Yes, as a 1099 contractor you can absolutely deduct mileage for driving between job sites (but not commuting from home to your first job site of the day or from your last job site back home). For 2025, you can either take the standard mileage rate or track actual expenses like gas, maintenance, etc. The standard rate is usually easier - just keep a log of business miles driven. Also keep those receipts for tools and work clothes! Those are legitimate business expenses you can deduct on Schedule C.

Make sure your boss is actually classifying you correctly! Some employers try to call people "contractors" to avoid paying employment taxes when legally they should be treating them as employees. If they control WHEN and HOW you do the work (vs just the end result), you might actually be misclassified.

Are you a W-2 employee? If yes, then unfortunately no - those home expenses aren't deductible for regular employees anymore. If you're a 1099 contractor, then yes you could deduct the business portion of those expenses (would need to calculate what % is for work vs personal use).

Would an email work instead of certified mail? I have all their texts demanding payment for the shirts, but I'm not sure I want to spend money on certified mail to these jerks.

Email isn't ideal because it's easier for them to claim they never received it. The certified mail creates an official record that they received your communication, which is important if this escalates further. The $4-5 for certified mail is worth it for the paper trail it creates. That said, if you do use email, make sure to request a read receipt and save all correspondence. The texts demanding payment are good evidence already, so keep those too. The key is documenting everything in case you need to prove harassment later or defend yourself if they try to send this to collections.

That's a good point - OP should look up the IRS Whistleblower Program. If the employer is systematically underreporting wages, the IRS takes that very seriously and you could potentially get a reward if your information leads to the recovery of unpaid taxes. The reward can be 15-30% of what the IRS collects!

Really? That's interesting. My HR department said the 3921 form was all I needed and that I'm responsible for figuring out the taxes. I'll double check with them about the W-2 reporting. If they won't issue a corrected W-2, is there any downside to reporting it as "Other Income" instead?

There's not really a downside to reporting it as "Other Income" - you'll pay the same amount of tax either way. The main difference is that Other Income isn't subject to FICA taxes (Social Security and Medicare), whereas if it were on your W-2, it would be. Many companies don't correctly report ISO disqualifying dispositions on W-2s because their payroll systems aren't set up to track when employees sell shares. That's why they issue the 3921 form but leave the tax reporting to you. Just make sure you have documentation of everything in case you're ever audited. The 3921 plus your brokerage statements showing the sale should be sufficient.

If you haven't exercised yet, you have options to possibly reduce taxes. The key is to try to get a qualifying disposition rather than disqualifying. To do this, you need to: 1) Hold the shares for at least 1 year after exercise AND 2) Hold the shares for at least 2 years after the option grant date If you meet both conditions, only the difference between sale price and strike price is taxed, and it's taxed as long-term capital gains (usually lower rates) rather than ordinary income.

Thanks for this warning! This is making me rethink our plan. Maybe instead of claiming 100%, we should just track the mileage super carefully and go with the actual percentage. I definitely don't want to deal with an audit. Do you know if we need to keep paper logs or if the delivery apps' records are enough proof?

The delivery apps aren't enough for the IRS if you get audited. You need a detailed mileage log showing starting and ending odometer readings for each delivery shift, dates, and business purpose. There are some good apps like MileIQ or Stride that make it easier. Also don't forget you can deduct more than just the car itself! Hot bags, phone mounts, portion of phone bill, extra car chargers - all that stuff is 100% deductible separately from your vehicle expenses. I even deduct part of my Spotify since I play music during deliveries lol.

That's somewhat misleading. Most food delivery people aren't driving vehicles over 6000 lbs - that's like a large SUV or truck. For regular cars, the Section 179 deduction is capped MUCH lower - around $19,200 for 2024 I believe. And remember you can't claim more in deductions than you earn from your delivery work!

You're right - I should have been clearer about the weight limitations. For most standard cars used for food delivery, there are lower caps on Section 179. For 2024, passenger vehicles are limited to around $19,200 for the first year if they weigh less than 6,000 lbs. And you made another great point - your total deductions can't exceed your business income, so if you're just starting out in delivery, you might not have enough income to take advantage of the full deduction in year one. Any unused portion can be carried forward to future years though!

Thanks for sharing your experience! Did you also report the fellowship stipend as "Other Income" like someone suggested above? And did you need to provide any additional documentation with your tax return?

Yes, we reported it as "Other Income" on Schedule 1 and labeled it as "Research Fellowship Stipend" in the description. This is the correct way to report it. We didn't need to attach any additional documentation to the tax return itself, but we did keep the letter from the university in our records in case of any questions. Most universities that regularly deal with international students and researchers have standard language they use for these letters that clearly explain the fellowship is not an employment relationship. Your husband should be able to request this from the international student/scholar office if you want extra peace of mind.

I used TurboTax last year for a similar situation and there was definitely an option to override. It's usually something like "I understand but want to continue without filing this form" somewhere on that screen. They make these warnings look scary but many are just precautionary.