Quick answer: Before tax season, Ashburn small businesses should reconcile their books through December, gather year end statements and payroll records, send W-2s and 1099-NEC forms by January 31, and note the March 1 Loudoun County deadlines. Then review common deductions and plan next year’s estimated taxes.
Tax season goes smoother when you prepare early. Whether you run a small business in Ashburn, elsewhere in Loudoun County or anywhere in Northern Virginia, this checklist covers the key steps to take before you file.
Know your key deadlines
Missing a deadline is one of the most common and expensive tax mistakes. For calendar year businesses, the main dates are:
- January 31: W-2s and 1099-NEC forms to workers and the IRS
- March 1: Loudoun County business license renewal and business property return
- March 15: partnership and S corporation returns
- April 15: individual and C corporation returns, plus first quarter federal estimated taxes
- May 1: Virginia individual returns and first quarter Virginia estimated taxes
- September 15 and October 15: extended deadlines for business and individual returns
Dates move to the next business day when they fall on a weekend or holiday. For local dates, see our guide to Loudoun County business taxes.
Gather your documents early
Starting early gives you time to find missing paperwork. Most small businesses will need:
- Year end profit and loss statement and balance sheet
- Bank, credit card and loan statements for every account
- Payroll reports, W-2s and W-3
- 1099s you received, and records of contractors you paid
- Records of equipment, vehicle and other large purchases
- Last year’s tax returns
Tip: If your books are not reconciled through December, fix that first. Accurate books make every other step faster. Our bookkeeping cleanup service can help.
Review common deductions
Many owners miss deductions simply because expenses were not recorded or categorized. Areas worth reviewing include:
Vehicle and travel costs
Business mileage or actual vehicle expenses, plus travel for client work. Good records are essential.
Home office
If you use part of your home regularly and exclusively for business, you may qualify for a home office deduction.
Equipment and software
Computers, tools, equipment and software subscriptions used in your business.
Retirement contributions
Contributions to certain retirement plans can lower your taxable income. Talk with your tax professional about which options fit.
Send 1099s on time
If you paid contractors for services, you may need to send them Form 1099-NEC by January 31. The reporting threshold went up for payments made in 2026. Read our 1099-NEC guide for the current amount and details.
Plan next year’s estimated taxes
Tax season is also the right time to look ahead. If you owed a large balance this year, adjusting your quarterly payments can help you avoid penalties next year. See our guide to quarterly estimated taxes in Virginia, or let our tax planning service set the right amounts.
→Related guideLoudoun County Business Taxes: BPOL, Business Property and Key DeadlinesIt covers the Loudoun County business license and equipment tax that come due on March 1.Tax season FAQs for Ashburn businesses
Does a tax extension give me more time to pay?
No. An extension gives you more time to file, not to pay. Any tax you owe is still due by the original deadline, or interest and penalties can apply.
Does Virginia give an automatic extension for individual returns?
Yes. Virginia gives individuals an automatic 6 month filing extension, but you must pay at least 90% of your tax by the original May 1 due date to avoid an extension penalty.
Do I need to send a 1099 to contractors I paid by credit card?
No. Payments made by credit card or through payment apps like PayPal are reported by the payment processor on Form 1099-K, so you do not send a 1099-NEC for them.
Do I need to send a 1099-NEC to an LLC?
Usually yes, if the LLC is taxed as a sole proprietorship or partnership. Payments to LLCs taxed as corporations are generally exempt, except payments for legal services. A Form W-9 tells you how the vendor is taxed.
How long should I keep business tax records?
The IRS generally recommends keeping records for at least 3 years after filing, and employment tax records for at least 4 years. Keep records for equipment and property until 3 years after you sell or dispose of them.
When to get help
If your books are behind, your business changed structure, you added employees or you simply want peace of mind, working with a professional can save time and money. Learn more about our business tax preparation and individual tax preparation services.
This article is general information and not tax advice for your situation. Tax rules change, so talk with a qualified professional before making decisions.
