Close the year cleanly.
Books current, a planning conversation before December 31, and records ready for filing season. Six steps in the order the calendar brings them, each linked to the page that covers it properly.
A clean close, not a January scramble.
Dates below are federal, checked against irs.gov, with the source beside each. If a due date falls on a weekend or legal holiday, the IRS moves it to the next business day. Massachusetts sets its own dates; confirm those with the Department of Revenue.
NOW THROUGH DECEMBER
Get the books current
Every other step on this page reads from the record. If the books are months behind or have never been reconciled, the planning conversation turns into reconstruction and the filing-season records arrive with gaps in them.
Catching up is a one-off project with a defined end: the record brought to a reliable state, current to a stated date.
BEFORE DECEMBER 31
Have the planning conversation while the year is open
Preparation reports a year that has closed. Planning looks at one still in progress, and that is only possible before December 31.
It is where the estimated-payment position gets checked, anything unusual in the year gets raised while it can still be acted on, and any open decision gets identified.
JANUARY
Make the fourth-quarter estimated payment
Federal estimated tax for the September 1 to December 31 period of 2026 is due in January. For self-employed owners it is the payment that lands right after the holidays, and the one most worth checking against current books rather than last year's return.
Massachusetts runs its own estimated-payment rules and schedule; confirm those with the Massachusetts Department of Revenue.
- Q4 2026 federal estimated tax: January 15, 2027
Source: IRS Publication 505
- Q4 2026 federal estimated tax: January 15, 2027
SETTLE BEFORE JANUARY
Know who produces your W-2s and 1099-NECs
Year-end forms for employees and contractors are one of the payroll tasks that has to be assigned to someone: you, a payroll provider, or an accountant. The expensive version of this is discovering in late January that each assumed it was the other.
If nobody has written down who produces them, settle it now. January 31 falls on a Sunday in 2027, so the federal due dates below move to the next business day.
- Form W-2 to employees and the SSA: February 1, 2027
Source: IRS General Instructions for Forms W-2 and W-3 (2026) - Form 1099-NEC filed with the IRS: February 1, 2027
Source: IRS Instructions for Forms 1099-MISC and 1099-NEC
- Form W-2 to employees and the SSA: February 1, 2027
JANUARY TO MARCH
Gather the records for filing season
A return is assembled from records that mostly already exist. What makes preparation slow is almost never complexity; it is missing information.
Start with the books closed through December, then the income, expense and payroll records that support them.
WHENEVER IT ARRIVES
If an IRS or Massachusetts notice arrives
Open it, note the notice number and the date printed on it, and keep it. The IRS's own guidance is that if a notice asks you to respond, you act by the due date it gives.
What each common notice means, and what clock it starts, is set out notice by notice.
- Respond by the due date on the notice
Source: IRS: Understanding your notice or letter
- Respond by the due date on the notice
General information for owner-led businesses, not advice for your specific situation. Which dates and forms apply depends on how your business is set up. Dates were checked against the IRS sources linked above in September 2026; rules and dates can change.
Find out where your year stands.
Tell us how the business is set up and how current the books are. We'll tell you what we'd look at first.
Please don't send Social Security numbers or tax documents through this form.