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.

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.