I can definitely relate to your anxiety about this! I was in almost the exact same situation two years ago - owed about $3,800 through TurboTax and was constantly checking my bank account waiting for the withdrawal. The anticipation is honestly the worst part when you're not used to owing taxes. Based on my experience and what I've learned since then, TurboTax automatic payments typically take 3-5 business days from your scheduled date to actually process. Since you scheduled for April 10th, you should see the withdrawal sometime between now and early next week. The most important thing to remember is that the IRS considers your payment made on April 10th (when you scheduled it), not when the money actually leaves your account, so you're completely protected from any late penalties. A few things that helped me get through the waiting period: - Keep a buffer in your account until you see the withdrawal (don't move money around yet) - Save screenshots of your TurboTax payment confirmation for your records - Try to check your account only once a day instead of multiple times (I know it's hard!) - Remember that TurboTax batches payments which adds 1-2 extra days compared to paying directly through IRS.gov You did everything correctly by scheduling before the deadline, so try not to stress too much. The IRS processing system is just naturally slow, especially during peak tax season. You're going to be fine!

I totally understand your anxiety! I went through something very similar last year when I owed about $2,650 through TurboTax - also my first time owing instead of getting a refund. The constant bank account checking is so real! From my experience, TurboTax automatic payments typically take 3-5 business days from your scheduled date. Since you scheduled for April 10th, you should see the withdrawal by early next week at the latest. The key thing that gave me peace of mind was understanding that the IRS considers your payment made on April 10th (when you scheduled it), not when the money actually comes out of your account. A few tips that helped me through the waiting: - Keep plenty of buffer money in your account until you see the withdrawal - Save screenshots of your TurboTax payment confirmation - Try to limit checking your account to once per day (I was checking like 20 times a day and driving myself crazy!) - Remember that TurboTax batches payments which can add an extra day or two compared to paying directly through IRS.gov You did everything right by scheduling before the deadline, so try not to stress too much. The waiting is definitely the hardest part, but you're covered! The IRS processing system is just slow, especially during tax season.

Has anyone dealt with leaving a company but negotiating an extension on the exercise period? Most standard option agreements only give you 90 days after leaving to exercise, but I've heard some companies are flexible on this, especially when options are underwater.

One additional consideration that might help with your decision - if you're planning to leave the company anyway, you could potentially negotiate with your employer to extend the exercise window beyond the typical 90-day post-employment period. This would give you more time to see how the company performs with that Q3 product launch you mentioned. Also, make sure you understand exactly what type of options you have (ISO vs NSO) as this affects the tax treatment. With ISOs, you generally have better tax advantages if you hold the stock for at least one year after exercise and two years after grant date to qualify for long-term capital gains treatment. Given that you're essentially guaranteed a loss if you exercise now, it might be worth having a conversation with your company about either repricing the options to current FMV or extending your exercise window. Many companies are becoming more flexible about this, especially in situations like yours where the employee would be financially penalized through no fault of their own.

Small thing to add - if you're using the standard mileage rate and deducting tolls separately, make sure you're only deducting the business portion of those tolls. If you use your car 70% for business and 30% personal, you can only deduct 70% of the tolls.

Great question! I went through this exact same situation last year with my freelance work. The good news is that toll expenses are definitely deductible separately from the standard mileage rate - they're specifically excluded from what the standard rate covers. Just a heads up though - make sure you're only deducting the business portion of those tolls. If you use your car for both business and personal driving, you'll need to calculate the percentage that's business use and only deduct that portion of your toll expenses. Also keep in mind that if you're an employee rather than self-employed, unreimbursed business expenses like this are generally not deductible under current tax law (suspended through 2025), unless you fall into certain categories like qualified performing artists or military reservists. Those EZ Tag receipts will be perfect documentation - just make sure to keep a detailed log of which trips were business-related so you can match them up with the toll charges. Good luck with your taxes!

Has anyone here actually had the IRS come after them for selling a personal car? I've sold like 5 cars over the years and never reported any of it on my taxes. Should I be worried about past sales?

This is a great question that trips up a lot of people! The key thing to understand is that when you receive a gift, you inherit the donor's "basis" (what they originally paid) for tax purposes. Since your car was originally purchased for $38k and you sold it for $15,800, you actually had a capital loss of about $22,200. However, the IRS has asymmetrical rules for personal-use property like cars - while capital gains would be taxable, capital losses aren't deductible. So you don't owe any capital gains tax (since you had a loss, not a gain), but you also can't use that loss to reduce other taxes. The good news is this is actually the most common scenario with personal vehicles since they typically depreciate over time. Just keep your documentation (bill of sale, any gift paperwork) in case you ever need to show the IRS how you calculated your basis, though it's unlikely to come up since there's no tax owed.

One thing people overlook in this discussion - if one of you has significant medical expenses (over 7.5% of your AGI), filing separately COULD be beneficial. My husband has ongoing medical issues, and his expenses easily exceed that threshold on his income alone. But when combined with my income, we couldn't deduct as much. We saved about $1,800 filing separately last year despite losing some credits. Just another angle to consider based on your specific situation. Tax software often misses these nuances.

Adding to the great advice already shared - as someone who's worked in tax preparation for over 15 years, I can confirm that for your specific situation (significant income disparity, three kids, homeownership), filing jointly is almost certainly your best bet. The key thing people don't realize is that when you have unequal incomes, the lower-earning spouse essentially "fills up" the lower tax brackets first, creating substantial savings. With your $120k/$40k split, you're getting maximum benefit from this effect. A few quick calculations based on your numbers: filing jointly, you'd likely qualify for the full $6,000 in child tax credits ($2,000 per child), plus potential additional child tax credit refunds. Filing separately, the higher-earning spouse would lose most or all of these benefits due to income phase-outs, while the lower-earning spouse couldn't claim all three children. My recommendation: run the numbers both ways using tax software, but I'd be genuinely surprised if separate filing saves you money. The math just doesn't work out in favor of separate filing for families with kids and significant income gaps like yours.