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Hey Mae! I completely understand your stress - I was in almost the exact same situation last year. Made about $365 selling old clothes and jewelry on Depop, everything for way less than what I originally paid for it. After going through the same confusion and panic you're experiencing, here's what I learned: since you're under $600 and sold everything at a loss, you most likely won't receive a 1099-K and don't need to report this as income. The IRS treats this as disposing of personal property at a loss, not generating taxable income. What really helped me understand this was realizing the key distinction - you bought these items for your own personal use and are just decluttering your closet, not running a resale business. That makes all the difference in how it's treated for tax purposes. My advice is to create a simple spreadsheet showing what you originally paid vs. what you sold each item for, just for your own records and peace of mind. I went through my old emails and credit card statements to piece together my purchase history - it was actually easier than I expected to find most of the info. At $350 with clear losses on every single item, you're really in a safe position. Try not to stress too much about it - you're handling this correctly and you're definitely not alone! This thread shows how common this exact situation is.
This is exactly what I needed to hear! I've been losing sleep over this whole situation and your experience with almost the identical amount ($365 vs my $350) is so reassuring. Reading through this entire thread has been incredible - it's amazing how many people have dealt with this exact same scenario. The distinction you made about personal decluttering vs. running a business really makes it click for me. I definitely wasn't trying to flip items for profit - I was literally just cleaning out my closet of designer pieces I bought years ago and never wear anymore. Everything sold for way less than what I paid originally. I'm absolutely going to create that spreadsheet you mentioned. I actually have most of my purchase records in my email since I shop online a lot, so it should be pretty straightforward to document everything properly. The peace of mind will definitely be worth the effort. Thank you so much for sharing your experience, and thanks to everyone else in this thread too! This community has been incredibly helpful and supportive. I feel so much better about my situation now and can finally stop stressing about it. At $350 with everything at a loss, it sounds like I'm definitely in the clear.
Mae, I completely understand your stress about this situation! I went through something very similar last year when I made about $320 selling old clothes and accessories on Depop - every single item sold for less than what I originally paid. After doing a lot of research and worrying for weeks, here's what I learned: at $350 with everything sold at a loss, you're very unlikely to receive a 1099-K and generally don't need to report this as income. The IRS treats selling your personal clothing items at a loss as disposing of personal property, not generating taxable income. The key factors in your favor are that you're well under the $600 threshold, sold everything below your purchase price, and these were personal items you bought for yourself (not business inventory). You're just decluttering your closet, not running a resale business. My recommendation is to keep simple records showing what you originally paid vs. what you sold items for - I created a basic spreadsheet with item descriptions, original cost, and sale price. I was able to find most of my purchase info by going through old emails and credit card statements, which was easier than I expected. Try not to stress too much! You didn't actually make any profit - you just recovered a small fraction of what you originally spent on clothes you weren't wearing anymore. Based on everything I've learned and what others have shared, you're in a really safe position tax-wise.
Has anyone tried using a tax professional instead of software for back taxes? I'm worried about making mistakes that could make my situation worse.
I used a CPA for 3 years of back taxes and it cost me nearly $1,200. The peace of mind was nice but honestly most of what they did I could have done myself with decent software. If your situation is complicated (multiple states, businesses, investments), a pro might be worth it. Otherwise, software is probably fine.
I went through this exact situation two years ago with 4 years of unfiled returns. Here's what I learned: 1. **Software choice**: I ended up using FreeTaxUSA after comparing costs. TurboTax wanted $140+ per year for my 1099 situation, while FreeTaxUSA was around $15-20 per prior year return. The interface isn't as polished as TurboTax, but it gets the job done. 2. **Filing order matters**: File in chronological order (2022 first, then 2023, then 2024). Some refunds from earlier years might offset what you owe for later years. 3. **Penalties**: The failure-to-file penalty is brutal (5% per month), but if you're getting refunds for any of those years, you won't owe failure-to-pay penalties on those. I qualified for first-time penalty abatement which saved me about $800. 4. **Keep copies of everything**: When you mail in the prior year returns, send them certified mail and keep tracking numbers. It can take 6-12 weeks for the IRS to process mailed returns. The whole process took me about 2 months to complete, but getting it done was such a relief. Don't let the fear of penalties stop you - the sooner you file, the sooner you can stop the failure-to-file penalties from accumulating. You've got this!
This is incredibly helpful, thank you for sharing your experience! I'm in almost the exact same boat - 3 years unfiled with mixed W-2 and 1099 income. Your point about filing in chronological order is something I hadn't considered but makes total sense. Quick question about the first-time penalty abatement - did you have to request that separately after filing, or was there an option to request it during the filing process? And did you need to provide any specific documentation to qualify for it? Also, when you say it took 2 months to complete, was that mainly waiting for the IRS to process everything, or was most of that time spent on actually preparing the returns?
As someone who works with tax issues regularly, I want to add a few practical points that might help newer traders navigate wash sales more effectively. First, regarding @Teresa Boyd's excellent point about cash flow - this is absolutely critical. I've seen many traders get blindsided by unexpected tax bills because they assumed their December losses would offset their gains, only to discover those losses were disallowed due to wash sales. One strategy that can help: if you're planning year-end tax loss harvesting, consider doing it earlier in December (or even November) rather than waiting until the last minute. This gives you more time to ensure you don't accidentally repurchase the same securities and create wash sales. Also, for those asking about tracking across multiple brokers - your brokers are required to report wash sales on your 1099-B, but they can only track what they can see within their own systems. If you have accounts at multiple firms, you're responsible for identifying and adjusting for wash sales that occur across those accounts. The IRS doesn't get a consolidated view either, so it's really up to you (or your tax software/professional) to catch these cross-broker wash sales. This is why keeping detailed records and using tools that can aggregate data from multiple sources becomes so important if you're an active trader. One last tip: if you're unsure about complex wash sale situations, don't hesitate to consult a tax professional who specializes in trader taxes. The cost of getting it wrong can far exceed the cost of professional advice.
This is incredibly helpful advice, thank you @AstroAlpha! As someone who just started trading this year, I really appreciate the practical timeline suggestions. The idea of doing tax loss harvesting in November rather than waiting until December makes so much sense - gives you that buffer to avoid accidentally creating wash sales. Your point about brokers only being able to track what they see within their own systems is eye-opening. I have accounts at both Fidelity and Robinhood, and I was naively assuming that somehow the wash sale tracking would just "work" across both platforms. Now I realize I need to be much more proactive about tracking this myself. The suggestion about consulting a tax professional who specializes in trader taxes is something I hadn't considered, but given how complex this is getting, it might be worth the investment. Do you have any recommendations for how to find tax professionals who actually understand active trading scenarios? I feel like my regular tax preparer would be out of their depth with wash sale complexities across multiple accounts. Thanks again for taking the time to share this practical guidance - it's exactly what newcomers like me need to hear!
@Giovanni Colombo great question about finding qualified tax professionals! Here are a few ways to find tax preparers who actually understand active trading: 1. Look for CPAs or EAs (Enrolled Agents) who specifically advertise "trader tax services" or "active investor tax preparation." Many will mention this specialization on their websites. 2. Check with your brokerage - many major firms like Fidelity, Schwab, and TD Ameritrade maintain referral lists of tax professionals familiar with trading complexities. 3. The American Institute of CPAs (AICPA) has a "Find a CPA" tool where you can filter by specialties including investment taxation. 4. Consider looking into firms that specialize in trader taxes - there are several national firms that work exclusively with active traders and can handle multi-broker wash sale situations remotely. A good trader-focused tax professional should immediately understand concepts like cross-account wash sales, mark-to-market elections, and the IRA wash sale rule @Ingrid Larsson mentioned. If they seem unfamiliar with these topics during your initial consultation, keep looking. You're absolutely right that your regular tax preparer would likely be out of their depth. Trading taxes are a specialized area, and the complexity only increases with multiple accounts and active trading strategies. The investment in proper professional help usually pays for itself by avoiding costly mistakes.
This is exactly the kind of guidance I was hoping to find! Thank you @QuantumQuasar for the specific resources and search tips. I had no idea that brokerages maintained referral lists for tax professionals - that's brilliant since they'd obviously want to connect their clients with preparers who understand their platforms and reporting. The point about testing a tax professional's knowledge during the initial consultation is really smart too. I'll definitely ask about cross-account wash sales and the IRA rule right upfront to see if they really know their stuff. I'm curious though - for someone like me who's just starting out with relatively simple trading (maybe 50-100 trades this year across two brokers), at what point does it make sense to invest in a specialized tax professional versus trying to handle it myself with good software? I don't want to overpay for services I don't need yet, but I also don't want to mess up my taxes in year one of trading. Has anyone here found that sweet spot between DIY and professional help for newer traders?
This is such a helpful thread! I'm new to survey sites too and had no idea about all these tax implications. I just signed up for a few platforms last week after seeing how much some people were making. One question I haven't seen addressed - what happens if you cash out through gift cards instead of PayPal or direct deposit? I was planning to take most of my earnings as Amazon gift cards since I shop there frequently anyway. Do I still need to report the full cash value of those gift cards as income, or is there some different treatment since it's not actual money hitting my bank account? Also, for those keeping detailed records throughout the year - are you tracking this manually or using any specific apps? I'm already feeling overwhelmed trying to keep track of earnings across multiple sites, and I've only been doing this for a week!
Great question about gift cards! Unfortunately, gift cards are still considered taxable income at their full cash value. The IRS treats them as compensation for your time and services, just like cash payments. So if you earn $100 in Amazon gift cards, you need to report $100 in income even though you never saw actual money in your bank account. For tracking, I personally use a simple Google Sheets spreadsheet with columns for: Date, Site Name, Activity, Amount Earned, Payment Method (cash/gift card), and Status (pending/paid). I update it weekly and it takes maybe 5 minutes. Some people use apps like Mint or YNAB, but honestly a basic spreadsheet works great and you can access it from anywhere. The key is being consistent with whatever method you choose - don't let it pile up or you'll be scrambling come tax time!
As someone who's been doing surveys for about two years now, I want to emphasize something that might not be obvious to newcomers - keep track of your time as well as your earnings! I started just like you, earning small amounts here and there, but once I hit that $600 threshold and had to start dealing with Schedule C, I realized I could also deduct certain expenses against this income. The time tracking helped me justify the business use percentage of my home office space, internet, and even my phone plan. Also, a practical tip that saved me during my first tax season: set aside about 25-30% of your survey earnings in a separate savings account throughout the year. Between federal income tax, state tax (if applicable), and the 15.3% self-employment tax, you'll owe more than you might expect. I learned this the hard way when I owed $180 on $800 of survey income and hadn't saved anything! The survey companies will usually send your 1099-NEC by January 31st if you earned $600+, but like others mentioned, you're required to report all income regardless. Good luck with your survey journey - it's actually pretty nice passive income once you get the tax part figured out!
This is excellent advice about setting aside money for taxes! I wish I had known about the 25-30% rule when I started. I'm curious about the time tracking aspect you mentioned - do you literally log every minute you spend on surveys, or do you do more of a weekly estimate? I'm trying to figure out the best way to document this for potential deductions without making it feel like a second job just to track the first side job! Also, when you mention home office deductions, does that work even if you're just using your kitchen table for surveys, or do you need a dedicated workspace?
Paolo Ricci
This is such valuable information, thank you for sharing! I'm currently dealing with something similar with TickPick - they've been sending me emails for about 2 weeks requesting my SSN after I sold some football tickets for $145 total (actually less than what I originally paid since I had to price them to sell quickly when I found out I couldn't attend). Reading through all these experiences has been incredibly helpful. I was starting to feel guilty about ignoring their emails, especially with subject lines like "Action Required for Tax Reporting" that made it sound so official and urgent. But seeing how consistent everyone's experiences have been across different platforms really validates my instinct that something wasn't right about providing my SSN for such a small personal transaction where I actually lost money. The tax professional's explanation about the $600 threshold and profit requirements was particularly enlightening - it's clear my situation doesn't come close to meeting any IRS reporting obligations. What bothers me most is how these platforms use official-sounding language to pressure people into giving up sensitive personal information when it's not actually required for most personal ticket sales. Your success story gives me confidence to continue waiting it out rather than cave to their pressure tactics. It's amazing how many people are dealing with this exact same issue - really shows these are standardized corporate data collection strategies rather than legitimate tax requirements. Thanks for helping all of us realize we have the right to protect our personal information while still following actual tax law!
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Diego Ramirez
ā¢Your situation with TickPick sounds exactly like what so many of us have been through! The fact that you actually sold at a loss makes this even more straightforward - there's definitely no taxable event when you lose money on a personal ticket sale, so their SSN request is completely unnecessary. Those "Action Required for Tax Reporting" subject lines are classic pressure tactics that these platforms use across the board. It's designed to make you feel like you're somehow non-compliant when you're actually just protecting your personal information appropriately. Based on everything we've learned in this thread, transactions like yours don't even come close to meeting IRS reporting thresholds. What's been most reassuring to me is seeing how consistent the outcomes are when people wait it out. Whether it's Ticketmaster, StubHub, TickPick, or other platforms, they all seem to use the same scare tactics, but their systems eventually process legitimate refunds automatically without the SSN when no actual reporting is required. Your instincts are absolutely right - there's no reason to hand over such sensitive information for a small personal transaction where you lost money. Based on everyone's success stories here, you should see your refund processed automatically soon. Stay confident in your decision to protect your personal information!
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Rajan Walker
This thread is incredibly helpful! I've been dealing with a similar situation with Ticketmaster for the past 3 weeks. They keep emailing me requesting my SSN for selling a pair of concert tickets at face value ($240 total) that I couldn't use due to a work conflict. Like many others here, those emails with urgent language made me feel like I was required to comply immediately, but something felt off about sending such sensitive information via email for a straightforward personal transaction with zero profit involved. Reading everyone's real experiences - especially seeing how consistently these refunds get processed automatically across different platforms - gives me so much confidence to wait it out rather than cave to their pressure tactics. The tax professional's explanation about the $600 threshold and profit requirements really clarified that my situation doesn't even come close to triggering any IRS reporting obligations. It's eye-opening to see how widespread this issue is and how these platforms use the same intimidation strategies regardless of whether your specific transaction actually requires any additional reporting. Thanks to everyone who shared their experiences - this is exactly the kind of community support that helps people make informed decisions about protecting their personal information while still following legitimate tax requirements!
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