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Do NOT skip filing!! I did that for 2 years when I first started freelancing and it was the worst financial mistake ever. By the time the IRS caught up with me (they always do), my original $4k tax bill had ballooned to over $9k with penalties and interest. Plus they can hold your future refunds, put liens on your property, and even levy your bank accounts if you ignore them long enough. The stress of wondering when they'd come knocking was horrible. Just file and set up a payment plan - it's super easy online and the minimum payment can be as low as $50/month depending on how much you owe. Way better than the alternative!
Was there any trouble with the IRS beyond the financial penalties? Like did they treat you differently or make things harder because you skipped filing?
No actual trouble beyond the financial hit, but they did put me on a shorter leash for a few years. They processed my refunds more slowly the next couple years and seemed to scrutinize my returns more carefully. I also couldn't qualify for their streamlined payment plans for a while - had to provide more financial documentation. The biggest issue was honestly just the unnecessary stress and the fact that I ended up paying more than double what I would have if I'd just filed on time and set up a payment plan from the start. The interest and penalties stack up way faster than most credit cards.
Another option nobody's mentioned - you could file your taxes on time but pay with a credit card. The processing fee is around 2%, which is probably less than the IRS penalties would be. Then you can continue with your debt payoff strategy while avoiding IRS penalties. Not ideal to add to credit card debt, but if you're close to paying off your cards anyway and the interest rate on the remaining one isn't terrible, it might be mathematically better than IRS penalties + interest.
This is actually not a terrible idea if you can qualify for a 0% intro APR card. I did this last year - got a card with 15 months at 0%, paid my taxes, then focused on paying off the card before the intro period ended. Saved me a bunch compared to the IRS installment plan interest rates.
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Your tax changes sound good, but don't forget to look at your state withholding too! I made the mistake of only adjusting my federal withholding when I got a raise last year, and ended up owing $1,200 to my state while getting a federal refund. The W-4 changes don't automatically adjust your state withholding in many states.
Andre Moreau
ā¢That's a really good point! How do you figure out the right amount for state though? Is there a calculator similar to the IRS withholding calculator?
Most states do have their own withholding calculators on their department of revenue or taxation websites. Just search for "[your state] withholding calculator" and you should find it. Some states like California and New York have particularly good calculators that will help you determine the right withholding amount based on your specific situation. If your state doesn't have a good calculator, a general rule of thumb is to withhold about 5-7% of your income for state taxes in high-tax states, or 3-5% in moderate-tax states, though this varies widely depending on your income level and state tax structure.
Zoe Stavros
Has anyone actually tried doing a projection with real numbers? I'm in a similar situation and wondering if I should pay someone to do this or use one of those tax planning spreadsheets I see online.
Jamal Harris
ā¢I've used https://smartasset.com/taxes/income-taxes to get a rough estimate. It's free and lets you play with different scenarios. Not super detailed but gives you a general idea of how changes affect your tax bill.
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Mei Wong
Check Box 7 on your 1099-R! That's the distribution code and it determines how the withdrawal is taxed. If it's code "G" for example, it means it was a direct rollover to another retirement account and not taxable. Also look at Box 2a to see if there's a taxable amount. If it shows $0, that might explain why TurboTax is saying you don't need to report it (though you still need to include the form on your return even if the taxable amount is zero).
AstroAce
ā¢Thanks for this tip! I just checked and Box 7 on my form has code "P" and Box 2a shows $0 as the taxable amount. Any idea what code P means? Could that be why TurboTax is telling me to file it next year?
Mei Wong
ā¢Code "P" is used for periodical payments from qualifying plans. If Box 2a shows $0 taxable amount, that would explain why TurboTax is saying you don't need to report it as income this year. However, even with a $0 taxable amount, you still need to include the 1099-R on your return. The software might be trying to tell you that you don't need to pay taxes on it this year, not that you should omit the form entirely. I'd suggest continuing through the TurboTax process - at some point it should ask you to enter the 1099-R information even if the amount isn't taxable.
Has anybody else noticed TurboTax has been extra glitchy this year? I had a similar issue with my 1099-R where it kept telling me conflicting things about when to file it. Ended up switching to FreeTaxUSA and everything worked fine there.
Amara Okafor
ā¢YES! TurboTax kept giving me weird prompts about my retirement distribution too. Switched to H&R Block online and it handled my 1099-R correctly right away. Something seems off with TurboTax this year.
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Zara Malik
One angle you might want to consider is having the foreign partner's LLC elect corporate status (Form 8832) AND then have that corporation qualify for benefits under an applicable tax treaty. Depending on the foreign partner's country of residence, this might reduce withholding rates. For example, if your foreign partner is from a country with a favorable tax treaty with the US (like the UK), a properly structured corporation might qualify for reduced withholding rates on certain types of income. However, this gets complicated fast because you need to consider: 1) Corporate tax at the US entity level 2) Withholding on distributions to the foreign owner 3) Branch profits tax considerations 4) Potential for treaty shopping challenges from the IRS
Thanks for this suggestion! Do you know if taking this approach creates any issues with the foreign partner's home country taxation? I'm concerned about creating unintended tax consequences for them.
Zara Malik
ā¢The impact on home country taxation depends entirely on which country your partner is from. Every country has different rules for how they tax their residents on foreign income, and how they treat entities that are disregarded or classified differently in the US tax system. For instance, if your partner is from a country with a territorial tax system, they might not face additional tax on US business income. But if they're from a country with a worldwide tax system, they'll likely need to report the income regardless of the structure, though foreign tax credits may be available to offset double taxation.
Luca Greco
I tried something similar a few years ago with a German partner in our consulting firm. We created a Wyoming LLC owned by the German individual, and had it be the official partner in our partnership instead of the German person directly. Our tax advisor initially thought this would work, but then we got a notice from the IRS saying we still needed to withhold under Section 1446 because the LLC was a disregarded entity. We ended up having to file amended returns and pay penalties and interest for the missed withholding. The IRS specifically cited Treasury Regulation 1.1446-3 which basically says they look through disregarded entities to the ultimate owner for withholding purposes. So based on my expensive lesson, your idea probably won't work unless the LLC elects to be treated as a corporation.
Nia Thompson
ā¢Our partnership faced this exact issue! Did you consider having the LLC elect corporate status? We're currently evaluating that option but concerned about the additional tax burden.
GalacticGuru
My brother got audited for not reporting his side business income (about $12k yearly from personal training). The penalties and interest ended up being way more than if he'd just paid the taxes originally. Plus he had to go back and try to recreate expense records from 2 years earlier which was a complete nightmare.
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Ethan Taylor
ā¢How did they catch him? Was it also through payment apps or did someone report him?
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GalacticGuru
ā¢It was actually through social media. He was advertising his training services on Instagram and Facebook, and someone (probably a competitor) reported him to the IRS. They have a whistleblower program where people can report suspected tax fraud. Once they started looking into him, they found the payment app transactions didn't match his reported income. It was really stressful for him, and he ended up having to hire a tax professional to help sort everything out, which was another expense on top of the penalties.
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Amara Nnamani
Does anyone know if buying equipment (like small soccer goals, training cones, etc.) would count as business expenses? I've spent like $600 on stuff for my similar setup.
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Giovanni Mancini
ā¢Yes! All of that counts as business expenses. Keep your receipts though. Also track mileage if you drive to buy supplies or meet clients anywhere outside your home. That adds up fast at the current deduction rate.
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