Should You Be Issuing 1099s to Your Contractors?

Here’s the deal: If you pay a contractor through Honeybook, Dubsado, Square or another payment processor, you don't need to issue them a 1099. That’s it. That’s the post!

Let’s unpack why:

Everything you need to know about issuing 1099s:

Platforms like HoneyBook, Stripe, Square, and Shopify report all payments made through them on a Form 1099-K. So, if you also issue your contractor a Form 1099-NEC, their income gets reported to the IRS twice — and that’s a paperwork mess no one wants. 😵‍💫

When Do You Need to Issue a 1099-NEC?

You only need to issue a 1099-NEC for payments you make outside of these platforms — think cash, checks, or direct bank transfers (wires or ACH).

What About PayPal?

Good question! Here’s the breakdown:

  • PayPal Goods and Services: No need to issue a 1099-NEC — PayPal handles it.

  • PayPal Friends & Family: Yes, you still need to issue a 1099-NEC, because it’s treated like cash (and let’s be real — you shouldn’t be using this for your business in the first place!).

Does This Happen Automatically?

Yes! If you’re paying contractors through a business payment platform like HoneyBook, there’s nothing more you or your accountant need to do. These platforms have you covered.

Now you know — and can breathe a sigh of relief! 😌

xx, Your Numbers Gal


1099s getting you down? The Contractor Clarity Kit to the rescue!

Learn how to track, pay, and issue 1099s for your contractors—the right way, without second-guessing or spreadsheets from hell.

What’s inside:

  • Comprehensive 45-minute workshop covering 1099 essentials and how to issue them online, plus access to our recommended tool for streamlined filing.

  • Practical resources like a Google Sheet tracker to help you stay organized year-round, making tax season far less stressful.

  • Lifetime access to all materials so you can revisit them whenever you need a refresh.

 

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Kelly Etz

Kelly Etz is a graphic designer, writer, and fisherman sweater enthusiast based in Chicago. She gets her best work done after 1am and spends too much money on fancy shampoo.

https://www.instagram.com/ketzdesign/
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