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One thing nobody mentioned yet is estimated tax payments for self-employment or investment income. If you've had a good year with extra income, you might need to make a Q4 estimated payment by January 15th to avoid penalties. This isn't technically a "tax reduction" strategy but can save you money in penalties!
Good point! I got hit with a penalty last year because I didn't realize this. Is there any kind of safe harbor rule that helps avoid the penalty even if you owe a lot?
If you have kids, look into contributing to a 529 college savings plan before year end. Many states offer tax deductions for contributions. Also, review any medical procedures you might need - sometimes it makes sense to bunch them in December if you're close to exceeding the medical expense deduction threshold (which is 7.5% of your AGI).
I went through bankruptcy with about $500k in IRS debt last year. Few things to keep in mind: 1) Make sure you file all required returns before bankruptcy. Any unfiled returns will definitely not be dischargeable. 2) Be careful about any transfers of assets in the years leading up to bankruptcy - the court looks back several years and can claw back anything they consider inappropriate. 3) Document EVERYTHING about your current financial situation very thoroughly. The courts are more skeptical when large tax debts are involved. 4) The IRS will scrutinize your case much more closely than a typical bankruptcy. They may send their own attorneys to challenge the discharge of tax debt. 5) Your trading accounts and history will be examined closely. Be prepared to explain any large withdrawals. Good luck! It's a stressful process but there is light at the end of the tunnel.
Thanks for sharing your experience! How long did the whole process take from filing to discharge? And if you don't mind sharing, were you able to get all of your tax debt discharged or just a portion?
The entire process took about 9 months from filing to discharge, which is longer than typical bankruptcies. The tax components definitely slow things down because the IRS reviews everything carefully. I was able to get about 80% of my tax debt discharged. The remaining 20% wasn't dischargeable because those taxes were from a year where I filed late and hadn't yet hit the 2-year mark from filing date. I ended up on a payment plan for that portion, but having 80% wiped out made that manageable.
Don't overlook the emotional toll this will take. Bankruptcy with the IRS involved is WAY more stressful than regular bankruptcy. I went thru this in 2022 and spent almost every night unable to sleep. Get some support - therapist, support group, whatever. The stress can be unbearable especially when ur young and feel like ur life is ruined. Also prepare for after bankruptcy. Trading might be harder without capital. Have a backup plan for income. The discharge feels amazing but then reality hits that you need to rebuild completely.
This is so true. I went through tax bankruptcy last year and the emotional side was the hardest part. Did you find that lenders were especially harsh because it was tax debt rather than credit cards or medical bills? I've been struggling to rebuild my credit because it seems like lenders see tax bankruptcy as a bigger red flag.
A big thing you need to figure out is your cost basis. Since you inherited the stock, your basis should be the fair market value on the date of death (or alternate valuation date if the executor chose that). This is called a "stepped-up basis." For a large inheritance like that, there should be estate documents that show the valuation. Make sure you have those before filing, because using the wrong basis could cost you thousands in deductions.
What happens if you can't find documentation of the exact value on date of death? My dad left me some stocks but passed away during COVID and everything's a mess with paperwork.
If you can't find the documentation, you can try to reconstruct it. You'll need to determine the date of death and then research what the stock was trading for on that day - most financial websites have historical price data. Get the closing price on that date and multiply by the number of shares. If it was a significant inheritance, the estate may have filed an estate tax return (Form 706) which would have the valuation. You can request a copy from the IRS with Form 4506. Another option is to contact the broker who handled the account - they often have historical valuations on record.
Everyone is talking about tax benefits, but has anyone considered that some of these failed bank stocks might actually recover some value? After Washington Mutual collapsed in 2008, the worthless stock (WAMUQ) actually traded up to about 50 cents from nearly zero as speculators bet on leftover assets.
Just wanted to mention that if you're only filing a few 1099-NECs, you can file them for free directly on the IRS website through the FIRE system. No need to buy forms or pay for services if you're comfortable navigating the government website.
I tried using the IRS site but got super confused. Is there a specific tutorial you followed to figure it out?
The IRS site is definitely not the most user-friendly, I'll admit. I found their tutorial in Publication 1220, but it's pretty technical. Here's what worked for me: create an account first, then go to the "Filing Information Returns Electronically" (FIRE) section. For simpler guidance, I actually ended up watching a YouTube tutorial someone made that walked through the process step by step. Just search "how to file 1099-NEC on IRS FIRE system" and you'll find several helpful videos that are much clearer than the official instructions.
Hey I went through this exact thing last month! I only had one contractor but got the 3-up form. I just filled out the top section and left the rest blank. Mailed it in and everything was fine. Don't overthink it!
Did you also e-file with the IRS or just mail the paper form? I'm trying to figure out the easiest way.
NebulaNova
Quick tip from someone who's been through this - if you have your last paystub of the year, it usually has your year-to-date info which is basically what goes on your W2! Most restaurants use standard payroll systems that calculate this automatically. Might be worth checking if you have that last stub somewhere.
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Sofia Ramirez
ā¢That's a great point! I don't think I saved my last paystub, but now I'm going to check my email to see if they sent electronic copies. I vaguely remember getting emails when a new paystub was available, but I usually just checked the deposit amount. If I can find that last one from December it would solve everything! Thanks for the suggestion!
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NebulaNova
ā¢Happy to help! Even if you can't find the December one, any paystub from late in your employment might be useful since it would have the year-to-date totals up to that point. You could then estimate the additional earnings for your remaining time there. And don't forget to check your spam folder - payroll emails often end up there.
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Keisha Williams
Has anyone here ever had the IRS penalize them for filing with Form 4852 instead of a W2? I'm worried my refund will get flagged or delayed if I go this route. My old employer is being difficult about sending my W2 and I need to file soon.
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Paolo Conti
ā¢I had to use Form 4852 two years ago and had zero issues. The IRS actually processes these pretty routinely. As long as your estimates are reasonable and you document your attempts to get the W2, you should be fine. My refund wasn't delayed at all. The employers are the ones who typically get in trouble, not you.
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