Just adding my experience - I took short term disability last year after surgery and realized months later that my company had taken taxes out of the payments but I had been paying the STD insurance premiums with after-tax dollars for years! I ended up having to file an amended return to get back about $900 in taxes. If you paid for the STD with after-tax money, double check your W-2 and paystubs. You might be paying taxes you don't actually owe.

I went through something very similar last year and want to share what I learned. The key thing is figuring out how your STD premiums were paid - this makes ALL the difference in how the benefits should be taxed. Here's what you need to check: Look at your pay stubs from before you went on disability and see if there's a line item for "STD" or "Short Term Disability" deductions. If those deductions were taken AFTER taxes were calculated on your gross pay, then the benefits you received should actually be tax-free. For bereavement leave, that's straightforward - it's always considered regular taxable wages since it's just paid time off from your employer. The tricky part is if your employer incorrectly treated tax-free STD benefits as taxable income on your W-2. This is surprisingly common because payroll departments don't always track the premium payment method correctly. If this happened to you, you'd need to get a corrected W-2 or file an amended return. I'd suggest calling your benefits department and specifically asking: "Were my STD premiums deducted pre-tax or after-tax?" Get that answer in writing if possible. If they were after-tax and your employer included the STD payments in your taxable wages, you're probably owed a refund.

You're totally fine to file Schedule C without any formal business registration! I've been doing freelance web development for 3 years now and started the same way - just picking up projects here and there with no LLC or business license. The IRS doesn't care about your business structure, they just want you to report the income you earned. Your $8,500 in earnings definitely qualifies as self-employment income, and those business expenses you mentioned (laptop, software, home office) are legitimate deductions as long as you use them for your graphic design work. Just make sure you can prove the business use percentage if the IRS ever asks. One tip: since you made over $400 in self-employment income, you'll owe self-employment tax (about 15.3%) on top of regular income tax, so don't forget to account for that when planning your payment. But the business deductions will help offset some of that burden.

I had the exact same concern when I started doing freelance consulting work! You definitely don't need a business license to file Schedule C - the IRS recognizes you as a sole proprietor automatically once you start earning income from self-employment activities. One thing that helped me feel more confident was organizing all my documentation before filing. Since you mentioned keeping records of payments through Venmo and direct transfers, I'd recommend downloading those transaction histories and creating a simple spreadsheet showing dates, clients, amounts, and brief descriptions of work performed. For expenses, keep receipts and note the business purpose. The home office deduction can be valuable, but make sure you understand the requirements - the space needs to be used regularly AND exclusively for business. If you work at your kitchen table sometimes, that won't qualify, but if you have a dedicated desk area only used for graphic design work, you're good to go. Also, don't forget you'll need to pay quarterly estimated taxes going forward if you expect to make similar or more income this year. The IRS expects self-employed folks to pay as they go rather than waiting until year-end. Good luck with your filing!

Has anyone actually calculated what this refund would be? I'm in a similar boat.

This is really helpful info! I was in a similar situation last year and want to add a few things based on my experience. First, make sure all 3 of your kids will qualify as "qualifying children" for the Child Tax Credit - they need to be under 17 at the end of the tax year and meet the relationship/support tests. Sounds like yours will qualify no problem. One thing to watch out for - the American Opportunity Credit has income limits too. For married filing jointly, it starts phasing out around $160,000, so you should get the full benefit at $65k income. Also, don't stress too much about the calculator differences. I found that some online calculators don't account for all the interactions between different credits, or they use different assumptions about your filing status or deduction amounts. The rough calculation that Natalie provided above looks pretty reasonable to me. With no withholding, you're essentially getting an interest-free loan from the government through these refundable credits. Just make sure you file on time to get your refund processed quickly!

The whole prize tax system is weird. My brother won a "free" trip to Hawaii valued at $8,500 on a radio show, then got hit with a $2,800 tax bill. He almost couldn't go because he didn't have the cash to pay the taxes. The radio station wouldn't adjust the value even though it was clearly inflated compared to what the trip would actually cost if you booked it yourself.

For anyone wondering, the prize tax rules are in IRS Publication 525. Contest winnings are considered "Other Income" and fully taxable at your normal income tax rate. This includes cash, goods, services, trips, cars, etc. You'll get a 1099-MISC if the value is $600+.

I dealt with this exact situation last year with my HSA through Bank of America. The key thing that helped me was creating a detailed spreadsheet tracking my contributions by date and the corresponding investment performance for each batch. What I did was go back through my HSA statements and identify exactly when I made the excess contribution (let's say it was my last $500 contribution in November). Then I tracked how my investments performed from that date forward until I discovered the issue. The pro-rata method others mentioned is correct, but I found it helpful to also document everything step-by-step in case the IRS ever questions it. I kept screenshots of my account balances, contribution dates, and the final calculation. One tip: when you call your HSA provider, specifically use the phrase "return of excess contributions with net income attributable" - this is the exact terminology they need to hear to process it correctly for tax reporting purposes. Don't let them just process it as a regular distribution or you'll get hit with taxes and penalties you shouldn't owe. The whole process took about 3 weeks from calculation to getting the money back, but it was worth doing it right to avoid tax headaches later.

I just went through this nightmare with my HSA provider a few months ago! The key is to be very persistent and document everything. Here's what worked for me: First, calculate the pro-rata earnings yourself using the method Paolo described above - it's actually not that complicated once you understand it. Write down your calculation with dates and amounts. Then when you call your HSA provider, don't accept "we can't help you" as an answer. Ask to speak to a supervisor or HSA specialist. I had to call three times before getting someone who actually knew how to process excess contribution returns properly. Most importantly, get everything in writing! Ask them to email you confirmation of the withdrawal amount and that it's being coded as a "return of excess contributions" rather than a regular distribution. This is crucial for tax reporting. One thing to watch out for - some providers will try to just process a regular withdrawal and tell you to "sort it out with taxes later." Don't accept this! It needs to be coded correctly from the start or you'll have major headaches come tax time. The whole process is frustrating but totally doable if you stay organized and persistent. Good luck!