‘Tis the Season… to Prep Your 1099s
- Maddie Craig
- 38 minutes ago
- 2 min read
– BY MADDIE CRAIG | 2025
Santa isn’t the only one who should be making a list (and checking it twice) this December.
If you paid independent contractors this year, it’s officially time to start prepping your 1099-NEC information.
Most business owners wait until January to deal with 1099s, and that’s exactly why January feels overwhelming. But a little prep in December can make the entire process smoother, faster, and far less stressful.
Here’s what you should be gathering right now so you’re ready when filing opens:
1️⃣ Make a List of All Contractors You Paid $600+ for Services
The IRS requires a 1099-NEC for any non-employee you paid:
$600 or more
For services
In 2025
Using a 1099-eligible payment method
This includes freelancers, subcontractors, bookkeepers, graphic designers, virtual assistants — anyone who isn’t on payroll.
2️⃣ Make Sure You Have a Signed W-9 for Each Contractor
This is a big one; and often forgotten until the last minute.
A W-9 provides:
Legal name
Business name (if applicable)
Address
Tax classification
EIN or SSN
Without a completed W-9, you can’t file a 1099-NEC correctly. If you haven’t collected W-9s yet, ask for them now - contractors tend to respond much faster outside the chaos of January too.
3️⃣ Calculate the Total Amount You Paid Each Contractor
Pull totals for any payments made through:
Check
ACH
Cash
In short: any method that isn’t debit/credit card or other processors like Venmo or PayPal, which may issue their own forms. Having these totals ready now makes filing in January a simple copy-paste situation instead of a frantic scramble.
A Little Prep Now = A Much Easier January
1099 season doesn’t have to be stressful. If you gather your list, W-9s, and totals now, you’ll be miles ahead once the filing deadline rolls around!
Meet The Author
Maddie Craig is the founder of Blue Cypher Bookkeeping, a detail-oriented bookkeeper, and definitely a “numbers nerd”! She is passionate about helping organizations understand the full story of their financials and using it to make more confident decisions and grow strategically. She has experience working with a wide array of clients, including small businesses and non-profit organizations. When not crunching numbers, she and her husband enjoy traveling, being active in the community, and sharing their love for good food with friends and family.
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