Don't forget about state estimated taxes too! Depending on your state, you might have different requirements than federal. My state (CA) absolutely hammered me with penalties because I made federal quarterly payments but forgot about state.

As a former tax preparer who now specializes in trader taxes, I want to emphasize something crucial that could save you thousands in penalties: since you've already earned $78,000 in trading profits through 8 months and haven't made any estimated payments yet, you're likely subject to underpayment penalties unless you act quickly. The IRS generally requires quarterly payments if you expect to owe $1,000 or more in taxes. With $78K in profits, you're definitely in that territory. However, you may still be able to minimize penalties by making a large estimated payment for Q3 (due September 15) and Q4 (due January 15). Here's what I'd recommend: Calculate roughly 25-30% of your profits for federal taxes (depending on your total income and deductions), plus self-employment tax of about 14.13% on your trading profits if you don't qualify for trader tax status. Don't forget state taxes if applicable. The key is to act now rather than wait until April. Even if you end up overpaying slightly, it's better than facing underpayment penalties plus interest. You can always get a refund when you file your return.

Something nobody mentioned is that you can do multiple backdoor Roth conversions in a year. If you do manage to get your trad IRA emptied out via the reverse rollover to your 401k, you could potentially do another backdoor Roth with additional non-deductible contributions up to the annual limit! I do this quarterly instead of all at once, and it's totally fine with the IRS.

Has anyone dealt with the paperwork for this? My accountant says there's a form 8606 I need to fill out for the backdoor Roth even if I fix the pro rata issue by year-end. Is that right?

Has anyone used TurboTax to handle severance packages? Do they have a special section for this or is it just entered as regular income? I'm in the same boat as OP and wondering which tax software handles this situation best.

I went through something very similar last year when I was laid off in February. The key thing to understand is that severance withholding often looks scary but it's usually just being overly cautious. My company withheld about 28% from my severance (federal + state), which felt like a huge chunk. But when I filed my taxes, I got most of it back because my total annual income was lower due to being unemployed for several months, just like your situation. One thing that helped me was keeping track of all my job search expenses - things like career coaching, resume services, networking events, interview travel costs, etc. These can sometimes be deductible and help offset the tax impact of your severance. The bottom line is that the IRS looks at your total annual income, not just individual payments. Since you were out of work for 8 weeks, there's a good chance you'll see a decent refund assuming they overwitheld on your severance. Just make sure to save all your tax documents and consider talking to a tax professional if the numbers seem off when you start preparing your return.

FYI - according to the My Tax Form website FAQ, they typically update at midnight Eastern time. So if your employer uploaded it today, it should be available at midnight ET tonight. That said, some employers only upload weekly, especially smaller companies.

Target employee here! I just got my W2 on My Tax Form this morning around 2 AM. I've been checking obsessively too lol. From what I've noticed working there for 3 years, Target usually uploads W2s in waves based on your employee number or store region. The first batch typically goes up around January 20th, with most everyone having theirs by January 28th. If you're still not seeing yours by January 29th, definitely call the Target HR hotline - sometimes there are issues with address changes or electronic consent that can delay individual W2s. Also make sure you're logged into the right My Tax Form account (the one linked to your Target employee profile). Hope this helps ease some of the anxiety!

Watch out for state tax issues too with your LLC sale! Federal is only part of it. Some states treat these sales differently and you might face surprising state tax bills. I sold my LLC in California and got hammered with state taxes I hadn't planned for because my accountant only focused on federal. Double check your state's treatment of goodwill and intangible assets before finalizing anything.

This is such a complex area that really deserves careful planning. One thing I'd add to the excellent advice already given - make sure you get a professional business valuation done before finalizing your sale structure. This isn't just helpful for negotiations, but it's crucial documentation if the IRS ever questions your asset allocation on Form 8594. A formal appraisal can help support the value you're assigning to goodwill versus tangible assets, which directly impacts whether you're paying capital gains or ordinary income rates. The cost of a good business appraiser (usually $3k-8k depending on complexity) is often a fraction of what you could save in taxes with proper allocation. Also, timing matters more than people realize. If you're close to a year-end, consider whether pushing the sale into the next tax year might help with your overall tax situation, especially if you have other capital gains or losses to consider. The interplay between federal and state taxes that others mentioned is real - I've seen people save five figures just by timing their sale strategically.