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Ask the community...

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Norah Quay

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Former payroll specialist here. Your W-2 is correct. When tips reported in Box 7 reach the Social Security wage base ($168,600 for 2024), Box 3 will be empty or show $0. This is because: 1. Social Security tax only applies up to the annual wage base limit 2. Your reported tips already hit that limit 3. Any additional income is not subject to Social Security tax 4. Box 3 is only for wages subject to Social Security tax that aren't tips In your case, all of your Social Security-eligible earnings were tips, so everything went in Box 7 up to the limit. Nothing needed to go in Box 3.

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Leo McDonald

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Does this mean the employee is paying less in taxes overall since not all income is subject to Social Security tax?

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Norah Quay

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Yes, it effectively means you're paying less in Social Security tax than you would if there wasn't a wage base limit. Social Security tax stops once you hit the annual limit ($168,600 for 2024), regardless of how much more you earn. However, Medicare tax continues to apply to all earnings with no cap, and you'll actually pay an additional 0.9% Medicare surtax on earnings above $200,000 for single filers. So while you get a break on Social Security tax, the Medicare portion continues and even increases at higher income levels.

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Wait I'm confused about Box 1 vs Box 3 vs Box 7... if your income is $400k and Box 7 is capped at $168.6k, shouldn't Box 1 show your full income of $400k? And then either Box 3 should show the difference or something?

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Box 1 shows total taxable wages, which would indeed be the full income (minus any pre-tax deductions like health insurance or 401k contributions). Box 7 shows tips that are subject to Social Security tax, which is capped at the wage base limit. Box 3 shows non-tip wages subject to Social Security tax. Since OP's tips already reached the Social Security wage base limit, there's nothing additional to report in Box 3.

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Omar Fawaz

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Don't forget about depreciation recapture! Even if you can use your PALs, you'll still have to recapture the depreciation you took (or were required to take) during the rental period. That gets taxed at 25% rather than your normal capital gains rate.

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Chloe Martin

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Is the depreciation recapture rate really 25%? I thought it was your ordinary income tax rate, but capped at 25%. So if your ordinary rate is lower than 25%, you'd pay the lower rate?

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Diego Rojas

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Has anyone used TurboTax to handle this specific PAL situation? I'm in literally the exact same boat (property rented in 2020-2021, vacant in 2022, then sold) and I'm trying to figure out if TurboTax will walk me through this correctly or if I need to go to a CPA.

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I used TurboTax last year for a similar situation. It does technically handle PALs, but I found it confusing. It asked a series of questions that didn't seem directly related to my situation, and I wasn't confident it was doing things right. Ended up going to a CPA who found several mistakes in what TurboTax had done. For something this specific, I'd recommend a tax pro.

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Jacob Lewis

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Another thing to consider with 1099 work is that you need to figure out your own health insurance, retirement, and you don't get paid time off or sick days. When comparing offers, factor in what these benefits would cost you. For health insurance, check your state's marketplace. For retirement, look into a SEP IRA or Solo 401k - you can actually save more for retirement as a self-employed person than as an employee. The best part about being a contractor is the tax deductions. Keep track of EVERYTHING related to your work - part of your internet, phone bill, any equipment, software subscriptions, professional development courses, mileage if you drive for work, etc. It all adds up!

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Liam Brown

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Thank you for mentioning health insurance - I totally forgot about that! The company did say something about a stipend for health coverage, but I should definitely calculate what that would really cost me vs. employer-provided insurance. Do you have any recommendations for tracking all those business expenses? Is it just like a spreadsheet or should I use some kind of app?

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Jacob Lewis

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I started with a spreadsheet but quickly found it too tedious to maintain. Now I use an app called QuickBooks Self-Employed that lets me connect my bank accounts and credit cards, then swipe left or right to categorize transactions as business or personal. It automatically calculates my quarterly tax payments too. If you're just starting out and don't want to pay for software yet, even something as simple as taking photos of receipts and saving them to a dedicated folder can work. Just make sure you have some system in place from day one - it's much harder to reconstruct everything at tax time if you haven't been tracking throughout the year.

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Just a heads up - make sure they're classifying you correctly! Some companies try to classify employees as 1099 contractors to avoid paying benefits and employment taxes, but there are specific IRS rules about who can legally be considered a contractor vs. employee. If they control WHEN and HOW you do the work (set hours, at their location, using their equipment, etc.), you might legally be an employee, not a contractor. Worth looking into before accepting the offer.

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Ethan Clark

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This is super important advice. I got misclassified as a contractor when I was really doing employee work and ended up paying thousands in taxes I shouldn't have had to pay. The IRS has a form called SS-8 you can file if you think you're misclassified.

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Independent Contractor vs. Sole Proprietor: Is There a Difference for IRS Filing?

I'm seriously confused about the difference between being an independent contractor and a sole proprietor according to the IRS. My situation is this: I occasionally work as a "patient advocate" for a medical foundation, sharing my experiences with a specific condition. It's completely random throughout the year with no regular schedule - just whenever they need someone with my background. I only make about $3,200 max per YEAR from this gig, usually less. My tax person has been putting this income on Schedule C for years, saying it has to go there. I looked at the IRS guidelines and I'm meeting the "independent in how I do the work" part, but not really the "regular and continuous business activity" part since it's so sporadic. Here's my problem - I'm involved in another situation where my lawyer (not a tax lawyer) is saying that filing Schedule C means I'm technically a "sole proprietor" not an "independent contractor," and that claiming to be an independent contractor elsewhere could make me look dishonest. I've read through all the "Small Business and Self-Employed Tax Center" info on the IRS website and I still can't figure out if there's actually any difference between these terms! I'm trying to get a meeting with a tax attorney but this other matter is urgent. Would really appreciate some insight on whether these terms are basically interchangeable or if I'm filing incorrectly. Should I not be using Schedule C for this kind of random work?

Sofia Torres

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Something nobody's mentioned yet - if you're really concerned about this from a legal perspective, you might want to consider forming an LLC. It's pretty simple and inexpensive in most states. That would make the distinction clearer since you'd be an LLC rather than a sole proprietor, but you could still be an independent contractor in terms of your relationship with clients. For tax purposes, a single-member LLC is typically treated as a "disregarded entity" and you'd still file Schedule C unless you elect different tax treatment.

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Jamal Harris

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That's an interesting suggestion! Would forming an LLC change anything about how I file taxes or would I still use Schedule C? And would there be any benefits for someone making such a small amount ($3k-ish per year) from this work?

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Sofia Torres

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You would still use Schedule C with a single-member LLC unless you elect to be taxed as an S-Corporation or C-Corporation. The LLC doesn't change your tax filing method by default - it's considered a "disregarded entity" for tax purposes when it has just one member. For someone making only around $3,000 annually from this work, an LLC probably isn't worth the administrative costs and annual fees unless you have significant liability concerns. The main benefit of an LLC is limiting your personal liability, but for patient advocacy work with minimal income, the protection may not justify the expenses. Some states have annual LLC fees of $800+ (California), while others are much cheaper ($50-100).

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Has anyone used TurboTax for this kind of situation? Does it automatically put you on the right forms? I'm starting to do some freelance work this year and trying to figure out if I should use software or hire someone.

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Ava Martinez

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I use TurboTax Self-Employed and it works great for this. It asks if you have self-employment income and then automatically puts you on Schedule C. It doesn't really distinguish between "independent contractor" and "sole proprietor" either - it just asks about your business income and expenses. The software walks you through all the deductions you might qualify for too.

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Capital Gains Tax When Paying Off Business Loan? Concerned My Accountant Misclassified Business Debt

I took over a small manufacturing business 8 years ago through probate when the previous owner passed without a will. As part of the inheritance arrangement, I agreed that the business would take responsibility for a personal debt the deceased owner had incurred to start the business. This debt was actually a Line of Credit that a family member had taken out against their assets to help fund the business initially. I've been making payments directly to the LOC, but have a formal agreement with the family member outlining the repayment terms. The LOC just reached the end of its initial term and was refinanced with a much higher interest rate. When I talked to my accountant about potentially paying off the remaining $68,000 balance completely, he dropped a bombshell - said I'd be hit with capital gains tax because he never classified this as business debt on our books, but kept it as personal debt. I'm frustrated and confused by this. My accountant claims "it actually benefited you because we added the loan amount to your capital account which allowed you to withdraw capital without triggering additional taxes." This doesn't make sense to me since I've never taken distributions exceeding our annual profits. Furthermore, we received a substantial ERC (Employee Retention Credit) payment last year, and I suspect my accountant is overlooking those funds in our capital account since we had to file amended returns. My accountant always seems completely overwhelmed when I ask questions. Can someone help me understand what the tax implications are of my accountant never properly classifying this as business debt when I inherited the company? Am I right to think this misclassification has negatively affected me? Would there be ANY advantage to keeping this classified as personal rather than business debt all these years? Any insights would be greatly appreciated!

Just to offer another perspective here: Your accountant might be partially right about the capital account benefit, but they're missing the bigger picture. When a business assumes a personal debt, it should be recorded as a liability of the business with a corresponding entry to your capital/equity account. What likely happened is that your accountant increased your capital account (correctly) but failed to record the liability on the business books (incorrectly). This artificially inflated your basis. Now when you want to pay off the loan, the business is essentially making a distribution to you because the liability isn't on the books. The proper correction would be to record the liability on the business books now (which would decrease your capital account) but then the debt payment would be a proper business expense, not a distribution. You might need to file Form 3115 to change accounting method rather than amending all previous returns. And yes, the ERC funds would absolutely increase your capital account and available business assets, so your accountant should be including those in the calculations.

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Joy Olmedo

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This explanation makes a lot of sense - thank you! So essentially, my accountant only did half the correct accounting (increasing my capital account) but missed recording the actual liability on the business books? If I understand correctly, I should be able to correct this going forward by properly recording the liability now, which would reduce my capital account but allow the business to pay off the debt as a legitimate business expense without triggering capital gains? Would this correction potentially trigger any penalties or raise audit flags?

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You've got it exactly right. Your accountant increased your capital account but failed to record the corresponding liability on the business books, which created this imbalance. Correcting this going forward is possible by properly recording the liability now. This would reduce your capital account (essentially correcting the artificial inflation), but then allow the business to properly pay off the debt as a legitimate business expense without triggering capital gains or being treated as a distribution to you. This type of correction typically wouldn't trigger penalties if properly disclosed as an accounting method change using Form 3115. The IRS recognizes that accounting methods sometimes need correction, and they provide this form specifically for that purpose. It's considered a voluntary correction rather than something that raises audit flags. Include a clear explanation of the circumstances of the inheritance and how the debt was always intended to be a business obligation based on your agreement. Having good documentation of the original intent (like your contract with the family member) will strengthen your position if there are any questions.

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Sasha Reese

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I think there's confusion about what your accountant actually did. Based on your description, it sounds like they treated the original loan amount as an owner contribution (increasing your basis/capital account) but never recorded the loan as a business liability. Each payment the business made toward the loan was likely treated as a distribution to you. This isn't necessarily "wrong" from a tax perspective - it's just one way to handle it. The alternative would have been to record the loan as a business liability with no impact on your capital account. Then payments would be business expenses. If the business has been profitable and generating basis, those distributions might have been tax-free. But now that you want to pay it off completely, there could be issues if the distribution exceeds your current basis. I'd suggest getting a copy of the business balance sheet and your capital account statement to see exactly what's been recorded over the years. That would clarify what's actually happening here.

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This makes sense, but wouldn't reclassifying the debt now as a business liability be better for tax purposes? Even if it means adjusting the capital account? I thought business interest expense was deductible while personal loan interest isn't (or is limited).

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