For golf influencers, I'd recommend establishing clear documentation standards from the start. Create a simple spreadsheet tracking each equipment purchase with columns for: purchase date, item description, cost, content where it was featured, and revenue attribution. The IRS looks favorably on taxpayers who can demonstrate a clear business purpose and profit motive. If your client is genuinely making income from this content and treating it as a business (not just a hobby), equipment purchases are much more defensible. One thing to watch out for: make sure they're not double-dipping by deducting equipment they later sell or give away. If they do equipment reviews and then sell the clubs, that sale price should be reported as income, and the original purchase becomes cost of goods sold rather than a business expense. Also consider depreciation for expensive items like club sets - depending on how long they plan to use them for content creation, it might be better to depreciate over several years rather than expense everything in year one.

One additional consideration I haven't seen mentioned yet - if your client does equipment reviews and receives free golf clubs/equipment from manufacturers for testing, they need to report the fair market value of those items as income. This actually strengthens the business expense argument for equipment they purchase themselves, since it demonstrates the review/testing activity is clearly income-generating. I'd also suggest having them maintain a content calendar that shows planned equipment purchases tied to upcoming video concepts. This proactive approach demonstrates business planning rather than just deducting personal golf expenses after the fact. For audit protection, consider having them sign a brief memo each time they purchase equipment outlining the intended business use. Something like "Purchased TaylorMade driver set for upcoming 'Best Drivers Under $500' video series, planned filming dates X-Y." Takes 30 seconds but creates contemporaneous documentation of business intent.

Has anyone here actually gotten audited specifically about S Corp health insurance treatment? I'm curious what the real-world risk is. I've been just paying health insurance personally and taking the self-employed health insurance deduction without running it through my S Corp payroll at all... which I'm now realizing might be incorrect after reading this thread.

Thanks for sharing your audit experience - that's exactly the kind of real-world insight that's helpful! It sounds like the IRS is definitely paying attention to this area. For anyone in a similar situation to @Sasha Ivanov, you'll want to correct this for future years. The proper flow should be: S Corp pays or reimburses health insurance premiums → those amounts get added to your W-2 as wages (but not subject to FICA/FUTA) → you then take the self-employed health insurance deduction on your personal return. Just paying personally and taking the deduction skips the crucial W-2 reporting step that the IRS expects to see. It's one of those things that might fly under the radar for a while, but if you do get audited, it's an easy thing for them to catch since the deduction on your personal return won't match up with any corresponding W-2 wages. The good news is this is usually fixable by amending prior year returns if needed, though you'll want to consult with a tax professional about the best approach for your specific situation.

This is a complex situation that requires careful attention to both timing and documentation. Given that you operated for nearly 3 months before the LLC was legally formed, you'll definitely need to address the pre-formation period separately from your QSub election timing. For the Form 8869, March 25th (your LLC formation date) is indeed the earliest possible effective date you can request. Since the deadline for that would have been June 9th, you'll need to file for late election relief under Rev. Proc. 2013-30. The good news is that the IRS is generally reasonable about granting relief for first-time filers who can demonstrate reasonable cause. A few critical steps you should take: 1. Prepare a reasonable cause statement explaining why you missed the deadline - unfamiliarity with the requirement is typically acceptable 2. Mark your Form 8869 clearly with "FILED PURSUANT TO REV. PROC. 2013-30" 3. Create formal assignment documentation for those $15,000 in pre-formation transactions 4. Verify your LLC operating agreement doesn't create multiple membership classes (which would disqualify QSub status) The pre-formation activities will need to be properly transferred to the LLC through an assignment agreement, and you'll want to ensure proper basis tracking for when everything eventually consolidates at the S-Corp level. Consider having both your attorney and accountant review the documentation to avoid any issues down the road. Don't let the complexity discourage you - these situations are more common than you might think, and with proper documentation and filing, you should be able to get everything straightened out.

I've been following this discussion and wanted to add a practical perspective from someone who went through a very similar situation last year. The advice about requesting late election relief is spot-on - don't try to work around it with a current effective date because that creates more complexity than it's worth. One thing I'd emphasize is to be very thorough with your documentation package when you submit Form 8869. Include copies of your LLC formation documents, your S-Corp documentation showing it owns 100% of the LLC, and a detailed timeline of events. The IRS processor reviewing your request will appreciate having everything in one place rather than having to ask for additional information. Also, when you're preparing that assignment agreement for the pre-formation activities, make sure it specifically addresses any equipment or assets you purchased during that January-March period. If you bought a computer, office supplies, or other business assets with personal funds during that time, those need to be properly transferred to the LLC with appropriate basis adjustments. The reasonable cause statement doesn't need to be elaborate - I used something simple like "Taxpayer was unaware of the QSub election filing requirement and deadline due to inexperience with entity taxation requirements" and it was accepted without issue. The key is being honest and straightforward rather than trying to craft some complex legal argument. Budget some time for this process - between preparing the documentation, getting everything reviewed, and potentially following up with the IRS, it took me about 2-3 months to get everything finalized. But it's definitely worth doing correctly rather than trying to shortcut it.

I'm going through the exact same thing right now! Just got my first paycheck last week and had the same panic seeing how much was taken out. Reading through this thread has been so reassuring - I thought I was the only one completely lost by all these deductions. Those abbreviations are absolutely terrible! Why can't they just say "Social Security" and "Medicare" instead of making us decode "OASDI/EE" and "MED/EE"? It's like they're trying to make it as confusing as possible. Based on everyone's advice here, I'm definitely going to check out that IRS withholding calculator this weekend. My federal withholding also seems way too high - I think I got scared during orientation and accidentally had them withhold extra money "just to be safe." Now I realize I'm basically giving the government a free loan when I could be using that money for rent, groceries, or actually starting to save! Thanks to everyone who shared their experiences - it makes me feel so much better knowing that paycheck shock is totally normal and that there are actually tools to help us figure this stuff out. Why don't they teach any of this in school?!

I totally feel your pain! When I got my first real paycheck, I had the exact same reaction - I actually called my mom thinking there was some kind of mistake because nearly 30% was gone. Those abbreviations are seriously the worst - I spent like an hour googling "OASDI/EE" because I thought it was some weird company-specific deduction! Everyone's already given you amazing explanations about what those taxes actually are, but I wanted to add that your situation is super fixable. That $392 federal withholding on a $2300 gross definitely seems too high for someone at your income level. I made a similar mistake on my W-4 - I was so paranoid about owing money at tax time that I basically told them to withhold extra "just in case." The IRS withholding calculator that everyone keeps mentioning literally saved me about $200 per month once I figured out how to use it correctly. And don't worry about looking clueless when you talk to HR about updating your W-4 - they deal with this stuff constantly and are usually really helpful. The silver lining is that if you've been over-withholding, you'll get all that extra money back as a refund. But you're absolutely right to want to fix it so you can actually use that money for rent, groceries, and maybe even start building an emergency fund instead of giving the government a free loan!

I'm dealing with a very similar situation this year - minimal income in Q1-Q3 and then a large retirement account rollover in Q4. Reading through all these responses has been incredibly helpful, especially the clarification about Form 1040-ES vs Form 2210. One thing I'm still confused about though - when you have zero or minimal income in the early quarters, do you need to formally notify the IRS that you're not making payments for those quarters, or do you just... not pay anything? I keep worrying that not sending in any payment vouchers will somehow trigger a penalty, even though my calculations show I don't owe anything for those periods. Also, has anyone here dealt with the situation where your "lumpy" income pushes you into a higher tax bracket for the year, but only for that final quarter? I'm trying to figure out if the annualized method properly accounts for the progressive tax rates when most of your income hits in one quarter.

This thread has been incredibly helpful! I'm in a similar boat with uneven income this year. One additional consideration I wanted to mention for anyone dealing with retirement account conversions or rollovers - make sure you understand the timing rules for when the income is considered "received" for estimated tax purposes. For traditional IRA to Roth conversions, the taxable income is generally considered received on the date of the conversion, not when you originally contributed to the traditional IRA. This matters for the annualized method calculations because it determines which quarter the income gets allocated to. Also, if you're doing a series of smaller conversions throughout the year to manage your tax bracket (rather than one large conversion), you'll need to track each conversion date separately for your quarterly calculations. I learned this the hard way when I assumed I could just lump all my conversions into one quarter for simplicity. The documentation advice from Hugh Intensity is spot on too - keep records of every conversion date and amount. Your brokerage should provide statements showing the exact dates, but it's worth keeping your own spreadsheet as backup.