---
title: The 7-Figure Owner's Year-Round Tax Playbook
updated: '2026-05-01T08:00:00Z'
description: >-
  Quarterly tax checklist and critical deadlines so $1M-$10M business owners
  never miss a savings window. Download your free strategic playbook today.
canonical: 'https://www.havenstoneadvisory.com/resources/guides/tax-playbook'
---

# The 7-Figure Owner's Year-Round Tax Playbook

Never miss a savings window. Use the planner and checklist to align payroll, purchases, retirement, and credits before deadlines hit.

## Q1 (January–March)
- Jan 15: Q4 estimated taxes due
- Jan 31: Send W-2s & 1099-NEC to employees/contractors
- Mar 15: File S Corp/Partnership returns or file extension
- Quarterly: Accountable plan reimbursements (mileage, home office, etc.)

## Q2 (April–June)
- Apr 15: Q1 estimated taxes due
- May 15: State franchise tax (e.g., TX) if applicable
- Jun 15: Q2 estimated taxes due
- By Jun: Mid-year entity/comp review (reasonable salary, §199A planning)

## Q3 (July–September)
- Aug: Capex review (§179/bonus timing before year-end)
- Sep 15: Q3 estimated taxes due
- Sep 15: Partnership/S Corp extension deadline

## Q4 (October–December)
- Oct 15: Individual & C Corp extension deadline
- Nov: Year-end payroll planning (bonuses vs. distributions)
- Dec 31: Finalize retirement & charity moves (401(k), DB plan, DAF)

Use the interactive estimator at: https://www.havenstoneadvisory.com/resources/guides/tax-playbook