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For last-minute tax reduction strategies, don't forget about 529 plan contributions! Many states offer tax deductions for contributions to these college savings plans, even if you open and fund one on December 31st. For example, my state (NY) allows deductions up to $5,000 per year for individuals or $10,000 for married couples filing jointly. You can name yourself as beneficiary if you don't have kids yet, and later change it. Just check your state's rules since not all states offer deductions.
Does contributing to a 529 reduce federal taxes though? I thought it was only state tax deductions in some states. We're really trying to minimize our federal tax bill since that's where the big surprise is coming from.
You're right - 529 contributions don't reduce your federal tax bill, only state taxes in states that offer the deduction. I should have been clearer about that. While this won't help with your federal tax surprise, it could still save you some money on state taxes depending where you live. For federal tax reduction, your options before year-end are more limited since you've already maxed your HSA. If you own a business or have any self-employment income, you could potentially make SEP IRA or Solo 401k contributions, which would reduce federal taxable income.
Strongly recommend reviewing your W-4 withholding ASAP to prevent this problem next year. The 2020+ version of Form W-4 doesn't use allowances anymore, so if you're still thinking in terms of "0 allowances" you might be using outdated forms or concepts. The new W-4 requires you to account for multiple jobs and specifically address additional income like investment earnings. There's a whole worksheet for this now. Your Roth conversion definitely needed adjustment on your W-4.
I've been self-employed for about 7 years now and have tried most of the major tax software. For 1099 income with retirement accounts, I've found TaxSlayer to be surprisingly good, especially for the price point. It handles self-employed 401k contributions correctly, separating employee and employer portions without the glitches you mentioned. The business mileage tracking is straightforward, and it lets you import from mileage tracker apps if you use those. Their support is also more knowledgeable about self-employment issues than H&R Block's in my experience.
Thanks for the TaxSlayer recommendation! How does it compare to FreeTaxUSA price-wise? And does it handle state filing too, or is that an extra charge?
TaxSlayer is slightly more expensive than FreeTaxUSA for the self-employed version, but still much cheaper than TurboTax or H&R Block. Last time I used it, the federal filing with self-employment was around $55, and state filing was an additional $35 per state. State filing is indeed an extra charge with TaxSlayer, similar to most tax software except for the truly free options that have significant limitations for self-employed people. The state module is comprehensive though and handles all the specific state deductions and credits relevant to self-employment income.
I switched from TurboTax to FreeTaxUSA last year for my 1099 work and solo 401k, and I'm never going back! The solo 401k was handled perfectly with clear sections for both employee and employer contributions. One thing nobody's mentioned yet that I found super helpful was the comprehensive audit assistance. Since 1099 workers get audited more frequently, I liked having that extra protection. And the customer service was shockingly responsive when I had questions - got answers within hours instead of days.
Did you find FreeTaxUSA easy to navigate for business expenses? I do photography as a side hustle and have a ton of different expense categories. TurboTax makes it so complicated I'm afraid I'm missing deductions.
Just a heads up - don't forget that even though your fiancee might not owe federal income tax because the prize value is below the standard deduction, she could still be on the hook for self-employment tax if this is considered self-employment income (like if she's a Mary Kay consultant herself). Self-employment tax kicks in once you make $400 or more in self-employment income, which is way lower than the standard deduction threshold. That includes the 15.3% for Social Security and Medicare that normally gets withheld from a W-2 job's paycheck.
Does winning a trip as a customer count as self-employment though? I thought self-employment was only if you're actually selling stuff or providing services. The post says she won it through her consultant, which makes it sound like she's just a customer who entered some kind of contest?
You're right about the distinction. If she's just a customer who won a prize, then it would be reported as "Other Income" on Schedule 1, not subject to self-employment tax. The key is how the 1099-MISC is filled out - Box 3 is for "Other Income" like prizes and awards, while Box 1 would be for self-employment income. The OP should check which box on the 1099-MISC has the amount listed. If it's in Box 3, then it's just regular income (not subject to self-employment tax). If it's in Box 1, then Mary Kay might be incorrectly classifying it as self-employment income.
Did you guys enter this trip as a prize when filing, or as a gift? Because I think gifts aren't taxable to the recipient (the giver pays any gift tax). Maybe there's a way to argue this was a gift from the Mary Kay consultant rather than a prize?
That's unfortunately not going to work. The IRS has very clear rules distinguishing gifts from prizes. A gift must be given out of "detached and disinterested generosity" with no expectation of benefit to the giver. When a company like Mary Kay gives a trip through a promotion or contest, it's clearly for business purposes (advertising, client retention, etc.), so it's a prize, not a gift. The 1099-MISC confirms this classification. Trying to reclassify it as a gift would likely raise red flags with the IRS.
Another thing to consider - if either of you has previous tax debts or is behind on certain government payments (like child support), filing jointly could put the refund at risk. When you file jointly, your entire refund could be seized to pay those debts even if they only belong to one spouse. You'd need to file an injured spouse form to try getting your portion back, which is a hassle.
Do student loans fall into this category? If your spouse has defaulted federal student loans, will they take your refund if you file jointly?
Yes, defaulted federal student loans can definitely lead to tax refund offsets. If your spouse has defaulted loans and you file jointly, the entire refund could be seized to repay those loans. Filing Form 8379 (Injured Spouse Allocation) can help you get your portion of the refund back, but it adds complexity and delays your refund by several months. If the student loans are in good standing or on an income-driven repayment plan, then you don't have to worry about refund offsets - it's only for defaulted loans. This is actually another situation where filing separately might make sense if one spouse has defaulted loans, as it protects the other spouse's refund entirely.
First time my husband and I filed together, we tried both options in TurboTax and found filing jointly saved us almost $2,000! But everyone's situation is different. When one spouse is a student, joint is usually better because you can claim education credits on a joint return. Consider running your numbers both ways before deciding.
Sarah Jones
I filed on January 29th and STILL haven't gotten my refund!!! The IRS Where's My Refund tool just says "still processing" for over 7 weeks now. I claimed the Child Tax Credit for my two kids. Anyone else waiting this long with CTC? Getting really frustrated!!
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Sebastian Scott
โขI claimed CTC for my kids too and got my refund after about 4 weeks. Did you also claim Earned Income Credit? That usually takes longer. You might want to try getting your tax transcript from the IRS website - sometimes it shows more details about what's happening with your return.
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Emily Sanjay
For those interested in extremely detailed stats: - E-filed with FreeTaxUSA on Jan 31 at 7:32pm EST - IRS acceptance email received Feb 1 at 9:14am - WMR updated to "approved" on Feb 15 - Direct deposit hit my bank Feb 17 at 3:42am Federal refund: $2,341 State refund: Still waiting, shows "processing" on state website Our return included W-2 income, 1099-INT, mortgage interest deduction, student loan interest, and HSA contributions. No tax credits. I've been tracking this data for years and this was about 3 days faster than last year!
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Jordan Walker
โขYou're even more detail oriented than me lol! Have you always used FreeTaxUSA? I've been thinking about switching from TurboTax to save some money.
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Emily Sanjay
โขI've used FreeTaxUSA for the last three years after switching from TurboTax. The interface isn't quite as polished, but it's completely adequate and handles all my tax situations correctly. The federal filing is free and state is only $15 compared to the $120+ I was paying with TurboTax for the same exact results. If you have a fairly straightforward tax situation (even with some common deductions and forms like I listed), it works great. The only people who might want to stick with the more expensive options are those with extremely complex situations like multiple businesses, complex investments, or unusual tax situations.
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