I have too many 1099s this year. What do I do?
Last year you knew everyone by name. This year half of them are new, the spreadsheet has columns you don't remember adding, and you're not sure who has a W-9 on file. The fix isn't another tab — it's getting out of the spreadsheet before January.
If any of this sounds familiar, you're in the right place:
- Your contractor count at least doubled this year
- You can't remember which contractors returned a W-9 and which never did
- You're not sure who crossed the threshold and who didn't
- The thought of doing this in January is making you want to outsource the whole problem
- Your accountant has stopped responding as quickly as they used to
Why the spreadsheet worked last year and won't this year
Spreadsheets scale linearly with the number of contractors but the cost of one mistake scales with the IRS penalty schedule. At 4 contractors the worst case is $1,360 in penalties. At 27 contractors with no W-9s on file it's $9,180 — and that's before the state filings, which most owners forget exist until the notice arrives. The spreadsheet didn't break. The math around it did.
What actually changes when you cross ~15 contractors
Three things stop being optional. First, you need a single place where W-9s live so you can prove you collected them in good faith. Second, you need year-aware threshold tracking because the OBBBA bumped the federal threshold from $600 to $2,000 for tax year 2026 — but some states didn't follow. Third, you need a deadline tracker that knows January 31 isn't the only date that matters. You don't need a payroll company. You need the three things above to stop being your job.
The honest cost of waiting until January
Every CPA we've talked to says the same thing: the contractors who never returned a W-9 in March will not return one in January. The window to chase missing W-9s is October through December. After that you're filing with what you have and documenting your good-faith request — which works, but only if you actually sent the request in writing.
What to do tonight
- 1Stop adding to the spreadsheet. Export it as a CSV so you have a clean record of where you were the night you decided to switch.
- 2Pull your top 5 highest-paid contractors. Confirm each one has a W-9. The ones missing are tomorrow's problem; capturing them tonight saves you weeks in January.
- 3Import the CSV into EarnDrift's free trial. The threshold and W-9 status columns auto-populate so you can see your real exposure in 5 minutes, not 5 weeks.
No card required. Cancels anytime. Honest 1–3 business day ACH timelines.