A Practical Look At 1099s

If you run a business, there’s a good chance 1099s show up on your to-do list each year.

They aren’t glamorous. They aren’t fun. But they do matter, and taking a practical, simple approach can save you time, money, and stress.

So… what is a 1099?

A 1099 is a tax form used to report certain payments made to non-employees.

Common examples include:

• Independent contractors
• Freelancers
• Virtual assistants
• Consultants and marketing professionals
• Bookkeepers, designers, website developers, etc.

Most of the time, when people talk about 1099s, they’re referring to the 1099-NEC, which reports non-employee compensation.

When are you typically required to issue one?

In general, you’ll likely need to issue a 1099-NEC if:

• You paid someone $600 or more during the year
• They are not your employee
• You paid them by cash, check, or bank transfer

(If you paid through a credit card or services like PayPal, those are usually reported separately by the payment processor.)

There are exceptions and special situations — so if you’re unsure, ask. It’s much easier to clarify than to fix later.

Want more detail? We put together a deeper breakdown here:
https://www.adminbooks.com/1099-filing-for-business-owners

What to gather now (so filing is easier later)

A little prep goes a long way.

Before you file, make sure you have:

• A completed W-9 from each contractor
• Total amount paid to them for the year
• Legal business name and current mailing address
• Whether they’re an individual, LLC, or corporation

Pro tip: Always request a W-9 before the first payment. Chasing paperwork months later is never fun.

Why 1099s matter

1099s aren’t just another form the IRS makes you file.

They help ensure income is reported correctly — and when they’re missing, penalties can add up.

Filing accurately and on time:

• Keeps your records clean
• Reduces risk of notices and penalties
• Protects your business from avoidable headaches

Our current offer: Free 1099 filing for new bookkeeping clients

If keeping track of this feels overwhelming — that’s exactly what we help with.

Through mid-January 2026, we’re offering:

🎉 Free 1099 filing for new monthly bookkeeping clients

We’ll take care of the bookkeeping and file any required 1099s for you, so nothing slips through the cracks.

If you want to talk through it or see whether this makes sense for your business, connect with us here:

👉 https://www.adminbooks.com/free-1099-filing

1099s don’t have to be confusing or stressful. With a practical plan — and the right support — they become one more task that gets handled correctly and on time.

And if you’d like some help staying on track, we’re here.