Arizona Fee Only

TAX-SMART INVESTING PLAYBOOK

A Checklist + Calendar Operating System for After-Tax Portfolio Management

Educational content only. Not financial, tax, investment, or legal advice.

WHO THIS PLAYBOOK IS FOR

This playbook is designed for individuals and households who:

  • Have $1M–$10M+ in investable assets
  • Hold assets across taxable, tax-deferred, and tax-free accounts
  • Want to reduce lifetime tax drag, not just this year’s bill
  • Prefer process and discipline over reactive decision-making

This is not about beating markets.

This is about keeping taxes from quietly beating you.

HOW TO USE THIS PLAYBOOK

This playbook has two integrated components:

  1. A Frequency-Based Checklist

    (what to review monthly, quarterly, annually, and after major events)

  2. A Month-by-Month Calendar

    (when to focus on specific tax-smart investing tasks)

They are designed to be used together.

Scoring System

  • 🟢 Green — Reviewed and addressed
  • 🟡 Yellow — Aware but not acted
  • 🔴 Red — Ignored, overlooked, or unknown

“Not applicable” is acceptable.

“Didn’t think about it” is not.

SECTION 1 — MONTHLY TAX-SMART INVESTING CHECKLIST

A. Market & Account Surveillance (10–15 minutes)

  1. Did any taxable holdings fall below cost basis this month?
  2. Are unrealized losses large enough to matter?
  3. Did volatility create harvesting opportunities?
  4. Did any holdings transition from short-term to long-term?
  5. Did dividends or capital gains post unexpectedly?
  6. Are automatic reinvestments creating wash sale risk?
  7. Did concentrated positions drift higher?
  8. Did cash balances grow unintentionally?
  9. Did any account drift from its intended role?
  10. Are there upcoming income or market events next month?

Scoring: 🟢 🟡 🔴

B. Monthly Tax Awareness

  1. Did taxable income spike unexpectedly?
  2. Did bonuses, RSUs, or deferred comp vest?
  3. Is investment income tracking above projections?
  4. Are capital gains being realized unintentionally?
  5. Were charitable gifts coordinated or random?
  6. Is state withholding aligned with income reality?
  7. Are estimated taxes still accurate?
  8. Are gains/losses being tracked in real time?
  9. Is Medicare IRMAA exposure increasing?
  10. Is this month increasing future tax friction?

Scoring: 🟢 🟡 🔴

SECTION 2 — QUARTERLY TAX-SMART INVESTING CHECKLIST

A. Tax-Loss Harvesting Discipline

  1. Have all taxable positions been reviewed for losses?
  2. Are losses harvested intentionally—not emotionally?
  3. Are replacement securities wash-sale compliant?
  4. Are harvested losses documented and tracked?
  5. Are losses being saved for higher-income years?
  6. Are losses offsetting gains strategically?
  7. Is harvesting coordinated with rebalancing?
  8. Are rebounds eliminating prior opportunities?
  9. Are losses improving after-tax outcomes?
  10. Am I harvesting losses while still realizing gains unnecessarily?

Scoring: 🟢 🟡 🔴

B. Rebalancing Without Tax Damage

  1. Has allocation drift exceeded tolerance?
  2. Can rebalancing occur inside tax-advantaged accounts?
  3. Are taxable sales truly necessary?
  4. Are new contributions used to rebalance?
  5. Are dividends redirected strategically?
  6. Is rebalancing increasing future tax exposure?
  7. Is risk increasing unintentionally?
  8. Are concentrated positions being reduced thoughtfully?
  9. Is rebalancing rule-based or emotional?
  10. Does the portfolio still match its intended function?

Scoring: 🟢 🟡 🔴

SECTION 3 — ACCOUNT LOCATION & ASSET PLACEMENT

A. Asset Location Review

  1. Are tax-inefficient assets sheltered?
  2. Are tax-efficient assets placed in taxable accounts?
  3. Are bonds placed intentionally—not by default?
  4. Are REITs and high-yield assets sheltered?
  5. Are growth assets protected from future taxation?
  6. Are high-turnover strategies isolated from taxable accounts?
  7. Is Roth space preserved intentionally?
  8. Are HSAs invested with long-term tax efficiency?
  9. Is asset location reviewed after major changes?
  10. Is asset location improving after-tax outcomes?

Scoring: 🟢 🟡 🔴

B. Account Role Clarity

  1. Does each account have a defined purpose?
  2. Are taxable accounts used for flexibility and liquidity?
  3. Are pre-tax accounts managed with future RMDs in mind?
  4. Are Roth accounts protected from unnecessary withdrawals?
  5. Are income-producing assets placed thoughtfully?
  6. Is cash positioned intentionally across accounts?
  7. Are accounts being duplicated unnecessarily?
  8. Are legacy-intended assets placed optimally?
  9. Are future withdrawals considered in placement decisions?
  10. Is account location reviewed annually—or ignored?

Scoring: 🟢 🟡 🔴

SECTION 4 — TAX COORDINATION & BRACKET CONTROL

  1. Do I know my current marginal tax bracket?
  2. Am I near a higher bracket threshold?
  3. Are capital gains stacking unintentionally?
  4. Is investment income triggering surtaxes?
  5. Are Roth conversions coordinated with market conditions?
  6. Are losses offsetting income optimally?
  7. Is income smoothing intentional?
  8. Am I creating avoidable state tax exposure?
  9. Is Medicare IRMAA monitored proactively?
  10. Are estimated taxes accurate?

Scoring: 🟢 🟡 🔴

SECTION 5 — ANNUAL TAX-SMART INVESTING CHECKLIST

Year-End Strategy

  1. Have all harvesting opportunities been evaluated?
  2. Have gains been realized intentionally?
  3. Are carryforward losses tracked correctly?
  4. Has rebalancing been completed tax-efficiently?
  5. Has asset location been reviewed?
  6. Are Roth conversions evaluated before year-end?
  7. Are charitable strategies optimized?
  8. Are required distributions planned—not rushed?
  9. Are tax documents reconciled with activity?
  10. Is next year’s strategy pre-planned?

Process Audit

  1. Did decisions reduce lifetime taxes?
  2. Were mistakes due to inattention or lack of structure?
  3. Did emotions override process?
  4. Were opportunities missed?
  5. Is the system improving year over year?
  6. Is documentation clean and accessible?
  7. Are assumptions still valid?
  8. Is coordination with tax professionals effective?
  9. Are future tax risks reduced?
  10. Is this system repeatable next year?

Scoring: 🟢 🟡 🔴

SECTION 6 — EVENT-DRIVEN CHECKLIST (RUN IMMEDIATELY)

Trigger after:

  • Market crashes
  • Bonuses or liquidity events
  • Business sale or inheritance
  • Tax law changes
  • Retirement transition
  • Death of a spouse

Immediate Questions

  1. Does this change tax strategy?
  2. Does it create harvesting opportunities?
  3. Does it require asset re-location?
  4. Does it affect RMD exposure?
  5. Does it affect Medicare premiums?
  6. Does it change withdrawal plans?
  7. Does it introduce new risks?
  8. Does it require professional input?
  9. Does it change long-term assumptions?
  10. Does it require immediate action?

SECTION 7 — TAX-SMART INVESTING CALENDAR

MONTH-BY-MONTH FOCUS

  • January: Baseline, cleanup, loss carryforwards
  • February: Asset location & account structure
  • March: Tax bracket & income tracking
  • April: Tax return review (strategic)
  • May: Rebalancing without tax regret
  • June: Midyear harvesting check
  • July: Income smoothing & projections
  • August: Stress testing & liquidity
  • September: Year-end planning window
  • October: Harvesting execution
  • November: Final adjustments
  • December: Close the books deliberately

Each month asks:

What changed?

What risks emerged?

What opportunities will disappear if I wait?

FINAL NOTE

This playbook is designed to:

  • Reduce surprises
  • Improve discipline
  • Lower lifetime tax drag
  • Replace reactive decisions with a system

Tax-smart investing is not seasonal.

It is continuous surveillance with intentional action.

EDUCATIONAL DISCLAIMER

This playbook is provided for educational and informational purposes only.

It does not constitute financial, tax, investment, or legal advice.

No recommendations are being made.

All financial decisions involve risk and should be evaluated with qualified professionals before implementation.

© Arizona Fee Only. All rights reserved.