Your Quarterly Tax Checklist: Never Miss a Deadline Again

Quarterly estimated taxes are one of the most misunderstood obligations for self-employed people and small business owners. Here's a practical checklist to keep you ahead of the IRS every quarter. WHY DO I OWE QUARTERLY TAXES? When you're employed, your employer withholds taxes from each paycheck. When you're self-employed or running your own business, no one does that for you. The IRS expects you to pay your taxes throughout the year — not just in April. THE 2026 QUARTERLY DEADLINES - Q1 (Jan–Mar): Due April 15 - Q2 (Apr–May): Due June 16 - Q3 (Jun–Aug): Due September 15 - Q4 (Sep–Dec): Due January 15, 2027 YOUR QUARTERLY CHECKLIST Before each deadline: ☐ Pull your income report for the quarter ☐ Subtract deductible business expenses ☐ Calculate your net profit ☐ Multiply by your estimated tax rate (typically 25–30% for self-employed individuals, including self-employment tax) ☐ Pay via IRS Direct Pay or EFTPS Throughout the quarter: ☐ Keep every receipt for business expenses ☐ Reconcile your bank accounts monthly ☐ Track mileage if you drive for business ☐ Save invoices and payment confirmations HOW MUCH SHOULD I PAY? A safe harbor approach: pay at least 100% of last year's tax liability (or 110% if your prior-year income exceeded $150k). This protects you from underpayment penalties even if your income increases. WHAT HAPPENS IF I MISS A DEADLINE? You'll owe a penalty — typically a small percentage of the underpayment per day. It's not catastrophic, but it adds up. Missing multiple quarters in a row can create a meaningful bill. Need help calculating your quarterly payments? That's exactly the kind of thing we help our clients with at Cherokee Bookkeeping.