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The Retirement Tax Playbook: A Practical 5-Season Strategy for Tax Planning in Retirement, Roth Conversions, Withdrawals, and Lifetime Tax Savings
Paperback
Series: Financial Planning
Publisher: Independently Published
Published: Aug 20 2026
Pages: 172
Weight: 0.52
Height: 0.37 Width: 6.00 Depth: 9.00
Language: English
Taxes don't retire when you do. Your tax strategy shouldn't either.
You can spend decades building your retirement savings-and then unknowingly give too much of it back through poorly timed withdrawals, unnecessary Roth conversions, higher Medicare premiums, or decisions made without considering what happens years down the road.
The Retirement Tax Playbook takes a different approach. Instead of a collection of disconnected tax tips, it gives you a practical 5-Season Strategy for how your tax decisions should change throughout retirement-plus a full toolkit of calculators, checklists, and worksheets you can use right away.
From the years before retirement to the years when RMDs and Social Security dominate your income-and eventually to survivor and legacy planning-this book helps you identify which decisions matter, when they matter, and how they affect one another.
The Five Seasons of Retirement
Accumulation Season - Position your savings and accounts before retirement.
Transition Season - Prepare for the shift from employment income to portfolio-based income.
Open Season - Recognize the valuable years when you have the most control over taxable income.
Income Season - Coordinate withdrawals, Social Security, RMDs, and Medicare premiums.
Legacy Season - Prepare for survivor taxes, inherited accounts, and the transfer of wealth.
Go beyond How much tax will I pay this year?
At the heart of the book is the Lifetime Tax Test-a framework for evaluating retirement decisions across multiple years, not just their immediate tax cost. You'll learn how to think through:
- Managing taxable income over time
- Roth conversions-when they may help, when they may not
- Withdrawal sequencing across taxable, tax-deferred, and Roth accounts
- Social Security taxation and how other income affects it
- RMDs and the tax consequences they create later
- IRMAA and how today's income affects future Medicare premiums
- Capital gains and your overall taxable-income picture
- HSAs, QCDs, and tax-efficient charitable giving
- Survivor tax planning and the shift to filing single
- Inherited retirement accounts and beneficiary tax rules
- Annual reviews that adapt your strategy as things change
Turn tax planning into an annual process-not a one-time decision
You'll get practical tools you can return to throughout retirement: the Lifetime Tax Test, the Annual Retirement Tax Review, the Retirement Tax Scorecard, decision frameworks, checklists, worksheets, and worked scenarios.
BONUS material Free with this book: The Retirement Tax Planning Toolkit
This book comes with a companion toolkit you can start using immediately, at no extra cost:
- An Excel Retirement Tax Control Center with eleven working calculators covering the Five Seasons, RMDs, IRMAA, Social Security, and capital gains
- Twelve checklists, one for each major decision point in the book
- Nine fillable worksheets, the paper companions to the calculators
- Nineteen letters, phone scripts, and planning templates
- A twelve-month retirement tax calendar
It's a direct download, instantly, no email address or sign-up required.
The goal isn't to predict every future tax rule or find a magic strategy that eliminates taxes. It's to help you make better decisions with the information you have today, while keeping tomorrow's consequences in view.
Whether you're approaching retirement, planning an early retirement, or already drawing retirement income, this book-and the toolkit that comes with it-gives you the framework and the tools to use your retirement savings wisely.
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