Don't forget that if you made over $60k, you probably should have been making quarterly estimated tax payments throughout the year. If you didn't, you might get hit with an underpayment penalty when you file.

This is such a common confusion right now! I went through the exact same thing with my Etsy payments processed through Square. The key thing everyone's mentioned is correct - you absolutely must report all that income regardless of getting a 1099-K. What helped me was creating a simple spreadsheet tracking my monthly Square deposits so I could cross-reference everything. Square's dashboard makes it pretty easy to pull annual totals, but I also kept screenshots of my year-end summary just in case I ever get audited. One thing I haven't seen mentioned yet - if you're using Square for a side business, make sure you're tracking ALL your business expenses too. Things like materials for your jewelry, packaging supplies, shipping costs, even the Square processing fees can be deducted. Those deductions can really add up and reduce your tax liability significantly. The quarterly payment thing Connor mentioned is super important too. I set up automatic transfers to a separate "tax savings" account now so I'm not scrambling come tax time.

Anyone know if the processing time differs for different types of FICA refunds? Mine is specifically for overpaid Medicare taxes (I'm over the Social Security limit but my company kept withholding). Form 843 submitted in February and still nothing.

My wife went through this last year. Her university incorrectly withheld FICA from her fellowship stipend. Form 843 submitted in July 2024 and the refund didn't come until April 2025!!! Almost 9 months. We called multiple times and kept getting told "it's in processing" with no other updates. And this was for a straightforward case with clear documentation from the university admitting their error.

Does anyone know if filing as Head of Household helps? I'm single without kids but I do financially support my elderly mother who lives with me. Would that status give me any of the tax advantages that married couples get?

As someone who's been single and dealing with this tax disparity for years, I completely understand your frustration. The system really does penalize singles in ways that don't make logical sense when you consider resource usage. One thing that helped me was learning about the Saver's Credit (Retirement Savings Contributions Credit) that many singles overlook. If your adjusted gross income is under $34,000 for 2022, you can get up to a $1,000 credit for contributing to retirement accounts. It's not much, but every bit helps when you're already paying higher rates. I've also started treating my tax situation more strategically - bunching charitable deductions in alternating years to exceed the standard deduction, timing capital gains and losses carefully, and even considering geographic arbitrage by moving to a state with no income tax if remote work allows it. The fundamental unfairness remains though. We're essentially subsidizing other people's life choices while getting fewer government benefits ourselves. It's particularly galling when you realize that Social Security benefits are also structured to favor married couples through spousal benefits that singles can never access, despite paying the same payroll taxes.

Don't forget to check if your state has different rules for business asset depreciation than federal. I deducted my laptop using Section 179 on federal, but my state has limitations on immediate expensing and required me to depreciate it. Caused me a headache when my state return got flagged.

Also important - make sure you're tracking business use vs. personal use! If you're using that laptop 70% for business and 30% for Netflix, you can only deduct 70% of the cost. IRS isn't stupid and this is a common audit trigger for home-based businesses.

I've given up trying to do this correctly in TurboTax and just hire a CPA every year. With RSUs, ESPP, and now some ISO and NSO options too, it's just too complicated. Last year I tried doing it myself and ended up with a CP2000 notice from the IRS saying I underreported my stock sales. Paid more in penalties than what a good accountant would have cost. Learn from my mistake!

I went through this exact same nightmare last tax season with my Fidelity RSU and ESPP sales! Here's what I learned after making several mistakes: The key insight is that your Tax Reporting Statement (1099-B) is what you'll enter into TurboTax, but you MUST use the Supplemental Information to correct the cost basis, especially for RSUs. The 1099-B often shows incorrect cost basis that doesn't account for the income you already paid taxes on when the RSUs vested. My process now: 1) Enter each transaction from the 1099-B exactly as shown, 2) When TurboTax asks for cost basis, use the adjusted numbers from your Supplemental Information instead of what's on the 1099-B, 3) Double-check that any ESPP sales are properly categorized as qualifying vs disqualifying dispositions. The supplemental statement is your friend - it contains the real cost basis calculations that prevent double taxation. Without using it, you'll likely overpay taxes significantly. I almost made a $2,000+ mistake before catching this! One more tip: Keep detailed records of both statements. If you ever get an IRS notice, having both documents makes it much easier to explain the discrepancies between what's reported on the 1099-B vs what you actually filed.