Has anyone used the IRS's "Offer in Compromise" program? I've heard you can settle for way less than you owe. With $70k in tax debt maybe that's better than a payment plan?

I went through something very similar - owed about $85k in back taxes after a stock windfall, then got laid off and couldn't deal with it for years. The stress was unbearable. Here's what I learned: Don't pay those tax resolution companies. I almost did the same thing and would have wasted $8k+ for services I could handle myself. First, get those returns filed immediately with your CPA. This stops the failure-to-file penalties which are brutal (5% per month vs 0.5% for failure-to-pay). Second, that $20k payment you made is definitely in the IRS system. When you file your 2020 return, make sure your CPA applies it to reduce your balance. You can verify this later with an account transcript. Third, with your new income level, you'll likely qualify for a standard installment agreement. The IRS will want financial disclosure (Form 433-F) for amounts over $50k, but they're usually reasonable about payment terms if you're compliant and honest about your situation. I ended up getting penalty abatement for about 60% of my penalties under the "reasonable cause" provision - the job loss and financial hardship were legitimate reasons. Saved me over $15k. The key is getting current with filing first, then dealing with collections. The IRS is actually pretty workable once you're compliant and communicating with them directly. Don't let the debt sit unfiled any longer - it only gets worse. You've got this! The fact that you're employed again and addressing it now puts you in a much better position than you think.

One more thing to consider - if you're earning that much at 14, you might want to look into opening a Roth IRA! You can contribute earned income (like your Patreon money) up to the annual limit or the total amount you earned, whichever is less. Starting retirement savings at your age would be AMAZING for long-term growth. Your parents would need to help set this up as a custodial account, but it's a fantastic way to start building wealth while getting tax advantages. Plus, you can actually withdraw your contributions (not the earnings) penalty-free if you need them for something like college.

Hey Luca! Great to see a young entrepreneur doing so well with their art! Just wanted to add a few practical tips from someone who's helped several teens navigate this: 1. **Quarterly estimated taxes**: Since you're making $450-500/month, you'll likely owe more than $1,000 in taxes for the year. This means you should consider making quarterly estimated tax payments to avoid penalties. Your first payment for 2025 would be due April 15th. 2. **Record keeping is CRUCIAL**: Start tracking everything now - income, expenses, receipts. Use a simple spreadsheet or app like QuickBooks Self-Employed. The IRS loves good records, especially for self-employment income. 3. **State taxes**: Don't forget about state income tax if you're in a state that has it! The rules can vary significantly by state for minor dependents with self-employment income. 4. **Consider forming an LLC**: Once you're consistently earning this much, your parents might want to look into forming a single-member LLC with them as the organizer. It can provide some liability protection and might make business banking easier. Keep up the great work with your art! It's awesome that you're thinking about taxes responsibly at 14. Your future self will thank you for getting this right from the start.

This is such a complex situation, and I really appreciate everyone sharing their experiences here! As someone who's been dealing with similar back tax issues, I wanted to add a few thoughts. First, regarding the statute of limitations - it's worth noting that while you generally can't get a refund after 3 years, the IRS can still apply overpayments as credits to other tax years even beyond that timeframe in certain circumstances. The key is how you handle the filing process. One thing I learned the hard way is that the ORDER you file multiple years matters tremendously. If you file 2017 first and request the overpayment be applied to 2018, then file 2018 showing that credit, it's processed differently than if you file them simultaneously or in reverse order. Also, don't forget about estimated tax payments you may have made for 2019 that could be applied back to 2018 if needed. The IRS has more flexibility with moving payments between adjacent tax years than most people realize. I'd strongly recommend getting everything professionally reviewed before filing - the potential savings from doing this right the first time far outweigh the cost of professional help. Missing these nuances could cost you thousands in lost credits or unnecessary penalties.

I've been following this thread as someone who went through a very similar situation with unfiled returns from 2016-2018. One thing I want to emphasize is the importance of acting quickly once you decide to file these old returns. The longer you wait, the more interest and penalties accumulate, and you risk losing additional credits. I procrastinated for an extra year after discovering my situation, and it cost me about $800 in additional interest that I could have avoided. Also, something that helped me was creating a simple spreadsheet tracking all my payments, estimated taxes, and what I owed for each year before I started filing. This gave me a clear picture of exactly how much I could recover and helped me set realistic expectations. When I finally filed, I was able to recover about 60% of what I thought I'd lost to the statute of limitations by following a strategic filing order and including the right forms. The key was understanding that while I couldn't get cash refunds for the older overpayments, I could still use them to offset other tax debts. Don't let the complexity paralyze you - even an imperfect filing is better than continuing to let these returns sit unfiled. The IRS is generally more willing to work with taxpayers who are making an effort to get compliant.

Great question! I was in a similar situation a few years ago and learned some hard lessons. With your combined income of around $63,000, you'll definitely want to be proactive about withholding. One thing to keep in mind is that restaurant work often involves tips, which are taxable income that may not have proper withholding. If you're serving tables, make sure to track all your tip income carefully and consider that when calculating your total annual earnings. The "different tax bracket" comment from your manager is referring to how your marginal tax rate increases as your income goes up. While you won't pay the higher rate on all your income (that's a common misconception), the additional $15K will likely be taxed at 22% instead of the 12% rate that covers most of your main job income. My recommendation: Use the IRS withholding calculator online to get specific guidance for your situation, or consider having extra tax withheld from your main job's paycheck. I'd rather get a refund than owe money when saving for a house down payment! Also, keep good records of any work-related expenses from the restaurant job.

Having been through this exact scenario myself, I'd definitely echo the advice about adjusting your withholding proactively. One thing I wish someone had told me when I started my second job - consider setting aside a small emergency fund specifically for potential tax surprises, even if you do everything right with withholding. With restaurant work, there are a few additional considerations beyond just the base wages. If you're in a tipped position, your employer might only withhold taxes on your hourly wage (which could be as low as $2.13/hour in some states) but not on your tips. This can create a significant underwitholding situation if your tips are substantial. Also, make sure both employers know about your multiple job status when filling out your W-4. There's actually a checkbox on the 2020 and newer W-4 forms (Step 2c) specifically for this situation. Don't be afraid to be conservative with your withholding - when you're saving for a house down payment, the last thing you want is to have that money tied up in an unexpected tax bill. The good news is that $63k total income is still very manageable from a tax perspective, and with proper planning you shouldn't have any nasty surprises come filing time!

Anyone else feel like the government is just trying to squeeze more tax money out of regular people with these new 1099-K rules? Most people using Venmo and CashApp are just normal folks splitting bills, not businesses trying to evade taxes! 😡

This is such a timely question! I went through the same panic last year when I first heard about the 1099-K changes. Here's what I learned after doing a lot of research and talking to a tax professional: The $600 threshold only applies to payments you RECEIVE that are marked as "goods and services" - not personal transfers like splitting dinner bills or paying rent to roommates. So if you're mostly sending money TO friends rather than receiving it FROM customers, you're probably fine. For the money you received from selling stuff on Facebook Marketplace, you'll only owe taxes if you made a profit. If you sold your old couch for $200 but originally paid $500 for it, that's actually a loss and not taxable income. My suggestion is to go through your transaction history ASAP and categorize everything: - Personal transfers (splitting bills, paying friends back) - Sales where you lost money (sold for less than you paid) - Actual profit from sales Keep screenshots and receipts as documentation. The IRS isn't trying to tax you on money that was never really income in the first place, but having good records will save you stress if questions come up later. Don't panic - most casual users aren't going to owe anything significant even if they do get a 1099-K!