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Slightly different approach - have you considered filing Form 1040X to amend your 2021 return? In some cases with ISOs and AMT, you can treat the options as never having been exercised if they became worthless within the same year or shortly after. Might be worth exploring as an alternative to the capital loss approach.
This advice is potentially misleading. You generally can't retroactively undo an ISO exercise through an amendment. The capital loss and AMT credit recovery approach is the standard IRS-approved method. The "treat as never exercised" approach typically only applies in very specific circumstances involving statutory stock options that weren't properly issued or were canceled within the same tax year as exercise.
I went through almost the exact same situation in 2020-2022. Exercised ISOs, paid massive AMT, then the company got acquired for pennies and common shareholders got zero. It's absolutely brutal financially and emotionally. A few things that helped me navigate this: 1. **Timing matters for worthless securities** - You claim the loss in the year the stock actually became worthless, not when you found out about it. For me, this was the date the acquisition closed and it was clear common shares had no value. 2. **Documentation is key** - I created a comprehensive file including: the original ISO agreement, exercise confirmations, any company communications about the acquisition, the final acquisition term sheet showing $0 for common shares, and a written timeline of events. The IRS wants to see that you can prove an "identifiable event" made the shares worthless. 3. **Don't forget about AMT credits** - This is where many people leave money on the table. The AMT you paid in 2021 generates credits that can offset regular tax in future years. Form 8801 is your friend here. The worthless stock loss actually helps trigger these credits since it reduces your AMT relative to regular tax. 4. **Consider professional help** - This situation is complex enough that a tax professional experienced with ISOs and AMT is worth the cost. The potential recovery often justifies the expense. The silver lining is that you can recover a significant portion of what you lost through proper tax planning. It takes time (capital losses are limited to $3K/year against ordinary income), but you will get relief.
This is incredibly helpful - thank you for sharing your experience! I'm particularly interested in your point about timing. My company was acquired in October 2022, but I didn't receive the final documentation showing common shares got $0 until January 2023. Should I claim the loss for 2022 (when the acquisition closed) or 2023 (when I had definitive proof)? Also, do you have any tips for calculating the adjusted basis correctly when AMT was involved? I want to make sure I'm not leaving money on the table with the basis calculation.
Dont forget about the qualified business income deduction (QBI) on Section 199A! If your reporting income on Schedule C you might qualify for this extra 20% deduction even if you have expenses that offset most of the income. Could actually work in ur favor!!!!
This is actually incorrect information. The QBI deduction only applies to net business income, so if you're reporting expenses that perfectly offset the 1099-NEC income (resulting in zero net income), there would be no QBI deduction available. Additionally, even if there were some net income, speaking at a single conference would likely fall under the specified service trade or business (SSTB) limitations for QBI.
This is a really helpful thread! I'm dealing with a similar situation where I got a 1099-NEC for what should have been expense reimbursements. Based on all the advice here, it sounds like Schedule C is the way to go to offset the income with the actual expenses. One question though - when reporting the expenses on Schedule C, do I need to follow the specific IRS categories (like separating meals at 50% deductible vs. full transportation costs), or since these were direct reimbursements can I just list them as "Other expenses" with a description? I want to make sure I'm not overcomplicating this but also want to be completely accurate in case of any questions later. Also really appreciate the suggestions about taxr.ai and Claimyr - it's reassuring to know there are resources available when you need specific guidance on these tricky situations!
Does anyone know if vehicle registration fees count toward the SALT cap? I pay almost $900 a year and TurboTax has a special section for this, but I'm not sure if it's part of the $10,000 limit.
This is really helpful info everyone! I've been wrestling with SALT deductions too since moving from a low-tax state to California. One thing I learned the hard way - if you have estimated tax payments, make sure you're allocating them correctly between federal and state portions. I was accidentally including my federal estimated payments in my SALT calculation and it threw everything off. Also, for anyone dealing with multi-state situations (like I was when I moved mid-year), each state's taxes still count toward the same $10,000 federal cap. So if you paid $6,000 to one state and $5,000 to another, you're right at the limit even though you dealt with two different tax systems. The timing of property tax payments can be tricky too - it's based on when you actually paid, not when the tax year was for. So December 2024 property tax payments go on your 2024 return even if it's for the 2025 tax year.
I'm genuinely curious why the $16,000 limit for QPA hasn't been adjusted for inflation. If it was set in the 1980s, that would be equivalent to around $45,000-50,000 today. Seems like the government has just let this deduction become useless for most actual performing artists.
It's because performing artists don't have a strong enough lobby in Washington. For comparison, look at how much the estate tax exemption has increased over the years - that benefits wealthy individuals who have substantial political influence.
The $16,000 AGI limit is indeed frustratingly outdated. It was established in 1986 and hasn't been adjusted since - that's nearly 40 years without any inflation adjustment! In today's dollars, that $16,000 would be worth about $44,000. The practical reality is that very few professional performing artists can survive on less than $16,000 annually, which makes this deduction almost useless for the people it was intended to help. Meanwhile, the standard deduction has increased regularly, and many other tax provisions get annual inflation adjustments. There have been some proposals in Congress over the years to either increase the limit or eliminate it entirely for QPA status, but they haven't gained enough traction. The performing arts community would benefit from more organized advocacy on this issue, as it affects thousands of working musicians, actors, and other performers who are caught in this outdated income trap. Until then, your best bet is exactly what others have suggested - maximize your legitimate Schedule C deductions for 1099 income and work with venues when possible to ensure proper worker classification based on the actual nature of your working relationship.
This is such valuable context, thank you! It's mind-blowing that a tax provision specifically designed to help working artists has been left to wither away for 40 years. $44,000 in today's money makes SO much more sense as a threshold. I'm curious - do you know if there are any current bills in Congress addressing this? It seems like with the gig economy exploding and more people doing freelance creative work, this would affect way more people now than it did in 1986. Maybe it's time for performing artists to band together and push for an update to this ridiculously outdated limit. In the meantime, I'll definitely focus on maximizing my Schedule C deductions for the 1099 work. At least that's something concrete I can do while we wait for Congress to catch up to reality!
Aileen Rodriguez
Have you checked your IRS transcript online? Sometimes it shows processing steps that WMR doesn't reveal. The combination of self-employment and credits often triggers what the IRS lovingly calls "additional review" (their euphemism for "we're going to take our sweet time"). š
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Miguel Ramos
Been in this exact situation for the past month! Filed February 10th with 1099-NEC income, CTC, and EIC. Finally got my refund deposited yesterday (March 6th) - so about 24 days total. My transcript updated with codes 846 and 571 about a week before the actual deposit hit my account. The waiting is absolutely brutal, especially when you're getting daily "any updates?" questions from family. What helped my sanity was checking my transcript instead of WMR - at least the transcript gives you SOME indication of movement even when WMR is stuck on that useless first bar. Hang in there - seems like most self-employed filers with these credits are hitting the 3-4 week mark this year. Your refund is coming! š¤
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