What about if I'm using my maiden name for business but my married name is on my social security card? Will that cause problems?

That's exactly the kind of situation that causes tax matching problems. You should use your legal name (the one on your Social Security card) on the first line of the W-9 form. If you're using your maiden name as a business name, you would put that on the second line "Business name/disregarded entity name." Ideally, you should consider filing for a proper DBA ("doing business as") with your local government if you're consistently using your maiden name for business purposes. This creates a clear paper trail between your legal name and business name.

You typically only need to provide a W-9 once unless your information changes (like a new address, name change, or tax ID change). Some companies have policies requiring annual updates just to ensure they have current information, but it's not an IRS requirement. It's not unusual for a client to request an updated form each year - they're just being thorough with their record-keeping. If nothing has changed in your information, you can just complete a new form with the same details.

Wait really? I've been driving for UberEats for 6 months and only counting miles when I have food in the car. So I can count ALL the miles when I'm logged into the app and available for deliveries?

Yes! Any miles driven while you're actively working (logged into the app and available) count as business miles, even if you don't currently have a passenger or food in the car. The IRS considers this "on the clock" time. The only miles you can't count are your personal trips or your commute to your starting point before logging in. But once you're logged in and working, those "empty" miles between rides or deliveries are absolutely deductible business miles. This is a huge thing many drivers miss! Make sure you're tracking all those miles - it can make a big difference in your tax bill.

I was worried about the same thing last year, so I asked my brother-in-law who's an accountant. He said just make sure you have good documentation for your mileage. Like a detailed log with dates and miles. The IRS knows rideshare drivers have high expenses, especially with mileage, so the low taxable income by itself isn't a red flag. Just make sure you can back up your numbers if they ask.

That's a relief to hear! I've been using MileIQ to track all my driving so I should have pretty good records. I guess I was just shocked at how much difference the deductions made. Thanks for the reassurance!

That's smart! Do you just use a regular spreadsheet or is there a template somewhere? Also, how do you handle documents that have multiple numbers on them like investment statements?

I just use a regular Excel or Google Sheets spreadsheet that I created myself. Nothing fancy, just those columns I mentioned. For complex documents like investment statements, I expand my tracking approach. I create sub-rows under the main document listing key figures (dividends, capital gains distributions, etc.) and note the specific form boxes where those numbers should go. Sometimes I even take screenshots of the tax software entry screens and note which box on my document goes to which field in the software. It's a bit more work upfront, but it saves me tons of confusion, especially for documents that have dozens of figures on them.

I used IRS Free File last year with W-2, some freelance income, and a small amount of stocks. It worked fine for me! Just make sure you go through the IRS website (irs.gov/freefile) rather than going directly to the tax company sites. If you go direct, they sometimes don't show the free options.

Omg you're right - we definitely go over 40 hours some weeks when there are more houses or deep cleans scheduled. I didn't even think about the overtime angle! How did you go about filing with the Department of Labor? Was it complicated?

Filing with the Department of Labor was surprisingly simple. I went to the DOL website and filed a wage complaint through their online system. You just need to provide details about your employer, your work hours, and how you were paid. After I submitted the complaint, a DOL investigator contacted me within a couple weeks. I shared my time records (I had kept my own log of hours worked in a notebook), and copies of payment records. They handled the entire investigation and calculated what I was owed. The whole process took about 3 months, but they recovered all my unpaid overtime plus damages.

While some workers might prefer contractor status for the deductions, that's not how tax law works. The IRS has specific criteria for worker classification regardless of what either party "prefers." If a worker meets the employee criteria (like OP clearly does), classifying them as a contractor is illegal tax evasion. Also, in this case, the workers can't even claim mileage deductions since the company provides the vehicles and pays for gas! They're getting all the downsides of contractor status (higher self-employment taxes, no benefits, no protections) with none of the advantages.

Is there anyway to estimate mileage after the fact if you didn't track it? I did some driving for Uber Eats but totally forgot to log miles.

Yes, you can estimate your mileage after the fact, but you need to be reasonable and have some basis for your estimate. If you have delivery history in your app, you can use that to reconstruct your mileage. Most delivery apps keep a record of your deliveries, so go through your history and map out the routes you took. Remember that you can count all business miles - driving to pickup locations, to customers, and returning to busy areas after deliveries. Just be careful not to include personal miles. If you're audited, the IRS will want to see some documentation, so create a log now with your best estimates and note that it's reconstructed. It's not ideal, but it's better than not claiming the deduction at all.

Keep ALL tax documents for at least 3 years after filing! That's the standard period the IRS can audit you. Some people recommend 7 years to be extra safe. Your tax person is right - don't throw them away!