Retirement Answer Man
Retirement Answer Man
Roger Whitney, CFP®, CIMA®, RMA, CPWA®
Your Social Security Playbook: Building Your Strategy- Single Filers
50 minutes Posted Sep 23, 2026 at 8:00 am.
Roger Whitney explains how solo filers can make a confident Social Security claiming decision without getting overwhelmed by complexity. He covers the biggest mistakes to avoid, introduces a practical decision-making framework, answers listener questions about survivor benefits, and closes with a simple action step for deciding when to revisit the issue.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN PODCAST
Intro: Why Social Security decisions get complicatedPRACTICAL PLANNING SEGMENT
Social Security claiming framework for solo filers: avoiding common mistakes, knowing when to begin, using the OODA framework, evaluating your plan and personal circumstances, checking survivor or divorced-spouse benefits, identifying your priorities, and testing your options against your retirement plan. LISTENER QUESTIONS
Karen asks how to switch from her own Social Security benefit to survivor benefits later.
Julie asks whether she should claim survivor benefits first while letting her own benefit grow.
Drew asks how retiring at 60 and claiming at 64 would affect his Social Security benefits.SMART SPRINT
If Social Security is still a green banana, use your full retirement age in your plan and set a date to revisit it; if it’s ripe, follow the protocol and make your claiming decision. ON THE BOOKSHELF
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Roger Whitney explains how solo filers can make a confident Social Security claiming decision without getting overwhelmed by complexity. He covers the biggest mistakes to avoid, introduces a practical decision-making framework, answers listener questions about survivor benefits, and closes with a simple action step for deciding when to revisit the issue.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN PODCAST(00:00) Intro: Why Social Security decisions get complicatedPRACTICAL PLANNING SEGMENT(02:55) Social Security claiming framework for solo filers: avoiding common mistakes, knowing when to begin, using the OODA framework, evaluating your plan and personal circumstances, checking survivor or divorced-spouse benefits, identifying your priorities, and testing your options against your retirement plan. LISTENER QUESTIONS(36:24) Karen asks how to switch from her own Social Security benefit to survivor benefits later.(39:06) Julie asks whether she should claim survivor benefits first while letting her own benefit grow.(40:54) Drew asks how retiring at 60 and claiming at 64 would affect his Social Security benefits.SMART SPRINT(46:50) If Social Security is still a green banana, use your full retirement age in your plan and set a date to revisit it; if it’s ripe, follow the protocol and make your claiming decision. ON THE BOOKSHELF(47:30) Roger recommends The Violin Maker, while Natalia gives Wild Dark Shore five out of five for its emotional depth and thrilling twists. REFERENCESSocial Security AdministrationLive Year-End Planning Session Sign up for the Noodle! The Violin Maker: Finding a Centuries-Old Tradition in a Brooklyn Workshop by John Marchese Wild Dark Shore by Charlotte McConaghyRock Retirement with Roger Whitney — YouTube channelSubmit a Question for RogerYouTube video: When Should a Single Person Claim Social Security?