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.

You're right, I haven't updated my W-4 since getting promoted. I assumed the payroll system would automatically adjust everything. How do I figure out the right amount to add for additional withholding? Is there a calculation or formula I should use?

Take the amount you owed this year ($1,300) and divide it by the number of pay periods remaining in the year. For example, if you're paid twice a month and it's currently April, you have about 16 pay periods left, so you'd add about $81 of additional withholding per paycheck ($1,300 ÷ 16). You might want to add a bit more if you expect your income to continue rising. The IRS has a tax withholding estimator on their website that can help you calculate this more precisely based on your specific situation. Remember that this adjustment only affects future withholding, not what you currently owe.

This is exactly right. I'm an accountant and see this all the time with sales people. The 22% supplemental wage withholding is just a simplified method employers use, but your actual tax liability is based on your total income for the year across all sources.

That's actually a really smart approach I hadn't considered! Did you have to push hard to get them to agree to it, or were they pretty understanding once you explained the situation?

They were surprisingly understanding. I just explained that for tax and professional liability reasons, I needed these workshops classified as paid professional services rather than volunteer work. I suggested a nominal fee ($75 per workshop in my case, which was about 25% of my normal rate for that time). They actually appreciated the more professional arrangement because it also clarified expectations on both sides. We created a simple addendum to my existing contract that specified exactly what these workshops would cover and what materials I'd provide. Having skin in the game made them value the workshops more, and it gave me actual income to report rather than trying to figure out complex tax deductions.

This is an important distinction! The IRS treats marketing expenses and regular business expenses somewhat differently. If these workshops are actually part of your contractual obligations, then all related expenses would be straightforward business expenses. Check your contract carefully to see if there's any language about community outreach or professional education being part of your duties. If so, you might have a stronger case for deducting related expenses.

What kinds of documentation do you recommend keeping for large medical expenses? My insurance company's explanation of benefits doesn't always match what I actually paid, and I'm worried about getting audited.

Documentation is crucial for medical deductions. Keep all receipts showing actual payment (not just bills or statements), explanation of benefits from insurance showing what wasn't covered, and bank/credit card statements proving payment. If there's a discrepancy between EOBs and what you paid, keep records explaining the difference. For unusual medical expenses (special equipment, home modifications, travel for treatment), get a letter from your doctor stating these were medically necessary. The IRS looks closely at large medical deductions, so documentation is your best defense. Organize everything by date and provider, and keep a spreadsheet summarizing all expenses. This preparation makes the process much smoother whether you use H&R Block or a CPA.

I've done both. Used H&R Block for years then switched to a CPA last year for a complicated medical situation with my special needs child. The CPA found almost $2,300 more in deductions than I would have gotten at H&R Block. She knew about specialized medical deductions for adaptive equipment and certain therapies that H&R Block missed in previous years.