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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.

Planning Cadence

How to use the tax playbook

This page is built for owners who need a simple quarterly system for estimated taxes, owner compensation, retirement funding, accountable-plan reimbursements, and year-end deduction timing.

Set the baseline

Compare prior-year safe harbor against current-year profit so quarterly payments are tied to real numbers instead of guesswork.

Review before deadlines

Use the quarter-by-quarter checklist to catch payroll, entity, retirement, and deduction decisions while there is still time to act.

Turn estimates into execution

Pair the playbook with clean monthly accounting so your tax plan reflects actual cash flow, margins, and owner draws.

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.

The planner compares the prior-year safe harbor to the current-year method and uses the lower. Prior-year safe harbor is generally 100% of last year’s total tax, or 110% if prior-year AGI exceeded the high-income threshold. Current-year uses 90% of this year’s projected tax.
Filing status, last year’s total tax (Form 1040), last year’s AGI (to check the 110% rule), this year’s projected total tax, and amounts already paid via withholding/estimates.
The selected method’s annual requirement is divided into four equal quarterly targets. The progress bar shows paid to date and the remaining annual amount.
No. It’s a federal educational planner and excludes state rules, penalty waivers, and irregular withholding timing. Confirm specifics with your CPA.
The full Playbook PDF + an editable checklist with quarter-by-quarter tasks, owner-pay/entity reminders, and links to IRS notices we rely on.
Yes. The estimator and downloadable materials are provided at no cost.

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

Related planning tools

These pages help turn quarterly estimates into a broader business-owner tax plan.

Entity Structure Matrix

Compare S-Corp, C-Corp, partnership, and sole proprietor tax layers before changing structure.

Open resource

Profit Routing Calculator

Model salary, distributions, retained earnings, taxes, reserves, and long-term wealth routing.

Open resource

Business Tax Strategy

Use a quarterly advisory cadence to turn estimates, payroll, and deductions into execution.

Open resource

Editorial review

Reviewed for tax accuracy

Educational tax content prepared by HavenStone Advisory and reviewed for technical accuracy. It is not individualized tax, legal, accounting, investment, or financial advice. Rules can change, and your facts matter, so confirm decisions with your CPA, attorney, or tax advisor before acting.

Reviewed by Mia Anne Pham Reeves, CPA

See our editorial policy or report a correction.

Verify reviewer CPA license through TSBPA

Primary references

Review standard

  • Primary-source references checked where rule-specific claims are made.
  • Article scope limited to educational information unless a client engagement exists.
  • Time-sensitive tax rules labeled with published, updated, or reviewed dates.

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.