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Just to add another perspective - when I liquidated my S Corp last year, the biggest issue was properly documenting the worthlessness of the business. My tax guy said it wasn't enough to just say "I'm closing down and taking a loss" - I needed to show evidence the business had no value. We created documentation showing failed attempts to sell the business, lack of revenue, negative cash flow, and competitive market conditions that made revival impossible. This packet of "worthlessness documentation" was crucial for supporting the deduction. Also, make sure you're tracking any personal expenses you covered for the business that weren't reimbursed - these can increase your stock basis and potentially increase your deductible loss.
How exactly did you document the "worthlessness"? Did you need an independent appraisal or was your own documentation sufficient? I'm in a similar situation but don't want to spend more money on an appraiser if I don't need to.
I used a combination of internal financial statements and business records rather than paying for an expensive appraisal. I created a documentation package that included monthly P&L statements showing consistent losses, screenshots of competitor pricing that showed we couldn't compete profitably, documentation of failed attempts to sell the business (emails with potential buyers or brokers), and a formal business memo explaining the market conditions that made continuation impossible. My CPA said the key was showing I had made legitimate efforts to make the business work or sell it before declaring it worthless. We also included bank statements showing the business accounts were depleted. This approach worked for me, but situations vary - if your business had substantial physical assets rather than just a website, you might need more formal valuation. The most important thing is showing you've exhausted reasonable options before taking the tax loss.
Quick question about timing - I'm in a similar situation but wondering whether I should liquidate this year or wait until January. Does it make a difference tax-wise? My income is higher this year than it will be next year.
If you're expecting lower income next year, it might make sense to delay the liquidation until January. Capital losses (which some of this likely will be) are more valuable in higher income years since they offset income. But if some qualifies as ordinary loss under Section 1244, that might be more valuable in a higher income year.
Just FYI for everyone, the paper forms aren't that complicated for a simple 1099-MISC situation. I filed mine manually last year with similar income. You need: - Form 1040 (the main tax return) - Schedule C (for reporting the business income) - Schedule SE (for self-employment tax calculation) The IRS has fillable PDFs on their website, and the instructions are pretty clear. The calculations for self-employment tax are a bit annoying but doable. Took me about 2 hours total. But honestly, with the free options others mentioned, software is probably easier unless you really want to understand the tax process.
Thanks for breaking down the forms! If I do decide to file manually, does Schedule C require me to track a bunch of expenses? I literally just got paid for working shifts operating rides, no expenses or anything.
Schedule C is where you report your business income and expenses, but you don't have to have expenses to file it. If you didn't have any business expenses, you can just put $0 in those sections. You'll report your total 1099-MISC income ($940) as gross income on Schedule C, then since you have no deductions, that same amount becomes your net profit. This net profit gets transferred to your 1040 and is also used to calculate your self-employment tax on Schedule SE. Keep in mind you'll owe about 15.3% for self-employment tax (covers Social Security and Medicare) on your earnings, so set aside roughly $144 if you haven't already. The tax software would calculate this automatically, which is one advantage of using it.
Don't forget to check your state's filing requirements too! Even if you use free federal filing, some states have separate requirements and fees. I had a similar situation with a small 1099 and found out I didn't need to file a state return at all in my state because my income was below the threshold. Saved me the $15-30 that most "free" services charge for state filing.
I think you're getting some overly complicated advice here. H&R Block has a guarantee that covers preparer errors. Just go back to the same office, ask for the manager, and explain what happened. They should handle the entire amendment process for you at no charge AND they should cover any interest or penalties that might result from their mistake. I used to work at a tax prep office (not H&R), and this kind of thing happened occasionally. The company should make it right without you having to do all this extra work yourself. Don't let them brush you off with "the IRS will catch it" because that's not how it works.
Thanks for this perspective! I called the H&R Block office this morning and asked for the manager. At first they tried to stick with the "IRS will catch it" line, but when I mentioned their guarantee that covers preparer errors, their tone completely changed. They've scheduled me to come in tomorrow where they'll handle the amendment for me and they're giving me a document stating they'll cover any related penalties. Should I bring anything specific to the appointment?
Bring all your original tax documents (W-2s, 1099s, etc.), your payment receipt showing how much you paid, and the final tax return they prepared. If you have any emails or documentation about the error being discovered, bring those too. Also ask them to provide you with written confirmation that they'll track the amendment until completion and notify you when the refund is expected. Get the manager's direct contact information in case you need to follow up. Don't leave without copies of everything they submit on your behalf, including the 1040-X form they prepare.
Don't wait for the IRS to "catch" anything! I made this mistake last year and waited 6 months before taking action myself. I finally called the IRS Taxpayer Advocate Service at 877-777-4778. They're an independent organization within the IRS that helps taxpayers resolve problems. Explain your situation and they can help guide you through the fastest way to get your refund. The key is to be proactive. Document everything, including the date and time you discovered the error and the name of the H&R Block preparer who admitted the mistake. This documentation will be crucial if there are any disputes later.
The Taxpayer Advocate Service is great but they're super backed up right now. I called them last month about a similar issue and they told me they're only taking cases with financial hardship or where you're facing immediate negative action from the IRS. Did you have to prove hardship to get their help?
Something nobody's mentioned yet - you might actually qualify for certain tax credits even with no income, which could mean getting money BACK when you file! For example, if you had any educational expenses last year, you might qualify for education credits. If you paid for healthcare, there might be credits available there too. And depending on your age and filing status, you might qualify for the Earned Income Tax Credit even with your business loss. Don't miss out on potential refunds just because you think you don't need to file with no income!
Do you know if you can get the earned income credit if your business operated at a loss? I thought you needed actual earned income to qualify for that. Also, would educational expenses count if they were related to improving business skills?
For the Earned Income Tax Credit, you generally do need some earned income to qualify, so a complete business loss might not help there - I should have been more specific. However, even minimal earned income (like side gigs) can sometimes qualify if you meet the other requirements. For educational expenses, if they were directly related to improving skills for your current business, they might be deductible as business expenses rather than qualifying for education credits. Business-related education can usually be deducted on Schedule C if you're a sole proprietor or flow through on partnership returns. This is actually where documenting business losses properly becomes important for future tax benefits.
Hey so I did almost the same thing last year, my small business tanked and I had basically no income. My tax person said to definitely file because not filing for multiple years can trigger automatic flags in the IRS system! Also they explained that living off savings is totally fine tax-wise since that money was already taxed when you originally earned it. You don't pay taxes again when you withdraw from your regular savings account. Made me feel way better about the whole situation!
Paolo Moretti
Don't forget to check if your school/university offers free tax advice! I was a research assistant during grad school and my university had free tax workshops specifically for students with stipends and research positions. They even had dedicated sessions for independent contractors vs. employees. Worth checking if yours has something similar!
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StarSurfer
β’That's a great idea! I didn't even think to check with my university. Do you know what department typically offers this kind of service? Would it be financial aid or something else?
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Paolo Moretti
β’Usually it's either through the financial aid office or the student services department. Some universities also have it through their business school or accounting program where accounting students (supervised by professors) provide tax help as part of their practical training. The best approach is to just email your university's general help desk or student services and ask if they offer tax assistance. If they don't have an in-house program, they might still know about local resources specifically for students.
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Amina Diop
One thing nobody mentioned - get a separate bank account for your business income and expenses! I learned this the hard way when I started freelancing. The IRS can be really picky about commingling personal and business finances. Also download a free expense tracking app now and start using it immediately. Take pictures of all receipts. You'll thank yourself next April when you're not trying to remember what every purchase was for.
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Oliver Weber
β’This is so important! And don't forget to keep track of any home office expenses. If you dedicate a space solely to your research work, you can deduct a portion of your rent and utilities.
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