New Year. New Ledger. No Excuses. The January Business & Tax Readiness Checklist

Shaylah Kiser
Jan 5
3 min read

By Kiser’s Legal Support Solutions

The confetti has settled.

The vision boards are up.

And the inbox is already loud.

Now comes the real beginning-of-the-year work—the kind that doesn’t get applause but keeps your business legitimate, defensible, and profitable.

January isn’t about vibes.

It’s about compliance, clarity, and control.

Let’s set the table properly.

Why January Is Non-Negotiable

January is your corporate reset. What you organize now determines:

Whether tax season is smooth or stressful
Whether your CPA can advise—or has to untangle
Whether your business looks polished or precarious

The IRS doesn’t care how small you are.

They care how accurate you are.

PART I: The Beginning-of-Year Business Checklist

1️⃣ Verify Your Business Identity (Before You Touch Taxes)

Start with the fundamentals:

Legal business name (exactly as registered)
EIN confirmation letter
Entity type (LLC, S-Corp, C-Corp, sole proprietor)
Active state registration
Current business address, phone, and email

If this information doesn’t match across platforms, filings get delayed—or flagged.

2️⃣ Review Prior-Year Financials (Not Perfect—Just Honest)

You don’t need final numbers yet, but you do need visibility:

Profit & Loss statement
Business bank statements
Business credit card statements
Outstanding invoices
Vendor payment summaries

This is where errors surface early—before penalties do.

PART II: Payroll & Contractor Reporting

Get Those W-2s and 1099s OUT

Deadlines live here. Handle this part cleanly.

Employees → W-2 Forms

If you had employees:

W-2s must be furnished to employees by January 31
W-2s must also be filed with the Social Security Administration by that deadline
If January 31 falls on a weekend or federal holiday, the deadline moves to the next business day

Before issuing:

Confirm legal names
Confirm Social Security numbers
Confirm wages and withholdings

Late W-2s = fines. No debate.

Contractors → 1099-NEC Forms

If you paid contractors:

1099-NEC applies if you paid $600 or more for services
Forms must be:
- Furnished to the contractor by January 31
- Filed with the IRS by January 31 (paper or electronic)
  
  Before issuing:

Ensure a completed W-9 is on file
Confirm name, address, and EIN/SSN
Confirm total payments

Important nuance:

Many payments to corporations are exempt—but key exceptions exist (including certain legal and medical payments). When in doubt, verify before assuming.