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Has anyone dealt with the "reasonable compensation" issue with an S-Corp? I'm getting conflicting advice from different accountants about how much I need to pay myself vs take as distributions.
That's because there's no hard and fast rule. I went through an audit last year for my S-Corp and the IRS looked at industry standards for my profession. They compared my salary to what others in my field typically make with similar experience. My advice: document WHY you chose your salary amount based on research you've done on comparable positions. That documentation saved me during my audit.
For graphic design specifically, I'd recommend checking the Bureau of Labor Statistics Occupational Employment and Wages data for "Graphic Designers" in your geographic area. The IRS often references BLS data during audits as it's considered authoritative government data. I also used Glassdoor and PayScale to document salary ranges, but made sure to filter by experience level and location. The key is showing you did your homework - I created a simple spreadsheet with 5-10 comparable positions and their salary ranges, then documented why I chose a specific amount within that range based on my experience and responsibilities. One thing that helped during my audit was showing that my total compensation (salary + distributions) wasn't unreasonably low compared to what an independent contractor in my field would charge for the same work. The IRS wants to see that you're not just minimizing salary to avoid employment taxes, but that there's genuine business reasoning behind your compensation structure.
To answer your second question about why we pay taxes on gross vs net - it's because the tax system is designed so that deductions are controlled by tax policy. If we taxed true "net" (after all your expenses), people would claim all sorts of personal expenses as deductions. Instead, the system defines specific deductions that are allowed (mortgage interest, certain business expenses, etc.) and everything else is considered part of your taxable income. It's not perfect, but it creates a more standardized system.
Thanks for explaining! I guess that makes sense when you put it that way. I was thinking of "net" as just what's left after pre-tax deductions like 401k and health insurance, but you're right that it could get really complicated if everyone defined their own version of "net income" for tax purposes. Is there any way to reduce what's in Box 1 besides the standard pre-tax deductions? I feel like I'm paying way more than I should.
Definitely! The most common ways to reduce your Box 1 wages are increasing your 401(k) or other retirement plan contributions, contributing to an HSA if you have a qualifying health plan, and taking advantage of other pre-tax benefits your employer might offer like dependent care FSAs, commuter benefits, or education assistance programs. If you're self-employed or have side income, there are even more options available like SEP IRAs and solo 401(k)s with much higher contribution limits. The key is finding deductions that actually benefit you in multiple ways - retirement contributions not only lower your taxable income now but also help you save for the future.
Box 1 on W-2 isn't actually gross or net - it's somewhere in between. It's your earnings minus pre-tax deductions like 401k, health insurance, HSA, etc. But it's not your take-home pay either because it's before federal/state/local taxes are withheld. The true gross income (what you earned before ANYTHING was taken out) isn't directly shown on a W-2. Box 3 and 5 are closest but even those might have some deductions taken out.
This is actually the clearest explanation I've seen. No wonder I'm always confused! Is there anywhere on the W-2 that shows what your actual take-home pay for the year was? Or do you have to add that up from paystubs?
The W-2 doesn't show your actual take-home pay anywhere - you'd need to add it up from your paystubs or calculate it yourself. Your take-home would be Box 1 minus federal taxes withheld (Box 2), state taxes (Box 17), Social Security tax (Box 4), Medicare tax (Box 6), and any other deductions like union dues or voluntary life insurance that aren't pre-tax. It's kind of annoying that there's no single box that just says "this is what you actually received in your bank account" but I guess the W-2 is designed more for tax purposes than personal budgeting.
I think there's another major issue with your strategy that no one's mentioned yet. It assumes you can accurately predict which stocks will rise and which will fall. Even professional fund managers struggle with this consistently. What happens if 70% of your picks fall and only 30% rise? Or if they all rise but in different proportions than expected? Your whole strategy depends on having enough losses to harvest when needed, but the market doesn't conveniently provide those when tax time comes around. I've had years where almost everything in my portfolio went up (great for returns, terrible for tax harvesting) and other years where I had plenty of losses but not enough gains to offset!
Great discussion everyone! As someone who's been implementing tax-loss harvesting for a few years, I wanted to add a practical perspective on timing and execution. One thing that's helped me is thinking about this strategy in quarters rather than just at year-end. I review my positions every 3 months to identify harvesting opportunities throughout the year. This helps avoid the December rush when everyone is doing the same thing (which can actually move prices unfavorably). Also, consider using broad market ETFs for your diversified positions instead of individual stocks. Something like VTI or ITOT for your "winner" bucket gives you instant diversification without the stock-picking risk that Romeo mentioned. Then you can use sector ETFs or individual stocks for more targeted loss harvesting when opportunities arise. The key insight I've learned is to make investment decisions first, tax decisions second. Don't let the tail wag the dog - if you have a great long-term position that happens to be down, don't sell it just for tax harvesting if you believe in the underlying investment thesis. One last tip: keep a spreadsheet tracking your wash sale windows. Nothing worse than accidentally triggering the wash sale rule and losing your tax benefit!
One thing nobody's mentioned - there's a potential workaround here. If her parents agree not to claim her (maybe because you're providing more support), they can file Form 8332 which releases their claim. This is usually used for divorced parents but can work in other situations too. My brother and his girlfriend worked this out with her parents - they calculated everything and determined he provided 48% of support while her parents provided 52%. But since he needed the tax break more as a young professional with student loans, her parents agreed to sign the form and let him claim her.
Is Form 8332 really applicable here? I thought that was specifically for custodial parents releasing a claim on their child to a non-custodial parent? Not sure it applies to non-child dependents.
You're right - I double-checked and Form 8332 is specifically for children of divorced/separated parents. My mistake! What my brother actually used was just a signed statement from her parents stating they wouldn't claim her that year, which they kept for their records in case of audit. The better approach is to properly calculate support and have the qualifying person make the claim. If it's close to 50/50, sometimes families do informally agree to alternate years, but there's no specific form for that with non-child dependents - just good documentation of the support calculation.
Don't forget there are two types of dependents: qualifying child and qualifying relative. GF would fall under qualifying relative, which means: 1. They don't need to be related if they lived with you all year 2. Their gross income must be under $4,700 3. You must provide over half of total support 4. They can't be claimed as a qualifying child by someone else The support test is the big one. Calculate EVERYTHING: - Housing (fair rental value of space) - Food - Utilities - Medical/dental - Education - Clothing - Transportation Car insurance, health insurance and phone are definitely part of support calculation, so add those to her parents' side.
Wait so even tho she's 22, her parents can still claim her as a "qualifying child" if she's a student? I thought there was an age limit?
Good catch! For qualifying child, the age limit is under 19, or under 24 if they're a full-time student. Since the girlfriend is 24 and still in school, she could potentially be claimed as a qualifying child by her parents IF she meets all the other tests (relationship, residency, support, joint return). But here's the key - if her parents can claim her as a qualifying child, then she can't be claimed as a qualifying relative by anyone else, even if they provide more support. That's the "tie-breaker" rule. So OP needs to first determine if the parents have a valid qualifying child claim before even calculating the support test for qualifying relative status. This is why having that conversation with her parents is so important - they need to figure out who has the stronger claim under which category.
Millie Long
One thing to be careful about with Section 1256 contract losses - make sure your client actually has "true" Section 1256 contracts. I had a situation where a client thought they had these contracts but they were actually just regular non-equity options that don't qualify for the special treatment. True Section 1256 contracts include regulated futures contracts, foreign currency contracts, non-equity options (broad-based indices), dealer equity options, and dealer securities futures contracts. If they were trading standard equity options on individual stocks, those wouldn't qualify.
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Eli Wang
ā¢Thanks for bringing this up! That's a good point. My client was trading futures contracts through a major brokerage, so they should qualify as true Section 1256 contracts. But I'll double-check their trading records to make sure everything is properly classified before proceeding with any carryback. Do you know if the brokerage typically designates which trades were Section 1256 contracts on their year-end statement? Or is that something I need to determine manually by looking at each transaction?
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Millie Long
ā¢Most major brokerages will identify Section 1256 contracts on their year-end tax statements, usually in a separate section specifically for these types of trades. They're reported differently because of the required 60/40 split between long-term and short-term capital gains treatment. If you don't see that clear designation, you might need to go through transaction by transaction. Regulated futures contracts, certain foreign currency contracts, and broad-based index options (like options on the S&P 500 index) are the most common Section 1256 contracts. Individual stock options aren't included, which is where many people get confused.
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KaiEsmeralda
Just to add another wrinkle to this discussion - don't forget about the Section 1256 election under 1256(d) that lets traders avoid the 60/40 split and mark-to-market rules for certain hedging transactions. If your client was using these contracts as hedges for their business rather than for speculation, they might qualify for this election, which would change how the losses are treated.
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Debra Bai
ā¢Can you explain what you mean by "hedging transactions" in this context? My husband has a small business importing goods from overseas and uses currency futures to lock in exchange rates. Would those qualify as hedging rather than speculation?
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Isaiah Thompson
ā¢Yes, currency futures used to lock in exchange rates for your husband's import business would typically qualify as hedging transactions! These are legitimate business hedges designed to reduce foreign exchange risk rather than speculative trading. For Section 1256 contracts used as hedges, the business can elect under Section 1256(d) to treat these transactions as ordinary business income/loss rather than capital gains/losses subject to the 60/40 split. This election must be made by the due date of the return (including extensions) and applies to all hedging transactions for that year. The key requirements are that the transactions must be: (1) entered into in the normal course of business primarily to manage risk, (2) clearly identified as hedging transactions in the business records before the close of the day they were entered into, and (3) the hedged risk must be with respect to ordinary property or ordinary obligations. Currency futures for import/export businesses are classic examples of qualifying hedges. Your husband should definitely consult with a tax professional about making this election if it would be beneficial.
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