10/16/2026
A little Friday thought for all the CEOs out there...
Every January scramble we have watched a business owner go through was avoidable back in October.
You know the version. It's late January, 1099s are due, and nobody has a current address or tax ID for half the contractors who got paid last year, so you're emailing people you haven't spoken to since June and hoping they get back to you before the deadline, and some of them won't.
The fix isn't complicated and it doesn't have to happen all at once. Pull the list of who you paid this year, check that you have a W9 on file for each one, and chase the few that are missing now, while it's still a small ask instead of an urgent one.
It's an hour in October or a week of stress in January, and since the deadline isn't moving either way, the timing is the only part of this you control. 🗓️