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Don't forget about estimated tax payments for next year! With income this high, you need to be making quarterly payments or you'll get hit with underpayment penalties. My business income jumped dramatically in 2023 and I got slapped with almost $4,000 in penalties because I didn't realize this. The IRS expects you to pay as you earn, not just at tax time.
This is actually really helpful - I had no idea about the quarterly thing. How do I figure out how much to pay each quarter if my income isn't consistent? My construction projects vary a lot month to month.
You have a couple of options for calculating your estimated payments. The safest method is paying 100% of your previous year's tax (or 110% if your income was over $150,000). This gives you a "safe harbor" from penalties even if you end up owing more. If your income fluctuates, you can use the "annualized income installment method" using Form 2210. This lets you make payments based on what you actually earned in each period rather than 25% each quarter. Most construction businesses have seasonal fluctuations, so this might work better for you. A good tax software or accountant can help you run these calculations.
Honestly at your income level, you should be talking to a tax ATTORNEY, not just a CPA. They can help you set up more advanced strategies like captive insurance companies, cost segregation studies if you buy commercial property, or even set up a management company with a defined benefit plan. These are all legit strategies but they need professional setup. I learned this the hard way after DIYing my taxes when my business hit 7 figures.
Completely agree - especially for construction. My brother's construction company got hammered in an audit because they hadn't structured things correctly. Not worth the risk when you're dealing with this kind of money. A good tax attorney will save you way more than they cost.
OP just to give you a different perspective - I work as a K9 handler in security and successfully deducted a portion of my dog training classes. The key was that I'm 1099 independent contractor, not a W-2 employee. I documented how the specific training skills directly related to my security contracts. If you're W-2, you're probably out of luck since the 2018 tax law changes eliminated most unreimbursed employee expenses. But if you're self-employed (filing Schedule C), you might have a case for a partial deduction. Just document everything like crazy in case of audit.
Thanks for this insight! I'm actually W-2 at my main job but I've been picking up some independent security gigs on weekends (about 10-15 hours per week) where I'm paid as a contractor. Would that change things since I'm partially self-employed? And what kind of documentation would you recommend keeping?
That definitely changes things! For the independent contractor work, you can potentially deduct a portion of the karate lessons that corresponds to your self-employment income. So if your 1099 work is 25% of your total income, you might reasonably deduct 25% of your martial arts training. For documentation, keep receipts for all classes, a log of your training hours, and most importantly, documentation showing how these specific skills are used in your contract work. I also keep client contracts that mention security skills required, emails discussing security requirements, and a written explanation of how each training element directly contributes to my services. The more specific you can be about the connection between the training and your security services, the better.
just a helpful hint - i'm a tax preparer and if you decide to deduct these, make sure you're tracking everything meticulously. i've seen too many clients audited for unusual deductions. the karate expense would go on Schedule C if you're a contractor, and you'd need to be able to show it's "ordinary and necessary" for your specific security business (not just helpful). one approach is to only deduct a reasonable percentage based on business use vs. personal benefit. like if you can demonstrate 40% business use, just deduct that portion. way less likely to trigger problems.
One thing nobody's mentioned yet - make sure you discuss who will claim any childcare expenses. My ex and I had a huge issue with this during our separation year. If you're the custodial parent and paid for childcare so you could work, you might qualify for the Child and Dependent Care Credit, which is significant. Also check if you're eligible for Earned Income Credit - the rules get complicated during separation years. And remember that alimony rules changed a few years back - it's no longer deductible by the payer or taxable to the recipient for divorces after 2019.
Thanks for bringing this up! I completely forgot about the childcare expenses. I've been paying for after-school care since we separated. Is there a specific form I need for the childcare credit? And does it matter if we've been splitting these costs or just whoever claims the dependent gets the credit?
You'll need Form 2441 for the Child and Dependent Care Credit. Generally, only the parent who claims the child as a dependent can claim this credit. However, there's a special rule for divorced/separated parents where the custodial parent can claim the credit even if they release the dependency exemption to the non-custodial parent. For expenses you've split, typically only the parent who claims the child can claim the credit for the expenses they personally paid. You can't both claim the same expenses. Keep good records of all payments you've made for childcare, including receipts with the provider's name, address, and tax ID number (EIN or SSN).
A word of warning - my ex and I thought we were being smart by filing separately during our separation. What we didn't realize is that if you file separately, BOTH of you have to either take the standard deduction OR itemize. You can't mix and match where one itemizes and the other takes standard. Also, if your divorce involves transferring property between you (like houses or investment accounts), don't do anything without understanding the tax implications first! Some transfers incident to divorce are tax-free, but timing matters.
Yep, ran into this exact problem. My ex itemized without telling me, so I had to itemize too even though standard would've been better for me. Ended up paying way more in taxes that year. Communication is key, even if it's just through your lawyers.
Don't forget that the IRS HAS to send you a Collection Due Process notice which gives you the right to appeal! This is super important because filing that appeal stops all collection activity while they review your case. You only have 30 days from the date on the letter though, not from when you receive it. I almost missed my window and would have been screwed.
What kind of reasons can you give for an appeal? Do you have to have some special circumstances or can anyone file one?
You don't need special circumstances to request a Collection Due Process (CDP) hearing - it's your right after receiving a final notice. You can appeal based on procedural issues (like if you believe you don't actually owe the tax), propose alternative collection methods (like an installment agreement), or claim financial hardship. Even if you know you owe the tax, requesting a CDP hearing buys you time to get your finances in order while collections are paused. During the hearing, you can propose an installment agreement, an Offer in Compromise, or request Currently Not Collectible status. The important thing is that it stops the immediate threat of a levy while you work things out.
From my experience, you usually get several notices before they actually levy anything. First some billing notices, then warning notices, then the official Notice of Intent to Levy (CP504 or LT11). I ignored all of them like an idiot and they eventually took $3,900 from my checking account. But it wasn't a surprise - they had warned me multiple times over about 6 months.
What happened after they took the money? Did they keep coming after you for more or was that the end of it?
Miguel Castro
Have you tried using the override function in TurboTax? I had a similar issue last year, and there's a way to tell the software to ignore certain validation warnings if you're confident your information is correct. Look for an option like "I'm sure my information is correct, continue anyway" or something similar on the error screen. Sometimes it's hidden behind a "more options" button. This worked for me when I had a situation where my state withholding was calculated differently than federal.
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Zainab Abdulrahman
ā¢Where exactly is this override option? I'm staring at the error screen right now and don't see anything like that. Is it only in certain versions of TurboTax?
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Miguel Castro
ā¢It's not always obvious - look for small text links near the bottom of the error message that say something like "I want to continue anyway" or "Override this warning." Sometimes you have to click on "Why am I seeing this?" first, and then the override option appears. If you're using the downloadable version, it might be under "Tools" ā "Options" ā "Error checking" where you can adjust the sensitivity level. For the online version, sometimes you need to click on a "More options" or "What should I do?" link that expands additional choices.
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Connor Byrne
Before you go crazy with workarounds, double check if you accidentally duplicated some income on your state return that's not on your federal. I made this exact mistake - entered my W-2 income twice on my California return but only once on federal. Drove me nuts for days until I spotted it!
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Yara Elias
ā¢This!! I had the same issue. Check if you accidentally entered a 1099 or W-2 twice in the state section. TurboTax's interface makes this so easy to do by accident.
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