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One thing nobody mentioned yet - KEEP YOUR OLD PHONE as a backup for your business! My tax person told me this creates a stronger case for the new phone being primarily for business use. If you're still using your personal phone for most personal stuff and the new one mostly for eBay, it's easier to justify a higher business use percentage.
That's actually brilliant advice. I never would have thought of that approach. It makes total logical sense though - if you have two phones and one is clearly used more for business activities, it strengthens your position.
Great discussion everyone! As someone who's been through this exact situation with my online business, I wanted to add a few practical tips that helped me: 1. **Screen time reports are your friend** - Both iPhone and Android have built-in screen time tracking that shows how much time you spend in each app. Screenshot these monthly and keep them in a folder labeled "Business Records [Year]". This creates concrete evidence of your business vs personal usage patterns. 2. **Document your business justification** - Write a simple one-page memo explaining WHY you need the phone upgrade for your business (bigger screen for barcode scanning, faster processor for inventory management, better camera for product photos, etc.). This shows the IRS that it's a legitimate business need, not just wanting a new toy. 3. **Consider your upgrade timing** - If possible, buy the phone early in the tax year so you can establish a full year of business usage patterns. This makes your deduction more defensible. 4. **Don't forget accessories** - Business-related phone accessories (cases, car mounts, portable chargers used for business) can also be deducted using the same business percentage. The key is being reasonable and consistent with your documentation. The IRS knows that business owners use their phones for both purposes - they just want to see that you're not claiming 100% business use when it's clearly mixed.
This is super helpful, especially the screen time tip! I never thought about using the built-in tracking as documentation. Quick question though - when you write that business justification memo, do you just keep it in your files or do you actually submit it somewhere? And how detailed should it be? I'm worried about over-documenting vs under-documenting if that makes sense.
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The 5500-EZ filing requirements are so confusing! I missed filing mine too and got hit with penalties. Does anyone know which tax software handles these forms properly? I use TurboTax for my regular taxes but they don't seem to support these specialized retirement plan forms.
None of the mainstream tax software handles 5500-EZ properly. I'm a bookkeeper and we use specialized software like Intuit Tax Online Pro or UltraTax for clients with these needs. For most individuals, you'll need to file it directly through the EFAST2 system on the Department of Labor website.
I went through this exact same situation last year! The panic is real, but you're not alone in missing this filing requirement. Here's what I learned from my experience: First, yes you do need to file Form 5500-EZ for plan termination even though it's been 2 years. The IRS considers a rollover to an IRA as terminating the Solo 401k plan. Since your combined plan assets were around $270k, you definitely exceeded the $250k threshold that triggers the filing requirement. The good news is that the IRS has reasonable cause provisions for late filings, especially when you can demonstrate that the failure was due to circumstances beyond your control - like not being informed by your financial institutions about this requirement. When you file, include a detailed reasonable cause statement explaining exactly what happened: the TD Ameritrade acquisition, Schwab's inability to support Roth 401ks, and the fact that neither institution informed you of the 5500-EZ requirement. Document everything with dates and reference any correspondence you had with them. I also recommend checking if you qualify for the DOL's Delinquent Filer Voluntary Compliance Program (DFVCP), which often results in reduced penalties for good faith late filers. Don't wait any longer though - the penalties do continue to accrue, and voluntary compliance always looks better than being contacted by the IRS first.
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Has anyone used an umbrella LLC with a separate tax election for the entity? My CPA suggested forming an LLC but then electing to have it taxed as an S-Corporation (Form 8832 followed by Form 2553). He said it gives the liability protection and flexibility of an LLC with the tax benefits of an S-Corp.
Yes, that's exactly what I did! It's actually quite common. You get the best of both worlds - the legal flexibility of an LLC with the tax treatment of an S-Corp. The state paperwork is simpler with an LLC (less corporate formalities like board meetings, etc.), but you still get the potential SE tax savings.
This is a great discussion thread! I'm in a very similar situation - household income around $380K and considering a side business. One angle I haven't seen mentioned much is the state-level implications. I'm in Texas (no state income tax), but for those in high-tax states like California or New York, the state treatment of S-Corps vs LLCs can significantly impact the overall analysis. Some states don't recognize S-Corp elections and will tax the entity at the corporate level regardless. Also, regarding the ownership question - even if your spouse isn't actively involved, there could be estate planning benefits to joint ownership, especially if the business becomes successful. If something happens to you, having your spouse as a co-owner can simplify business continuity compared to having to transfer a sole proprietorship through probate. Has anyone factored in the potential exit strategy implications? If you plan to eventually sell the business or bring in outside investors, the corporate structure (even if taxed as S-Corp) might be more attractive to buyers than an LLC structure.
Great points about state implications and exit strategy! I'm actually in New York and can confirm that the state treatment does add complexity. NY generally follows federal S-Corp elections, but we have that additional $325 minimum tax plus the fixed dollar minimum tax that varies by income level. Regarding the estate planning angle - that's something I hadn't considered but makes a lot of sense. Even if the business starts small, if it grows significantly over time, having both spouses involved from the beginning could save substantial transfer costs later. The exit strategy point is particularly interesting. I've heard from business brokers that buyers often prefer acquiring corporations over LLC interests due to cleaner transfer mechanics and more familiar legal structures. Have you found any specific resources that compare how different entity structures affect business valuation or saleability?
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11 One thing nobody mentioned - if your 1099 income is below $400 for the year, you don't need to file Schedule SE because you won't owe self-employment tax. Saved me some paperwork last year!
2 That's good to know! Is there a similar threshold for Schedule C? Or do you still need to report all 1099 income on Schedule C regardless of the amount?
You still need to report all 1099 income on Schedule C regardless of the amount, even if it's just $1. The $400 threshold only applies to self-employment tax (Schedule SE). So you'd file Schedule C to report the income, but if your net self-employment earnings are under $400, you can skip Schedule SE. The income still gets added to your total income on Form 1040 though, so it could still affect your regular income tax liability.
Great question! I went through this exact same confusion last year. You definitely need to mail all the schedule forms along with your 1040 and W-2. The schedules aren't just supporting documents - they're integral parts of your tax return that show how you calculated the numbers on your main form. Make sure to arrange them in the correct order: Form 1040 on top, then your schedules (typically Schedule 1, then C, then SE), and attach your W-2 Copy B where indicated. Use one staple in the upper left corner and send everything via certified mail so you have proof of delivery. Don't worry about messing up - you're asking the right questions! The IRS processing centers are used to handling returns with multiple income sources. Just double-check that you've signed and dated everything before mailing.
Mateo Martinez
Does anyone know if bonuses are treated differently for Social Security tax purposes? I'm getting a $40k bonus in December and I'll have already earned about $155k in regular salary by then.
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Aisha Hussain
•Bonuses are treated the same as regular wages for Social Security tax purposes. They're included in your total earnings that are subject to the $168,600 limit. In your case, if you've earned $155k in regular salary and then get a $40k bonus, only $13,600 of your bonus would be subject to Social Security tax (to reach the $168,600 limit). The remaining $26,400 of your bonus would be exempt from the 6.2% Social Security tax, though it would still be subject to Medicare tax.
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Andre Laurent
Great question about the 2025 Social Security tax maximum! Just to add some additional context to what others have shared - the $168,600 wage base limit is set by the Social Security Administration and applies to all earned income, including salary, wages, bonuses, and self-employment income. One thing that catches people off guard is that if you have multiple jobs throughout the year, each employer withholds Social Security tax independently without knowing about your other income sources. This can result in overpayment, but as others mentioned, you can claim the excess as a refund when filing your return. Also worth noting: if you're self-employed in addition to having W-2 income, the limit applies to your combined earnings. So if your W-2 wages already reach the $168,600 threshold, you won't owe Social Security tax on your self-employment income (though you'll still owe Medicare tax). The annual adjustments to this limit have been pretty substantial lately - it jumped from $147,000 in 2022 to $168,600 in 2025, so it's definitely worth keeping track of if you're in that income range!
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