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Farnoosh Tarabi
Smart tax moves Every solopreneur needs to
know you're listening to so Money with award winning money guru Farnoosh Tarabi. Each day get a 30 minute dose of financial inspiration from the world's top business minds, authors, influencers and from Farnoosh yourself, looking for ways to save on gas or double your double coupons. Sorry, you're in the wrong place. Seeking profound ways to live a richer, happier life. Welcome to so Money.
Lisa Green Lewis
Solopreneurs are so busy you could leave out a 1099, but also what could be costly is leaving out receipts for items that are deductible. You don't want to forget anything directly related to your business. And then I've also seen business owners, sometimes they're hesitant to take certain deductions because they think it's going to be like an audit red flag when in reality less than 1% of people are audited. But I've seen that like with the home office deduction, people think that's a red flag.
Farnoosh Tarabi
This episode is brought to us by TurboTax experts for business. Welcome back to so Money everybody.
I'm Farnoosh Tarabi.
If you've ever had that moment, maybe it's late at night, you're catching up on emails, finally feeling proud of the income you're generating on your own. And then it hits you. Wait a minute, what does this mean for my taxes? Because no one really prepares you for this part of entrepreneurship. Not the forms, not the deadlines, and definitely not feeling that you might be leaving money on the table or worse, doing something wrong. Whether you're freelancing, consulting, running a side hustle, or fully self employed, tax season can feel like the one place where confidence quickly turns into confusion. So today we're tackling this head on. This bonus episode is all about helping you feel more in control of your taxes. Because this is something so many self employed listeners and small business owners are thinking about right now. And it's no wonder then that this episode is brought to you in partnership with TurboTax Experts for Business. And that and the good news, you don't have to figure it out alone. Joining me is Lisa Green Lewis, CPA and TurboTax expert with more than two decades of experience helping individuals and business owners navigate the tax code and uncover opportunities to save. She's also been self employed herself, so she understands firsthand the realities of wearing all the hats and how easy it is for taxes to slip to the bottom of the list. We're going to get into the biggest mistakes Solopreneurs make the deductions you might be missing and how to approach your taxes in a way that actually feels manageable, maybe even empowering. Lisa also shares how TurboTax connects you with experts who understand your specific industry. So you can file with confidence and stay focused on what matters most, which is growing your business. Let's get into it. Lisa Green Lewis, welcome to Sew Money.
Lisa Green Lewis
Thank you for having me.
Farnoosh Tarabi
All right. We are talking about the topic du jour.
Lisa Green Lewis
Yes.
Farnoosh Tarabi
And we're specifically talking about taxes with the entrepreneur solopreneur worker in mind. And I'm right there with everybody. And it's just, it's really overwhelming, especially if you are just new to your business, even if you're familiar with doing your taxes, but doing your taxes as a solopreneur or a side gigger, it can be very overwhelming, especially right now. What do you think think is the most overwhelming part of it actually for those who are newbies?
Lisa Green Lewis
Yeah, I think people are busy trying to run their businesses and so as you grow, you have more transactions to keep track of income, your expenses. That can be overwhelming as well as even just knowing. I know people just starting out, sometimes they start with a hobby and it becomes a business and they don't even realize that they're self employed. They don't realize what that really means, what deductions they can take. There, there can be a lot to it. That is where TurboTax definitely comes in. With our TurboTax business, we make it really easy whether you want to do your taxes yourself or you can have a TurboTax business expert do your taxes for you.
Farnoosh Tarabi
Oh my gosh, take the wheel. I think from my own experience, the organization goes a very long way coming up with whatever your system is for tracking your expenses, tracking your receipts. There's so much to also just get informed about. And especially this year there are some, there are some changes to the tax law. We won't get into them, but just, you know, you always feel like you're leaving a credit on the table or a deduction on the table. And so obviously that's where having some help can be invaluable. Let's start simple. If I earn income outside of a traditional job, I don't own a full on business yet, but I'm making some money on the side. What do I need to understand right away about how I'm taxed differently and how I maybe should go about filing my taxes differently?
Lisa Green Lewis
Yes. So the first thing you should know, when you have an employer, they're taking taxes out of your paycheck. When you're self employed, if you are expected to owe $1,000 or more, you have to pay quarterly estimated taxes. So it's really important to track not only your income but your business expenses directly related to those activities because that can lower your taxes. So you want to make sure that you're keeping track of everything you're eligible for.
Farnoosh Tarabi
And there's a threshold. Right. At which point you must report your income. It doesn't mean you're necessarily going to get taxed on every dollar. But can you clarify that for people too? Because people are get confused about that.
Lisa Green Lewis
Yeah. So if you're self employed, it's at net income of $400 and that is the point at which you're required to also pay self employment taxes.
Farnoosh Tarabi
Got you. Okay, let's talk basic steps. Let's keep it basic. Some we're running up against the deadline right now and people are anxious. What are a few foundational steps for solopreneurs in just say the first year to stay on top of their taxes and avoid surprises? What's part of that organization system we were talking about earlier, we were touching on?
Lisa Green Lewis
Yeah, you just want to figure out what works for you. It doesn't mean like tracking every week or biweekly, but you just need to do it. So you want to start tracking your income, all of your expenses. That would be the first step. And I know with intuit we have QuickBooks that can help you track your income and expenses and that information can automatically export into your tax return. Or if you have one of our tax experts do them for you, you can give them that information. Now we've also, we have our AI integrated with our human expertise and intelligence. And new this year, it can actually extract information from your spreadsheets and categorize your business expenses. And also getting to that when you're self employed, you want to separate your business and personal expenses would be a key step that you want to take.
Farnoosh Tarabi
Yeah, a lot of people don't initially get the business checking account or savings account or business credit card. Do you feel like there's a certain amount of income you want to be making before you do that? Or it's just always a good practice to get ahead of that. No matter where you're at in the
Lisa Green Lewis
beginning, I think it's always a good practice just to get ahead of it. If you didn't. There's plenty of people that dive into self employment and they just get busy and they don't do it. It's not the end of the world. But I would say from the beginning, do it. And it could have benefits. If you open a business credit card, you may be getting points for your business. And there's those deductions that you can deduct directly from your business. So if you're traveling for your business expenses, like hotel or whatever, you could put that on those credit cards and it'll be easy to track. And you may be getting points for your business on those credit cards, for sure.
Farnoosh Tarabi
You said earlier about estimating your payments every quarter. Let's say you didn't do that in 2025 and now with the tax filing deadline approaching, what's the penalty for that?
Lisa Green Lewis
Yeah, so you get a penalty every quarter for not doing that. One thing I want to bring up that people don't realize. It's a tip that people are so surprised to find out about. You can annualize your income. The IRS does know that people typically don't make the same amount of income every quarter. So you can recognize that your income in the quarter that you earned it. So let's say in the first quarter you didn't earn any money. But being self employed, you were required to do quarterly estimated taxes. But when you annualized, you could recognize your income in the quarter you earned it. And you won't get a penalty in that quarter. And by the way, when you use TurboTax, it will annualize your income for you if you choose that option. And then if you have a tax expert do your taxes for you, they'll do that for you as well. So you don't need to go to an outside tool.
Farnoosh Tarabi
Great.
Okay, let's talk mistakes.
We've all made them. And sometimes you don't make a mistake and you get a letter from the IRS saying, where was that 1099? And that's happened to me. It was right there. I claimed that income. And then you have to go through the work of not correcting it, but just re informing them, which is. It can be scary to get a letter from the irs. But if you have support, and this is where I had help, someone helping me with my taxes, it was helpful too, to get that corrected. But what are some common mistakes that you see especially solopreneurs making and the ones that are the costliest, quite frankly.
Lisa Green Lewis
Yeah. So as you mentioned, solopreneurs are so busy you could leave out a 1099. But also what could be costly is leaving out receipts for items that are deductible. You don't want to forget anything directly related to your Business. And then I've also seen business owners, sometimes they're hesitant to take certain deductions because they think it's going to be like an audit red flag, when in reality, less than 1% of people are audited. But I've seen that, like with the home office deduction, people think that's a red flag, but absolutely, if you have a dedicated space in your home or wherever it is for your business, you should feel empowered to take that deduction because it could be a substantial deduction. It's a portion of your rent or mortgage interest, property taxes, utilities, and depreciation based on the amount of space you're using for your business. And the irs, they do know people have been hesitant. So they also created the simplified method, which is the flat $1,500 deduction that you could get because they know people were hesitant to do it or didn't want to collect the documents that were related to the individual amounts that you get. But definitely, if, like you said, as long as you. If you have backup information and receipts, then you should take those deductions.
Farnoosh Tarabi
Yeah, that was a nice. I remember that was a nice news bulletin when that came up.
Lisa Green Lewis
Yeah.
Farnoosh Tarabi
Because you're right. I think that was one of the things that I was hesitant because you'd have to measure and then. How much am I really using this? A hundred percent for work? Especially if it's like a corner in your bedroom or.
Lisa Green Lewis
Right.
Farnoosh Tarabi
And then you felt like you were gonna get penalized or red flags and.
Lisa Green Lewis
Yeah.
Farnoosh Tarabi
I think people just were like, it's not worth it.
Lisa Green Lewis
Yes. And they didn't want to take the time.
Farnoosh Tarabi
I was definitely in that camp. What are some other mistakes that are maybe less obvious, but you see all the time behind the scenes, even people make a lot of, like, spelling errors, math errors, when they do it themselves. And that's gonna cost you because then your return might not even get filed because of that. And then you have to wait for your. Your refund, potentially have to resubmit. But other things, other mistakes people make that are costly.
Lisa Green Lewis
Yeah. They could be not inputting something correctly or something related to a form that the IRS has. The forms that report your income, like W2S, 1099s. The IRS gets a copy of that. If something doesn't match up there. Not to worry. I know you said people do tend to get scared when they receive a letter from the irs, but not all correspondence from irs. It doesn't mean an audit. Sometimes they're just checking something. Sometimes if you leave out some income, if it's not a substantial amount, they'll make an adjustment on your return. So you might just get an adjustment letter. And that is just telling you this is what they see according to their records. And they want to know that whether or not you agree with what they included.
Farnoosh Tarabi
What do you think, speaking of getting nervous and worked up, what are some things that people get really worked up about? I hear this from the accounting world that the IRS is actually more forgiving than we give them credit sometimes. How would you, what would you say to someone who's like, I'm really nervous about filing my taxes, I'm worried I'm going to do it wrong and it's not going to work, it's not going to go through. Give us a pep talk.
Lisa Green Lewis
Yes, I would say just get it done. Especially this year we're seeing filers are expected to see $1,000 increase in their refund with the new tax laws. So that's something to think about. Like you said, the irs, they will work with you and if you leave something out, they'll make an adjustment. It's not like you're going to get audited. They'll just make an adjustment and also confirm with you if you agree with that.
Farnoosh Tarabi
All right, let's talk about saving money and some of the most overlooked deductions or credits. Just overall opportunities that solopreneurs might miss, especially if they're new to this and haven't filed taxes as solopreneurs in the past or they just didn't know they existed because I don't know, they just didn't know. There's a lot that we don't know because it's just such a vast topic.
Lisa Green Lewis
Yeah, exactly. And there's so many people just diving into self employment and they don't even realize that self employed or what they can deduct. Some of those include like startup costs. So if you have any costs related to doing research on your business, advertising, marketing, website development, anything directly related to your business travel, those are some that people miss. Some other ones, if you have kids and you employ kids that are under 18, you may be able to forego the some of the taxes that you have to pay as an employer. So that's something to think about for your kids under 18. There's also a lot of people are surprised to find if you have a car that you use for your business, there could be big deductions there. I know under the new tax law, the section one, what's known as section 179 deduction so that is for business equipment up to $2.5 million that you can deduct. But some heavy trucks fit under that classification. And so people are often surprised to find that out. And even if it isn't a heavy truck, if it's £6,000 and under £14,000, you can deduct up to $31,300 for that vehicle so that you have to use it over 50% for your business in order to do that. But those are some that people are like blown away. And then we have the new. I mentioned the business equipment deduction, but we also. There are business owners out there that may get tips. If you're a rideshare driver. Yes. Or a beautician or esthetician, professions like that. We have the new deduction for qualified tips and that deduction is up to $25,000.
Farnoosh Tarabi
Yeah, that's a huge one. And always wondering, like people buying their fancy SUVs, luxury SUVs. It's for the business.
Lisa Green Lewis
Yes.
Farnoosh Tarabi
Huge write off. That's so true. We see. I see like sometimes I see those reels on Instagram and they're very popular. Yeah, that's a huge deduction.
I can't.
Lisa Green Lewis
It is if you are. If you're using it for over 50% of your business.
Farnoosh Tarabi
Yeah.
If you work in real estate.
Lisa Green Lewis
Real estate agents take their clients. Definitely. Or rideshare drivers. They're using their car so much.
Farnoosh Tarabi
Brilliant. All right, let's talk about how working with a turbo tax expert can help you uncover these deductions. Because it's a lot to track, but if you've got the power of technology and an expert who's in this all the time helping you, it's hard to miss any.
Any deductions.
Lisa Green Lewis
Right, Exactly. If you want your taxes fully prepared by our TurboTax full service experts, you can connect with them virtually and now in person. So we've opened 20 retail stores and 600 service centers, so you can go into those stores and have your taxes fully prepared and you'll be matched with an expert that's experienced in your specific industry. And that's something you really want because there are so many new different industries now. They'll be able to uncover deductions that you didn't even know exist that are related to your specific industry.
Farnoosh Tarabi
That's a really good reminder. Yeah. Because it's like with any other expert. Right. Whether it's like a certified financial planner, you want to work with somebody who understands kind of your goals, your specific life circumstances. And similarly, like a tax Expert that understands your industry, your niche, your business. And so how does that work? Do you have a way for someone to connect those dots? Like in the search for an expert, is it like I work in real estate, so I want to work with an expert that knows that industry and that's how it works. It's just connected like that?
Lisa Green Lewis
Yes, it so virtually it would be connected like that with an AI concierge when you're online and then when you go into our store, we actually have people that are tax concierge. So they will talk to you, get information on your industry. They'll also help you just get started. Because that's one of the biggest barriers for people starting their taxes is just knowing what documents to get together. So they will do that as well and then match you with the right expert experience in your industry. And then same with online. The AI concierge will help you organize your documents and get them together and then match you with the right expert and then with our TurboTax full service experts once you use them. So let's say this year you do use them. You'll be able to connect with them throughout the year and ask any questions. Self employed people and solopreneurs, they come up with questions all year long. So you can connect with them and ask them whatever tax questions come up and which is especially useful. We talked about quarterly estimated taxes. You might want to ask them, will I be able to deduct this business equipment that I'm thinking about buying and can it help me lower my taxes at quarterly estimated tax time?
Farnoosh Tarabi
Yes. Yes. Let's bring this to light. So if you're a consultant, freelancing or have a side business, what are some habits? You know, I feel like tax season is a good time to just think about what I wish I had done throughout the year. We learned that. And then what are the systems I can put in place going forward or the habits I can start to practice to really optimize my tax return. So what would be your advice for that freelancer in terms of those smart tax habits?
Lisa Green Lewis
I would say create a schedule, whatever works for you. But for tracking your income and expenses, whether it's bi weekly, once a month or quarterly, but just so you're not doing it at that one time of the year at tax time. Like when I was an auditor at a tax firm, we had someone, they had a lot of transactions, they had a, a big business, but they would come to us at one time of the year and bring all their documents at tax time to do their Accounting and then their taxes. And that's something you want to avoid so that you save money and don't miss out on anything.
Farnoosh Tarabi
Right. I always say, you know, the more legwork you do, the more organized you are. Of course that makes your life easier come filing. But if you are working with a service, time is money and the more you arrive at the, the tax work the tax filing without any kind of system and things are just dangling, that's going to take time to mine that and to get organized. And of course now you're under the time pressure too. So I find that procrastination usually does lead to missed opportunities and overlooking things. So for all the reasons like come up with your system, let this last year, but let it be bygone. Okay, well, wasn't an ideal year, but maybe also you did do some things well like doubling down on that in the 2026 tax year is really going to help you come this time next year. You mentioned you were an auditor and we touched on auditing earlier in the conversation. Can you tell us like what are the audit red flags if we are curious? Don't do this, don't do that, be careful about that.
Lisa Green Lewis
Yes. I think for self employed and businesses you don't want to overstate your expenses. They have to make sense for your income. Like one of them is like the travel or meals and entertainment. If they're extravagant expenses, that's something you want to avoid. And then just definitely have your receipts in order in case you're ever asked to substantiate anything. And then if you do have a business meeting, you just want to have documentation, you want to document the date, what the business purpose was. Just make sure you have that.
Farnoosh Tarabi
Yeah. Who was there, you know, when I was filing my expenses, let's say for when I worked at a company and you would go out to lunch with colleagues and it was a valid expense to be deducted, but the company would require not just the receipts, but who was there. Yes, what you talk about and you know, and obviously if it was a lunch, you're not ordering two bottles of wine. So just make it right, make it as business appropriate as possible. All right. Now TurboTax offers year round expert support. How can solopreneurs take advantage of that? Not just at tax time, but throughout the year.
Lisa Green Lewis
Yes. So if you use our TurboTax full service experts to get your taxes done, then you can contact them throughout the year to ask any tax questions that you have.
Farnoosh Tarabi
What are the most common questions that
come up throughout the year? You Mentioned obviously like purchases is one of them, is it deductible? Is it worth getting for the business? But what are some other kind of like mid year questions that stop solopreneurs in their tracks?
Lisa Green Lewis
I think just knowing what is deductible, there's confusion around that. I hear self employed people all the time saying oh yeah, I've heard from this person that I can deduct these clothes that I wear in this interview or personal items. And so definitely there's a lot of confusion out there. People are turning to social media for answers or different other platforms of people that aren't as experienced. So I definitely hear those type of questions and mainly just what can be deducted and understanding that yeah, social media
Farnoosh Tarabi
can create a lot of confusion around this for sure. If you could give one piece of advice to those of us listening, especially our solopreneurs in the audience who are feeling a little stressed or a lot stressed right now about their taxes, what
would you want them to know? What would you tell them today?
Lisa Green Lewis
I would tell them you still have time to get your taxes done if you have not started and TurboTax is here to help you whether you want to do your taxes yourself or get your taxes done by a tax expert. Our tax experts have an average of 13 years experience and then the ones the TurboTax full service business experts are experienced in your specific industry as well.
Farnoosh Tarabi
And what are your thoughts on filing an extension? I think sometimes it's got to be done and but you got to be careful. So this means you don't owe any money, you got to pay your taxes
Lisa Green Lewis
if you owe it, right? Yeah, I would say if you have all of your documents together, I wouldn't lean on filing an extension if you have everything together. And a lot of people have a misconception that filing if they owe money. Filing an extension is an extension to pay, but it's just an extension to extend your time to file. So if you're leaning into that for that reason, just make sure you know that you still have to pay what you owe and then who knows, by the time you do your taxes with all the deductions that are available, you may not owe any money. You may be getting a refund which
Farnoosh Tarabi
then also gets dragged out. Yeah, the earlier you file, the earlier you get that refund. And I was reading that the average refund this year is like several thousands of dollars. So that's not a little bit that can be very helpful to everybody right now. Paying off their debt, saving more, investing just a little parting advice. The sooner you file, maybe the sooner you will have money in your bank account.
Lisa Green Lewis
Yes, for sure. And you can invest in yourself and your business as well.
Farnoosh Tarabi
For sure. Lisa Green Lewis thank you so much.
Lisa Green Lewis
Thank you for having me.
Farnoosh Tarabi
Huge thanks to Lisa Green Lewis for those invaluable tips. Now, whether you're a first time filer or looking to stay tax compliant as you grow your brand, remember you don't have to do it alone.
Thanks for listening to our bonus episode
today brought to you in partnership with TurboTax Experts for Business. To learn more and find an expert to help you with your filing needs, visit turbotax.com business I hope your day is so money.
Episode Title: Bonus: Smart Tax Moves Every Solopreneur Needs to Know
Date: April 7, 2026
Host: Farnoosh Torabi
Guest: Lisa Green Lewis, CPA and TurboTax Expert
This bonus episode of So Money dives deep into the essential tax strategies every solopreneur should know. Host Farnoosh Torabi is joined by Lisa Green Lewis, a CPA and seasoned TurboTax expert, to discuss best practices for staying organized, maximizing deductions, and steering clear of common (and costly) tax mistakes. Drawing from decades of experience — and Lisa’s hands-on familiarity with both entrepreneurship and tax code — the conversation is packed with actionable advice, myth-busting insights, and reassuring words for anyone navigating their first (or fifteenth) self-employed tax season.
On Overwhelm:
On Home Office Deduction:
On IRS Letters:
On Social Media “Tax Advice”:
Final Pep Talk for Procrastinators:
This episode offers both practical how-tos and an empowering perspective, reminding solopreneurs that organization and support are the best antidotes to tax-time stress.