Just wanted to share my experience as someone who's been through this exact situation! I started selling digital content (similar situation to yours) about two years ago and was terrified about the tax implications. The biggest thing that helped me was realizing that from the IRS perspective, this is just self-employment income like any other side business. Whether you're selling feet pics, tutoring, or making crafts - the tax treatment is identical. Here's what I learned that might help: 1) Keep meticulous records from day one. I use a simple spreadsheet tracking every payment received and any business expenses (props, camera equipment, editing apps, etc.) 2) The alias situation is totally manageable. I've been using a stage name for two years with no issues. Just make sure you can clearly document that the income belongs to you. 3) Consider your payment platform carefully. I had to switch away from PayPal after they became problematic about content policies, even for non-explicit material. 4) Set aside 30% of earnings immediately for taxes. I put mine in a separate savings account so I'm not tempted to spend it. 5) Don't overthink the business description on tax forms. "Digital Content Creation" or "Photography Sales" works perfectly fine. The privacy concerns are valid, but remember that tax records are confidential. Future employers won't see your tax returns or know what specific products you sold to earn income. You've got this! Student loans are crushing, and there's no shame in finding creative legal ways to pay them down faster.

I want to emphasize something important that others have touched on but bears repeating - you absolutely need to treat this as legitimate self-employment income from day one, regardless of what you're selling. I work as a tax preparer and see people in similar situations regularly. The IRS doesn't care about the nature of your legal business - they care about accurate reporting and proper tax compliance. Here are some key points: 1) Document everything meticulously. Bank statements, payment platform records, expense receipts - keep it all organized by tax year. 2) If using an alias, maintain clear documentation linking that alias to your SSN. Screenshots of payment transfers, account statements, anything that shows the connection. 3) Open a separate bank account for business income, even if it's under your real name. This separation makes record-keeping much cleaner and shows the IRS you're treating this professionally. 4) Calculate and pay quarterly estimated taxes if you expect to owe $1,000+ annually. Use Form 1040-ES or work with a tax professional to avoid underpayment penalties. 5) Track deductible expenses: photography equipment, props, software subscriptions, portion of internet/phone bills used for business, even a portion of rent if you use part of your home exclusively for this work. The privacy concerns are understandable, but tax filings are confidential. Your Schedule C will simply show "Digital Content Creation" or similar - no one will know specifics about your products. Consider consulting with a tax professional for your first year to ensure everything is set up correctly. The peace of mind is worth the cost, especially when dealing with student loan debt stress. You're taking a proactive approach to your financial situation - that's commendable. Just make sure you're protecting yourself legally and financially from the start.

This entire discussion has been absolutely invaluable! As someone who's been lurking in this community for a while but never posted, I felt compelled to jump in because I'm facing a very similar situation. My house was destroyed in a wildfire 4 years ago, and like many others here, I've been sitting on the vacant land ever since. Reading through everyone's experiences and advice has finally given me the confidence to move forward with selling. A few key takeaways that really helped clarify things for me: **Documentation is everything** - I'm going to start with the title company suggestion to get my old property tax assessments. That seems like the fastest route to get the land-to-structure ratio I need. **State tax implications matter** - I hadn't even considered this since I moved states after the fire. Definitely need to research my specific situation there. **Professional guidance is worth it** - Between the retroactive appraisal option and the various tax planning strategies mentioned (loss harvesting, timing, etc.), it's clear this is complex enough to warrant getting expert help. One question I still have: for those who successfully sold their vacant lots, how did you handle the actual real estate transaction? Did you use a regular residential agent, or is there a better approach for selling vacant land? I'm wondering if the marketing and pricing strategies are different than what I'm used to from regular home sales. Thanks again to everyone who shared their knowledge and experiences - this community is amazing!

This has been such a comprehensive and helpful discussion! As someone new to this community, I'm amazed by how much practical knowledge everyone has shared. I wanted to add one more angle that might be relevant - if you're planning to sell your vacant land and potentially buy another property, consider looking into Opportunity Zone investments. If your land sale generates a significant capital gain, you might be able to defer or even eliminate some of that tax burden by investing the proceeds in a Qualified Opportunity Fund. The Opportunity Zones program allows you to defer capital gains taxes until 2026 (or when you sell the Opportunity Zone investment, whichever comes first), and if you hold the Opportunity Zone investment for at least 10 years, any appreciation on that investment is completely tax-free. This could be particularly attractive if you were already considering investing in real estate or business ventures in designated Opportunity Zones. The investment has to be made within 180 days of the land sale, so it requires some advance planning, but the tax benefits can be substantial. Of course, like everything else discussed here, this strategy has its own complexities and isn't right for everyone. But given how much money some of you might be looking at in capital gains taxes, it could be worth exploring alongside the other strategies mentioned like 1031 exchanges and loss harvesting. Anyone have experience with Opportunity Zone investments in this type of situation?

Just a heads up, if they're controlling when and how you work (scheduled shifts, supervision, etc.), you're almost certainly misclassified. Companies do this ALL THE TIME to save money. I was in the same situation with a call center job last year. After filing the SS-8 form, the IRS determined I was an employee, not a contractor. The company got hit with back taxes and penalties, and I got a nice refund check for the extra self-employment taxes I paid! Don't let them get away with it!!

This is exactly why I always tell people to be very careful about contractor classifications! The key thing to remember is that being classified as 1099-NEC means you're paying both the employer AND employee portions of Social Security and Medicare taxes (15.3% total), whereas W2 employees only pay 7.65% with their employer covering the other half. Based on your description - having supervisors, following their schedule, taking calls during set shifts - you sound like you might be misclassified. True independent contractors typically have more control over how, when, and where they do their work. The good news is that if you are misclassified and can prove it through Form SS-8, you could get back thousands in overpaid self-employment taxes. The IRS looks at factors like behavioral control, financial control, and the type of relationship you have with the company. Your situation has several red flags for employee classification rather than contractor.

I went through this same problem last year! Tax laws are so confusing... I used TurboTax Free Edition and it walked me through everything. Since your income is under $12k, you should qualify to file completely free. Just make sure you go directly through the IRS Free File program so you don't get upsold on paid services.

I've been helping people with tax questions for years, and yes, you absolutely need to file. Unemployment compensation is 100% taxable income at the federal level, regardless of the amount. The $12,000 filing threshold doesn't apply when you have unemployment income - it's always reportable. The silver lining is that with your low total income ($11,230), you'll likely qualify for the Earned Income Tax Credit (EITC) which could actually get you money back even though you didn't have taxes withheld. The EITC is designed to help working people with low to moderate income, and your W-2 wages of $650 plus the $180 contractor work should qualify you. Also, don't forget about the standard deduction of $13,850 for 2023. Your income is actually below that threshold, so you might not owe any federal tax at all, but you still need to file to report the unemployment and claim any credits you're eligible for. I'd recommend using the IRS Free File program since your income qualifies you for completely free tax preparation software. Don't let anyone charge you for filing with your income level!

Just went through this exact process with my consulting LLC that elected S-Corp status. A few key points that might help: 1) You're absolutely right to be frustrated about the $850 fee for zero-activity returns, but unfortunately it's required. However, you can significantly reduce costs by doing some of the prep work yourself. Since you had no business activity, your Form 1120-S will basically be all zeros except for basic entity information. 2) For the EIN notification, I sent a simple letter to the IRS Business & Specialty Tax Line at the Cincinnati processing center. Include your business name, EIN, date of dissolution, and a brief statement that the entity has been dissolved. Keep a copy for your records. 3) Don't forget about your state requirements - many states require a final franchise tax return even with zero activity, and some have specific dissolution tax forms. The penalties for missing these can be worse than just filing them. 4) One money-saving tip: if both LLCs are in the same state and have similar structures, see if your accountant will give you a discount for preparing both final returns together. Mine knocked off about 20% for the second entity since most of the work was duplicated. The whole process is definitely a pain for inactive businesses, but better to close them properly than deal with ongoing compliance issues down the road.

I'm going through a similar situation right now with my small consulting LLC that I'm dissolving. Reading through all these responses has been incredibly helpful - especially learning that you don't actually "cancel" an EIN but just notify the IRS of the dissolution. One thing I wanted to add that might help others: if you're looking to save money on the final tax returns, consider asking your accountant if they offer a flat fee for "zero activity" final returns. I found one who charges $275 for S-Corp final returns when there's literally no business activity to report - just filling in the basic entity info and checking the "final return" box. Also, for anyone else dealing with this, make sure you check if your state has any annual report filings that need to be completed before dissolution. I almost missed my state's final annual report, which would have kept the entity technically "active" even after filing articles of dissolution. The certified mail suggestion for the EIN notification letter is spot on too - that return receipt is your proof that the IRS received your notification. Worth every penny for the peace of mind.