That's good to know about the Social Security cap, though like you said we're both under it individually. I didn't realize the Child Tax Credit could be that significant! Would we need to adjust our W-4s again after the baby is born to account for the credit, or does that automatically reduce what we owe at tax time?

You'd need to update your W-4s again after the baby is born to account for the Child Tax Credit. It doesn't happen automatically during the year - it would only reduce what you owe when you file your taxes otherwise. On your W-4, you would indicate the dependent in Step 3, which would then reduce your withholding throughout the remainder of the year. When you update your W-4s, you'll probably want to do it soon after the baby is born to maximize the withholding adjustment for the rest of the year. Just be aware that the Child Tax Credit begins to phase out at higher income levels (starts phasing out at $400,000 for married filing jointly), but based on your income you should still qualify for at least a partial credit.

I second this approach. With our W-2 income plus investment income, quarterly estimated payments have been a lifesaver. The peace of mind knowing we won't have a surprise tax bill is worth the extra effort. Just make sure you're paying at least 100% of last year's tax liability (or 110% if your AGI was over $150,000) to avoid underpayment penalties.

Do you need to keep special documentation beyond the invoices from the production company? My accountant mentioned something about needing to document the "business purpose" but wasn't clear what that meant exactly.

Beyond the invoices, I'd recommend keeping a simple log that documents the business purpose of each video. Nothing complicated - just a spreadsheet with video titles, publication dates, and a brief note about how each relates to your business (like "demonstrates expertise in X service" or "explains process relevant to potential clients"). This extra documentation isn't strictly required, but it's extremely helpful if you ever get audited. I learned this the hard way when I had to justify some marketing expenses during a review. Having a clear business purpose documented for each expense makes the process much smoother.

Which category in TurboTax did you use for this? I'm trying to enter similar expenses and getting confused about where they belong.

This tripped me up too! I didn't realize they changed it this way. Is this true for all the quarterly forms now or just the 941?

This change is primarily for Form 941, but the IRS has been moving toward more form-specific versions for several reporting requirements. Form 941-X (the amended return) still requires you to check which quarter you're correcting. Some other quarterly forms still use the traditional checkbox method, but the IRS seems to be gradually transitioning more forms to the quarter-specific model. Always best to download the most current version directly from IRS.gov or use up-to-date tax software to be sure.

They won't reject it as long as you used the correct quarterly form. I did the same thing - printed it out and manually marked the box even though it was greyed out. The IRS agent I spoke with said it's fine because they can tell which quarter you're filing for based on the form version itself. They're just trying to phase out that manual selection to reduce errors. So you should be good!

Do you think there's any legitimate way my coworker and I could structure this that wouldn't violate policies? What if he just gave me the money as a birthday gift with no strings attached, and then months later I happen to donate to that charity?

Even with separation in time, the arrangement is still designed to circumvent company policy, which is problematic regardless of how it's structured. Most corporate ethics policies look at intent, not just technical compliance. A legitimate alternative would be for your coworker to donate their full intended amount directly to the charity, and you could separately donate to the same charity if you genuinely support their cause. This way, both donations would be legitimate, the company match would apply appropriately based on actual employee giving, and there would be no ethical concerns. The charity might receive slightly less overall, but without any risk to your employment or tax standing.

Great point! When I worked in nonprofit development, we had several approaches for donors in this exact situation. Some options included spreading the donation across multiple tax years, involving family members who could make legitimate donations, or exploring donor-advised funds which sometimes have their own matching programs.

Most of what I sold were collectibles I'd been buying and flipping, so definitely not personal items sold at a loss. I was buying things specifically to resell at a higher price, so based on what you're saying, it sounds like I would owe taxes on this income. I'm guessing this would count as a business activity?

Yes, that definitely counts as business activity since you were buying with the intention to resell at a profit. That would be subject to both income tax and self-employment tax (15.3% on top of regular income tax). But the good news is you can deduct all your legitimate business expenses - the cost of the items you purchased to resell, any shipping supplies, eBay and PayPal fees, mileage driven to purchase inventory or ship items, a portion of your internet if you're listing from home, etc. These deductions can substantially reduce the taxable profit.

That's only for goods and services payments though right? If you use friends and family that doesn't get reported.

Correct, it's only for goods and services payments. But using Friends and Family for business transactions is against PayPal's terms of service and can get your account limited or banned. Plus, as a buyer, you lose purchase protection when using Friends and Family. More importantly, deliberately using Friends and Family to avoid tax reporting could be considered tax evasion if the IRS can prove intent. Many platforms are getting better at detecting when people are trying to circumvent the system, so it's a risky strategy that can lead to bigger problems down the road.