Thanks for the suggestion! I'm hesitant to start over with new software since I'm pretty far along in TurboTax, but it might be worth it to avoid mailing. Did you have to manually re-enter everything when you switched to FreeTaxUSA or is there some way to transfer the information?

Unfortunately, you do have to re-enter everything manually when switching between tax software platforms. There's no universal transfer system between different companies. It's definitely a pain, especially if you're already far along in TurboTax. One shortcut though - if you have last year's tax return PDF (even from TurboTax), most software can import some basic information from it like personal details and employer information. You'd still need to enter this year's specific numbers manually, but it saves some time on the setup.

I second this! In my case it was vehicle expenses for my delivery gig. When I changed from "actual expenses" to "standard mileage rate" it suddenly allowed e-filing. The tax amount was basically the same but for some reason one method triggered paper filing and the other didn't.

I haven't tried Stride - does it integrate directly with any tax filing software? The project-based spreadsheet approach is interesting too. How time-consuming do you find it to maintain throughout the year?

Stride generates tax reports you can download, but doesn't directly integrate with filing software like TurboTax. You'll still need to transfer the info, but at least it's all calculated and organized. The spreadsheet takes me about 10 minutes a week to maintain. I just update it every Friday with that week's expenses and receipts. The key is consistency - if I wait more than a week, it becomes a pain to remember details. The project-based approach has actually helped me adjust my pricing too, since I can see exactly how much each type of shoot costs me in expenses.

I was literally about to comment about my receipt shoebox system! But seriously, I switched to Expensify last year and it's way better than my old "system." The receipt scanning feature saves so much time, and it's actually pretty accurate at pulling the data.

Thanks for pointing this out! My company only does reimbursements after I submit receipts, so it sounds like I'm good. But do you know how advances are treated differently?

Advances can be tricky. If you receive money before incurring the expense, it might be considered an "advance" rather than a reimbursement. If you don't provide adequate documentation afterward or don't return unused funds, the IRS might consider it a non-accountable plan. In a non-accountable plan situation, the advance would be included in your W-2 income, and you'd have to claim any eligible expenses as miscellaneous itemized deductions (which are currently suspended until 2026). Much worse tax treatment than a proper accountable plan reimbursement.

I've been using Expensify for the past year and it's been great. You can snap photos of receipts on the go and it automatically extracts the info. Makes submitting to accounting super easy too.

Does Cash App Taxes handle things like education credits too? My kid is working but also in college and I'm worried about missing out on education tax benefits.

Yes, Cash App Taxes does handle education credits like the American Opportunity Credit and Lifetime Learning Credit. It covers most common tax situations that students and young adults encounter. For more complex situations though, you might want to double-check with another resource or consider upgrading to a paid version of software. But for a basic return with some education credits, the free version should work fine.

Yes! This is super important! I didn't file my first year working because I made under the threshold, then learned later I would've gotten a refund of everything withheld. Such a waste!

Any app recommendations for tracking mileage? I've been using a paper log but it's a pain.

I personally use MileIQ, but there are several good ones like Everlance and Stride. The key is finding one that automatically detects drives and lets you easily classify them as business or personal. Make sure whatever app you choose lets you export detailed reports that include start/end locations, odometer readings, and business purpose. The app I mentioned even lets you add notes for each trip which is super helpful if you get questioned about specific drives later. Most have free versions that work fine if you don't drive tons of miles.

Thanks, you're right - I do get a 1099-NEC that includes everything (services + mileage all together). So based on what you're saying, I should be able to deduct the full mileage at the standard rate since I'm paying taxes on the entire amount, including what was meant as "reimbursement"?

Yes, that's exactly right. Since your 1099-NEC includes both your service payments and mileage reimbursements as one lump sum, the IRS considers it all taxable income. Therefore, you are absolutely entitled to deduct all your business mileage at the standard rate on your Schedule C. Just make sure your mileage log is detailed and accurate to support your deduction if you're ever questioned. Include dates, destinations, business purpose, and mileage for each trip.