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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 You can download the current version directly from irs.gov rather than using any forms that might be outdated on tax preparation websites.
Some practical advice from someone who's been an indie contractor for 7 years: 1. Immediately open a separate business checking account and business credit card. Keep ALL business transactions separate from personal. 2. Track EVERYTHING. Every mile driven for business, every coffee with a potential client, every subscription, every piece of equipment. 3. Pay quarterly estimated taxes ON TIME to avoid penalties. I use a separate savings account and transfer 30% of each payment I receive. 4. A good CPA will likely save you more than they cost. Interview a few who specialize in self-employment. 5. Consider a SEP IRA or Solo 401k - you can contribute WAY more than with a regular 401k, which offsets some of the self-employment tax pain.
Thanks for the solid advice! For the quarterly taxes, is it just a flat 30% of income or does it vary based on what expenses I've had that quarter? Also, do most banks offer business accounts to sole proprietors or do I need an LLC first?
The quarterly tax amounts should ideally be based on your actual profit for that quarter (income minus expenses), but many contractors use a simplified approach of setting aside a percentage of gross income to make it more manageable. The 30% is just a rule of thumb - your actual percentage might be higher or lower depending on your state tax situation and deductions. Most banks absolutely offer business accounts to sole proprietors - you don't need an LLC first. You'll typically need your Social Security number and possibly a DBA ("doing business as") registration if you're operating under a business name that's not your personal name. I'd recommend shopping around as some banks offer free business checking while others charge monthly fees.
The others gave good advice on the tax side, but the critical thing I learned about contract work: GET DISABILITY INSURANCE. Like yesterday. When you're an employee, you probably have some short/long term disability coverage and workers comp. As an indie, if you get sick or injured, you get $0. Disability insurance is expensive but without it, one bad accident could financially ruin you. Same goes for health insurance if they're not offering benefits. The marketplace plans might be more expensive than you're used to with employer coverage.
Can confirm this 100%. I broke my wrist in a bike accident last year and couldn't code for 8 weeks. No income coming in but rent and bills still due. The disability insurance I had grumbled at paying for? Saved me from emptying my emergency fund.
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.
Fatima Al-Farsi
There's no catch except that you need to do the work to claim what you're owed! I missed out on the Earned Income Credit for two years because I didn't know I qualified. Amending those returns got me over $3k back. The real "catch" is that some amendments require more documentation than others. Education credits especially - make sure you have your 1098-T forms from your school and receipts for textbooks/required materials. The student loan interest is easier since your loan servicer should have sent 1098-E forms showing interest paid.
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Carmen Ruiz
ā¢Thanks for mentioning documentation! I think I have all my 1098-Ts from school but not sure about textbook receipts from 3 years ago. Will the IRS reject my amendment if I'm missing some of the receipts?
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Fatima Al-Farsi
ā¢The IRS won't automatically reject your amendment if you're missing some receipts, but you should be prepared to substantiate your claims if they ask questions. For textbooks, if you don't have the original receipts, look for credit card statements, bank statements, or emails confirming your purchases. For education credits, the 1098-T is the most important document, as it shows your enrollment and amounts paid to the institution. The IRS is more likely to focus on verifying that information rather than every individual book purchase. Do your best to create a reasonable estimate of your textbook costs if you can't find all receipts, and keep notes on how you calculated those amounts.
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Dylan Wright
One thing nobody has mentioned - if you amend and get a bigger refund, you might also be entitled to interest! The IRS pays interest on refunds that are more than 45 days old from the filing deadline or the date you filed, whichever is later. I amended 2 years of returns last year and got about $3400 back plus another $126 in interest. Not a huge amount but hey, free money on top of free money lol. The interest is taxable income tho, so remember that for next year's taxes.
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Sofia Torres
ā¢Does the IRS automatically add the interest or do you have to request it specifically? And do you know what the current interest rate is?
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