One thing to keep in mind is that most RSUs are taxed at vesting (your company probably withheld shares for taxes when they vested). So your actual cost basis for tax purposes is the FMV on vesting date, not zero. This means your older RSUs that are "lower than current price" might actually represent a loss if the current price is lower than when they vested! In that case, selling them would give you a capital loss you can use to offset other gains. Check your vesting statements carefully!

Great advice from everyone here! One additional consideration for @Kristin Frank - if you're in a higher tax bracket this year but expect to be in a lower bracket next year (maybe due to job change, retirement, sabbatical, etc.), it might make sense to delay selling the older RSUs to take advantage of the lower long-term capital gains rate when your overall income is lower. Also, don't forget about the Net Investment Income Tax (NIIT) - if your modified adjusted gross income exceeds $200K (single) or $250K (married filing jointly), you'll pay an additional 3.8% tax on investment income including capital gains. This could influence the timing of when you sell. The tools others mentioned like taxr.ai sound really helpful for modeling different scenarios, especially when you factor in state taxes and these additional considerations!

One thing I haven't seen mentioned yet is quarterly estimated tax payments. Since you're making "decent money" after 8 months, you'll likely need to make quarterly payments to avoid underpayment penalties. The IRS expects you to pay as you earn, not just at year-end. For 2025, if you expect to owe $1,000 or more in taxes on your golf business income, you should be making quarterly payments. The deadlines are January 15, April 15, June 16, and September 15. You can use Form 1040ES to calculate what you owe. Also consider opening a separate business checking account if you haven't already. It makes tracking so much easier and looks more professional if you ever get audited. You can deduct the monthly fees as a business expense too. Keep up the great work with the side business - sounds like you're really building something solid!

Great thread everyone! As someone who's been through the home business learning curve, I wanted to add a few practical tips that helped me stay organized: 1. **Monthly reconciliation** - Set aside time each month to categorize expenses and reconcile your business account. Don't wait until tax time! I use a simple spreadsheet with columns for date, vendor, amount, category, and business purpose. 2. **Photo documentation** - Take pictures of receipts immediately and store them in a cloud folder organized by month. I've saved myself multiple times when paper receipts faded or got lost. 3. **Business purpose notes** - For any expense that could be questioned (like those golf rounds for testing clubs), write the business purpose directly on the receipt or in your expense tracking. "Tested driver repair for Client X" is much better than trying to remember 6 months later. 4. **Mileage log app** - Use an app like MileIQ or even just the notes app on your phone to track business mileage in real-time. I tried keeping a paper log and failed miserably. The key is building these habits now while your business is growing. It's so much easier to maintain good records from the start than to reconstruct everything later. Sounds like you're already thinking about this stuff the right way - that puts you ahead of most new business owners!

Make sure you explore all possible deductions/credits to offset some of this conversion income! Unemployment often makes people eligible for credits they wouldn't normally get. Check if you qualify for the Earned Income Credit, education credits if you took any classes, or increased medical expense deductions (threshold is lower when income drops). Also, since you were laid off, don't forget to deduct any job search expenses that might be eligible. Every little bit helps when facing a big tax bill from Roth conversions!

I'm really sorry to hear about your situation - getting hit with unemployment and a massive tax bill at the same time is incredibly stressful. Since you can't undo the conversion, here are a few additional strategies to consider: First, if you haven't already, make sure you're maximizing your 2023 deductions. Since you were unemployed for part of the year, you might qualify for larger medical expense deductions (they need to exceed 7.5% of AGI), and any charitable contributions you made could help offset some of the conversion income. Second, consider whether you have any capital losses in taxable investment accounts that you could harvest to offset some of the ordinary income from the conversion. While capital losses primarily offset capital gains, you can use up to $3,000 per year to offset ordinary income, with any excess carrying forward to future years. Finally, when you do speak with the IRS, emphasize your unemployment situation. They're often more willing to work with taxpayers facing genuine financial hardship. Document everything about your job search efforts and financial situation - this will support any hardship claims. The combination of an installment plan, penalty abatement if you qualify, and maximizing all possible deductions should help make this more manageable. Hang in there!

Have you tried checking your IRS account transcript online first? Sometimes that gives you more info than the "Where's My Refund" tool. Go to irs.gov and create an account if you don't have one - you can see your account transcript which shows all the processing codes and might explain why it's delayed. Could save you hours on the phone if it's something simple like a math error or missing form. If the transcript shows something you can't figure out, at least you'll have specific codes to ask about when you do get through to an agent.

I've been dealing with this nightmare too! After weeks of trying everything - calling at different times, using various menu tricks, even trying the practitioner line - what finally saved me was a combination approach. First, I used taxr.ai to decode my transcript and found out exactly what was holding up my refund (turned out to be an identity verification flag I had no clue about). Then I used Claimyr to actually get through to an agent who could resolve it. The transcript analysis showed me exactly what to ask for when I got on the phone, so I wasn't just saying "where's my refund?" The agent was able to clear the verification in 10 minutes once they knew what the specific issue was. Total game changer having that detailed info beforehand rather than going in blind!

I've been dealing with a similar situation and wanted to share what finally worked for me after reading through all these great suggestions. The key combination that got me through was: calling 800-829-1040 at exactly 7:00 AM Eastern on Wednesday, using @Emma Bianchi's phone tree navigation steps (especially the part about NOT entering your SSN when first prompted), and having patience when the system says high call volume. I also want to echo what @Giovanni Greco said about checking your IRS online account transcript - I found mine had been updated with the information I was waiting for in the mail, which saved me from having to wait for the physical letter. You can access it at irs.gov under "Get Your Tax Record." One thing that helped my sanity during this process: I kept a log of when I called and what happened each time. It helped me identify that Tuesday-Thursday mornings really do have better success rates than Mondays or Fridays. Don't give up - the system is definitely broken, but persistence does pay off eventually!

I've been lurking here for a while dealing with my own IRS phone nightmare, and this thread is incredibly helpful! Just wanted to add that I finally got through last week using a combination of these strategies - called 800-829-1040 at 7:05 AM on Thursday, followed Emma's phone tree navigation exactly (the part about not entering SSN initially was crucial), and got connected after about 40 minutes on hold. The agent was actually very helpful once I got through and explained that the delays are even worse than usual this year due to staffing issues. She also confirmed that many of the letters people are waiting for are now available in the online account system before they're mailed out. For anyone still struggling: don't give up! The system is broken but these tips really do work. Wednesday and Thursday mornings seem to be the sweet spot, and having all your info ready (SSN, filing status, tax year, and specific questions) makes the actual call much smoother once you get connected.