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Ask the community...

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Zoe Walker

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Just FYI - I'm a small business owner who's been using Solo 401ks for years, and there's a weird exception that might apply to your situation. If you're a sole proprietor, the "employee" contribution is technically coming from you as the owner anyway. Some providers will code these contributions differently in their system. I've seen cases where you can make the full contribution up to the tax filing deadline and just specify how much is employee vs employer when you file your taxes. But this varies by provider and how they report to the IRS.

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That's interesting! So are you saying some providers might actually allow employee contributions after December 31st, or is it more about how they classify the contributions internally? Has this approach ever caused issues with the IRS for you?

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Zoe Walker

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It's more about how they classify contributions internally. The IRS rules are still the same (employee contributions by Dec 31, employer by tax filing deadline), but some providers don't track the distinction in their system - they just report the total contribution amount. This approach hasn't caused me problems, but it requires careful record-keeping on your end. You need to document what portion was intended as employee vs employer when you file your taxes. The risk is if you exceed your allowed contribution limits for either category. I always consult with my tax professional to ensure my allocations are correct before finalizing my tax return.

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Elijah Brown

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I wanted to point out something that hasn't been mentioned yet. The SECURE 2.0 Act made changes to retirement plans, but it did NOT change the fundamental deadlines we're discussing here. Employee deferrals (the money you contribute as an employee) still need to be elected and set aside by December 31st of the tax year. Employer contributions (the profit-sharing component) can still be made until your tax filing deadline including extensions. What the SECURE Act (the first one) changed was allowing people to ESTABLISH the plan until the tax filing deadline, whereas previously the plan had to be established by December 31st. But this didn't change the actual contribution deadlines for plans that were already established.

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Thanks for clarifying this! A lot of people confuse the deadline for establishing the plan with the deadline for contributions. I learned this the hard way last year when I set up my Solo 401(k) in February for the previous tax year, thinking I could still make employee contributions. Expensive lesson!

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One option nobody's mentioned yet is setting up a Charitable Remainder Trust if you're charitably inclined. You could put some or all of the settlement into a CRT, take a partial tax deduction now, receive income for life, and then have the remainder go to charity. I did this with a $420k settlement and it worked out great - reduced my immediate tax hit, created a steady income stream, and eventually will support causes I care about. You'd need to talk to an estate planning attorney to set it up properly though.

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Jay Lincoln

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How much of a tax deduction did you actually get from doing this? And what percentage of the settlement amount do you receive as income each year? I'm trying to figure out if this makes financial sense.

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My tax deduction was about 25% of the amount I put into the trust, so roughly $105,000, which I was able to use that year and carry forward some to future years since it exceeded my deduction limits. I receive about 5% of the trust value each year as income, which is around $21,000 annually. You can set different percentages based on your needs - anywhere from 5% to 50% technically, though most are in the 5-8% range. The payments can be fixed or variable depending on how you structure it. The key benefit was avoiding a massive tax hit in a single year while still having access to income from the full amount.

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Has anyone used a Section 1031 exchange for settlement money? My brother-in-law mentioned it but I'm not sure it applies to legal settlements.

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Ryan Vasquez

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Unfortunately, Section 1031 exchanges only apply to business or investment real estate, not to settlements. Your brother-in-law is probably confusing it with other tax deferral strategies. For your settlement, you're better off looking at the options mentioned above like non-qualified assignments or potentially a charitable trust if that aligns with your goals. Section 1031 wouldn't be applicable to settlement funds.

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Thanks for clearing that up. I had a feeling he might have been mixing things up. Appreciate the quick correction - saved me from going down a useless research rabbit hole!

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Carmen Diaz

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Have you considered just using TurboTax or H&R Block software? They have specific sections for adjusting cost basis on stock sales. I did my own with about 15 stock sales last year and it wasn't that difficult. The software walks you through it and you can manually override the reported basis.

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I tried this route and it was a nightmare. The software technically "allows" you to adjust basis, but doesn't help you calculate what the correct basis should be. I ended up paying a CPA $350 to fix my return after I'd already spent hours trying to figure it out myself.

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AstroAce

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Just to add another data point - I paid $275 last year for almost the identical situation (3 W2s, some interest, and about 20 stock sales with basis issues). This was with a small local CPA firm, not a chain. Big chains like H&R Block would probably charge more. Location matters too - I'm in a low-cost Midwest city. If you're in SF or NYC, $300 is practically a steal.

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Jabari-Jo

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Another option is to just increase the withholding at your main job to cover the additional income from the teaching gig. My accountant suggested this approach because it's simpler than dealing with multiple withholding adjustments.

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Anna Kerber

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I do this too! Way easier to just have my primary employer take out an extra $200 per paycheck than mess with the withholding on smaller jobs. Just calculate your expected additional tax from all side gigs, divide by the number of paychecks from your main job, and add that amount to your withholding.

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Jabari-Jo

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Thanks for confirming this approach! It's worked really well for me. One thing to add - if you go this route, make sure you're not having too much withheld just because it's easier. I review my withholding about halfway through the year to make sure I'm on track.

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I adjunct at a community college too! For my $500ish biweekly checks, I have them withhold $100 for federal taxes. My spouse and I are in the 22% bracket with our combined incomes, and this has worked out almost perfectly for the past two years. You could try a similar percentage. Just remember that teaching income stacks on top of your other income for tax bracket purposes, so it's getting taxed at your highest marginal rate. Don't make the mistake I made the first year where I only had 10% withheld because I thought that's what the bracket would be if it was my only job!

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That's really helpful to hear from someone in almost the exact same situation! I think I'll start with having them withhold $100 from each check and see how that looks. Thanks for the perspective!

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Amina Diallo

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You might want to check your credit report too. If your father put a business in your name without permission, there's a chance he might have taken out business loans or credit cards too. You should get a full credit report from all three bureaus to make sure there aren't other financial issues tied to your name that you don't know about. Also, while I understand not wanting to get your father in trouble, please remember that you're the victim here. This could affect your financial future for decades if not addressed properly. Whatever path you choose, make sure you're protecting yourself first.

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TechNinja

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I hadn't even thought about checking my credit report. That's a really good point. Do you know if business debts always show up on personal credit reports? And if I do find something, should I dispute it the same way as the tax debt?

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Amina Diallo

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Business debts can absolutely show up on your personal credit report, especially if the business was a sole proprietorship or if your father used your personal information to guarantee any loans. Even with corporations or LLCs, lenders often require personal guarantees from owners for small businesses. If you find unauthorized accounts or loans, you would dispute them differently than tax debt. For credit report issues, you'd file disputes directly with the credit bureaus using their fraud departments. You may also need to file a police report for identity theft, which some creditors require before removing fraudulent accounts. This is separate from the IRS process, but equally important for your financial health.

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GamerGirl99

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Has anyone considered that maybe the father didn't do this maliciously? Maybe he thought he was helping his kid establish credit or a business history? I'm not saying what he did was right - it definitely wasn't - but before going straight to identity theft claims and potentially sending your dad to jail, maybe have an honest conversation with him first?

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Intent doesn't really matter when you're talking about $105K in tax debt that could follow this person for life. Even if the father meant well (which seems doubtful), he's essentially saddled his child with a massive financial burden without consent. That's not something you do to someone you care about, regardless of intention.

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