A missed date is one of the easiest ways to pay a penalty or lose work you didn’t need to: an estimated tax payment missed, a license that lapsed, a 1099 sent late. By the end of this lesson you’ll have one calendar with the federal tax dates, your own renewal dates, reminders set ahead of each, and a year-end checklist for your accountant.
This lesson is an introduction, not tax or legal advice. The federal dates below are from the IRS and apply to individuals, including sole proprietors. Your state, city, business structure and trade add their own dates. Confirm your full list with your accountant and your licensing board.
The federal dates for a sole proprietor
| Date | What | Source |
|---|---|---|
| January 15 | Estimated tax payment for September 1–December 31 of the year before | IRS |
| January 31 | Form 1099-NEC to each person you paid for services, and filed with the IRS (see below) | IRS instructions |
| April 15 | Your individual tax return, with Schedule C for the business, and the estimated tax payment for January 1–March 31 | IRS |
| June 15 | Estimated tax payment for April 1–May 31 | IRS |
| September 15 | Estimated tax payment for June 1–August 31 | IRS |
The IRS: “If the due date for making an estimated tax payment falls on a Saturday, Sunday, or legal holiday,” the payment is on time “if you make it on the next day that’s not a Saturday, Sunday, or legal holiday.”
Who pays estimated tax: generally, individuals, including sole proprietors, who “expect to owe tax of $1,000 or more when their return is filed” (IRS). Your accountant will tell you whether you need to and how much. Pay from the tax savings account described in bookkeeping for contractors.
How to pay: the IRS says “You may pay within your online account, Direct Pay with bank account, by phone or from your mobile device using the IRS app.” Its payment page lists every option. Save the confirmation of each payment in your Money folder.
Many states also have their own estimated income tax with their own dates; ask your accountant whether yours applies.
If your business is a partnership, an S corporation or a corporation, or you have employees, there are other forms and dates. Ask your accountant for that list.
1099s for the people you pay
If you pay a subcontractor or another business for services, you may have to send them a Form 1099-NEC. The IRS says: “Use Form 1099-NEC to report nonemployee compensation” (IRS). For payments made in 2026, the IRS instructions say to report nonemployee compensation “of $2,000 or more” (the threshold was lower for earlier years), and “You are required to furnish the payee statements and file with the IRS by January 31.”
What makes January easy:
- Get a Form W-9 from every subcontractor before you pay them the first time. It gives you their legal name and taxpayer ID.
- Pay them from the business account, never in cash without a record.
- Keep a running total per person during the year.
- In early January, send the totals and W-9s to your accountant, or file yourself if you’ve been shown how.
Some payments, such as those to most corporations or by card, may not need a 1099 from you. Your accountant will sort out which.
Your own renewal dates
These differ for every business. Find each date once, write it down, and put it on the calendar:
| Renewal | Where to find the date |
|---|---|
| Contractor or trade license | Your license, or your state licensing board’s lookup |
| Continuing education for your license, if required | Your licensing board |
| Local business license | Your city or county |
| State business registration or annual report (LLCs and corporations) | Your secretary of state |
| General liability and other insurance policies | Your policy declarations page |
| Workers’ comp, if you have employees | Your policy |
| Contractor bond, if required | Your bond paperwork |
| Vehicle registration and commercial auto insurance | Registration card; auto policy |
| Sales tax filings, if your state taxes your work | Your state’s tax department |
| Trade certifications that expire | The certifying organization |
| Domain name and website hosting | Your registrar |
Set reminders ahead of every date
A date on the calendar only helps if you see it in time:
- 60 days before each renewal: ask for quotes or paperwork, and check for continuing education.
- 14 days before each tax date: check the tax savings account and confirm the amount with your accountant.
- The day before: pay or file.
Put all of them in the calendar you already use every day, not a separate app you’ll forget.
Year-end checklist for your accountant
In early January, send your accountant:
- Your bookkeeping reports for the year, or access to your software, with every account reconciled to December 31
- Bank and card statements for every business account
- Every 1099 you received (for example from platforms or commercial customers)
- Totals and W-9s for everyone you paid for services
- Estimated tax payments you made, with dates and amounts
- Vehicle mileage or expense records, and receipts for equipment and other large purchases
- Your questions, and any changes coming next year (hiring, a new vehicle, a new structure)
Deductions are your accountant’s call; contractor tax deductions you shouldn’t miss is a list to bring to the conversation.
Your next action
This week:
- Put the five federal dates in your calendar for the next 12 months, with a reminder 14 days before each.
- Fill in the renewal table with your own dates, and set a reminder 60 days before each.
- Ask your accountant whether you need to pay estimated tax, how much, and which other dates apply to you.
- Collect a W-9 from every subcontractor you’ve paid this year.
FAQ
When are estimated taxes due for contractors?
For individuals, including sole proprietors, the IRS lists April 15, June 15, September 15 and January 15 of the following year. If a date falls on a weekend or legal holiday, the payment is on time on the next business day. Your accountant will tell you whether you need to pay and how much.
Do I need to send 1099s to my subcontractors?
If you paid someone for services in your business, you may have to send a Form 1099-NEC by January 31. For payments made in 2026, the IRS threshold is $2,000. Collect a W-9 before the first payment and ask your accountant which payments need a 1099.
What happens if my contractor license lapses?
It depends on your state. Working without an active license where one is required can bring fines, and in some states it can affect your right to be paid for the work; your licensing board can tell you the rules where you work. Check your renewal date and continuing education with your licensing board, and set a reminder 60 days ahead.
Keep the paperwork in order with MotionOps
MotionOps is field service software for contractors. Invoicing & Payments keeps a record of every invoice and payment, Field Expense Tracking records purchases by job, and MotionOps works with QuickBooks Online, so your year-end reports for your accountant are easier to pull together.
See all features or compare plans. When you’re ready for your first jobs, book a MotionOps demo.
Contractor Starter Hub: Business Administration Essentials, lesson 4 of 5
- Previous lesson: Get Paid Faster and Keep Your Projects on Track + Free Template
- Next lesson: Weekly Admin Checklist for Contractors: A Routine That Fits in Two Hours
- Download for this lesson: Business Deadline Calendar (spreadsheet)
- All five lessons: Business Administration Essentials
