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Just a heads up - don't forget to consider state filing requirements too! Depending on your state, you might need to file additional self-employment forms at the state level. I learned this the hard way last year š
I'm in almost the exact same boat - W-2 from my day job plus a 1099-NEC from some freelance work I picked up. After reading through all these responses, I'm definitely leaning toward checking out FreeTaxUSA instead of paying the premium for TurboTax Self-Employed. One thing I'd add is to make sure you track any business expenses related to your 1099 work - things like equipment, supplies, mileage, or even a portion of your internet bill if you worked from home. These can really help offset the self-employment tax burden. I wish I had been better about tracking expenses throughout the year instead of scrambling to remember everything now at filing time. Thanks everyone for sharing your experiences - this thread has been super helpful!
Great point about tracking expenses! I'm new to this whole 1099 situation too and didn't realize how many things could be deductible. Do you know if there's a minimum threshold for business expenses to be worth claiming? I probably only have a few hundred dollars in expenses from my side work but wasn't sure if that was worth the hassle of itemizing everything on Schedule C.
Anyone have experience with the IRS payment plan options? If I've already missed two quarters, should I just pay a big chunk now or try to set up some kind of plan?
I went through this last year. Your best bet is to make a large payment now for what you've missed, then get on schedule for the remaining quarters. The IRS payment plans are more for when you file your taxes and can't pay the bill in full. For quarterly estimated payments, you're better off catching up and staying current.
Great advice in this thread! Just to add - if you're already behind on quarters like the OP, don't panic but definitely act fast. I was in a similar spot with about $180k in 1099 income and no quarterly payments made. What saved me was calculating my total tax liability for the year and making one large estimated payment immediately to cover what I should have paid in Q1 and Q2, then getting on a proper quarterly schedule for the rest of the year. The key is using Form 1040-ES to calculate what you actually owe. For $270k in income, you're probably looking at around $60-70k in total tax liability (including self-employment tax), so you'd want to pay roughly $15-17k per quarter. The sooner you catch up, the less the penalties will accumulate. The IRS Direct Pay system makes it pretty straightforward once you know your numbers.
Thanks for breaking down the numbers! That $60-70k total tax liability estimate is really helpful. I'm wondering though - when you made that large catch-up payment, did you have to specify which quarters it was for, or does the IRS just apply it to your account? I'm worried about making a mistake with the paperwork since I've never dealt with estimated payments before.
Just wanted to add another perspective - I'm a Canadian freelance developer and I've been working with EU clients for years. My accountant advised me to get VAT numbers for my high-volume EU countries through a fiscal representative service. It was expensive but worth it for me because I have many B2C clients in those countries. If you're mainly dealing with B2B clients though, the reverse charge mechanism means you don't need to register or collect VAT. One practical tip: always ask new EU clients for their VAT registration number upfront and include it on your invoice. This documents that they're a business client subject to reverse charge.
How much did the fiscal representative service cost you? I've been looking into this but the quotes I'm getting seem ridiculously high.
I pay approximately ā¬800-1200 per year per country for the fiscal representation service, which includes quarterly VAT filings. It's definitely not cheap, which is why I only registered in countries where I have significant B2C business. For countries where I have just a few clients, it wouldn't be cost-effective. If you're getting higher quotes, it might be worth shopping around. There are firms that specialize in digital businesses and offer more competitive rates. Also, the OSS system now allows you to register in just one EU country and file VAT for all EU sales through that single registration, which can significantly reduce costs.
This thread has been incredibly helpful! I'm also a Canadian freelancer and had been worrying about this exact issue with my growing EU client base. One thing I'd add for other Canadians reading this - make sure you're also considering the impact on your Canadian tax obligations. Even though you might not need to collect EU VAT, you still need to report all international income to CRA. I learned this the hard way during my first audit. Also, for invoice templates, I found that including a clear statement about the reverse charge helps avoid confusion with EU business clients. Something like "VAT reverse charged - Customer to account for VAT according to local regulations" seems to work well. Thanks everyone for sharing your experiences and the tool recommendations. It's so reassuring to know other Canadian freelancers have navigated this successfully!
This is such valuable advice about reporting international income to CRA! I'm new to freelancing and hadn't even thought about the Canadian tax implications of working with international clients. Can you share more about what that audit experience was like? I want to make sure I'm doing everything correctly from the start. Also, that invoice template language is perfect - I've been struggling with how to word that part professionally. Do you have any other invoice best practices for international clients that you learned through experience?
I'm really sorry for your loss, Dmitri. This is such a difficult situation to navigate while you're grieving. From my experience as a tax preparer, you're absolutely right that you can file married filing jointly for their final return since they were married at the time of death. Here are a few additional things to keep in mind: 1. Make sure to get a federal tax ID number (EIN) for each estate if you haven't already - you'll need these for any estate tax returns or if the estates generate income after death. 2. Check if they had any estimated tax payments due for 2024. As executor, you'll need to make those payments to avoid penalties on their final return. 3. Don't forget about state taxes - you'll likely need to file final state returns as well, and some states have different rules for deceased taxpayers. 4. If they had any joint bank accounts or investment accounts, make sure you understand which income gets reported on their final personal return versus potential estate returns. The IRS Publication 559 has detailed guidance on tax issues for survivors, decedents, and estates. It's dense reading but covers scenarios exactly like yours. You're doing the right thing by being thorough about this.
Thank you so much for the detailed guidance, Dmitry. I hadn't thought about the estimated tax payments - that's a great point. They usually made quarterly payments so I should check if Q4 2024 was paid before they passed. One question about the EIN numbers - do I need separate EINs for each spouse's estate even though they were married? And when you mention "estate income," does that include things like interest that accrued on their bank accounts between their deaths and when I closed the accounts? I'll definitely get Publication 559. The IRS website can be overwhelming when you're trying to find specific guidance, so having a comprehensive resource will be really helpful.
Yes, you'll typically need separate EINs for each spouse's estate if they had separate wills or if their assets weren't entirely joint. Even though they were married, each person's estate becomes its own legal entity for tax purposes. And you're exactly right about the interest income - any interest, dividends, or other income generated on their accounts between their date of death and when you closed/transferred those accounts would be reported on the estate's Form 1041, not on their final personal return. This includes things like final paychecks, pension payments, or investment income received after death. For the estimated taxes, definitely check their 2024 payment history. If Q4 wasn't made before they passed, you as executor can still make that payment to avoid underpayment penalties on their final return. The IRS generally allows reasonable time for executors to catch up on these obligations. Publication 559 really is your best friend here - it has worksheets and examples for situations exactly like yours. Take your time with it, and don't hesitate to reach out to a tax professional if some of the estate tax implications get complicated.
I'm sorry for your loss, Dmitri. This is definitely a complex situation, but you're on the right track asking these questions. One important detail I haven't seen mentioned yet - since your sister passed in March and her husband in October, you'll need to be careful about how you handle any income or deductions that occurred between those dates. Income that your brother-in-law received between March (when your sister died) and October (when he passed) should still be included on their joint final return, but you'll want to make sure you're not double-counting anything. Also, if either of them had health insurance premiums or medical expenses that were paid after your sister's March death but before your brother-in-law's October death, those can still be deducted on the joint return since they were still married filing jointly for the full tax year. The IRS Form 1041 instructions have a helpful section on "Income in Respect of a Decedent" that might be relevant if they had any retirement accounts or other assets that generated income after death. It's worth reviewing even if you end up not needing to file estate returns. You're doing a great job handling this responsibility during such a difficult time.
Thank you for pointing out the timing issue between the two deaths, Kiara. That's something I definitely need to pay attention to. Just to make sure I understand correctly - any income my brother-in-law earned or received between March and October (like his pension payments or any part-time work income) would still go on their joint final return, right? And if he paid any of my sister's outstanding medical bills during that period, those medical expenses could still be deducted on their joint return? I'm also wondering about their joint savings account. After my sister passed in March, my brother-in-law continued to receive interest on that account until he died in October. Would that interest income all be reported on their final joint return, or would some of it need to be split out somehow since she had already passed? This is definitely more complicated than I initially thought, but I really appreciate everyone's guidance here.
Emma Thompson
Another factor that could explain the difference is if you have student loan interest deductions. If you're paying student loans and she isn't, you can deduct up to $2,500 in student loan interest, which would reduce your taxable income and potentially explain part of that $1,350 refund difference. Also worth checking if either of you contributed to a traditional IRA during the tax year - that's another above-the-line deduction that reduces taxable income. Even a $1,000 IRA contribution could create a meaningful difference in your final tax liability compared to someone who didn't contribute.
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Jamal Thompson
ā¢That's a great point about student loans! I do pay about $180/month in student loan interest, so that deduction probably helps. I hadn't thought about IRA contributions either - I should look into that for next year. It's interesting how all these little differences add up to create such a big gap in our refunds even though our base salaries are so similar.
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Liam O'Connor
This is a really common situation that confuses a lot of people! The key thing to understand is that a refund isn't necessarily "good" - it just means you overpaid your taxes throughout the year. Your coworker who owes $15 actually had her withholding dialed in almost perfectly. Looking at all the responses here, it's likely a combination of factors: your 401k contributions (which reduce taxable income), different health insurance situations, student loan interest deductions, and possibly different W-4 setups. The 8% 401k contribution you mentioned is probably the biggest factor - that's over $5,000 less in taxable income compared to your coworker. If you want to get more money in your paychecks instead of waiting for a big refund, consider updating your W-4 to account for these deductions. The IRS withholding calculator can help you figure out the right amount to have withheld so you break even (or close to it) next year.
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Javier Morales
ā¢This is such a helpful breakdown! I'm new to understanding taxes beyond just filing them, and this thread has been really eye-opening. It sounds like the original poster (@Victoria Jones is) actually in a pretty good financial position with the 401k contributions and student loan payments, even if it means a bigger refund. I m'curious though - when people talk about updating the W-4 to get the withholding right, "is" there a risk of accidentally owing a lot at tax time if you miscalculate? I d'rather get a refund than have to come up with a big payment in April, but I also see the point about getting more money throughout the year.
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