?

  That's really good to know. And if someone does want to hire an accountant or a tax attorney for whatever reason, not necessarily because they owe money this year, but they're just looking for someone to help them with their taxes or a tax issue, how do you do your research? How do you find a good accountant or attorney?

• 15:56Speaker 08

  I would say, look at their qualifications. Make sure that they are licensed, because people had returns done by what they thought was a CPA, was in fact a non-accredited individual that just...

• 16:10Marielle Segarra?

  Just some guy?

• 16:10Speaker 08

  Just some guy. And, you know, that caused a lot of nightmares for the unsuspecting taxpayer that hired that guy. So, don't end up in that situation, but definitely look at the credentials of the person, of their firm, is it reputable? And that's how I would look for them.

• 16:27Speaker 07

  Yeah, the only other thing that I would want to add is that enrolled agents are a great resource for some people. Enrolled agents are individuals who are qualified to have taken tests before the IRS to essentially be tax preparers and represent people before the IRS. So, you don't need to be a CPA, you don't need to be an attorney. And there are a lot of really smart enrolled agents, and, you know, I tell people to look for those as well, where if you're looking for an accountant and you might not need one, or might not necessarily be able to afford the cost of what a CPA costs, enrolled agents are a great option, because they generally charge even less than the CPA does.

• 17:08Speaker 07

  And again, if you know that $250 or $300 for your return gives you that peace of mind, then great, pay an enrolled agent to help out.

• 17:18Marielle Segarra?

  All right. Hana, Leo, thank you so much for this.

• 17:22Speaker 08

  Thank you for having us.

• 17:23Speaker 07

  Thank you for having us.

• 17:26Marielle Segarra?

  Okay, it's time for a recap. A few takeaways from our conversation. One is to file your taxes by the deadline to avoid penalties and interest. You can probably do this on your own or using free tax software if you have a simple situation, like you just have a W-2. But you might want to hire an accountant if you freelance or own your own business. Number two, if you work remotely, pay close attention to the state tax laws where you work and where you live, because you might have to pay income taxes in two states. But in some cases, you can get a tax credit to make up for that double payment. And number three, if you can't afford your tax bill, there are several options available to you: payment plans, coming to a compromise with the IRS, non-collectible status.

• 18:10Marielle Segarra?

  If you need help figuring all this out, you can reach out to Taxpayer Advocate. It's an independent organization within the IRS that can help you understand your rights, communicate with the agency, and figure out next steps. And if you're having problems with your state taxes, your state might have a Taxpayer Advocate office, too.

• 18:29Marielle Segarra?

  For more Life Kit, check out our other episodes. We've got tips on lowering your next tax bill and advice on paying off your debt. You can find those at npr.org/lifekit. And if you love Life Kit and you want even more, subscribe to our newsletter at npr.org/lifekitnewsletter. And just a reminder that signing up for Life Kit Plus is a great way to support our show and public media, and you'll get to listen to every episode sponsor-free. So please, go find out more at plus.npr.org/lifekit.

• 19:00Marielle Segarra?

  This episode of Life Kit was produced by Margaret Serino. Our visuals editor is Beck Harlan, and our digital editor is Malika Gharib. Megan Cain is our supervising editor, and Beth Donovan is our executive producer. Our production team also includes Andy Tagel, Claire Marie Schneider, and Sylvie Douglas. Engineering support comes from Patrick Murray. I'm Mary El Segarra. Thanks for listening.

• 19:24Speaker 00

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