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WARNING: Be careful about reasonable cause. My husband tried this last year for his consulting business and it got REJECTED. He had to file as a sole prop for half the year and then as an S-corp, which meant TWO different tax returns and a ton of accounting headaches. The IRS is getting stricter about these late elections. Make sure your reasonable cause is actually reasonable and not just "I didn't know about it." We learned the hard way that "I was busy with client work" isn't good enough. If you're serious about making this work, talk to an actual tax pro who specializes in business formation, not just random internet advice.
I went through this exact situation 2 years ago as a freelance web developer. Here's what I wish someone had told me upfront: The timing is crucial, but you have more flexibility than you might think. You can form your LLC in August and still get S-corp treatment for your entire 2023 income, BUT you need to act fast once the LLC is formed. My recommendation: Form the LLC immediately in August, get your EIN the same day (you can do this online), then file Form 2553 within 2-3 weeks. Even if you're technically "late" by a few days, a simple reasonable cause statement explaining you're a first-time business owner unfamiliar with the election deadlines will likely be accepted. The key advantage is that once approved, you'll file a single 1120-S for the entire year instead of splitting between Schedule C and S-corp returns. This saves you significant accounting complexity and costs. One important note: Make sure you have reasonable justification for the salary vs. distribution split once you're an S-corp. The IRS expects you to pay yourself a "reasonable" salary for the work you do, with the remaining profits taken as distributions (which aren't subject to self-employment tax). Don't overthink this - thousands of freelancers make this transition successfully every year. Just don't wait until December to start the process!
This is really helpful advice! I'm also a freelancer (marketing consultant) and have been putting off the LLC formation because the timing seemed so complicated. Your point about acting fast once the LLC is formed makes total sense. Quick question - when you say "get your EIN the same day," do you mean online through the IRS website directly? I've seen some services that charge fees for EIN applications, but it sounds like you did it yourself for free? Also, did you run into any issues with quarterly estimated taxes during the transition year, or does the S-corp election smooth that out too?
Just wanted to add some perspective as someone who's been doing gig work for a while - the tax situation isn't as scary as it seems once you get organized! The key is treating this like a real business from day one. I use a simple spreadsheet to track my daily earnings, miles driven, and any expenses. At the end of each week, I calculate roughly 30% of my profit and transfer it to a separate "tax savings" account. For tracking mileage, I highly recommend using an app like Stride or MileIQ that automatically tracks your drives. Manual tracking gets tedious and you'll inevitably forget to log trips. One thing that surprised me: even though you're paying self-employment tax (which feels like a lot), you're also earning Social Security credits that count toward your future benefits. So it's not just money disappearing - you're building toward your retirement too. The $600 threshold just determines whether DoorDash sends you a 1099 form, but you're technically required to report ALL income regardless of whether you get a form. Keep good records and you'll be fine!
This is really helpful advice! I'm new to gig work and the automatic mileage tracking apps sound like a lifesaver. Quick question - when you say "profit" for the 30% calculation, do you mean total earnings minus just mileage deduction, or should I subtract other business expenses too before calculating what to set aside for taxes? Also, I hadn't thought about the Social Security credits aspect - that actually makes the self-employment tax feel less painful knowing it's contributing to future benefits. Thanks for putting it in perspective!
Great question! When I calculate the 30% to set aside, I use my profit after ALL business expenses - so total earnings minus mileage deduction, phone bill percentage, equipment costs, etc. This gives you a more accurate estimate of your actual taxable income. For example, if you earn $500 in a week but have $150 in mileage deduction and $20 in other business expenses, your profit is $330. I'd set aside about $100 (30% of $330) for taxes rather than $150 (30% of $500). The apps make such a difference! I tried manual tracking for like two weeks and kept forgetting to start/stop the timer. Now it just runs automatically when I'm driving and I can categorize trips later. Much less stressful than trying to recreate your mileage from memory at tax time. And yes, the Social Security angle really changed my perspective too. As gig workers we're essentially self-employed business owners building our own retirement credits. Makes the extra tax burden feel more like an investment in your future rather than just money going down the drain!
As someone who's been dashing for about 8 months, I'd say it's definitely worth it if you approach it right from the start. Here's what I wish someone had told me when I was at your stage: First, don't stress too much about the $600 threshold - others have explained it well, but just know you're still a ways from hitting it based on your current earnings. What I found most helpful was setting up systems early: 1. Download a mileage tracking app immediately (I use Stride - it's free and designed for gig workers) 2. Open a separate savings account just for taxes and transfer 25-30% of your weekly profit there 3. Keep a simple log of any equipment you buy (phone mount, insulated bags, etc.) The tax situation seems overwhelming at first, but it's really manageable once you get organized. I actually ended up owing less than I expected because the mileage deduction is pretty generous - I drive about 70% of my total earnings in deductible miles. One tip: don't just focus on gross earnings when deciding if it's "worth it." Track your profit after expenses for a few weeks to see your real hourly rate. That'll help you decide if you want to continue and which times/areas are most profitable for you. You're smart to think about this stuff early rather than scrambling at tax time like a lot of people do!
This is such solid advice! I'm in a similar situation as the original poster - just started doing delivery work and feeling overwhelmed by all the tax stuff. The separate savings account idea is brilliant - I keep telling myself I'll set money aside but never actually do it. Quick question about the mileage tracking - does Stride track automatically or do you have to remember to turn it on each time you start dashing? I'm worried I'll forget and mess up my records. Also, when you say 70% of earnings in deductible miles, does that include driving TO the restaurant areas at the start of your shift, or just the actual delivery miles? Thanks for breaking this down in such a practical way. Makes it feel way less intimidating!
@d73f89d17d35 Great advice! Just wanted to add that Stride does track automatically once you set it up - it uses your phone's GPS to detect when you're driving and categorizes trips. You can always edit/classify them later if needed. For deductible miles, you can actually deduct ALL business-related driving - so yes, that includes driving TO your first restaurant, between deliveries, AND driving home from your last delivery if you wouldn't have been in that area otherwise. The key is that it has to be for business purposes. I keep a simple rule: if I'm driving because of DoorDash (getting to hotspots, between orders, etc.), I count those miles. Personal detours obviously don't count, but most of your driving during a dash session will be deductible. The separate account thing really is a game-changer. I set up an automatic transfer so every Sunday I move my "tax money" over. Takes the guesswork and willpower out of it!
I filed my Form 7202 amendments in late January 2025 for both 2020 and 2021, so I'm about 10-11 weeks into the process now. Reading through all these detailed experiences has been incredibly reassuring - I was starting to worry that something was wrong with my filing since I hadn't heard anything yet, but it's clear that I'm still well within the normal timeframe. Like most of you, I'm self-employed (run a small accounting practice) and qualified for the family leave credits when I had to stay home with my two kids during the virtual learning periods. The potential credits are substantial - around $8,900 for 2020 and $11,200 for 2021 - so the waiting has been pretty anxiety-inducing. The "Where's My Amended Return?" tool still shows "received" for both years, but based on everyone's shared timelines, it sounds like that's completely normal until around week 15-16. I'm planning to start checking more frequently once I hit that milestone. One thing that really stands out from reading everyone's experiences is how consistent the 16-22 week timeline seems to be, regardless of when people filed. It's frustrating that it takes so long, but at least it appears to be a predictable process rather than just random delays. Carlos, since you're at the 3-week mark, it sounds like we're all in this together for the long haul! Thanks to everyone who shared their detailed timelines - it really helps to know what to expect and that legitimate claims do eventually get processed and paid out.
I'm in almost the exact same boat as you Natasha! Filed my Form 7202 amendments in early February 2025, so I'm about 9 weeks in now. Like you, I'm self-employed (freelance writer) and had to care for my kids during school closures while trying to keep my business afloat. Reading through everyone's experiences here has been such a lifesaver - I was getting really anxious thinking my amendments got lost or rejected, but seeing the consistent 16-22 week timeline from people who actually received their payments gives me so much peace of mind. The amounts I'm expecting are similar to yours - around $7,800 for 2020 and $10,400 for 2021. It's really helpful to see that the "Where's My Amended Return?" tool showing "received" for this long is totally normal. I've been checking it obsessively every few days, but now I know not to expect any status changes until we hit that 15-16 week mark that everyone mentions. Carlos, thanks for starting this thread - it's been incredibly valuable to hear from so many people who've gone through this process. We're definitely all in this waiting game together, but at least now we know what to expect!
I'm about 8 weeks into this process myself - filed my Form 7202 amendments for both 2020 and 2021 in mid-February 2025. Like many of you, I'm self-employed (freelance IT consultant) and qualified for the family leave credits when I had to care for my kids during school closures. Reading through everyone's detailed timelines has been incredibly helpful and reassuring! I was starting to get worried since I haven't heard anything yet, but seeing the consistent 16-22 week pattern from people who actually received their payments gives me much more realistic expectations. The potential amounts for me are around $9,400 for 2020 and $12,800 for 2021. The "Where's My Amended Return?" tool still shows "received" for both years, but based on all the experiences shared here, that seems completely normal until around week 15-16. I'll stop checking it obsessively and wait until I'm closer to that milestone! One thing I really appreciate from this discussion is how everyone emphasizes that legitimate claims do eventually get processed - it just takes patience. The waiting is definitely stressful when you're talking about substantial amounts, but knowing there's a predictable timeline helps manage the anxiety. Carlos, thanks for asking this question - this thread has become such a valuable resource for all of us going through this process! We're definitely all in the long wait together, but at least now we know we're not alone and that the process does work.
I'm just starting this journey myself - filed my Form 7202 amendments about 2 weeks ago for both 2020 and 2021. As someone completely new to this process, reading through everyone's experiences has been both enlightening and a bit overwhelming! Like many of you, I'm self-employed (run a small catering business) and had to deal with caring for my kids when schools closed while trying to keep my business running during COVID. The potential credits I'm looking at are around $6,200 for 2020 and $8,900 for 2021. I have to admit, I went into this thinking it would be similar to a regular tax refund timeline - maybe 6-8 weeks. Seeing that everyone is talking about 16-22 weeks is definitely an adjustment to my expectations! But it's actually really comforting to see so many people sharing their successful outcomes, even if the wait is long. I appreciate everyone being so detailed about their timelines and what to expect with the "Where's My Amended Return?" tool. As a newcomer, knowing that it will likely show "received" for months before changing is really helpful for managing my anxiety about the process. Carlos, thanks for starting this discussion - it's become such a valuable resource for all of us navigating this lengthy but ultimately successful process!
One more thing on this topic - capital loss carryovers can potentially be used on back-to-back separate and joint returns. Like if you filed as single with carryover losses, then got married, you CAN bring those losses to your joint return. But what's weird is if you file jointly with losses, then get divorced, each spouse gets half the carryover. My ex and I had about $18k in carryovers when we split, and we each took $9k to our separate returns.
Is this officially documented somewhere? Going through a divorce now and we have carryover losses from some terrible investment decisions we made together. Would be nice to know the official position on splitting these up.
For the divorce question about splitting capital loss carryovers - yes, this is covered in IRS Publication 504 (Divorced or Separated Individuals). When spouses who filed jointly get divorced, any unused capital loss carryovers from the joint returns are generally allocated 50/50 between the former spouses on their subsequent separate returns, unless they agree to a different allocation in their divorce decree. However, if one spouse can demonstrate they were responsible for a larger portion of the losses (like if they managed all the investments that generated the losses), they might be able to claim a larger share. But absent specific documentation or agreement, the IRS default is 50/50 split. The key thing is to make sure this gets addressed in your divorce settlement so there's no confusion later when you're both trying to claim the carryovers on separate returns.
This is really helpful information! I had no idea that capital loss carryovers could be split in divorce situations. Makes me wonder - what happens if one spouse remarries and files jointly with their new spouse? Can those carried-over losses from the previous marriage be used on the new joint return? Or do they stay tied to the individual who originally incurred them? Also, does anyone know if there are any time limits for making the allocation agreement in the divorce decree, or can former spouses go back and amend how they want to split the losses even after the divorce is final?
Yuki Tanaka
The actual stats on audit rates might make you feel better. For small Schedule C filers (under $100k), the audit rate is around 0.9%. Even with multiple years of losses, unless you have other major red flags, your chances remain relatively low. Make sure you can document that your expenses were legitimate business costs, not personal expenses, and you should be okay.
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Anastasia Sokolov
ā¢Thanks for sharing those stats - that does make me feel better. Just curious, where did you find those numbers? And what would be considered other "major red flags" besides the consecutive losses?
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Yuki Tanaka
ā¢I got those stats from the IRS Data Book which they publish annually. The latest numbers show small business audits have been declining due to IRS budget constraints, though that may change with recent funding increases. Major red flags beyond consecutive losses include unusually large deductions compared to income (especially home office, vehicle, travel, meals), round numbers that suggest estimation rather than actual record-keeping, substantial cash-based income, and claiming 100% business use for vehicles. Also, mathematical errors or inconsistencies between forms can trigger automated reviews that sometimes escalate to audits.
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Carmen Ortiz
Has anyone here actually been audited for a small business with losses? I'd love to hear a firsthand experience about what happened and how it went.
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MidnightRider
ā¢I was audited back in 2023 for my crafting business that had losses for 4 years. It was a correspondence audit (mail only). They asked for receipts for all my expenses and evidence it was a real business (website screenshots, business cards, show applications). It was stressful but I had good records and they accepted everything. Whole process took about 5 months.
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Ravi Malhotra
ā¢That's really helpful to hear from someone who actually went through it! Five months sounds like a long time but at least it was just correspondence and not an in-person audit. Did they question the legitimacy of your business being a "real" business versus a hobby, or did they focus more on the specific expense deductions? I'm trying to figure out what kind of documentation would be most important to keep organized.
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