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Just to add some clarification - it also matters if the settlement had punitive damages vs compensatory damages. Punitive damages are almost never deductible, while compensatory might be depending on what they're compensating for. If your settlement agreement breaks down what's what, that's super helpful for determining tax treatment.
Thanks for this - my settlement does break down different amounts. About $21k was compensatory for financial losses and about $7k was listed as "other damages." Is there a way to deduct at least the compensatory part?
Based on your breakdown, if the $21k compensatory damages were related to financial losses from a business activity or investment property, then yes, that portion would likely be deductible in the appropriate section (Schedule C for business, Schedule E for rental property, etc.). The $7k listed as "other damages" is more ambiguous and would depend on the specific nature of those damages. If they're punitive damages, those typically aren't deductible. If they're for emotional distress without physical injury, those generally aren't deductible either. But if they relate to a business loss in some way, they might be.
Make sure you keep really good records of the settlement! If you get audited, you'll need to show the settlement agreement and proof of payment. I got audited 2 years ago over a business settlement deduction and having all my paperwork saved me big time.
Do cancelled checks count as proof or do you need more than that? I paid my settlement in 3 installments and have the cancelled checks but wondering if I need more documentation.
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Quick note that might help - make sure you're tracking ALL your business expenses carefully. I'm a small seller too, and I use a spreadsheet to track: - Cost of materials - Shipping supplies - Platform fees (Etsy, eBay, etc) - PayPal fees - Portion of internet/phone used for business - Home office space (if you have dedicated space) - Mileage when you go buy supplies You'd be surprised how quickly these add up and can reduce your taxable income. I learned this the hard way my first year and paid way more than I needed to!
Do you need receipts for absolutely everything? I haven't been great about keeping track so far. Also, how do you calculate the portion of internet/phone to deduct?
Yes, you should keep receipts for everything - the IRS can ask for documentation if you're ever audited. But if you've lost some, bank/credit card statements can sometimes work as backup. For internet/phone, you need to determine what percentage is used for business. For example, if you estimate 30% of your phone use is for business communications with customers, you can deduct 30% of your phone bill. Just be honest and reasonable with your estimates. Some people keep a log for a few weeks to establish a usage pattern. Same concept applies to your home office - you calculate what percentage of your home's square footage is used exclusively for business, then deduct that percentage of rent/mortgage, utilities, etc.
I see a lot of comments about filing, but nobody mentioned the Qualified Business Income Deduction (Section 199A). If your net income from your business is under certain thresholds, you might qualify for a deduction of up to 20% of your business income! This is separate from your regular business expense deductions. Also, consider making estimated quarterly tax payments if you expect to owe more than $1,000 in taxes. This helps avoid an underpayment penalty when you file your annual return.
Omg this tax stuff is so complicated. Im making bracelets and selling them on etsy too and i had no idea about any of this!!! How do you even make quarterly payments? And what's this 199A thing?
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One thing I learned from my CPA friend - create a simple coversheet/checklist with everything you're providing them. It makes it super obvious if something is missing and gives them a quick overview of your situation. My friend says clients who do this tend to get their returns done faster because they don't have to keep coming back asking for missing documents. It also helps you keep track of what you've already given them vs what you still need to track down.
Do you have a template for this coversheet you could share? I'm trying to visualize what should be on it besides just a list of documents.
I don't have a specific template, but I include these sections: Personal Info (names, SSNs, address), Income Documents (list all W-2s, 1099s by source), Deduction Documentation (charitable contributions, home office, etc.), Credits (child tax credit info), Estimated Tax Payments (dates and amounts), and Questions (things I specifically want the CPA to address). I also add a section for "Changes from Last Year" that highlights anything new (like your new baby) so they immediately know what's different.
I've been using a CPA for years and the best thing I started doing was keeping a "tax events" note on my phone. Whenever something happens that might affect taxes (bought something for business, made a donation, started using part of house for work), I just jot it down with the date. By tax time I have a chronological list of everything that happened.
Smart! What app do you use for this? Just regular notes app or something specific for tracking expenses?
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Just coming from an accounting perspective - one thing to consider is that a tax refund isn't free money, it's YOUR money that you overpaid throughout the year. If you contributed 90% of the payments, then logically, most of that refund is just returning YOUR overpayment. I always tell my clients to think about it this way: if you had both filed separately, what would each of your refund/payment situations look like? That can sometimes clarify who "generated" the refund. That said, I've seen couples handle this many different ways: 1. Split based on income percentage 2. Split based on tax payment percentage 3. Split 50/50 regardless 4. Put the whole refund toward a shared goal/expense There's no absolute "right" answer - it depends on your overall financial arrangement.
What about if one spouse is a stay at home parent? They technically didn't contribute any tax payments, but they're enabling the working spouse to earn income. Should they get 0% of the refund?
That's an excellent question and highlights why this isn't a simple mathematical equation. In a stay-at-home parent situation, that spouse is providing substantial economic value to the family through unpaid labor that enables the working spouse to earn income. In that case, I generally advise clients to view family finances (including tax refunds) as fully shared resources rather than trying to split based on direct financial contribution. The non-working spouse is contributing significantly to the family economy in non-monetary ways. Most of my clients in this situation treat the refund as joint family money and make decisions about it together, recognizing both partners' contributions to the family's overall financial situation.
My husband and I solved this by just having separate bank accounts AND a joint account. Our tax refund always goes into the joint account and is used for shared expenses/goals. That way we never fight about who gets what portion of it. Or sometimes we use the refund for a vacation together! That way it's something we both benefit from equally.
This is exactly what we do! Joint refund goes to joint expenses or something fun we do together. No arguments ever. We actually have our refund automatically split into savings for our annual vacation. Tax time = vacation planning time lol
I really like this approach. We've been talking about saving for a home renovation, so maybe using the refund for that would be a good compromise where we both benefit. That would definitely avoid the whole percentage split issue entirely. Do you find that system works well overall for managing finances? We've been mostly separate but are considering more joint planning.
Sebastián Stevens
Just a quick tip from my experience moving from India to the US mid-year last year: make sure you're clear about your residency status for tax purposes! There's something called the "substantial presence test" that determines if you're a resident alien or nonresident alien for tax purposes. Since you arrived in November, you might actually be considered a nonresident alien for 2023 tax purposes, which would change how you file. If that's the case, you might need to file Form 1040-NR instead of the regular 1040, and the joint filing with your spouse might be more complicated. FreeTaxUSA should have a questionnaire that helps determine your status, but just make sure you're clear on this before you start the actual filing process.
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Molly Hansen
•Thank you for bringing this up! I hadn't even considered the resident vs. nonresident alien distinction. Do you know if there's any advantage to being classified one way or the other? And will FreeTaxUSA automatically determine which forms I need based on my answers?
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Sebastián Stevens
•There can definitely be advantages depending on your specific situation. Generally, if most of your income was earned outside the US (which sounds like your case), being a nonresident alien means you only pay US tax on US-source income. As a resident alien, you'd be taxed on worldwide income. FreeTaxUSA will guide you through questions to determine your status and should select the appropriate forms. However, there's a special provision where nonresident aliens married to US citizens can elect to be treated as residents for tax purposes, allowing you to file jointly. This is often beneficial but depends on your specific numbers. The software should walk you through this option as well once it determines your status.
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Bethany Groves
Has anyone compared FreeTaxUSA to TurboTax for handling foreign income? I'm in a similar situation (moved from South Korea last year) and wondering which software handles international situations better?
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KingKongZilla
•I've used both. TurboTax is more hand-holdy with foreign income but WAY more expensive when you need the premium version for international situations. FreeTaxUSA has all the same forms and capabilities but the interface is slightly less polished. Functionally they both work fine - I switched to FreeTaxUSA and saved about $70.
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