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Need help catching up on multiple years of unfiled taxes and handling other financial responsibilities

I'm not going to sugarcoat my situation - I've let things slide for way too long. I could list all my reasons, but they're not excuses for the hole I've dug myself into. I need to start climbing out. I'm 32F and have multiple years of unfiled taxes (I did manage to file this year through H&R Block). I've moved between three states without updating my vehicle registration. Haven't seen a dentist in about 8 years. Credit card debt is piling up. I think I might have a medical bill in collections, but I'm not even sure how to check (tried paying online but couldn't find it - maybe because it was a billing error that got fixed?). My out-of-state driver's license expires next month, but I'm worried that getting it updated will trigger questions about all those unfiled taxes. Currently living in TX. I'm finally addressing my core issues (tendency to avoid problems and some addiction struggles), and now I need to deal with the fallout. I seriously have no clue where to start untangling this mess. I'm willing to pay someone to help sort it out, but my experience with H&R Block wasn't great. Should I hire a tax attorney? Can I handle this myself if I find the right resources? I've spent enough time beating myself up over this, but I'm finally at a point where I can ask for help. Any guidance would be incredibly appreciated. Please skip the judgment part - I know I messed up badly. I'm ready to face the consequences but don't need reminders of how dumb this was. I've told myself that plenty already. Thanks for any help.

Just wanted to add something important about your credit card debt - while you're tackling the tax issues, don't ignore this! Credit card interest compounds quickly and can become a bigger problem than the taxes. Consider calling your credit card companies and asking about hardship programs. Many have options they don't advertise that can lower your interest rate or even pause payments temporarily while you get back on your feet. Just be honest about your situation.

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QuantumQuest

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That's a great point. I've been ignoring my credit card statements because they stress me out, but that's obviously making things worse. Have you had any personal experience with these hardship programs? I'm wondering how understanding they actually are.

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I went through this myself during 2020. I called all three of my credit card companies - two offered to reduce my interest rate by about half for 6 months, and one actually gave me a 3-month payment pause without additional interest accumulating. The key is to call before you miss payments. They're much more willing to work with you if your account is still in good standing. Be prepared to explain your situation briefly and have a specific request in mind. Sometimes they'll offer options right away, but other times you need to directly ask "Do you have any hardship programs available?" or "Can you reduce my interest rate while I get back on track?

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For the medical bill concern, I'd recommend pulling your credit reports ASAP. You can get free weekly reports from all three bureaus at www.annualcreditreport.com (the only government-authorized source). If you find the bill in collections, don't panic! Medical collections have less impact on your credit score than other types of debt, and new scoring models even ignore paid medical collections.

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Adding to this - if you do find a medical collection, call the collection agency and ask for "debt validation" before you pay anything. They're required by law to prove the debt is yours. I've had medical bills dropped completely because they couldn't provide proper documentation.

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One important thing I learned as a widow who lost my husband mid-tax year: keep an eye on potential medical expense deductions. With both your husband's treatment and your own surgeries, you might qualify to deduct medical expenses that exceed 7.5% of your adjusted gross income when filing jointly. This includes health insurance premiums, prescription costs, hospital stays, transportation to medical care, and lots of other expenses people often don't realize are deductible. Make sure to gather all medical receipts from both of you for the year.

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Thank you for mentioning this. I honestly hadn't even thought about the medical deduction angle. Between his cancer treatments and my surgeries, we easily spent over $15,000 out of pocket even with insurance. Do things like hospital cafeteria meals and parking at medical facilities count too? I had so many appointments and hospital stays.

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Yes, many of those related expenses do count! Transportation costs to and from medical treatments (including parking fees at hospitals and medical facilities) are deductible. While regular meals generally aren't deductible, if you had to stay overnight for medical care, some meal costs might qualify. Also track any home modifications made for medical reasons, medical equipment purchases, and even mileage driven to pharmacies and doctor appointments. The IRS allows 22 cents per mile for medical travel in 2024. Many people miss these "secondary" medical expenses that can really add up over a year of intensive treatment.

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Mason Davis

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Has anyone mentioned the Qualifying Widow(er) status yet? This wouldn't apply for 2024 (the year your husband passed), but for the next two tax years (2025 and 2026), you might qualify to file as a "Qualifying Widow(er) with Dependent Child" if you have a dependent.

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That won't help in this case. OP specifically mentioned they don't have any children/dependents, so they wouldn't qualify for the Qualifying Widow(er) status in future years.

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Ethan Taylor

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Have you checked your withholding throughout the year? Most ppl don't realize their employer often adjusts their withholding based on the latest IRS tables. So you might be getting slightly bigger paychecks throughout the year but a smaller refund. Check your last paystub from last year vs. this year and see if there's a difference in what they're taking out.

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I actually just dug through my pay stubs after seeing your comment. You're right - they were taking out about $45 less per month in federal taxes this year compared to last year. That accounts for like $540 of the difference. Still doesn't explain all of it, but that's a big chunk I hadn't noticed. So essentially I was getting more in my checks but then less in my refund? That's so confusing.

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Ethan Taylor

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That's exactly what happens for a lot of people. The tax system is designed to try to get you to break even - ideally you'd owe nothing and get nothing back. When tax laws change, they adjust the withholding tables, which changes how much comes out of each check. The rest of your missing refund might be from expired tax credits or deductions. The past few years had some temporary tax benefits due to COVID that have now expired. It sucks when your refund drops, but getting more in each paycheck throughout the year is actually better financially - you get to use your money sooner rather than letting the government hold it interest-free.

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Yuki Ito

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Does anyone know if the standard deduction is going up for 2025? I heard something about inflation adjustments but not sure if that's true or how much it would be.

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Carmen Lopez

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Yes, the standard deduction adjusts for inflation every year. For 2025, it's supposed to be around $14,600 for single filers and $29,200 for married filing jointly. That's up from 2024. Doesn't help you for your current return, but at least it'll help reduce your taxable income a bit next year.

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One tip nobody's mentioned yet - if you made under $58,000 last year, you might qualify for the Earned Income Tax Credit even as a single person with no kids. Check if you're eligible! Could mean several hundred dollars in your refund. Also, don't forget to check if you're eligible for any education credits if you were in school part of last year before graduating. The American Opportunity Credit can be worth up to $2,500 and Lifetime Learning Credit up to $2,000 depending on your education expenses.

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Andre Dupont

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Thank you for this! I had no idea about the Earned Income Tax Credit. My income from June-December was only about $25,000 since I started mid-year. Would I still qualify even though my annual salary is higher?

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Yes, the EITC is based on your actual income earned during the tax year, not your annualized salary. Since you only worked part of the year and earned about $25,000, you would likely qualify for some amount of EITC. The exact amount depends on your filing status and a few other factors, but it could add several hundred dollars to your refund. When you file, make sure whatever software or service you use checks your EITC eligibility with your actual earned income for the year.

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Make sure you're filing as independent if your parents aren't claiming you! This was my biggest mistake my first time. My parents had always claimed me, but we didn't communicate clearly and we BOTH ended up claiming me which caused a huge headache with the IRS. Check with your parents about this asap! The rules are basically if you provided more than half of your own financial support and didn't live with them for more than half the year, you should file independently.

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This happened to my sister! The IRS sent letters to both her and my parents, and they had to figure out who should actually claim her. Took months to resolve.

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One aspect of C-corp compensation that hasn't been mentioned yet is the dividend strategy. If you're moving to part-time and the business is profitable, you could consider a combination of reasonable salary + dividend distributions to shareholders. The benefit is that while dividends are subject to double taxation, they don't incur payroll taxes. For a company with stable profits like yours, establishing a dividend policy might make sense if you're looking to provide regular returns to your investors as well. Just make sure your salary comes first and is defensibly "reasonable" before you start declaring dividends. Documentation is key!

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Xan Dae

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What about accumulated earnings tax though? If the C-corp retains too much profit without a business purpose, couldn't they get hit with that penalty?

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You're absolutely right to bring that up. C-corporations that accumulate earnings beyond the reasonable needs of the business ($250,000 is generally the threshold) can face the Accumulated Earnings Tax, which is a 20% penalty tax. However, if the company can demonstrate specific, definite, and feasible plans for the retained earnings - like future expansion, equipment purchases, paying down debt, or even building reserves for contingencies - these can justify keeping cash in the business. It's important to document these plans in your corporate minutes and have financial projections to support them.

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Have you considered the option of electing S-Corp status instead? Since you mentioned that you're not planning to raise more capital and are running this as a smaller operation now, an S-Corp could potentially give you more tax flexibility. The main benefits would be avoiding double taxation and having more options for taking profits out of the business. You'd still need to pay yourself a reasonable salary, but the remaining profits could pass through without the additional layer of corporate tax.

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I've thought about S-Corp, but we have some complications - we have foreign investors from the angel round, and I believe S-Corps can't have non-US shareholders? Also, if we did ever want to raise more money in the future or pursue an acquisition by a larger company, my understanding is that C-Corp is more attractive to those types of buyers.

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