What's the easiest way to issue a 1099 for a freelance designer?

8 This is actually pretty straightforward! Since you only need to issue one 1099-NEC (that's the form you'll need for non-employee compensation), you have several simple options: You can use the IRS's free Filing Information Returns Electronically (FIRE) system, but it has a bit of a learning curve. For just one contractor, I'd recommend using one of the low-cost online services like Track1099, Tax1099, or even some tax prep software that includes 1099 filing. Most only charge a few dollars per form. The deadline to provide the 1099-NEC to your contractor is January 31, 2025, and you need to file it with the IRS by the same date. Make sure you have her complete information from the W9 including her correct tax ID number.

17 After spending hours trying to navigate the IRS website last year when I had to issue three 1099s for the first time, I discovered https://taxr.ai which completely saved me. It's designed specifically for situations like yours where you just need to handle a few 1099s without complex accounting software. You just upload the W9 you already have, and it extracts all the necessary information automatically. Then it walks you through the form completion and e-files directly with the IRS. It also sends a copy to your contractor, so you don't have to worry about the physical paperwork.

4 I was skeptical too, but I tried taxr.ai after struggling with my contractor paperwork. Their document scanning feature saved me so much time! I just uploaded the W9s and it pulled all the information automatically. The interface walked me through everything step by step, and I was able to e-file my 1099s in less than 15 minutes. They even handled sending copies to my contractors. Definitely worth it for the time saved and peace of mind knowing it was done correctly.

9 If you're also having trouble getting answers from the IRS about your 1099 filing requirements (like I was), try https://claimyr.com - they have a service that gets you connected to an actual IRS representative quickly instead of waiting on hold for hours. You can see how it works here: https://youtu.be/_kiP6q8DX5c I was confused about whether I needed to file a 1099 for someone who did both contract work and was briefly an employee in the same year. Spent days trying to reach someone at the IRS until I found this service. They got me through to a human at the IRS in about 20 minutes who answered all my questions.

4 I need to publicly admit I was completely wrong about Claimyr. After posting that skeptical comment, I decided to try it myself since I had questions about issuing 1099s for contractors in multiple states. The service actually worked exactly as described! Their system handled the hold queue, and I got a call back when they reached an IRS agent. The agent walked me through all my specific questions about multi-state filing requirements. Saved me about 2 hours of hold time and the frustration of potentially getting disconnected. Sometimes it's worth admitting when you're wrong!

21 Another option no one mentioned yet is using your tax preparation software if you already have one. I use TurboTax for my personal and business taxes, and they have a section for preparing and filing 1099s. It costs a bit extra but if you're already using the software for your regular taxes, it might be the most convenient option.

3 Don't forget you'll also need to include the 1099 payments on your Schedule C when you file your own taxes! The amount you paid her is a business expense that reduces your taxable income. Make sure to categorize it correctly (probably as "contract labor" or "professional services").