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Curious what tax software people recommend for filing the partial year returns after conversion? I'm going through this exact scenario and usually use TurboTax Business but not sure if it handles this situation well.
I appreciate everyone sharing their experiences here. Just want to add a few additional considerations that might help with your decision timing: 1. **Quarterly estimated taxes** - If you're making quarterly payments as a C Corp, converting mid-year will complicate your Q3 and Q4 estimates since you'll need to calculate them based on your new entity structure. 2. **Employee benefits** - If you have employees or provide yourself benefits through the C Corp (health insurance, retirement plans), these will need to be restructured. Some benefits that were tax-deductible for the C Corp might not be for an LLC. 3. **State franchise taxes** - Many states charge annual franchise taxes for C Corps that are calculated differently than LLC fees. Converting mid-year might still leave you liable for the full year's C Corp franchise tax in some states. The timing really depends on your specific situation, but given the complexity everyone's outlined here, waiting until your accountant returns might be worth the delay. Two weeks could save you from making a costly mistake, especially since you'll need professional help with those dual tax filings anyway.
Great question! This is actually a pretty common scenario for people with mixed income sources. The answer depends on how your employer handles your health insurance premiums. If your $420 is deducted pre-tax from your paycheck (which is most common), you've already received the tax benefit and can't deduct it again for your 1099 income. However, if it's deducted post-tax, you may be able to claim a partial self-employed health insurance deduction on Schedule 1 of your 1040 (not Schedule C). The deduction would be proportional to your self-employment income vs. total income. To check: Look at your pay stub - if the health insurance comes out before taxes are calculated, it's pre-tax. If it comes out after, it's post-tax. You can also verify by checking if your W-2 Box 1 (taxable wages) is lower than your gross pay by more than just the health insurance amount. Even if you can't deduct the health insurance, make sure you're tracking all your other legitimate business expenses for your consulting work - they add up quickly!
This is exactly the kind of detailed explanation I was hoping for! I'm going to check my pay stub tonight to see if my health insurance is pre-tax or post-tax. I had no idea there was a difference or that it would affect my ability to deduct it for my freelance work. The proportional deduction based on self-employment income vs total income makes total sense too. Thanks for breaking this down so clearly - it's way more helpful than the IRS publications I was trying to wade through!
I had this exact same situation when I started doing freelance graphic design while working my regular job! The confusion about health insurance deductions with mixed income sources is so real. What really helped me was creating a simple spreadsheet to track everything - not just the health insurance question, but all my freelance expenses. I was surprised how much I could legitimately deduct once I started paying attention: software subscriptions, equipment depreciation, client meeting costs, even a portion of my home office space. For the health insurance specifically, I ended up working with a CPA who explained that since my employer premiums were pre-tax, I couldn't double-dip. But she helped me identify so many other deductions I was missing that it more than made up for it. The key thing I learned is to keep meticulous records from day one of your freelance work. Even small expenses add up over the year, and come tax time you'll be glad you tracked everything properly!
This is such great advice about keeping detailed records! I'm just starting my freelance journey and already feeling overwhelmed by all the tax implications. Could you share what categories you track in your spreadsheet? I want to make sure I'm capturing everything from the beginning rather than scrambling at tax time. Also, how did you find a CPA who really understood the mixed W-2/1099 situation? It seems like a lot of tax preparers don't deal with this combo very often.
Has anyone had luck with state efiling for prior years? I know the IRS doesn't allow it, but I'm wondering if some states might have different rules? I'm in California if that matters.
California FTB (Franchise Tax Board) has the same rules as the IRS - prior year returns need to be paper filed. I tried to efile a 2021 return last month and had to mail it in. Most states follow similar protocols to the federal system.
I went through this exact same situation last year! Unfortunately, as others have mentioned, you really can't efile prior year returns through any service - it's just not allowed by the IRS regardless of who prepares them. What I ended up doing was printing my completed TurboTax returns and sending them via USPS Priority Mail with tracking. It actually wasn't as slow as I expected - my returns were processed within about 6-8 weeks, which is pretty standard for paper filing. One tip that helped me: I called the IRS processing center for my area about 3 weeks after mailing to confirm they received my returns. You can find the right number on the IRS website based on where you're mailing your returns. It gave me peace of mind knowing they actually got them and were in the system. The certified mail route that Connor mentioned is also a good option if you want extra proof of delivery, though it does cost a bit more than regular Priority Mail.
That's really helpful to know about the 6-8 week processing time! I was expecting it to take much longer based on horror stories I've read online. Did you have any issues with your returns or did they process smoothly? I'm also wondering - when you called to confirm they received your returns, did they give you any kind of reference number or just confirm they were in the system?
In addition to what others have said, make sure you're tracking ALL your expenses, not just mileage! I do all these delivery apps too and was leaving money on the table my first year. Deductible expenses: - Phone bill (% used for gig work) - Phone holder/mount for car - Hot bags (if you bought your own) - Portion of car insurance - Parking fees while waiting for orders - Dashcams (safety equipment) - Cleaning supplies for your car - Masks, hand sanitizer, etc. If you use the actual expense method instead of standard mileage rate, you can also deduct gas, maintenance, repairs, etc., but usually the standard mileage rate is better.
Wait, you can deduct hot bags? I bought like 3 different ones trying to find one that actually keeps food warm. Also, what percent of your phone bill do you usually deduct?
Yes, hot bags are definitely deductible! They're business equipment necessary for your delivery work. I deducted all three bags I bought too - keep those receipts! For phone bill percentage, I calculate it based on how much I actually use my phone for gig work versus personal use. I track my delivery hours versus total phone usage time. For me, it works out to about 30-35% since I do deliveries part-time. Some people just estimate, but I'd recommend being conservative and keeping records in case you get audited. Also don't forget phone accessories like car chargers, portable battery packs, and phone cases if you bought them specifically for delivery work!
Great thread! I went through this exact same confusion last year with DoorDash, Uber Eats, and Postmates. One thing I learned the hard way is to make sure you reconcile your bank deposits with what the platforms report. DoorDash's 1099-NEC was straightforward, but Uber's tax summary sometimes includes tips and other payments that might not match exactly with your bank records due to timing differences. I had to go through my statements month by month to make sure I wasn't missing any income or double-counting anything. Also, even though you can combine everything on one Schedule C, I'd suggest keeping a simple spreadsheet that breaks down your income by platform just for your own records. It helps you see which apps are actually worth your time and makes it easier if you ever need to answer questions about your income sources. The business code 492000 that Anastasia mentioned is spot on - that's what I used and had no issues with the IRS.
This is such helpful advice about reconciling bank deposits! I'm dealing with this exact issue right now - my Uber summary shows one amount but my actual deposits don't quite match up. Did you find any specific patterns in the timing differences? Like were tips always delayed by a certain number of days or was it more random? Also, your point about the spreadsheet breakdown is smart. I've been thinking it would help me figure out which time slots are most profitable for each app too, not just which apps overall.
Cass Green
Something nobody's mentioned yet - you should check if the debt collector properly renewed the judgment. In most states, judgments expire after a certain period (often 7-10 years) unless the creditor files paperwork to renew it. If yours was from 2013 and they never renewed it properly, it might have expired. You can check this by contacting your county clerk's office and asking about any judgment renewals filed against you. If they didn't renew it and the original judgment has expired, you might be able to challenge the garnishment on those grounds. I went through something similar with an old credit card judgment from 2010. They tried to garnish my bank account in 2022, but I discovered they never renewed the judgment which expired after 10 years in my state. The court immediately terminated the garnishment order when I pointed this out.
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Khalil Urso
ā¢Thank you for this suggestion! I hadn't even thought about checking if they properly renewed the judgment. I'll definitely contact my county clerk tomorrow. Do you happen to know if I need any specific information when I call them? I'm not even sure what the case number would be since I never received the original paperwork.
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Cass Green
ā¢You'll need to provide your full legal name as it would appear on court documents. Some counties have online systems where you can search by name, while others require you to call or visit in person. They can usually find judgments against you just with your name and possibly your address. If they locate the judgment, ask specifically about renewal filings. The clerk should be able to tell you if and when any renewals were filed. If the original judgment has expired without renewal, get documentation of this to present to both the creditor and the tax authorities.
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Finley Garrett
Just want to add that if the majority of your income is from SSD, you might qualify to file Form 982 "Reduction of Tax Attributes Due to Discharge of Indebtedness" which can help if you're considered insolvent. This might not stop the current garnishment but could prevent future tax consequences if some of your debt gets discharged. Also, many states have homestead exemptions or wildcard exemptions that protect certain amounts of your assets and income from creditors, even after a judgment. These vary dramatically by state though - where are you located? Might be able to point you to specific state resources.
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Madison Tipne
ā¢Not OP but I'm in Florida dealing with similar issues. Would love to know what protections might apply here. I'm on SSDI with about $22k annual income and just got a garnishment notice for a debt from 2014.
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