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Nia Jackson
One thing that hasn't been mentioned yet - you should also be aware that your W-2 job will handle the employer portion of Social Security and Medicare taxes (7.65%). With your 1099 income, you pay the full 15.3% as self-employment tax. So even if the income tax withholding seems comparable, you're actually paying less in total taxes on your W-2 earnings compared to the same amount of 1099 income. This is why some people prefer W-2 jobs even if the stated pay is a bit lower.
Omar Hassan
ā¢That's a really good point! So with my W-2 job, I'm actually saving that 7.65% that I'd otherwise have to pay if it were 1099 income? Does this mean I should try to increase my W-2 hours rather than taking on more photography clients if I want to maximize my after-tax income?
Nia Jackson
ā¢Yes, you're saving that 7.65% on every dollar of W-2 income compared to 1099 income. Whether you should increase W-2 hours vs. taking more photography clients depends on several factors. If both pay roughly the same hourly rate before taxes, then yes, you'd keep more of your W-2 earnings after tax. However, if your photography business pays significantly more per hour, or if you can deduct legitimate business expenses, self-employment might still be more profitable despite the higher tax rate. Also consider that your photography business might have growth potential that your W-2 job doesn't.
NebulaNova
Don't forget about the W-4 form! When you started your W-2 job, you filled one out to tell your employer how much to withhold. If you're worried about owing a lot at tax time, you can submit a new W-4 and have additional money withheld from each paycheck to cover taxes on your 1099 income too.
This is what I do! Instead of making quarterly payments for my side gig, I just have my day job withhold extra. You can put a specific dollar amount on line 4(c) of the W-4. Super convenient.
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This sounds a lot like what the IRS calls "not engaged in for profit" activities. I'm not a tax pro, but I've dealt with this. To be blunt, I think your accountant's advice is questionable. The key issue is whether your LLC has a genuine profit motive as its primary purpose. The fact that you're using it to increase your W-2 income rather than generate its own profit is problematic. The IRS usually expects to see a profit in 3 out of 5 consecutive years. You might want to consider restructuring this arrangement - maybe have your LLC bill your employer directly for the marketing services? That would establish a clearer business purpose and direct income stream.
Would it make a difference if OP created detailed documentation showing that the business plan is to eventually transition to serving clients directly? Like showing a 3-5 year plan with projections for when the LLC would start generating its own income? I'm wondering if having that kind of evidence of profit motive would help.
Yes, having detailed documentation would definitely help. The IRS looks at nine factors when determining if an activity is engaged in for profit, and one of those is whether you operate in a businesslike manner with complete and accurate records. A formal business plan with realistic projections showing a path to profitability is great evidence of profit motive. Also helpful would be documentation showing how specific marketing activities connect to potential future income. Just make sure the plan is realistic and that you're actually following it - the IRS will be skeptical of plans that seem designed just to justify tax deductions.
I think everyone is missing that this is actually a Schedule C issue, not really an LLC issue. Since a single-member LLC is a disregarded entity, you're filing a Schedule C with your personal return. The real question is: can you deduct these business expenses on Schedule C when they're indirectly increasing your W-2 income rather than generating Schedule C income? The answer is complicated. You'd need to prove you have a legitimate business (not a hobby) with a clear profit motive. The fact that you intend to eventually serve these clients directly might help establish that. But I think there's a more immediate problem: the expenses you're incurring need to be ordinary and necessary for YOUR business. If your business doesn't have income yet, the IRS might question how these expenses are necessary for a non-existent business rather than just supporting your employment.
That makes sense. So what if OP restructured to have the LLC provide marketing services directly to their employer? Would that create a cleaner separation and establish the LLC as a legitimate business with its own income stream?
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One thing nobody's mentioned yet - if you win big on certain games (slot machines, bingo, poker tournaments, etc.) and the winnings are above certain thresholds, the casino might withhold federal income tax immediately (usually 24%). This is separate from whether they issue a W-2G. Check if any of your bigger wins had taxes already withheld because you'll want to claim that on your return.
Connor Byrne
ā¢Is there a simple way to calculate how much I should set aside for taxes on my gambling winnings throughout the year? I'm worried about getting hit with a big tax bill next April.
For most people, setting aside about 30% of your net gambling profits should cover the federal taxes, but you should also account for state taxes if your state has income tax. Remember that gambling winnings are added to your other income, so they're effectively taxed at your highest marginal tax rate. If you're already in a higher tax bracket from your regular job, your gambling winnings could be taxed at 32% or higher federally. It's always better to set aside too much than too little - you can always keep the extra if you overestimated.
Yara Elias
Just a heads up, I'm a regular poker player and one big mistake I see new players make is not tracking sessions properly. The IRS allows poker players to track by session (meaning you can combine wins and losses from the same day at the same casino/site) which is usually better than reporting each hand separately. But sports betting is different - you have to report each winning bet separately, not as a session. This tripped me up my first year.
Could you expand on what counts as a "session" for online poker? If I play multiple sit-n-gos in one day on the same site, is that all one session? Or is each tournament separate?
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Isabel Vega
I'm actually a freelancer who files Schedule C and this exact thing happened to me 2 years ago. One of my clients didn't send a 1099-NEC for about $800 of work and then included it on the next year's form. Here's what I did: I reported ALL the income in the year I actually received it (keeping my own records as proof), then when they incorrectly issued the 1099 the following year, I contacted them immediately with proof of when I was paid. They issued a corrected 1099-NEC for both years. It was annoying but fixable!
Did you have any issues when filing your taxes the following year when the incorrect 1099 showed up? I'm worried the IRS computers will automatically flag a mismatch if the client reports it wrong next year.
Isabel Vega
ā¢I did have a small issue the following year - I received a letter from the IRS asking about "unreported income" because the amounts didn't match. I responded with a letter explaining the situation and included my proof (bank statements showing the deposit date in the previous year, copies of invoices, and screenshots of the payment confirmations). I also included documentation showing I had already reported and paid taxes on that income in the correct previous tax year. The IRS accepted my explanation and documentation, and the matter was resolved without penalties. That's why keeping detailed records is so important in these situations.
Everyone's focusing on reporting the income (which is correct), but don't forget the client is actually making a mistake that could cause THEM problems too. The IRS requires payers to issue 1099-NECs for the calendar year when payment was actually made. If they paid you in 2024, they legally need to issue the form for 2024, not 2025. Maybe explain this to them? They could face penalties for incorrect reporting.
This is an excellent point! The client might not realize they're setting themselves up for potential issues. The IRS can penalize businesses for failing to file required information returns or filing incorrect ones.
Andre Dubois
just wanna add that CP2000s often have a "respond by" date that's usually 30 days from when they sent it. make sure you don't miss this deadline!!! if u need more time u can call and ask for an extension but they're not required to give u one. speaking from experience, trust me u don't want the headache of dealing with an expired notice š©
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CyberSamurai
ā¢And make SURE you send it certified mail with return receipt if you're mailing your response! I learned this the hard way when the IRS claimed they never received my response to a similar notice.
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Zoe Alexopoulos
Don't overlook the possibility that this could be a scam. Real IRS notices have a notice number, info about your rights as a taxpayer, and never ask for gift cards or wire transfers. The IRS also doesn't initiate contact through email, text or social media. If you're unsure if it's legitimate, you can call the IRS directly at 800-829-1040 to verify.
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Zara Khan
ā¢It definitely came through regular mail with all the official letterhead and notice numbers. I'm pretty sure it's legit - just confusing! Thanks for looking out though. I've heard about those scams where they call and threaten to arrest you if you don't pay with gift cards right away.
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