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This is actually a fairly common issue with new LLCs. Here's what's important: If you've been filing and paying taxes consistent with S-corp status for 2021 (meaning you filed Form 1120-S and issued yourself a W-2 as an employee-owner), you have a much stronger case for retroactive election. When filling out Form 2553, check Box D1 in Part I for the January 1, 2021 effective date. In Part III (Late Election Consent), explain that you've been operating with the understanding that you were an S-corporation and have filed all relevant tax documents accordingly. The IRS is generally pretty reasonable with the relief provision if you've been consistent in your tax treatment.
Thanks for this info! I did file Form 1120-S for 2021 and issued myself W-2s, so sounds like I've been operating consistent with S-corp status. I was just confused about whether I could put January 1 as the effective date when my LLC wasn't technically formed until March. I'll definitely check Box D1 and explain the situation in Part III as you suggested. Do you think I should attach anything else to the form when I send it in? Like copies of my 2021 tax filings to prove I've been operating as an S-corp?
Yes, you should absolutely attach copies of your 2021 Form 1120-S and any W-2s you issued yourself as supporting documentation. This demonstrates to the IRS that you've been operating consistently as an S-corporation. Also consider attaching a brief cover letter referencing the IRS notice you received and explaining your intention to address this with the late-filed election. I'd also recommend sending it certified mail so you have proof of submission. The IRS can be slow to process these, so having documentation of when you submitted everything can be important if they follow up again before processing your election.
Something nobody's mentioned yet - make sure you're using the CURRENT version of Form 2553. The IRS updated it in December 2023 and they're pretty strict about using the correct version.
Good point! I made this mistake last year and they rejected my filing, adding another 2 months to the process. You can download the current version directly from irs.gov rather than using any forms that might be outdated on tax preparation websites.
Don't forget that if your losses exceed your gains by more than $3K, you might want to consider tax loss harvesting strategies for future years. Since you can only deduct $3K against ordinary income per year, having a large carryover loss can be a tax planning opportunity.
Can you explain what you mean by tax loss harvesting? I'm in a similar situation with about $8K in losses this year.
Tax loss harvesting means strategically selling investments that have declined in value to realize losses that can offset capital gains or up to $3,000 of ordinary income per year. Since you already have $8K in losses, you'll use $3K this year against ordinary income, then have $5K carrying forward. In future years, if you have investments that have appreciated significantly and you want to sell them, your carried-over losses will offset those gains, potentially reducing or eliminating the tax impact. Just be careful of the wash sale rule - don't buy substantially identical securities within 30 days before or after selling at a loss.
Just a quick tip from someone who messed this up last year - make sure you're tracking your loss carryovers yourself and don't rely solely on your tax software to remember them year to year. I switched tax software and almost forgot about my carried-over losses! Keep a spreadsheet or something with your tax records.
Learned this the hard way too. Does anyone know if turbotax carries this info forward correctly if you use them consecutive years?
16 Has anyone used the annualized income installment method (Form 2210 Schedule AI)? My income is super uneven throughout the year and my accountant mentioned this but said it's complicated.
22 I use it every year for my seasonal business. It's definitely more work but WORTH IT if your income is lumpy. Instead of being required to pay equal amounts each quarter, you calculate based on what you've actually earned by the end of each quarter. My Q1 and Q2 payments are tiny, then Q3 and Q4 are massive when we hit our busy season. Your accountant is right that it's complicated though. You basically have to do a mini tax return for each quarter. I wouldn't try it without professional help the first time.
4 Just remember that corporate estimated taxes work differently than individual estimated taxes! My LLC is taxed as an S-Corp and I got slammed with penalties because I didn't realize the rules were different for the corporate portion vs. the pass-through income. Talk to a tax pro who specializes in your specific business structure before making any decisions.
Something else to consider that nobody mentioned - if you choose to have the withholding spread across multiple paychecks instead of taking it all at once, it might prevent you from dipping below your normal take-home pay too dramatically. Taking it all at once could really hurt your cash flow for that pay period. Also check if your employer is withholding for state taxes too. Some employers only adjust federal, and then you still end up owing a lot at the state level.
That's a really good point about spreading it out. I think I'll do the 5 paycheck option since that would be way less disruptive to my monthly budget. Do you think I need to specifically ask HR about the state tax withholding or would they typically handle both?
Definitely ask HR specifically about state taxes. In my experience, some payroll systems don't automatically adjust state withholdings when federal is increased. Just tell them you want to make sure both federal AND state taxes are being withheld appropriately for the HRA payment. They should be able to handle that for you.
There's one more benefit to having them withhold it now that nobody's mentioned. If you're planning to itemize deductions, the state and local tax (SALT) deduction is limited to $10,000. By having taxes withheld in 2023, those withholdings count toward your 2023 SALT deduction limit. If you wait and pay when you file in 2024, those tax payments would count toward your 2024 SALT limit instead.
Nalani Liu
Don't forget to keep track of your mileage if you're driving to special locations for your pics! I've been doing this type of work for a few years and mileage deductions add up fast. Also track any pedicures, foot care products, special socks/shoes bought specifically for your photoshoots.
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Axel Bourke
ā¢Wait seriously? You can actually write off pedicures as a business expense for feet pics? That seems too good to be true lol
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Nalani Liu
ā¢Absolutely! If the pedicures are specifically for your photoshoots and business purposes, they're a legitimate business expense. Think of it like this - if a hand model gets manicures for photo shoots, that's a business expense. Same principle applies to foot modeling/pics. Just make sure you're being honest about the business purpose and keep good records. I keep a separate calendar where I note when I got pedicures specifically for photo sessions versus personal ones. Same with any special foot care products or accessories I buy exclusively for shoots. The key is that these expenses must be "ordinary and necessary" for your specific business - which in the case of foot content, professional foot care definitely qualifies!
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Aidan Percy
Heads up, you might need to look into copyright protection for your content too. Not tax advice exactly but related to running your business properly. I had someone steal my pics and resell them which was both annoying and cut into my taxable income. Might be worth watermarking or using content protection services.
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Fernanda Marquez
ā¢Are the costs for copyright registration and protection software tax deductible? Seems like they would be but just checking.
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