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Ask the community...

  • DO post questions about your issues.
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  • DO NOT post call problems here - there is a support tab at the top for that :)

Emma Davis

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One thing nobody mentioned yet - make sure you're tracking your mileage if you drive anywhere for your freelance work! I'm a freelance photographer and the mileage deduction saved me thousands on my taxes last year. You can't deduct regular commuting, but any driving to client sites, for supplies, to networking events, etc. is deductible. For 2025 the standard mileage rate is 67 cents per mile which adds up fast. Just keep a log in your car or use an app like MileIQ.

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What about if I mostly work from home but occasionally go to coffee shops to work? Would those miles count?

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Emma Davis

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No, unfortunately trips to coffee shops to work generally don't count as business mileage since they're considered a personal choice rather than a business necessity. The miles that do count would be things like driving to meet a client, traveling to a location for a project, picking up supplies specifically for your business, or attending a conference related to your field. The key distinction is whether the travel is necessary for your business rather than a preference about where you do your regular work.

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Don't forget to look into health insurance premium deductions if you're self-employed! My accountant showed me that I could deduct 100% of my health insurance premiums on my 1099-NEC income. It's not part of your business expenses on Schedule C, but a separate deduction on the 1040 form itself.

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Wait really? I've been filing 1099-NEC income for 3 years and had no idea about this. Is there a minimum income requirement to qualify?

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Another tip - take pictures of EVERYTHING before you mail it. Last year I had to prove what I sent and thankfully had photos of all my documents. Also write down the certified mail tracking numbers somewhere safe in case you lose the receipt.

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That's really smart! Should I also make photocopies or are pictures enough? And should I mail it from the post office or can I just drop it in a mailbox?

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Pictures are generally enough if they're clear and show all the information, but if you want to be extra cautious, photocopies are good too. Personally, I just take clear photos of each page with my phone and save them in a dedicated folder. I strongly recommend going to the post office counter rather than using a dropbox, especially for tax documents. At the counter, you can get a stamped receipt with the tracking number. For something as important as your tax return, that extra confirmation is worth the few minutes in line.

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My advice is to try again with e-filing! You don't actually need last year's AGI if you never filed before or can't access it. There's usually an option to enter "0" or check a box that says you didn't file last year. Much faster for getting your refund (about 21 days vs 6-8 weeks for paper returns).

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Sayid Hassan

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This is actually correct! I work as a tax preparer and there should be an option to indicate you don't have last year's AGI. Which software are you using? I can tell you exactly where to look for this option.

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Bro just max out your 401k if you can - that'll definitely lower your taxable income. My income jumped last year and I got destroyed on taxes until I realized I could pump more into my 401k. I upped my contribution to like 15% and it dropped my tax bill significantly. Way simpler than the backdoor Roth stuff everyone's talking about.

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But wouldn't that only help for next year? OP already owes for this year's taxes, so isn't it too late to increase 401k contributions for the tax year that already ended?

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You're totally right and I should have been clearer. For the current tax bill that's already calculated, increasing 401k won't help since those contributions had to be made during the calendar year. For the IRA though, you actually have until the tax filing deadline (usually April 15) to make contributions that count for the previous year. So while the 401k ship has sailed for last year, you can still make that IRA contribution up to the filing deadline and potentially benefit from the backdoor Roth strategy others mentioned. My bad for not being specific about the timing difference.

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Something nobody's mentioned yet - if you're self-employed even part-time, look into an SEP IRA instead. Higher contribution limits ($66,000 or 25% of income, whichever is less). I switched from traditional to SEP last year and was able to shelter way more income.

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Zara Ahmed

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Does that work if you have a regular job too? I have W-2 employment but also make about $15k from a side hustle. Would that qualify?

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A little more background on this: In 2020, the IRS split non-employee compensation from the 1099-MISC form and created the 1099-NEC specifically for contractor work. This has caused TONS of confusion for companies. Your father's former employer is probably just confused about which form to use now. The key thing is whether you provided any services to them. If not (which is clearly the case as a beneficiary), then it should be 1099-MISC.

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That explains the timing! The first two years I got the MISC, and then after 2020, they switched to NEC. Do you know which box on the 1099-MISC it should be reported in? My accountant seemed uncertain about this too.

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Beneficiary payments like what you're receiving should typically be reported in Box 3 of the 1099-MISC, which is for "Other Income." This box is specifically for income that isn't from services provided as an independent contractor and doesn't generally trigger self-employment taxes. When you talk to your accountant about filing amended returns, make sure they understand this distinction. Some tax software automatically assumes any 1099 income is subject to self-employment tax, so your accountant needs to manually ensure these payments are characterized correctly as "Other Income" rather than self-employment income.

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Emma Morales

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I work in payroll and see this mistake ALL the time. The 2020 form change has created so much confusion. Your best bet is to contact whoever is handling the payments (likely HR or the benefits department) and explain that beneficiary payments should go on 1099-MISC Box 3, not 1099-NEC. Most companies actually want to get this right because incorrect filing causes problems for them too!

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As an accountant, I second this. The confusion between these forms is one of the most common issues I see with clients. The company should be able to issue corrected forms once you explain the situation.

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One thing that hasn't been mentioned is that you should also consider your tax situation holistically. If you're consistently getting $12k refunds, it may not just be your W4 that needs adjusting. Do you have significant deductions that maybe aren't being accounted for in your paycheck withholding? Things like mortgage interest, charitable donations, or business expenses can dramatically affect your final tax bill. Also, if you've had major life changes (marriage, kids, buying a house), you should completely redo your W4 rather than just tweaking it.

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Lucas Parker

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I do have some substantial deductions - I own my home and have mortgage interest, plus I make regular charitable contributions. I also contribute the max to my 401k. Would all of these affect how I should fill out my W4? I'm not married and don't have kids, so I'm filing as single.

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Yes, those substantial deductions are likely a big part of why you're getting such large refunds! The default withholding calculations don't account for itemized deductions like mortgage interest and charitable contributions. Your 401k contributions should already be excluded from your withholding calculations automatically since they're pre-tax, but the itemized deductions need to be handled separately on your W4. You should enter the approximate amount of your itemized deductions that exceed the standard deduction on line 4(b) of your W4. This will reduce your withholding to account for these deductions.

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Caleb Bell

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Has anyone actually used the IRS's Tax Withholding Estimator on their website? I found it super helpful for figuring out my W4. It asks you questions about your tax situation and then gives you the exact numbers to put on each line of the W4. Totally free too.

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I tried that but found it confusing because you need to have so much info on hand - like exactly how much you've had withheld so far this year and projected income for different sources. It was accurate when I finally got through it, but took me like an hour to complete.

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