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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 (Jan-Mar)

  • Jan 15Q4 estimated taxes due
  • Jan 31Send W‑2s & 1099‑NEC
    to employees/contractors
  • Mar 15File S‑Corp/Partnership returns
    or file extension
  • QuarterlyAccountable plan reimbursements
    mileage, home office, etc.

Q2 (Apr-Jun)

  • Apr 15Q1 estimated taxes due
  • May 15State franchise tax (e.g., TX)
    if applicable
  • Jun 15Q2 estimated taxes due
  • By JunMid‑year entity/comp review
    reasonable salary, §199A planning

Q3 (Jul-Sep)

  • AugCapex review
    §179/bonus timing before year‑end
  • Sep 15Q3 estimated taxes due
  • Sep 15Partnership/S‑Corp extension deadline

Q4 (Oct-Dec)

  • Oct 15Individual & C‑Corp extension deadline
  • NovYear‑end payroll planning
    bonuses vs. distributions
  • Dec 31Finalize retirement & charity moves
    401(k), DB plan, DAF

Deadlines can shift for weekends/holidays and differ by state. Confirm each year.

Quarterly Estimated Tax Planner

Compares prior‑year safe harbor to current‑year (90%) and uses the lower amount.

Your figures

Plan

Selected method:
Prior-year safe harbor
Annual requirement
$49,500
Quarterly target
$12,375
Paid40%
Remaining this year: $29,500

This planner does not apply state rules, penalty waivers, or irregular withholding timing. Verify with your CPA.

Educational planner. Confirm federal/state specifics with your CPA.

Get the full playbook (PDF + editable checklist)

Quarter-by-quarter deadlines, owner pay/entity reminders, and links to IRS notices we rely on.

Common questions

How the planner applies safe harbor rules, calculates quarterly targets, and what’s included.

Related video

Tax Landmines: The Quick Take

One missed date can trigger three penalties. Here are the seven IRS deadlines every business owner must hit, plus two simple ways to set quarterly estimates so you never guess again.

Read the full blog post

Lock in a smarter 12-month tax plan

Turn your estimate into action. In one session we will set precise quarterly payments, dial in owner pay and payroll, map credits and deductions, and give you a step-by-step timeline so you stop overpaying and stay compliant.