October doesn’t feel like a deadline month. Tax season is behind us, the holidays haven’t hit yet, and for a lot of small and medium-sized businesses it’s the calm before the storm — which is exactly why it’s the month bookkeeping quietly falls apart.
Here’s the task almost everyone overlooks: collecting W-9 forms from every contractor, freelancer, or vendor you’ve paid $600 or more this year. Landscapers, cleaning crews, IT help, subcontractors — if you paid them and they’re not a corporation, you’re required to send them a 1099 by January 31. The catch is that W-9s (their name, address, and tax ID) have to come from them, and chasing that paperwork in January, while you’re also closing out the year, is where most small and medium-sized businesses lose weeks they don’t have. October is the month to send that request while people are still easy to reach.
A few other things worth doing now, before Q4 gets busy:
Catch up your reconciliations. If any bank or credit card account hasn’t been reconciled since summer, close that gap now. Doing three months of catch-up in October is manageable. Doing five in December is not.
Look at your chart of accounts. Pull up your profit and loss for the year so far and ask whether anything’s been miscategorized — expenses dumped into “Miscellaneous,” personal charges mixed into business accounts, that kind of thing. Fixing it now means your year-end numbers, and your tax preparer’s job, are accurate the first time.
Think about equipment purchases before December 31. If you’ve been planning to buy a vehicle, machinery, or major equipment, talk to your bookkeeper or CPA about the timing now. Section 179 deductions can make a real difference to what you owe, but only if the purchase — and the paperwork — happens before year-end.
If your business is seasonal, forecast your cash flow for the season ahead. With snowbirds returning and foot traffic picking back up, this is the month to make sure you have enough cash on hand to cover payroll and inventory before the revenue catches up.
None of this is complicated. It just has to happen before the last week of December, when every other business owner is trying to do the same thing at once.
Marianne Kirwan is President/CEO of Accredited Bookkeeping LLC, providing bookkeeping, payroll, and advisory services to small and medium-sized businesses, nonprofits, and franchise operations.
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