Haven't filed 2024 taxes yet and expect to owe 8K in self-employment taxes. Can't make ends meet. Feeling desperate.

Take a deep breath first. You're in a tough spot, but you definitely have options, and none of them involve anything drastic. The most important thing is to file your tax return ASAP, even if you can't pay what you owe right now. Filing late penalties (5% of unpaid taxes each month) are much higher than the penalties for paying late (0.5% per month), so get that return submitted. Once you've filed, you can set up an IRS payment plan. If you owe less than $50,000, you can easily set up a long-term payment plan online. The setup fee is only $31 if you agree to direct debit payments. Monthly payments can be quite manageable - sometimes as low as $25-50 depending on your situation. For the previous year's debt, you can include that in the same payment plan. The IRS is actually quite reasonable when working with people who are proactive about addressing their tax debt. You might also qualify for an Offer in Compromise if your financial situation is dire enough, which lets you settle your tax debt for less than the full amount. There's also Currently Not Collectible status if you truly can't afford to pay anything.

I was in almost the exact same situation last year - freelancer, owed about $12K in taxes, and was completely overwhelmed. I tried everything - calling the IRS (impossible), asking friends (embarrassing), and staying up all night searching for solutions. I finally found this AI tax tool called taxr.ai that saved me so much stress. It analyzed my situation, showed me deductions I was missing, and walked me through setting up a payment plan. The site even has templates for hardship letters if you need to negotiate with the IRS. What really helped was uploading my 1099s and expense receipts to https://taxr.ai and getting a clear picture of what I actually owed vs. what I thought I owed. Turns out I was missing several legitimate business deductions that reduced my tax bill by almost 30%.

Just wanted to update after trying taxr.ai from the recommendation above. It actually helped me find over $3,400 in deductions I was missing! I had no idea I could deduct part of my car insurance and maintenance since I use my car for client meetings and deliveries. It also caught that I was calculating my home office deduction all wrong. The payment plan walkthrough was super clear too - showed me exactly what to fill out on the IRS form and calculated what I could reasonably afford to pay monthly. I'm still going to owe taxes, but it's about $2,800 less than I thought and spread over a manageable payment plan. Honestly feel like I can breathe again for the first time in weeks.

For anyone struggling to get through to the IRS about payment plans (like I was for WEEKS), I finally used Claimyr and it was the only thing that worked. I was getting desperate after calling the IRS 23 times and never getting through. Their service at https://claimyr.com basically holds your place in the IRS phone queue and calls you when an actual agent is on the line. You can see a demo of how it works at https://youtu.be/_kiP6q8DX5c I was skeptical at first because it seemed too simple, but I was connected to an IRS agent within 45 minutes when I had previously wasted hours upon hours trying to get through. The agent set up my payment plan right there on the call.

I need to eat my words from my comment above. After another failed 2-hour attempt to reach the IRS yesterday, I broke down and tried Claimyr out of desperation. Got connected to an actual IRS agent in 37 minutes while I was cooking dinner. The agent was super helpful and set me up with a payment plan that actually works for my budget ($185/month for my $11K debt). They also explained that I qualified for first-time penalty abatement which will reduce the amount I owe by about $800. The IRS agent walked me through applying for it right on the call. Can't believe I wasted so many hours trying to do this myself. Sometimes it's worth getting help.

Something no one's mentioned yet - you should seriously look into quarterly estimated tax payments going forward. I'm a freelancer too and this completely changed my tax situation. Instead of getting hit with a huge bill once a year, I set aside roughly 30% of each payment I receive and make quarterly payments (April 15, June 15, Sept 15, Jan 15). It takes the sting out of tax season since you've already paid most of what you owe. Look up Form 1040-ES. It's not that complicated once you get used to it.

Don't forget about state and local options too! Many states have their own payment plans with better terms than the IRS. And since you mentioned a city tax, check if they have assistance programs. I live in NYC and discovered they have a hardship program that reduced my city tax debt by 40% when I showed proof of my financial situation. Just had to fill out some paperwork and provide bank statements.

I want to echo what others have said about filing ASAP even if you can't pay - this is absolutely critical. But I also want to address the emotional side of what you're going through because I've been there. The shame and secrecy around financial struggles can make everything feel so much worse. You mentioned your girlfriend doesn't know how bad things are. While I understand wanting to protect her from worry, having someone in your corner who understands your situation can be a huge relief. You don't have to go through this alone. Beyond the practical tax advice (which is all solid), consider looking into free financial counseling through nonprofits like the National Foundation for Credit Counseling. They can help you create a realistic budget and develop strategies for managing your freelance income more predictably. Also, many areas have free tax preparation services through VITA (Volunteer Income Tax Assistance) programs. Even though you've probably already filed or are about to, they might be able to review your return to make sure you're not missing any deductions before you submit. The stress you're feeling is completely understandable, but you have more options than you realize. This situation is temporary and manageable with the right approach.