Don't forget that if you're due a refund from any of the years you didn't file, you only have 3 years from the original due date to claim it. After that, the money is gone forever. But if you OWE money, there's no time limit for the IRS to collect! Not fair but that's how it works.

I went through this exact same situation about two years ago - four years of unfiled returns with gig work income mixed in. The anxiety was eating me alive until I finally bit the bullet and dealt with it. Here's what I learned: The IRS actually wants to work with you more than you think. I ended up qualifying for First Time Penalty Abatement which wiped out a huge chunk of the penalties. The key is being proactive about fixing it rather than continuing to avoid it. For your income level and situation, you'll likely owe some back taxes but it won't be catastrophic. The failure-to-file penalties are the killer (5% per month up to 25%), but once you get those abated, you're mostly looking at the actual tax owed plus interest. My biggest regret was waiting so long to address it. Every month you wait, more interest accrues. I'd definitely recommend getting professional help - an Enrolled Agent was worth every penny for me. They knew exactly which forms to file and how to minimize the damage. You've got this! It's scary but totally manageable once you start the process.

Something nobody has mentioned - check if your state has different rules about carryovers when converting from C to S. Some states don't fully conform to federal treatment of S-Corps and may allow carryover of certain attributes that the federal rules prohibit. For example, California has its own set of rules for S corporations that sometimes differ from federal treatment. Might be worth exploring if your state gives you more flexibility than the federal rules.

This is a tough situation, but you're not completely out of options. First, definitely verify the timing of your S election - if it was made within the first 2 months and 15 days of your tax year, you can still revoke it with unanimous shareholder consent. Beyond that window, you'd need to show reasonable cause. Before making any decisions, I'd strongly recommend getting a second opinion from a tax attorney who specializes in corporate conversions. The $270k carryover is substantial enough that it's worth exploring all possibilities, including: 1. Whether any exceptions might apply to your specific situation 2. Asset restructuring strategies (like the equipment holding company idea mentioned above) 3. State-level treatment that might differ from federal rules 4. Alternative tax benefits you might qualify for post-conversion The decision to stay C-Corp vs convert to S-Corp involves many factors beyond just this carryover. You'll want to model out the long-term tax implications of both scenarios before deciding whether to proceed with or revoke the election.

Check if your mailbox is locked or if there's any forwarding issues with your address. Sometimes refund checks get returned to IRS if there's a delivery problem. Also double check the mailing address on your return matches exactly what's on file with USPS. Hope you get it soon!

I'm in the exact same situation! My transcript shows it was mailed 6 days ago and I've been refreshing my Informed Delivery every morning hoping to see it. The waiting game is brutal when you're expecting money lol. From what I've read here it sounds pretty normal though - seems like most people get theirs within that 5-7 day window. Fingers crossed we both get ours soon! 🤞

One trick I learned from an accountant friend - keep a separate log for your hobby sales that clearly documents each sale with dates, amounts, and context (like "church fundraiser" or "neighbor request"). This helps establish the occasional/non-commercial nature of the sales if questioned. Also track your expenses separately from any business activities. When my wife started selling her paintings occasionally, we created a simple spreadsheet showing that she was actually spending more on supplies than she was making from sales, which helps support the hobby classification. The key is showing you're not primarily motivated by profit.

This is such a common confusion point! I went through this exact same situation with my ceramics hobby last year. What really helped me was understanding that sales tax and income tax are completely separate systems with different rules. For sales tax: Most states require you to collect it on tangible goods regardless of whether it's a hobby or business. The transaction itself triggers the requirement, not your profit motive. For income tax: The key is proving it's truly a hobby. I keep detailed records showing I'm not profit-motivated - my supply costs usually exceed my sales, I only sell when people specifically ask, and I don't advertise or actively seek customers. One thing that wasn't mentioned yet - if you do need to get a sales tax permit, some states offer simplified filing options for occasional sellers. Mine lets me file annually instead of quarterly since my sales are so infrequent. Definitely worth asking your state about when you call them. The most important thing is consistency in how you document and report everything. Good record-keeping will protect you if there are ever questions about your classification.

Quick question for those with more experience - does anyone know if you can switch between standard mileage deduction and actual expenses year to year? I'm getting a newer car soon specifically for Uber and wondering what's best.

Great discussion everyone! As someone who's been doing rideshare driving for 2 years, I wanted to add a few practical points that might help the original poster. First, regarding the LLC question - you're right that it doesn't change your tax situation for deductions, but one thing to consider is that some insurance companies offer better commercial auto rates to LLCs versus individual drivers. It's worth shopping around. Second, about the "100% business use" claim - be really careful here. The IRS scrutinizes this heavily. Even driving to get gas, going to the car wash, or driving to your first pickup of the day can count as personal use in their eyes. Most tax professionals recommend being conservative and claiming something like 90-95% business use to avoid audit triggers. Finally, don't forget about other deductions beyond the vehicle! Phone bills (business portion), toll fees, parking costs, and even roadside assistance memberships are all deductible. These can add up to significant savings even if you're taking the standard mileage deduction.