VERY basic question regarding a W-9 form for freelance work

So if I did work for multiple clients and filled out W-9s for all of them, will each one send me a separate 1099-NEC? Also, what happens if they paid me less than $600? Do I still need to report that income somewhere?

Yes, each client who paid you $600 or more should send you a separate 1099-NEC form. If they paid you less than $600, they aren't required to send a 1099, but you still need to report that income on your tax return. The IRS requires you to report all income regardless of amount or whether you received a form. For income without a 1099, just keep good records of what you were paid. You can track this in a spreadsheet or accounting software, and bring those records to your accountant along with any 1099s you receive. Remember to track business expenses for all your freelance work too, even for clients who paid less than $600.

Does it work for people who have both W-2 income and freelance stuff? My main job gives me a W-2 but I do freelance on the side and have a bunch of W-9s I've filled out. Getting kind of nervous about tax season.

I'm skeptical about AI tax tools. How does it actually determine what's deductible vs what might trigger an audit? I've been burned before with software that claimed I could deduct things that later caused problems.

Yes, it definitely works for mixed income situations. I'm actually in the same boat with a full-time job plus freelance work, and it handles both income types and helps make sure you're allocating expenses correctly between your different income sources. Regarding deductions, I was skeptical too! The tool uses the actual IRS guidelines to analyze expenses. It doesn't just blindly suggest deductions - it asks specific questions about each expense to determine if it truly qualifies. It's actually more conservative than some CPAs I've used, flagging things that might increase audit risk rather than pushing the boundaries.

How does this actually work? I don't understand how they can get you through when everyone else is waiting for hours. Sounds like they're jumping the line somehow?

Yeah right. This sounds like BS. Nobody can get through to the IRS that fast. I spent 3 days trying last year and gave up. If this worked everyone would be using it.

It uses a technology that continuously redials and navigates the IRS phone system until it secures a place in line, then it calls you when an agent is about to be available. It's not jumping the line - you still wait your turn, but the system does the waiting instead of you having to stay on hold for hours. It's actually a legitimate service that many tax professionals use themselves. The reason everyone doesn't use it is simply because most people don't know it exists. I was skeptical too until I tried it and had an IRS rep on the phone answering my questions about my missing 1099 forms in minutes instead of waiting all day on hold.

Do you have a template for this spreadsheet you could share? I'm doing freelance work for the first time this year and I'm trying to get organized before tax season.

I don't have a template to share but it's pretty simple to create. I just use columns for: Client Name, Project Description, Date Paid, Amount, Payment Method, W-9 Submitted (Y/N), 1099 Expected (Y/N), and 1099 Received (Y/N). I also have a separate tab for business expenses with columns for: Date, Vendor, Description, Amount, Payment Method, and Category (like "Software," "Equipment," etc). Nothing fancy but it keeps everything organized when it's time to do taxes.

Technically you're supposed to report all income, even small amounts. But realistically the IRS is more concerned with larger amounts. You should definitely start reporting your income going forward though. The IRS has been increasing focus on gig/freelance work.