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Daryl Bright

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I'm in a similar situation as a new freelancer, and this thread has been incredibly helpful! Just wanted to add one thing that might help with the quarterly payment anxiety - you can actually adjust your payments throughout the year if your income changes significantly. I started doing freelance writing this year and was worried about committing to quarterly payments when my income is so unpredictable. Turns out you can increase or decrease your estimated payments if you realize you're making more or less than expected. The IRS just wants you to make a good faith effort to pay as you go. Also, if you have any W-2 income from other work, you can ask that employer to increase your withholding instead of making separate quarterly payments. Sometimes that's easier to manage than keeping track of four separate payment due dates. The 15.3% self-employment tax definitely stings at first, but think of it as building your Social Security credits for the future. Every quarter you pay SE tax, you're earning credits toward your eventual Social Security benefits. It's not just money disappearing into a black hole - you're actually investing in your own retirement security. Keep all those receipts and track everything! Even if individual expenses seem small, they really do add up over the course of a year.

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Felix Grigori

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This is really reassuring about being able to adjust quarterly payments! I was stressed about committing to a fixed amount when my handyman work is so seasonal - busy in spring/summer, pretty quiet in winter. Knowing I can adjust up or down based on actual income makes it feel much more manageable. The point about building Social Security credits is a great perspective shift too. I hadn't thought about it that way - it does make the 15.3% sting a little less when you frame it as investing in future benefits rather than just a tax penalty. Since you mentioned W-2 withholding as an alternative - I do have a part-time job that gives me a W-2. Would increasing withholding there be simpler than quarterly payments? I'm wondering if it's easier to just have more taken out of my regular paychecks rather than remembering four separate due dates throughout the year.

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@029bdb4f51ee Yes, increasing your W-2 withholding is often much simpler! Since tax withholding from your regular job applies to all your tax liability (including self-employment tax), you can just have extra federal taxes withheld from your paychecks to cover what you'll owe on your side gig income. The big advantage is you don't have to worry about quarterly due dates or calculating estimated payments. Just figure out roughly how much SE tax you'll owe for the year (around $980 based on your income level), divide by the number of paychecks you get, and have that extra amount withheld. So if you get paid bi-weekly (26 paychecks), you'd need about $38 extra withheld per paycheck to cover your SE tax. Much easier than remembering January 15, April 15, June 15, and September 15 quarterly deadlines! You can update your W-4 with HR anytime during the year, so you could even start this mid-year and just have a bit more withheld to catch up. The IRS doesn't care whether your tax payments come from withholding or estimated payments - they just want to receive the money throughout the year rather than all at once in April.

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Zane Gray

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I've been following this thread as someone who went through the exact same confusion last year! All the advice here is spot-on - you definitely owe self-employment tax on that $6,400. One thing I wanted to add that might help for next year: consider getting a business checking account even for your small-scale operation. I kept mixing my handyman earnings with personal money and it made tracking everything so much harder. Having a separate account makes it crystal clear what's business income and what expenses you can deduct. Also, since you mentioned doing neighborhood work within walking distance, don't forget you can still deduct mileage if you drive to buy supplies for specific jobs, even if it's just to Home Depot and back. At 65.5 cents per mile for 2023, those short trips add up. The quarterly payment advice everyone's giving is solid, but here's another option: if you expect to make similar amounts next year, you could also consider getting a basic business license and possibly looking into whether any of your regular clients would be willing to treat you as a vendor and send 1099s. It won't change your tax obligation, but having that documentation can make the whole process feel more legitimate and organized. The SE tax bite is rough the first time, but once you plan for it, it becomes just another part of doing business. Good luck with your filing!

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The business checking account suggestion is really smart! I can see how mixing everything together would make tax time way more complicated. Even though my operation is pretty small-scale, having that clear separation would definitely make tracking income and expenses much easier. I hadn't thought about the mileage deduction for supply runs - that's a great point. I probably made at least a dozen trips to hardware stores for various jobs last year, and at 65.5 cents per mile, even short trips could add up to meaningful deductions. I should start keeping a simple mileage log in my car. The business license idea is interesting too. A few of my regular clients have asked if I could send them invoices instead of just taking cash payments. Having everything more official might actually help with getting repeat business and referrals, plus make the tax side more straightforward. Thanks for the practical suggestions!

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Ava Martinez

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I can completely understand your stress about this situation! As someone who's been through similar S-Corp election concerns, I want to reassure you that what your accountant did is likely correct and actually quite common. The January 1st effective date on your Form 2553 is probably intentional and falls under Revenue Procedure 2013-30. This IRS procedure specifically allows newly-formed corporations to elect S-Corp status retroactively to the beginning of the tax year, even when the corporation wasn't legally formed until later in the year. What this means for you: Your corporation still legally exists only from June 5th forward, but the S-Corp tax election applies retroactively to January 1st for tax purposes. This gives you clean S-Corp treatment for the entire 2024 tax year and means you'll only need to file one 1120-S return instead of dealing with multiple entity types for different parts of the year. The "late filing" concern is also addressed by this same procedure - when newly-formed corporations make retroactive elections like this, the IRS automatically considers there to be reasonable cause for filing beyond the normal 2-month+15-day window. My recommendation: Have a conversation with your accountant to confirm this was their strategy and ask them to ensure they include the proper explanatory statement with your first 1120-S filing. This documentation helps protect you if the IRS ever has questions about the election timing. You're not in trouble - this is actually smart tax planning that simplifies your first year of business operations!

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Jason Brewer

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This is such valuable information, Ava! I'm new to business ownership and had never heard of Revenue Procedure 2013-30 before reading this thread. Your explanation really helps clarify why accountants use this approach - it makes total sense that the IRS would want to simplify things for new businesses rather than force complicated split-year filings. I'm curious though - when you mention the explanatory statement that should be included with the first 1120-S, is there specific language that needs to be used, or is it more of a general explanation of the circumstances? I want to make sure I ask my accountant the right questions when we discuss this. It's amazing how much this thread has reduced my anxiety about S-Corp elections! I was really worried I had made some major error, but it sounds like this is just standard practice that most new business owners don't know about until they go through it themselves.

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Ava Thompson

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@Jason Brewer Great question about the explanatory statement! From my experience, there isn t'a specific required template, but the statement should generally explain that the corporation was newly formed during the tax year and that the S election is being made under Revenue Procedure 2013-30 for reasonable cause. Most accountants will include language like: The "corporation was incorporated on [date] and is making this S election retroactively to January 1st of the tax year under Rev. Proc. 2013-30. The late filing is due to the corporation being newly formed during the tax year. The" key is referencing the specific revenue procedure and explaining the timing circumstances. Your accountant should know the standard language to use, but it s'definitely worth confirming they plan to include this documentation. Having it properly documented from the start gives you protection if any questions arise during future IRS interactions. You re'absolutely right that this thread has been incredibly educational - I wish I had known about these procedures when I first went through S-Corp formation!

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I completely understand your concern about the January 1st effective date - I had the exact same reaction when I first saw this on my own Form 2553! But after going through this situation myself and working with multiple tax professionals, I can assure you that what your accountant did is not only correct but actually represents smart tax planning. What you're seeing is a retroactive S-Corp election under Revenue Procedure 2013-30, which the IRS specifically designed for newly-formed corporations like yours. The key insight is that your corporation doesn't need to have existed on January 1st for the S election to be effective from that date - it's purely a tax designation that applies once your corporation legally exists on June 5th. The practical benefit is huge: instead of potentially dealing with different entity classifications for different parts of 2024, you get clean S-Corp treatment for the entire tax year with just one 1120-S filing. The IRS created this procedure specifically because they recognize that many businesses incorporate mid-year but benefit from consistent tax treatment. Regarding the timing concern, Revenue Procedure 2013-30 also addresses the "late filing" issue automatically. When newly-formed corporations make this type of retroactive election, the IRS considers there to be reasonable cause for filing beyond the normal 2-month+15-day window. I'd recommend having a follow-up conversation with your accountant to understand their strategy, but more importantly, confirm they plan to include the proper explanatory statement with your first 1120-S return. This documentation references Rev. Proc. 2013-30 and explains the circumstances, which protects you if the IRS ever has questions. You're not in trouble - this is actually a routine and beneficial election that thousands of new S-Corps make every year!

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Thank you so much for this detailed explanation, Aisha! As someone who's completely new to business ownership and S-Corp elections, this thread has been incredibly educational. I had no idea that Revenue Procedure 2013-30 even existed or that the IRS had specific provisions designed exactly for situations like this. Your point about the distinction between legal existence and tax treatment really helps clarify what seemed like a contradiction. I was getting hung up on how a corporation could have an effective date before it legally existed, but now I understand that these are two separate concepts that work together for administrative efficiency. I'm definitely going to have a more informed conversation with my accountant now about their strategy and make sure they include that explanatory statement with the first 1120-S filing. It sounds like having proper documentation upfront is crucial for avoiding any potential issues down the road. This whole experience has been a great learning opportunity about how complex tax regulations can actually work in favor of new businesses when you understand the underlying procedures. Thanks again for sharing your expertise!

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I'm dealing with a similar foreign asset reporting situation and wanted to share what I learned after consulting with an international tax attorney. The key distinction here is that Form 8938 and FBAR serve different purposes - 8938 is part of your tax return while FBAR is filed separately with FinCEN. The "quiet disclosure" concern is real. When you suddenly report foreign assets that weren't previously disclosed, it can trigger questions about why they weren't reported before. The IRS has sophisticated matching systems that can identify patterns like this. For your $275k in assets, you're definitely above the reporting thresholds. My attorney explained that while some people do get away with quiet disclosures, the formal Streamlined Filing procedures provide legal protection and closure. The penalty (5% for domestic taxpayers) might seem steep, but it's often much less than the potential penalties for continued non-compliance if discovered later. The fact that your accountant "shrugged it off" is concerning - this is exactly the kind of situation where specialized expertise matters. I'd strongly recommend getting a second opinion from someone who specifically handles international tax compliance before deciding your approach.

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This is really helpful advice, thank you! I'm curious about the timeline for the Streamlined Filing procedures - how long does the process typically take from submission to resolution? Also, during that period, are you still at risk of penalties or does filing give you some protection while it's being reviewed? I'm trying to weigh the peace of mind factor against just hoping nothing comes of continuing forward correctly.

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I've been through this exact situation with foreign assets around the same value range. The stress is real, but let me share what worked for me after making the same mistake. First, your accountant's casual approach is a red flag. International tax compliance isn't something to "shrug off." I initially tried the quiet disclosure route too - just started filing Form 8938 correctly going forward without addressing prior years. But the anxiety was killing me, especially after learning that FATCA reporting means the IRS likely already has visibility into many foreign accounts. I ended up using the Streamlined Domestic Offshore Procedures about 6 months after my initial "quiet" filing. Yes, there's a 5% penalty on the highest aggregate balance, but here's what sold me on it: legal certainty. Once you complete the streamlined filing and pay the penalty, you get formal closure. No more sleepless nights wondering if the IRS will come knocking. The process took about 4 months from submission to receiving my closing letter. During that time, I felt much more secure knowing I was in an official compliance program rather than hoping my quiet disclosure wouldn't be noticed. Given your asset level ($275k), the streamlined penalty would be around $13,750 - painful but manageable compared to the potential penalties and legal costs if things go sideways later. My advice: bite the bullet and get the peace of mind. The stress relief alone was worth it for me.

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This is exactly the kind of real-world experience I needed to hear. The anxiety factor is huge - I've been losing sleep over this too. Your timeline of 4 months for the streamlined process is helpful to know. Can I ask what documentation you had to gather for the streamlined filing? I'm wondering how intensive the paperwork process is compared to just filing the forms going forward. Also, did you need to get certified translations for any foreign bank statements, or were English summaries sufficient? The $13,750 penalty calculation is sobering but you're right that it's probably less than what I'd spend on legal fees if this becomes a bigger issue later. Did you handle the streamlined filing yourself or work with a specialist?

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Ali Anderson

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Just wanted to share my experience - I had a similar issue and ended up valuing each of my furniture pieces individually (all under $5k) in Section A. Make sure to take photos of everything you donate in the future! I now take pictures of all donation items next to that day's newspaper and keep a spreadsheet with estimated values. Makes tax time so much easier.

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Zadie Patel

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This is smart. Do you use any specific apps to keep track of your donations throughout the year? I always scramble at tax time trying to remember what I gave away.

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I've been through this exact situation! The key is understanding that Form 8283 has different requirements based on individual item values, not total donation value. Since your most expensive piece was $3,000, you should definitely use Section A, which is much simpler. For future donations, I recommend taking photos of items before donating and keeping a detailed list with estimated values. Also, when you drop off at Goodwill, ask if they can note on your receipt that you're donating items over $500 total - this can help with their signature requirement later. One tip that saved me: if you can't get back to the original Goodwill location, try calling their regional office. They often have staff who are more familiar with tax form requirements and can coordinate with your local store. Most Goodwill locations will sign the form if you explain it's for tax purposes and show your original receipt. Don't stress too much about the timing - as long as you file the form with your return and have reasonable documentation of the values, you should be fine. The IRS is generally more concerned with inflated valuations than missing signatures for legitimate donations.

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Ayla Kumar

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This is really helpful advice! I'm curious about your suggestion to ask Goodwill to note on the receipt that you're donating items over $500 total - do they actually do this? I've never thought to ask for specific notations on donation receipts, but it sounds like it could save a lot of headaches later. Also, when you say "regional office," how do you find the contact information for that? Is it different from the corporate number? I'm planning some larger donations this year and want to get ahead of any potential Form 8283 issues.

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I went through this exact same panic last year! First-time 1099 worker, no quarterly payments, the whole deal. Here's what actually happened: I ended up owing about $4,200 in taxes but qualified for the Earned Income Tax Credit which gave me back $1,800, so my net owed was much less scary than I expected. A few things that saved me: Track down EVERY possible business expense - I found I could deduct my car mileage for client meetings, part of my cell phone bill, even some meals when meeting with clients. Also, look into whether you qualify for any tax credits based on your income level. The Earned Income Credit alone can be worth thousands if you're under certain income thresholds. For the underpayment penalty, I was honest with the IRS that this was my first year as a contractor and I didn't know about quarterly payments. They reduced my penalty significantly. The key is showing good faith - maybe make a quarterly payment now even though you've missed the others, and definitely start making them next year. Don't stress too much - worst case scenario, the IRS has very reasonable payment plans if you end up owing more than you can pay at once.

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This is so reassuring to hear from someone who went through the exact same situation! I'm definitely going to dig deeper into my expenses - I hadn't even thought about car mileage or meal deductions. Quick question: for the Earned Income Tax Credit, is there a specific income limit I need to be under? With $42k in income, I'm wondering if I might still qualify. Also, when you say you were honest with the IRS about not knowing about quarterly payments, did you have to call them directly or was there a way to explain this on the tax forms themselves?

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@Natasha Ivanova For the Earned Income Tax Credit in 2024, the income limits are around $56,844 for single filers with no children, so with $42k you should definitely qualify! The credit phases out as income increases, but you re'well within the range. The exact amount depends on your filing status and whether you have kids. For the quarterly payment explanation, I actually included a brief note with my tax return filing explaining it was my first year as a contractor. You can attach a statement to Form 2210 which (calculates underpayment penalties explaining) the circumstances. I wrote something like First "year as independent contractor, unaware of quarterly payment requirements, will comply going forward. The" IRS does have some discretion with first-time penalties, especially if you show you re'making an effort to comply. Also, definitely track that mileage! I use a simple app on my phone to log business trips. Even short drives to meet clients or pick up supplies add up quickly over a year.

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Aaron Lee

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As someone who's been doing 1099 work for several years now, I want to reassure you that your situation is totally fixable and much more common than you think! First-time contractors almost always miss the quarterly payment thing - I certainly did. Here's the reality check: with $42k income minus your $3,800 in expenses, you're looking at roughly $38,200 in net self-employment income. You'll owe self-employment tax (about 15.3%) plus regular income tax on this amount. However, don't forget that you get to deduct half of the self-employment tax you pay, which helps reduce your overall tax burden. The good news is that there are likely more deductions you haven't thought of yet. Beyond your laptop and internet, consider: software subscriptions, professional development courses, co-working space fees, business insurance, professional memberships, office supplies, and even a portion of your phone bill if you use it for work. For the quarterly payments you missed - yes, there will likely be some penalties, but they're calculated as interest on what you should have paid throughout the year. It's not as scary as it sounds, and the IRS does offer reasonable payment plans if needed. My biggest advice: don't try to wing this on your own for your first year. The peace of mind from using proper tax software designed for self-employment or hiring a tax pro who understands 1099 situations is absolutely worth the investment. You've got this!

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Aisha Khan

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This is such a comprehensive and reassuring breakdown! I really appreciate you mentioning the deduction for half of the self-employment tax - I had no idea that was a thing. That could make a significant difference in the overall tax burden. One thing I'm curious about is the professional development courses you mentioned. I took a couple of online courses this year to improve my skills for my 1099 work, but they weren't directly required by any client. Do those still count as legitimate business deductions? Also, how do you typically track and document something like "office supplies" when most of my purchases are just random items from Target or Amazon that I use for work? The advice about not winging it solo definitely resonates. I've been trying to figure this all out myself but I'm starting to realize that might be penny wise and pound foolish for my first year doing this.

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