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Just a heads up - I work in the high-ticket sales industry too and saw a company get absolutely hammered for this exact issue last year. The IRS determined ALL their 1099 sales reps were actually employees and hit them with back taxes, penalties, and interest going back 3 years. The company tried to claim the reps had "independence" but the IRS didn't buy it because they: 1) Had to attend mandatory meetings 2) Were required to use company scripts 3) Had to work specific hours 4) Used company CRM and tools 5) Were subject to performance reviews Sound familiar? Several reps got significant tax refunds since they'd been paying the full self-employment tax when they should've only been paying the employee portion. The company ultimately had to lay off about 30% of staff to cover the penalties.
Do you know if the reps had to pay back any of the business deductions they'd claimed? I've been deducting home office, internet, phone, etc., as a 1099 and I'm worried if I get reclassified I'll owe a ton for those past deductions.
From what I understand, the reps didn't have to pay back deductions they had legitimately claimed while operating under the 1099 status. The IRS generally doesn't penalize workers in these situations since you were filing based on the classification given to you by the company. However, going forward after reclassification, they could no longer claim those business deductions as W-2 employees. That's definitely something to consider in your calculations - while you save on the employer portion of FICA taxes as a W-2, you lose those valuable business deductions. In some cases, especially if you have significant legitimate business expenses, remaining a 1099 might actually be more financially beneficial despite the higher self-employment tax.
Has anyone successfully negotiated higher pay when transitioning from 1099 to W-2? I'm making about $17k/month as a 1099 sales rep, and I've calculated that I'd need at least a 9% raise to break even after losing my business deductions if I become a W-2 employee.
Yes! I managed to negotiate a 12% increase in my commission rate when my company reclassified me from 1099 to W-2 last year. The key was coming prepared with exact numbers showing: 1) The taxes they'd now be paying (7.65% of your income) 2) The benefits costs they'd incur 3) The exact business deductions I'd be losing 4) Market rates for W-2 sales reps with my performance level I presented it as a business case rather than a demand. They actually appreciated the transparency and realized keeping top performers was worth the adjustment.
That's really helpful, thanks for the specific percentage figure and the breakdown of what to include in the negotiation. I'll definitely put together that kind of detailed analysis before approaching them. I'm curious though - did your overall take-home pay end up being higher, lower, or about the same after the transition? And did you notice any benefits to being W-2 beyond just the tax situation?
Just to add another perspective - I'm a corporate accountant (not giving tax advice) and see this confusion all the time with employees. Stock compensation generally has two tax events: 1. When you RECEIVE the shares - taxed as ordinary income 2. When you SELL the shares - taxed as capital gains on any appreciation Your employer should have included the fair market value of the stock when granted on your W-2 and withheld taxes accordingly. The 1099-B is often wrong because brokerages don't know what's been reported on your W-2, so they put $0 as the cost basis. You need to adjust this manually.
What about if the stock value dropped between when I received it and when I sold it? Can I claim a loss in that case? My employer gave us stock at $75/share but by the time I sold it had dropped to $58.
Yes, if the stock value dropped between when you received it and when you sold it, you can absolutely claim a capital loss. In your example, if your stock was valued at $75 per share when granted (and that amount was included in your W-2 income), but you sold at $58 per share, you would have a capital loss of $17 per share. This loss can be used to offset capital gains from other investments, and if your total capital losses exceed your gains, you can deduct up to $3,000 of the excess loss against your ordinary income. Any remaining loss can be carried forward to future tax years.
Has anyone actually found where in TurboTax to adjust the cost basis? I'm having the same issue but can't find where to change it from $0 to what was reported on my W2.
In TurboTax, when you enter your 1099-B information, there should be a screen that says something like "Review your 1099-B entries" after you input the initial information. On that screen, you can select the specific stock transaction and click "Edit" or "Update." There should be a field labeled "Cost basis" where you can manually enter the correct amount instead of using what's on the form.
One thing nobody's mentioned yet - your friend should request his Wage and Income Transcripts from the IRS for all those years. This will show all income that was reported to the IRS on 1099s, W2s, etc. This gives you a starting point to know what income the IRS already knows about. You can request these transcripts online at irs.gov or by filing Form 4506-T. This helps ensure you don't miss any income that was reported to the IRS, which would definitely trigger notices or audits.
Can you get these transcripts if you haven't filed for several years? I thought your online access gets restricted if you're not in compliance?
You're right that online access might be restricted for non-filers. In that case, you can still get them by mail using Form 4506-T. It takes a few weeks but gives you exactly what income the IRS has on record. Even if your friend can't access his own transcripts directly, a tax professional with proper authorization (Form 2848 Power of Attorney) can access these transcripts on his behalf through the tax pro's account. This is another reason working with a professional is valuable in catch-up situations.
Just wanted to add that I was in a similar situation (6 unfiled years as a freelancer) and the process wasn't nearly as scary as I thought. Definitely start with current year and work backwards, and be proactive about setting up payment plans if he owes. The IRS is actually pretty reasonable if YOU reach out to THEM before they come looking for you. It's when you ignore their notices that things get ugly with liens and levies.
Has anyone considered that the Tax Cuts and Jobs Act significantly changed tax brackets, deductions, and credits between 2017 and 2018? I know OP is talking about 2023-2024, but if your tax preparer is using outdated forms like 1040EZ (which doesn't exist anymore), they might not be the most reliable. Different withholding tables + partial year work + 401k contributions can absolutely cause dramatically different refunds. Remember a refund just means you overpaid throughout the year - it's not free money!
Wait, so if these forms don't even exist anymore, why would my preparer mention using different forms? Now I'm really confused and wondering if I should find a new tax person. Do you have any suggestions for how to find a good tax preparer?
I'd be concerned if your preparer is actually referring to these outdated forms, as they haven't been used since 2017. They might be using simplified language to describe your tax situation, but it's a red flag if they're literally talking about filing these forms recently. For finding a good preparer, I recommend looking for an Enrolled Agent (EA) or CPA who specializes in individual taxes. Ask friends for recommendations, check Google reviews, and interview potential preparers before hiring. Ask questions like: How long have you been preparing taxes? What continuing education do you complete? How do you stay current with tax law changes? A good preparer should be able to clearly explain why your refunds differed and shouldn't mind questions.
One thing nobody's mentioned - check if your state withholding was different between the two years! My refunds were super different between years and it turned out my state withholding had doubled accidentally. The federal return looked similar but the state refund was huge one year.
Good point! I had something similar happen when I moved from Illinois to Indiana mid-year. The state portion made a massive difference.
Malik Thompson
Don't forget to check if your school sent you a Form 1098-T, which shows how much you paid in qualified tuition and related expenses. You'll need this form when claiming the LLC. Sometimes schools mess up and don't include all eligible expenses on the form, so compare it against your actual receipts and payment history! If your MAGI is under $80k (single) or $160k (married filing jointly), you'll get the full credit amount based on your expenses. Once you hit those thresholds, the credit starts to phase out.
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Isabella Ferreira
ā¢Is the 1098-T required to claim the credit? My school is weird and doesn't always send them on time.
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Malik Thompson
ā¢While the 1098-T is helpful documentation, it's not technically required to claim the Lifetime Learning Credit. If you don't receive one or it's incorrect, you can still claim the credit using your own records of qualified education expenses. Keep documentation like receipts, cancelled checks, credit card statements, and any official statements from your educational institution showing you paid qualified expenses. The burden is on you to prove eligibility if audited, so good record-keeping is important even without the 1098-T.
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CosmicVoyager
Has anyone tried claiming both American Opportunity Credit AND Lifetime Learning Credit in the same year? I have expenses for two different students (me and my wife).
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Ravi Kapoor
ā¢You can definitely claim both credits in the same tax year, but not for the same student. If you and your wife are both in school, you could potentially claim AOC for one person and LLC for the other, depending on eligibility. That's a great way to maximize education tax benefits on one return!
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