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Has anyone run into issues with the hobby loss rule with something like D&D sessions? I'm worried the IRS might consider my similar side gig a hobby rather than a business.
The key to avoiding the hobby loss rule is showing that you're running your D&D sessions as a business with the intent to make a profit. Keep good records, have separate business accounts, track all expenses properly, create a business plan, and be professional about how you operate. The IRS generally uses a "3 out of 5" guideline - if you show a profit in 3 out of 5 consecutive years, they typically consider it a legitimate business. Since OP mentioned they were "hit hard with taxes," it sounds like they're profitable, which helps their case significantly.
That makes sense, thanks! I've been profitable 2 of the last 3 years, so I think I'm on the right track. I do have separate tracking for all my game master income and expenses, but I should probably open a dedicated bank account to make it even clearer.
I went through the S-Corp route with my freelance writing business and can confirm it saved me several thousand in self-employment taxes, BUT - and this is a big but - it only made sense once I was consistently making over $70k. The accounting and filing fees cost me about $1,200/year plus the extra time dealing with payroll. Stick with Schedule C for now, maximize your legitimate deductions, and revisit the business structure question when your income grows. The tax savings need to outweigh the additional costs and complications.
Anyone try TaxAct? They have HSA forms and actually do efile for real. I've used them for years with no problems and they're cheaper than TurboTax. Just a suggestion for next year.
Thanks for the recommendation! I've heard good things about TaxAct from a coworker too. Did you find their interface easy to use? I'm not super tax-savvy and need something that explains things clearly.
Their interface is pretty straightforward and they explain tax concepts in plain English. They use a question-based approach that helps catch things like HSA contributions without you needing to know which specific forms are required. The help sections are quite clear with examples, and if you get stuck, they have decent customer support through chat. For someone who isn't tax-savvy, they offer good guidance without overwhelming you with jargon. Their review system also catches common errors before you file.
I had a simular issue with that same software!!! They also missed my student loan interest deduction completely. I ended up disputing the charge with my credit card company and got a full refund. Then I used FreeTaxUSA which was actually free for federal filing and only $15 for state. They had all the right forms including 8889 for HSA stuff.
Since this hasn't been mentioned yet - you should know that profit sharing contributions are completely discretionary year to year, which is incredibly valuable for professional practices with fluctuating income. Some years you can contribute the full 25%, other years you can reduce or skip it entirely depending on cash flow. Also, make sure the plan documents are properly amended to include the profit sharing component. This is something your plan administrator needs to handle formally - you can't just start making profit sharing contributions without updating the plan design. One thing your CPA might not have emphasized: the timing of cash flow matters. The S Corp needs sufficient profits distributed from the LLC to make these contributions. Planning the timing of distributions from LLC to S Corp becomes important if you want to maximize these retirement contributions while maintaining adequate operating capital.
Thanks for this insight. The discretionary nature is really appealing since her income can vary quite a bit. Do you know if there's a deadline for deciding whether to make a profit sharing contribution for the current tax year? Like could we wait until March 2025 to decide about 2024 contributions?
You can actually wait until your S Corp's tax filing deadline including extensions to make the profit sharing contribution for the prior year. So for 2024 contributions, if your S Corp files for an extension, you could have until September 15, 2025, to make the decision and the actual contribution. This flexibility is one of the biggest advantages of profit sharing plans for professionals with variable income. Just make sure the plan documents are amended before the end of the plan year in which you first want to make profit sharing contributions. The plan has to allow for profit sharing before you can actually make those contributions.
Wait, I'm confused about something! You said the LLC already handles your wife's regular 401K contribution before the money reaches the S Corp. Does that mean she's technically an employee of the LLC rather than the S Corp? Because that would change everything about how this works. If she's getting a W-2 from the S Corp (which it sounds like she is), then the LLC shouldn't be handling any 401k deductions - that should all be happening at the S Corp level. The way you described it sounds like there might be a potential compliance issue with how things are currently structured.
Another option worth exploring is a mega backdoor Roth if your employer plan allows after-tax (not Roth) contributions and in-service distributions or in-plan Roth conversions. The limits are much higher than regular backdoor Roth - you could potentially put away $40k+ extra beyond your regular 401k limit. Not all plans offer this though, so check with your HR or benefits department. The key words to ask about are "after-tax contributions" (different from Roth) and either "in-plan Roth conversions" or "in-service distributions.
Would I have to pay taxes on the conversion from after-tax to Roth though? I'm confused about how this is different from just doing a backdoor Roth IRA.
You only pay taxes on the growth between the time you make the after-tax contribution and when you convert it to Roth. If you convert frequently (some plans even allow automatic conversions), this tax amount is minimal. The main difference from a backdoor Roth IRA is the amount you can contribute. A backdoor Roth IRA is limited to $7,000 per year (2025 limit for those under 50). With the mega backdoor Roth, you could potentially contribute up to around $43,500 more (the exact amount depends on your plan and the total annual 401k limit of $70,000 for 2025 minus your regular contributions and employer match).
Something nobody has mentioned - simple taxable brokerage account might actually be better in some cases? I use one alongside my 401k. The benefits: no contribution limits, complete flexibility to withdraw anytime without penalties, and long-term capital gains tax rates (which are lower than ordinary income rates for most people). Plus you can tax-loss harvest during market downturns, which isn't possible in retirement accounts. Just buy tax-efficient ETFs that don't distribute much in dividends and hold long-term.
Great point about the flexibility! But don't you lose a lot to taxes on dividends and capital gains compared to Roth growth that's completely tax-free?
Zachary Hughes
Another thing to consider - if your child has earned income, you might want to help them open a Roth IRA! They can contribute the lesser of their earned income or $6,500 (2025 limit). Since your child probably has a low tax rate now, a Roth can be an amazing long-term investment vehicle. I started my daughter on this when she got her first 1099 income at 15, and she's already building a nice nest egg. Just make sure the income is legitimate and documented in case the IRS questions it.
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Admin_Masters
ā¢That's a great idea! I hadn't even thought about retirement accounts. Would we need to wait until after we file taxes to open the Roth IRA, or can we do it now based on the 1099 amount?
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Zachary Hughes
ā¢You can open and fund the Roth IRA anytime between January 1, 2025 and the tax filing deadline (usually April 15, 2026) for the 2025 tax year. You don't need to wait until after filing taxes. Remember that the contribution limit is based on earned income after business expenses. So if your teen's net self-employment income ends up being $550 after deducting the computer and software expenses, their maximum Roth contribution would be $550 for the year, not the full $1,400 from the 1099-NEC.
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Mia Alvarez
Don't forget your kid might need to make quarterly estimated tax payments if they continue this self-employment gig! My son got hit with an underpayment penalty because I didn't realize this applied to him.
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Carter Holmes
ā¢I think there's a safe harbor exception for dependents with small amounts of income? My accountant told me my daughter didn't need to worry about quarterly payments for her babysitting income until it was more substantial.
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