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I went through almost this exact situation a few years back and want to reassure you that it's really not as bad as it feels right now! Missing one year happens to more people than you'd think, especially during major life transitions. Since you mentioned you were probably due a refund with your $45k W-2 job, you're actually in the clear on penalties. The IRS is pretty understanding when they owe YOU money - they just hold onto it until you file. Here's what worked for me: I gathered all my tax documents from that missed year (W-2, any 1099s, bank interest statements, etc.) and filed using TurboTax's prior year option. Yes, I had to pay for it even though I normally used the free version, but it was worth it for the peace of mind. Got my refund about 3 weeks after e-filing. Then I filed my current year return normally - no issues whatsoever. The IRS really does treat each tax year independently. The key is just to get that 2023 return filed ASAP so you can get your refund and put this behind you. Don't let the anxiety keep you frozen - once you actually sit down and do it, you'll probably be surprised how straightforward it is for a basic W-2 situation like yours.
@361f93487b1b - Thank you so much for sharing your experience! It's really reassuring to hear from someone who went through the exact same situation. The fact that you got your refund in just 3 weeks after e-filing the late return is encouraging. I'm definitely feeling much more confident after reading through all these responses. It sounds like the consensus is that my situation is pretty straightforward since I was just a W-2 employee and likely due a refund. I'm going to gather up my 2023 documents this weekend and get that return filed, then focus on getting my 2024 taxes done before the April deadline. @b4ff4b44430f - I hope you're feeling better about your situation too! Seems like we're both going to come out of this just fine. Sometimes life gets chaotic and things slip through the cracks, but at least we're addressing it now rather than letting it pile up for another year. Thanks everyone for all the helpful advice and reassurance!
Hey Mateo! I can totally relate to your situation - life gets chaotic and sometimes important things like taxes fall through the cracks. The good news is you're definitely not as screwed as you think! Since you mentioned you were probably due a refund from your W-2 job, you're actually in a really good position. Here's the deal: if you were owed money, there are no penalties for filing late. The IRS basically just holds onto your refund until you claim it, and you have up to 3 years from the original due date to do so. For your situation, I'd recommend: 1. File your 2023 return ASAP - you can still get that refund! 2. File your 2024 return normally by the April deadline 3. Each tax year is treated separately, so you don't need to fix 2023 before filing 2024 The most important thing is to not let anxiety paralyze you. For a straightforward W-2 situation like yours, it's much simpler than it seems. Just gather your 2023 W-2 and any other tax documents from that year, and you can file using any standard tax software (though you'll likely need to pay for prior year filing even if you normally qualify for free options). You're handling this responsibly by addressing it now rather than letting it pile up. Take a deep breath - you've got this handled!
Don't forget that if you're married, having your spouse be an employee of the company (a real employee with actual duties) can open up some options. You could potentially provide health benefits to employees without running into the 2% shareholder limitations. This only works if your spouse isn't also a shareholder though.
Thanks, this is an interesting idea. My spouse does already help with some administrative tasks, but I haven't formally hired them. Would they need to be W-2 or could they be contracted? And what minimum hours would they need to work for this to be viable?
They would definitely need to be a legitimate W-2 employee with regular duties, regular pay, and appropriate documentation. Using a contractor arrangement wouldn't work for this purpose. There's no specific minimum hour requirement in the tax code, but the employment needs to be genuine and the compensation reasonable for the work performed. I'd recommend at least 15-20 hours weekly to establish a clear employment relationship. Make sure to document job duties, have a formal employment agreement, and maintain records of work performed. The IRS does scrutinize family employment situations, especially when benefits are involved, so you want everything to be properly documented and legitimate.
One thing I haven't seen mentioned yet is the importance of timing when implementing these strategies. If you're going to start having your S-Corp pay health insurance premiums directly, you need to make sure this is consistent throughout the entire tax year. You can't just start doing it partway through the year for the expenses you've already paid personally. Also, keep in mind that if you do switch to having the corporation pay premiums directly, you'll need to adjust your officer compensation accordingly since this will increase your W-2 wages. This might push you into a higher tax bracket, so run the numbers carefully. For those considering the spouse employment route, remember that you'll also need to factor in the additional payroll taxes and potential workers' compensation requirements depending on your state. Sometimes the administrative burden can outweigh the tax benefits, especially for smaller operations.
This is really valuable timing information that I wish I had known earlier! I'm currently mid-year and have been paying my health insurance premiums personally. Does this mean I'd have to wait until next tax year to start having the S-Corp pay them directly, or is there a way to handle the transition properly? Also, regarding the higher tax bracket concern - while the W-2 wages would increase, wouldn't the self-employed health insurance deduction on my personal return essentially offset that increase? I'm trying to understand if there's actually a net tax difference or if it's more about cash flow timing.
Here's a simple breakdown of the main sections on a Robinhood 1099-B: 1A: Short-term transactions with basis reported to the IRS 1B: Short-term transactions with basis NOT reported to the IRS 1D: Proceeds from broker transactions (total sales amount) 1E: Cost basis (what you paid) 1G: Gain or loss (what you're actually taxed on) The large number in 1D is just the total dollar amount of ALL your stock sales combined - like if you bought $1000 of stock and sold it at $1100, then that $1100 goes in 1D, but you're only taxed on the $100 profit.
What about wash sales? My 1099 has some adjustments in a column labeled with a "W" and I'm not sure what to do with those.
Wash sales happen when you sell a stock at a loss and then buy the same or a substantially identical stock within 30 days before or after the sale. When this happens, you can't immediately claim the loss for tax purposes. The "W" column on your 1099 indicates the amount of loss that was disallowed due to wash sale rules. The cost basis of your replacement shares is increased by this amount, which means you'll eventually get the tax benefit of that loss when you finally sell the replacement shares (assuming you don't trigger another wash sale). When entering this information into tax software, make sure you include the wash sale adjustment exactly as shown on your 1099. Most tax programs have specific fields for this. If you have multiple wash sales, it can get complicated quickly, which is why some people use specialized tax software or services for investment income.
I used to be a tax preparer and saw this confusion ALL THE TIME. One thing not mentioned yet: check if your Robinhood 1099 has supplemental information pages. They often include a summary that breaks down your actual taxable gains/losses more clearly than the main form. The IRS only cares about your profits/losses, not the total amount of money that moved through your account. The big number in section 1D freaks everyone out, but it's just the sum of all your sales, regardless of whether you made or lost money on those transactions.
Do you have to report every single transaction or can you just report the summary totals? I made like 50 trades last year and don't want to enter them all individually.
You typically don't need to enter every single transaction individually. Most tax software (like TurboTax, FreeTaxUSA, etc.) allows you to import your 1099-B directly or enter summary totals by category - short-term gains/losses and long-term gains/losses. The key is making sure your totals match what's reported on your 1099-B forms. If you have basis reported to the IRS (covered securities), you can usually just enter the summary amounts. For non-covered securities, you might need more detail, but even then you can often group similar transactions together. Just make sure you keep your detailed transaction records in case the IRS ever asks for them during an audit, but for filing purposes, summary totals are usually fine.
Check your account transcript not return transcript. Sometimes return transcript takes longer to update but account transcript will show processing status
tried both, nothing yet :
Same boat here - filed and accepted 2/5, no transcript updates yet either. I've been checking daily (probably too much lol). From what I've read on here and other forums, the IRS is still ramping up their systems for the season. Early filers often get caught in this limbo period. Try not to stress too much about it, though I know that's easier said than done when rent's coming up! Keep checking your transcripts every few days but don't drive yourself crazy with daily checks.
Keisha Williams
As someone who just went through this exact situation with my occasional photography sales, I can confirm that getting an EIN for privacy protection is totally legitimate and won't force you into business status. The IRS allows individuals to obtain EINs for various reasons beyond just business formation. Here's what I learned from my research and talking to a tax professional: 1. Having an EIN doesn't automatically require Schedule C filing - the determining factor is whether your activity meets the IRS criteria for a business (profit motive, regularity, time investment, etc.) 2. You can absolutely report the income on Schedule 1, Line 8 as hobby income even with an EIN. Just make sure to be consistent in how you treat the activity. 3. When you receive the 1099-NEC (which they'll likely issue for $600+), include a brief statement with your tax return noting that the 1099 income is being reported as hobby income on Schedule 1. This prevents automated IRS matching notices. 4. Creating an LLC isn't necessary for just getting an EIN - you can apply for one as a sole proprietor for privacy purposes. One thing to consider though: since hobby expenses aren't deductible anymore (thanks to 2018 tax law changes), you might actually save money by treating it as business income on Schedule C if you have legitimate photography expenses. The self-employment tax might be offset by equipment deductions, but run the numbers for your specific situation. The key is being consistent in your treatment and having a clear understanding of your intent with the activity.
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Kayla Jacobson
ā¢This is really helpful! I'm in a similar situation where I occasionally sell nature photos but definitely don't want to turn it into a business. Quick question - when you say "include a brief statement with your tax return," do you mean just attach a note explaining the hobby income, or is there a specific form or format the IRS expects? I want to make sure I do this right to avoid any issues down the road.
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Rachel Clark
ā¢Great question! There's no specific IRS form for this - just a simple written statement attached to your return works fine. I typed up something like: "The 1099-NEC income from [Company Name] totaling $XXX is reported as hobby income on Form 1040, Schedule 1, Line 8 as this represents occasional sales from my photography hobby, not a business activity." Keep it brief and factual. You can either attach it as a separate page or include it in the "Additional Information" section if you're e-filing. The goal is just to help the IRS computers understand why the 1099 income isn't appearing on Schedule C. Most tax software will let you add statements like this during the filing process. The key is being proactive about explaining the discrepancy rather than waiting for the IRS to send you a notice asking about "missing" business income!
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Mia Green
This is exactly the kind of situation where getting an EIN makes perfect sense! You're absolutely right to be cautious about sharing your SSN with companies - identity protection is important. To answer your specific questions: 1. No, getting an EIN doesn't automatically require Schedule C filing. The IRS determines business vs. hobby status based on your actual intent and activity patterns, not whether you have an EIN. 2. Yes, you can definitely report this as hobby income on Schedule 1, Line 8 even with an EIN. Just be consistent in treating it as a hobby. 3. You don't need an LLC at all - you can apply for an EIN as a sole proprietor specifically for privacy purposes. One practical tip: when you receive the 1099-NEC (which they'll issue for $600), consider adding a brief statement to your tax return explaining that the 1099 income is reported as hobby income on Schedule 1, Line 8. This helps prevent any automated IRS notices about mismatched income. Since this is truly a one-off payment and you want to keep things simple, the hobby income approach with an EIN for privacy protection sounds like the perfect solution for your situation. You'll protect your personal information while avoiding unnecessary business complications.
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