I appreciate the suggestion! In this case, I actually paid the hospital directly rather than gifting money to my dad, but that's good to know for future reference. Would it have made any difference tax-wise if I had sent him the money first and then he paid the hospital? Or is the end result the same either way?

The end result would be exactly the same tax-wise. Whether you pay the hospital directly or give your father the money to pay, the IRS views it the same way - as a gift to your father. Neither approach would give you a tax deduction. The only practical difference is that paying directly ensures the money is used for its intended purpose, and sometimes hospitals offer cash discounts or payment plans when working directly with them. But from a tax perspective, there's no advantage to either approach.

This sounds like tax fraud. You can't just claim personal expenses as business expenses by making up fake work. The IRS specifically looks for this kind of thing in audits.

What percentage of my phone bill can I reasonably deduct? I use it for personal stuff too obviously.

For your phone bill, you need to determine what percentage is used for business purposes. If you use your phone for DoorDash about 30% of the time, you can deduct 30% of your bill. Be honest but don't shortchange yourself. Some dashers keep track for a typical week to establish a pattern, then apply that percentage to the whole year. The same concept applies to other mixed-use items. Just make sure you can explain how you arrived at your percentage if asked. And always keep your monthly phone bills as documentation - digital copies are fine.

In my experience as a full-time dasher for 3 years, standard mileage is almost always better for delivery drivers. The rate for 2024 is 67 cents per mile which really adds up when you're putting 20k+ miles a year for deliveries. Plus it's way simpler than tracking all your actual expenses and calculating depreciation.

Thanks for mentioning this! I'm in New York - do you know if I need to file anything special with the state here? I definitely have plenty of evidence (emails, company handbook they gave me, etc). Should I be reaching out to the company about this or just handle it on my tax forms?

New York has pretty strong worker protection laws. You'll want to look into filing the IT-2104 form which is NY's equivalent of the W-4 for your state taxes. Also consider filing a report with the NY Department of Labor about the misclassification - they take these cases seriously and can help recover the employer portion of taxes you shouldn't have to pay. Regarding contacting the company, it depends on your relationship with them. Some people have success simply explaining the situation to their former employer and requesting they issue a corrected W-2. Others find this creates conflict. If you need them as a reference, consider how approaching them might affect that relationship. Either way, you can still file correctly on your end using Form 8919 even if they refuse to correct their mistake.

Yes! I got a favorable determination but it took forever (9 months). The key was documenting everything thoroughly in the initial filing. I included copies of emails showing they controlled my schedule, photos of the company equipment I was required to use, their employee handbook they made me follow, etc. The more evidence you provide upfront, the faster and more likely you'll get a favorable ruling.

7 Omg thank you for mentioning this! I just checked my W2 and there's like $300 in box 4 and $75 in box 6. SPRINTAX never mentioned anything about this. Do I need to file something special to get these back??

9 You need to file Form 8843 along with a special statement requesting a refund of incorrectly withheld FICA taxes. SPRINTAX should have this capability, but sometimes you need to specifically indicate your FICA exempt status. If they missed this, you can either restart your SPRINTAX return and make sure to answer the FICA questions correctly, or use a different service that better handles J1 visa FICA exemptions. This could easily explain why your friends got larger refunds if they properly claimed their FICA exemptions and you didn't.

13 This is so confusing! I worked 4 months and made about $12,000 total. My employer is a big company that hires tons of J1s every year so I assumed they knew what they were doing with the withholding. Is there any way to know if they did it right?

This! I had Robinhood show completely wrong basis amounts for some options I exercised last year. How do you correct this on your tax forms if the 1099 is wrong?

You need to file Form 8949 and check box C for short-term transactions with incorrect basis. Then you'll list the transaction as reported on your 1099-B, but you'll make an adjustment in column g to correct the basis amount. In the code column, you'll enter "B" which means that the basis was reported incorrectly by the broker. Keep detailed records of your actual trade confirmations showing the correct basis in case you're ever audited. It's definitely more work, but it ensures you're not overpaying taxes because of broker reporting errors. Most tax software has a way to enter these adjustments, though it's not always obvious where to find that section.

Robinhood's tax docs are still a mess. I switched to TDA and it's night and day difference. Their reporting actually makes sense and properly tracks wash sales.