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Vince Eh

Why do I pay Self-Employment tax AND Federal Taxes as a 1099 contractor? Aren't Social Security & Medicare already included?

Last year hit me like a ton of bricks when it came to taxes. I totally messed up my savings plan and got slammed with a way bigger tax bill than I ever thought possible. I sat down with a tax person who pointed out I missed a bunch of stuff in my calculations, especially this whole Self-Employment tax thing. I get why my Federal Tax estimate was off (basically my combo of W-2 work and my 1099 gigs pushed me into a higher bracket than I realized), but I'm confused about why I have to pay this additional Self-Employment tax on top of everything. Isn't Social Security and Medicare already coming out of my Federal Taxes? What gives? I found a Self Employment Tax Calculator online to help me plan better for next year's tax season, but I still don't really understand the WHY behind this extra tax. Between Federal, State, and Self-Employment taxes, I'm having to save like 44% of every payment I receive (I know deductions will bring this down but I'd rather overestimate than be caught short again). That seems insanely high considering I only make around $78k a year total. Can someone explain this to me like I'm 5? Why am I getting double-taxed here?

The reason you're paying both isn't because you're being double-taxed - it's actually closing a gap in how employment taxes work. Here's the simple version: When you're a W-2 employee, your employer pays half of your Social Security and Medicare taxes (7.65%), and you pay the other half through payroll withholding. You never see the employer portion on your paystub because it doesn't come out of your check. As a 1099 contractor, you're effectively both the employer AND employee. The Self-Employment tax (15.3%) is basically you paying both halves of those FICA taxes. Your federal income tax is completely separate - it doesn't include Social Security or Medicare contributions at all. The good news is you can deduct half of your self-employment tax when calculating your income tax, which helps offset the extra burden a little.

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Vince Eh

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Oh wow that actually makes so much sense! So I'm not being double-taxed, I'm just covering what an employer would normally pay? Does that mean my effective rate is higher than someone making the same amount but as a W-2 employee? Is this why so many contractors charge higher rates than employees?

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You're exactly right - you're simply covering what an employer would normally pay on your behalf. Your effective tax rate is indeed higher than a W-2 employee making the same amount, which is precisely why contractors typically charge 25-30% more than employees. This higher rate compensates for both the additional tax burden and the lack of benefits (health insurance, paid time off, retirement contributions) that employees receive. As a contractor, you're responsible for all of these expenses yourself, so the higher rate helps offset these additional costs.

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I was in your exact situation last year - totally blindsided by how much I owed! After doing a bunch of research, I found this amazing tool called taxr.ai (https://taxr.ai) that saved me so much headache with my 1099 work. It analyzes all your income sources and explains exactly what taxes you'll owe and why. What really helped me was how it broke down the self-employment tax vs regular income tax and showed me all the deductions I was missing. Before using it, I was saving way too little and would've been screwed again this year.

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Ezra Beard

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How accurate is it with calculating the estimated payments? I'm new to freelancing and already worried about getting hit with penalties for underpayment.

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Does it actually help identify deductions specifically for contractors? I've been using regular tax software but feel like I'm missing a ton of write-offs that could lower my tax burden.

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It's extremely accurate with estimated payments! I've been using it for quarterly estimates and it adjusts based on your actual income each quarter, so you're not overpaying or underpaying. It even reminds you when payments are due so you avoid those annoying penalties. The deduction finder is what really saved me money. It's specifically designed for contractors and freelancers, so it catches all those business expenses regular tax software might miss. It found over $3,200 in deductions I hadn't even considered - home office, portion of internet/phone, mileage for client meetings, even some software subscriptions I use partially for work.

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Just wanted to update after trying taxr.ai that the previous commenter recommended. Seriously a game-changer for understanding my contractor taxes! I was in the same boat as you - totally confused about why I was paying so much in taxes. The tool broke everything down and showed me that I was missing TONS of deductions. It identified about $4,800 in legitimate business expenses I could deduct that I had no idea about. The best part was seeing exactly how much to set aside each month for taxes based on my actual income instead of just guessing. My effective tax rate dropped from around 42% to 31% after all the proper deductions. Wish I'd found this before filing last year!

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If you're struggling with tax questions like this, you're definitely not alone. I spent HOURS on hold with the IRS trying to get clarity on self-employment taxes last year. Complete waste of time until I found Claimyr (https://claimyr.com). They have this service that gets you through to an actual IRS agent in minutes instead of waiting for hours. I was super skeptical at first, but you can see how it works in their demo video: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with explained everything about self-employment taxes and confirmed I could deduct my home office and a bunch of other expenses I wasn't sure about. Saved me a ton in taxes and the peace of mind was worth it.

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Aria Khan

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Wait how does this actually work? I've literally spent cumulative days of my life on hold with the IRS and never get through. Is this legit?

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Everett Tutum

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This sounds like a scam. There's no way anyone can magically get you to the front of the IRS phone queue. They're a government agency - nobody gets special access.

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It's not complicated at all - they use a system that continually redials and navigates the IRS phone tree until it gets through, then connects you when an agent is actually available. You don't have to sit there listening to hold music for hours. It just calls you when there's a live person ready to talk. I was definitely skeptical too, which is why I mentioned watching the demo. I thought it might be a scam at first, but it's just clever technology solving a common problem. They don't have "special access" - they're just automating the painful waiting process so you don't have to do it yourself. The IRS has no idea you're using a service - you're just another caller who got through the queue.

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Everett Tutum

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I need to eat my words about Claimyr being a scam. After struggling with a complex question about self-employment deductions that no one could answer clearly, I was desperate enough to try it. It actually worked. Got connected to an IRS agent in about 22 minutes (instead of the 3+ hours I spent last time trying on my own). The agent walked me through exactly how to handle my specific situation with 1099 income mixed with W-2 income. For what it's worth, they also confirmed what others have said about the self-employment tax - it's covering both the employee and employer portions of Social Security and Medicare. The agent also pointed out some deductions I was missing that will save me about $2,100 this year.

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Sunny Wang

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Don't forget that you can deduct 50% of your self-employment tax on your federal tax return! That helps offset the pain a little bit. Also, track EVERYTHING for your 1099 work - mileage, home office, supplies, software, portion of internet and phone, etc. All those deductions add up and can significantly lower your taxable income. When I first started contracting, my effective tax rate was around 40% but after properly tracking deductions it's now closer to 30%. Don't be afraid to get aggressive (but legal) with your business deductions!

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What's the safest way to handle home office deductions? I've heard they're audit triggers and I'm paranoid about getting flagged by the IRS.

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Sunny Wang

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Home office deductions are perfectly safe if you're legitimately using the space exclusively for business. The key is "exclusive use" - the area must be used ONLY for business, not a guest bedroom or family space that you sometimes work from. For the safest approach, use the simplified method - it's $5 per square foot up to 300 square feet ($1,500 max deduction). No receipts needed, super clean. The regular method might get you more deduction but requires tracking actual expenses and calculating percentages, which is where people often make mistakes that can trigger audits.

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ugh this whole system is so rigged against independent workers! big corporations get all these loopholes but we get stuck with this "self employment" tax that's just a fancy way of saying "we're taxing you extra for not having a traditional job" 🙄

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Melissa Lin

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It's not really "extra" tax though. Employees pay the same total amount, it's just hidden because their employer pays half. The real issue is all the work we have to do to track everything and file correctly.

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Quick tip - if you expect to owe more than $1000 in taxes for the year, you need to make estimated quarterly tax payments to avoid underpayment penalties. I learned this the hard way and got hit with penalties my first year contracting. Easiest way is to use the IRS Direct Pay system and select "estimated tax" as the reason. You'll need to calculate roughly what you'll owe each quarter based on your income. Quarters are due April 15, June 15, Sept 15, and Jan 15 of the following year (weird schedule, I know).

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The confusion is totally understandable! Think of it this way - when you're a W-2 employee, you see 7.65% deducted from your paycheck for Social Security and Medicare, but your employer is secretly paying another 7.65% that you never see. So the total is actually 15.3%, you just don't realize it. As a 1099 contractor, there's no employer to pay that hidden half, so YOU have to pay the full 15.3% as self-employment tax. Your federal income tax is completely separate - it's based on your income bracket and has nothing to do with Social Security/Medicare. The bright side? You can deduct half of that self-employment tax (the "employer" portion you're paying) when calculating your federal income tax. Plus, all those business expenses you can write off as a contractor often make up for the extra tax burden. Just make sure you're tracking everything - home office, mileage, equipment, software subscriptions, etc. At $78k with mixed W-2 and 1099 income, 44% savings rate does seem high. You might want to run the numbers more precisely or consult with a tax professional to make sure you're not over-saving (though better safe than sorry after last year's surprise!).

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