Four dates every small business owner should circle

I keep a paper calendar on the wall next to my desk, and four dates on it are circled in cobalt ink every single year. If you own a business, they belong on yours too.

January 15

The last estimated tax payment for the year before is due. If you’re self-employed, nobody withheld tax from your pay, so the IRS expects you to send it in four times a year. Miss one and you’ll pay interest on the shortfall.

March 15

Returns for S corporations and partnerships are due. This one catches people because it comes a full month before the date everybody remembers. If your business files its own return, this is your real deadline.

April 15

Personal returns are due, along with the first estimated payment for the new year. Yes, both on the same day. Plan for two checks, not one.

June 15 and September 15

I’m cheating a little here, because these are two dates, but they do the same job: the second and third estimated payments. They fall in summer, when nobody is thinking about taxes, which is exactly why they get missed.

A note on weekends

When a deadline lands on a Saturday or Sunday, it moves to the next business day. Our tax calendar page does this math for you and shows how many days are left until the next one.

Every client of ours gets a reminder two weeks before each date that applies to them. Nobody should learn about a deadline from a penalty notice.