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One thing nobody's mentioned yet - if you're self-employed, you should definitely be making quarterly estimated tax payments to avoid this problem in the future. Pay as you go through the year (April, June, Sept, and Jan of the following year) and you won't end up with a huge bill at tax time. I learned this the hard way too. Got hit with a $8k tax bill my first year of self-employment and couldn't pay it all at once. Now I put aside 25-30% of every payment I receive and make quarterly payments. No more surprises!

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Yuki Watanabe

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Do you set aside a separate bank account for this? I've tried to do quarterly payments but always end up spending the money I should be saving for taxes.

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Yes, I have a separate savings account specifically for taxes! This was game-changing for me. Every time I get paid, I immediately transfer 30% to this account. I don't even think of that money as mine - it's already the government's money that I'm just holding temporarily. Some banks let you create sub-accounts with different names, which helps mentally. I named mine "NOT MY MONEY - TAXES" to remind myself not to touch it except for quarterly payments. Having it separate from your main checking account removes the temptation to spend it.

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Don't forget that if you paid penalties and interest on your 2023 taxes, those are treated differently than the tax itself. While the $13,500 tax payment isn't deductible on your 2024 return, any interest you paid on late taxes might be deductible if you itemize. Penalties are never deductible though. If you paid through the IRS payment system, you should be able to see the breakdown of what portion was tax, what was penalty, and what was interest. Might be a small silver lining!

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Andre Dupont

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Wait really? Interest on tax payments can be deducted? That's amazing, I paid about $400 in interest because I was on a payment plan. Do you know which form this goes on?

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do u have an actual accountant or just a tax preparer? big difference tbh. my "accountant" last year was just a lady at a strip mall tax place & she missed tons of stuff. real accountant this year saved me like $3,200 by finding actual business deductions & doing proper income splitting

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Juan Moreno

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This is so true! I used to go to one of those chain tax places and when I finally switched to a CPA, the difference was huge. Worth every penny, especially for self-employment stuff.

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Amy Fleming

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make sure ur quarterly estimated payments are higher next year!! that was my mistake too. if ur income is increasing, u need to adjust estimates. i use the safe harbor rule - pay 110% of last year's tax & avoid penalties even if u end up owing more.

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Carmen Ortiz

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Here's what our CPA firm is doing for clients with this issue: 1. We're creating a workpaper that clearly separates business meals into two categories: pre-1/1/2023 (100% deductible) and post-12/31/2022 (50% deductible) 2. For clients with good recordkeeping, we're using the actual dates of each meal 3. For clients with less detailed records, we're doing a pro-rata allocation based on 9 months at 100% and 3 months at 50% The IRS hasn't specifically addressed this fiscal year issue in any publications I've seen, but the calendar-specific language in the original legislation is pretty clear that the enhanced deduction ends 12/31/2022.

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Have any of your clients using the pro-rata approach been audited yet? I'm worried that might be seen as too simplified if the actual spending pattern wasn't evenly distributed throughout the year.

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Carmen Ortiz

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None of our clients using this approach have been audited yet. You raise a valid concern though. If a client's business is seasonal or their meal expenses fluctuate significantly throughout the year, a pro-rata allocation wouldn't be appropriate. In those cases, we recommend either analyzing the actual receipts or using a reasonable allocation based on their business patterns (like quarterly sales figures or similar metrics that would correlate with business meal activity).

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Zoe Papadakis

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Has anyone heard if Congress might extend the 100% meal deduction? I heard rumors they might bring it back since restaurants are still struggling in many areas. Would hate to spend hours implementing a split approach if they're just going to retroactively extend it again.

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Luca Marino

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I haven't seen any serious legislation proposed to extend it. There was some industry lobbying from restaurant associations, but it doesn't seem to have gained traction. I'd proceed with the split approach rather than counting on a retroactive extension.

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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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Sophia Miller

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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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Sophia Miller

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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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Mia Rodriguez

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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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