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Something important to consider that nobody has mentioned yet: make sure that loan was actually made with the expectation of repayment. The IRS looks at whether you had a reasonable expectation of being paid back when you made the loan. If they determine you never really expected to get paid back (like if your friend had terrible credit or no income), they might classify it as a gift rather than a loan that went bad. Also, keep in mind that nonbusiness bad debts are treated as short-term capital losses even if the loan was for more than a year. This means you're limited to offsetting capital gains plus up to $3,000 of ordinary income per year. If your loss is bigger than that, you'll carry the remainder forward to future tax years.
Ava Johnson
ā¢Does having a written loan contract automatically prove it wasn't a gift? Or does the IRS look for other evidence too? Like what if the friend never made any payments at all?
A written loan contract is definitely helpful but doesn't automatically prove it wasn't a gift. The IRS looks at the entire situation. They consider factors like: Was there a reasonable expectation of repayment? Did you charge interest? Were there regular payment schedules? Did you make efforts to collect when payments weren't made? If your friend never made any payments at all, that might raise more red flags with the IRS. However, if you can show you took reasonable steps to collect (demand letters, texts/emails requesting payment, etc.), that helps demonstrate you genuinely intended it as a loan. Documentation is key - the more evidence you have showing you treated this as a serious financial transaction, the stronger your case.
Miguel Diaz
I went through almost the identical situation last year with a cousin. Loaned $6,500, got back $2,000, and then nothing despite dozens of texts and calls. I claimed the bad debt deduction and it did work, but here's a tip: document EVERYTHING. I made a simple timeline of all attempts to collect (with screenshots of texts and emails). Also, I did send a certified demand letter as a final step which helped prove I made reasonable collection efforts. The tax software I was using (TurboTax) actually had a specific section for bad debts under capital losses. My refund went through without any issues, but I've heard these deductions can sometimes trigger additional review, so having good documentation ready is important.
Zainab Ahmed
ā¢Did you have to provide all that documentation when you filed or just keep it in case of an audit? My tax software doesn't seem to have any place to upload proof.
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Lindsey Fry
7 I work in payroll, and there's one important thing to keep in mind: your last paycheck might not include adjustments for taxable fringe benefits. Things like group term life insurance over $50k, personal use of company car, or certain bonus payments sometimes get added at year-end during W2 processing. Also, if you received any non-cash benefits throughout the year (like equity compensation or awards), those typically won't show on your regular paychecks but must be included on your W2.
Lindsey Fry
ā¢12 What about 401k contributions? My last paystub shows my total contributions for the year, but does the W2 report this differently? Really confused about where this should appear.
Lindsey Fry
ā¢7 Your 401k contributions are handled in a specific way on the W2. Your paystub will show your contributions, but on the W2, your Box 1 wages (taxable federal wages) will already be reduced by your pre-tax 401k contributions. The actual 401k contribution amount will typically appear in Box 12 with code D. So when comparing your paystub to your W2, remember that your W2 Box 1 should be lower than your gross wages by at least the amount of your 401k contributions (plus any other pre-tax deductions like health insurance).
Lindsey Fry
3 Has anyone used TurboTax's W2 import feature? I'm wondering if I should just wait for my official W2 to use that or if I should manually enter everything from my paystub.
Lindsey Fry
ā¢15 Definitely wait for your official W2 to use the import feature. I tried entering from my paystub last year and ended up having to amend my return because of some differences with taxable benefits that weren't on my paystub. The import feature is super convenient but only works with the actual W2.
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For your first year with Uber income, make sure you're keeping all your receipts and tracking expenses properly going forward. I started driving last year and wish someone had told me this sooner. The Uber tax summary doesn't include a lot of deductions you're entitled to. Track EVERYTHING - car washes, portion of phone bill, mileage between passengers (not just with passengers), snacks/water for riders, car repairs, etc. I use a separate credit card just for Uber-related expenses to make it easier to track.
Chloe Green
ā¢Thank you for this! I haven't been great about tracking so far... is there any way to reconstruct expenses from earlier in the year or am I just out of luck on those deductions?
You can definitely reconstruct some expenses! Go through your credit card and bank statements to find business-related purchases. For mileage, the Uber app keeps a record of your trips that you can use as a starting point, though it won't have the miles driven to pickup locations. Many drivers who don't have complete records use a reasonable estimate based on the data they do have. Just make sure you start keeping detailed records going forward. I recommend apps like Stride or Hurdlr that can track mileage automatically and categorize expenses. Much easier than trying to sort it all out at tax time!
Don't forget about quarterly estimated taxes! This was my big mistake my first year as an Uber driver. Since there's no withholding on your Uber income like there is with your W-2 job, you might need to make quarterly payments to avoid penalties.
Natalie Wang
ā¢But if your W-2 job withholds enough to cover your additional Uber income, you might not need to make quarterly payments, right? How do you know if you need to do this?
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If you have a Traditional or Roth IRA, you can sometimes make tax payments through the same investment firm for free. I use Fidelity and they let me make federal and state estimated tax payments with no fees.
Owen Jenkins
ā¢Wait seriously??? I have Fidelity and had no idea they offered this. How do you access this feature?
Lilah Brooks
Don't forget to account for the safe harbor rules when making estimated tax payments! As long as you pay either 100% of last year's tax liability (110% if your AGI was over $150,000) or 90% of your current year's liability, you won't face underpayment penalties even if you end up owing more. This was a lifesaver for me because my income fluctuates a lot month to month as a contractor, so calculating exact quarterly estimates was driving me crazy.
That's really helpful! So if I made $80k last year and paid $12k in taxes, as long as I pay $3k per quarter this year ($12k/4), I won't get hit with penalties even if I end up making more? That makes planning so much easier.
Lilah Brooks
ā¢Exactly right! For your situation with $80k income and $12k tax last year, paying $3k per quarter will definitely keep you safe from underpayment penalties, even if your income jumps to $100k or more this year. It's one of the few tax rules that actually makes life easier for freelancers and contractors. Just remember if your income does increase dramatically, you'll still owe the additional tax when you file your return - you just won't have the extra penalty on top of it.
Amelia Cartwright
One thing nobody mentioned yet - you should also check if any of these artists are in countries with tax treaties with the US. Some countries have specific rules about how commissions are handled. For example, I work with artists in Canada and there's different documentation requirements than for artists in, say, Brazil.
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Aurora Lacasse
ā¢That's a good point! Do you know if there's a resource where I can look up which countries have tax treaties with the US? Most of my artists are from Japan, South Korea, and a few from the UK.
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Amelia Cartwright
ā¢The IRS has a complete list of tax treaties on their website. Japan, South Korea, and the UK all have tax treaties with the US, which is good news for you! For these countries, you still need the W-8BEN, but the artists might qualify for reduced withholding rates or exemptions depending on the specific treaty. This is another reason to make sure you get those forms completed properly - they allow the artists to claim treaty benefits if applicable.
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Chris King
I messed up this exact situation last year and got hit with a CP2000 notice. Make SURE you keep proof of payments and all communications with these artists. The IRS flagged my contractor payments because I couldn't prove some were to foreign individuals. Even if you can't get W-8BENs from everyone, save emails, payment receipts, anything showing they're international.
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Rachel Clark
ā¢What happened with the CP2000? Did you have to pay penalties or just provide the documentation after the fact?
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