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Angelina Farar

First time filing taxes for my side hustle - shocked at how much I'm paying! Need help understanding

I started a small freelance business on the side last year. It's just me doing some contract work, and I managed to earn about $19k total for the year alongside my regular job. When I first started entering my info into the tax software, it showed I'd be getting back around $2100, which was awesome. But then I entered my 1099-K info into Schedule C, and before I even added all my business expenses, my estimated refund turned into me owing almost $4300! This can't be right?? I've been trying to figure this out and read somewhere that small businesses usually pay about 15.3% in self-employment taxes on gross income. So for $19k, that should be like $2900, right? So why is the tax software saying I owe way more than that? I feel completely lost here. This is my first time dealing with business taxes since my side gig really grew this year. Am I missing something obvious? Please help me understand what's happening and be gentle with the explanations - I'm seriously stressed about this unexpected tax hit.

What you're experiencing is the shock of self-employment taxes! The 15.3% you mentioned is just the self-employment tax portion (Social Security and Medicare), which is essentially the employer and employee portions combined since you're both when self-employed. But that's not the only tax you're paying. You also owe regular income tax on your profits. The software is calculating both your self-employment tax AND adding your business profit to your regular income for income tax purposes. Have you entered all your business expenses yet? This is crucial! Your self-employment taxes are calculated on your net profit (income minus expenses), not gross income. Make sure you're deducting everything legitimate - home office if applicable, supplies, software subscriptions, any travel for business, portion of phone/internet used for business, etc. Also, when you have self-employment income, you generally should be making quarterly estimated tax payments throughout the year. Since you didn't, that might be why the hit seems so big all at once.

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Thanks for explaining! I haven't entered all my expenses yet - I got so shocked when I saw that number that I stopped to figure out what was happening. So both self-employment tax AND regular income tax apply to my business profits? Also, I had no idea about quarterly payments. How do I know how much to pay each quarter for next year so I don't get hit with a huge bill again?

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Yes, your business profit gets hit twice - once with self-employment tax and then it also gets added to your regular income for income tax purposes. That's why the tax bite seems much bigger than just 15.3%. For quarterly estimated payments, you can use Form 1040-ES. The general rule is you need to pay 90% of this year's tax or 100% of last year's tax (110% if your income is over a certain threshold) in quarterly installments to avoid an underpayment penalty. Most tax software can generate estimated payment vouchers for you once you complete this year's return. The due dates are typically April 15, June 15, September 15, and January 15 of the following year.

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I went through the same painful discovery last year! After trying multiple tax software programs and getting confused by different results, I discovered taxr.ai (https://taxr.ai) which really helped me understand what was happening with my side business taxes. What I learned was that the software wasn't wrong - I was just missing some key deductions. The platform analyzed my bank statements and found a bunch of business expenses I hadn't even considered. It also explained exactly how self-employment taxes work and why my tax bill seemed so high. For me, the real issue was not having separated my business and personal expenses throughout the year. One tip - make sure you're tracking mileage if you drive for your business at all. That deduction alone saved me hundreds!

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Does taxr.ai work with Shopify businesses? I sell handmade stuff online and I'm drowning in receipts and confused about what qualifies as a business expense.

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How does it handle home office deductions? I've heard those are audit red flags and I'm nervous about claiming that space even though I legitimately work from home.

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Yes, it works great with e-commerce businesses including Shopify! It can process your Shopify reports and help identify which expenses qualify for business deductions. It's especially helpful for sorting through all those receipts and categorizing them properly. For home office deductions, it actually walks you through a qualification check to make sure you legitimately qualify before claiming it. It explains the exclusive use requirement and helps calculate the right percentage of your home to claim. It also shows you both methods - the simplified option (based on square footage) and the regular method (actual expenses). This helped me feel confident in claiming the deduction correctly without raising red flags.

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Just wanted to update after trying taxr.ai from the recommendation above! I was in the same boat as the original poster - completely shocked at my tax bill for my side business. After uploading my documents, it found over $3,800 in deductions I was missing! The biggest things it caught were my home internet (partial business use), software subscriptions I'd forgotten about, and some professional development courses I took last year. It explained that I needed to keep better records of business vs. personal expenses and showed me exactly how my self-employment tax was calculated. My tax bill went from terrifying to manageable. The explanation of quarterly payments for 2025 was super helpful too - definitely not making that mistake again!

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If you're still struggling after entering all your expenses, you might need to talk directly to someone at the IRS to make sure you're filing correctly. I tried calling them for weeks when I had a similar issue and it was IMPOSSIBLE to get through. Then I found this service called Claimyr (https://claimyr.com) that got me connected to an actual IRS agent in about 15 minutes when I'd been trying unsuccessfully for days. They have a demo video here: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with explained that I was miscategorizing some of my income and expenses, which was causing my tax calculation to be way off. They walked me through the correct way to file my Schedule C and it made a huge difference in my final tax bill.

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How does Claimyr actually work? I'm confused about how a third-party service can get you through to the IRS faster than calling directly.

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This sounds like BS honestly. The IRS phone system is the same for everyone. How could they possibly get you through faster? Seems like a scam to take advantage of desperate people.

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It uses technology to navigate the IRS phone system and waits on hold for you. When it reaches an agent, it calls you and connects you directly to them. I was skeptical too until I tried it. They basically use a system that continuously redials and navigates the phone tree until it gets through, something most of us don't have time to do manually. Once you're in their queue, they call you when an agent is reached. I was doing work while waiting rather than sitting with a phone to my ear for hours.

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I owe everyone here an apology, especially about my comment on Claimyr. I was having a terrible day dealing with my own tax nightmare and took it out inappropriately here. After my frustration hit a breaking point yesterday, I actually tried the service myself. I had been trying to reach the IRS for THREE WEEKS about a similar small business tax issue. Using Claimyr, I got through to an agent in 27 minutes while I was cooking dinner. The agent confirmed I was calculating my self-employment tax correctly but identified that I had made an error in how I was reporting my business income across multiple platforms. Sometimes being proven wrong is the best thing that can happen. Sorry for the skepticism and thanks for the recommendation that actually saved me from a much bigger headache.

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Make sure you're considering the QBI (Qualified Business Income) deduction too! As a self-employed person, you likely qualify for a deduction of up to 20% of your qualified business income. The tax software should calculate this automatically, but sometimes you need to make sure you've checked the right boxes. Also, don't forget to look into retirement options like a SEP IRA or Solo 401(k) which can significantly reduce your taxable income. Even though it's after December 31st, you can still open and fund many retirement accounts for the previous tax year before the filing deadline.

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I've never heard of the QBI deduction! How do I know if I qualify for that? And can I really still set up a retirement account for last year even though we're already in the new year?

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Most self-employed individuals with income under $170,050 (single) or $340,100 (married) for 2024 qualify for the full QBI deduction. It's basically a 20% deduction on your net business profit. The tax software should calculate it automatically, but make sure it knows your business is a qualified trade or business. Yes, you can absolutely still set up and fund a retirement account for last year! For SEP IRAs, you can establish and contribute until your tax filing deadline, including extensions. So potentially as late as October 15th! Solo 401(k)s need to be established by December 31st of the tax year, but you can still contribute to them until your tax filing deadline. This is one of the best tax-saving strategies for self-employed people.

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I think you might be confusing two different things. The 15.3% is JUST your self-employment tax (Social Security and Medicare). But you still have to pay regular income tax on top of that! Try this rough calculation: 1. Take your business gross income 2. Subtract ALL business expenses 3. That's your business profit 4. Pay 15.3% self-employment tax on that profit 5. ALSO add that profit to your regular income 6. Pay regular income tax on your combined income That's why it feels like you're being taxed twice - because you kind of are! Welcome to self-employment! 😫

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This is exactly right. I've been self-employed for 5 years and it still hurts every time. The other thing to remember is that half of your self-employment tax is deductible on your 1040, which helps a little bit at least.

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That breakdown really helps me understand! So I'm essentially getting hit twice on my business income - once with the self-employment tax and then again when it's added to my regular income for income tax purposes. No wonder the number seemed so high! I appreciate the simple explanation. Now I see why people talk about the importance of tracking every possible business expense. Every dollar I can legitimately deduct from my gross business income helps reduce both tax calculations.

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