Retirement Answer Man

Latest Episodes:

Year-End Planning Checklist for Retirees Oct 14, 2026

Show notes

Episode Overview

Year-end planning doesn't have to become a giant project. Roger walks through the key items every retiree should put eyes on before December 31st -- not to do everything, but to avoid the unforced errors that sneak up on you. He also takes listener questions on coordinating Social Security survivor benefits, weighing a teacher pension lump sum against a higher annual payment, what happens to capital losses when there are no gains to offset, and how to build enough confidence to actually pull the trigger on retirement.

Outline Of This Episode Of The Retirement Answer Man

(00:00) Year-end planning is about avoiding unforced errors -- not turning the checklist into a project
(00:42) Rock Retirement Club open enrollment runs October 15-21 -- rockretirementclub.com
(01:40) October theme in the club: year-end planning

PRACTICAL PLANNING SEGMENT

(03:35) Life check: pull up your 2027 plan of record and ask what's changed
(05:01) What spending ideas are floating around that aren't in the plan yet?
(06:00) Re-check your retirement paycheck: is your contingency fund and income reserve where it needs to be?
(08:24) Tax-related action items
(16:18) Deadline-driven items: required minimum distributions
(17:15) Annual gifting limits ($19,000 per person in 2026)
(17:45) Charitable giving strategies: cash, appreciated assets, and qualified charitable distributions for those 70.5+
(18:42) ACA subsidies: if your income changed this year, now is the time to check -- not at tax time
(20:38) ACA and Medicare open enrollment

LISTENER QUESTIONS

(22:49) Jim asks about coordinating spousal and survivor Social Security benefits
(25:09) Brian asks whether to take a teacher pension lump sum or a higher annual pension
(29:19) Rose asks what happens to capital losses when there are no gains to offset
(32:36) Bacher asks how to assess confidence in being financially ready to retire

SMART SPRINT

(41:29) In the next seven days, run through a year-end checklist -- just to put eyes on things. You may not have to do anything, but you'll be glad you looked.

ROCKIN' RETIREMENT IN THE WILD

(42:26) Roger just got back from his annual golf trip to Traverse City -- a good reminder of why investing in friendships is worth it

REFERENCES

The Perfect Portfolio with Peter Lazaroff Oct 07, 2026

Show notes

Peter Lazaroff, Chief Investment Officer of PlanCorp and author of The Perfect Portfolio, joins Roger to explore what makes a portfolio “perfect.” The answer isn’t a mathematically optimized portfolio—it’s one that serves your life. They discuss how to align investments with your goals and purpose, manage risk, evaluate stocks and bonds, and create a simple investment process you can actually stick with.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN PODCAST

(00:00) Roger welcomes Peter Lazaroff to discuss The Perfect Portfolio, shares what’s happening inside the Rock Retirement Club, and explores why the right portfolio is the one that serves your life.

INTERVIEW WITH PETER LAZAROFF

(2:58) Roger introduces Peter Lazaroff, author of The Perfect Portfolio, and they discuss what makes a portfolio “perfect,” why there is no one-size-fits-all approach, and how your goals, preferences, risk capacity, and purpose should shape your investment strategy.
(12:12) Peter explains why the purpose of your money should drive your investment strategy and how to think about risk capacity, time horizons, and different goals.
(20:00) Roger and Peter begin filling in the pieces of the asset allocation, discussing indexing, factor investing, and how to approach the different components of a portfolio.
(40:32) Peter shares practical steps for implementing an investment strategy, including creating an investment policy, automating decisions, and connecting each investment to a specific purpose.

LISTENER QUESTIONS

(47:33) Dan: How can he find his complete Social Security earnings history?
(48:48) Maggie: Are future Social Security benefit estimates adjusted for inflation and cost-of-living adjustments?
(51:09) Jay: When should he file Form SSA-44 if he expects an IRMAA surcharge from a one-time income event?
(53:05) Renee: How should an ultra-short-term bond fund fit into a five-year retirement income floor?

SMART SPRINT

(1:00:14) Look at your entire portfolio and connect each investment to the goal it is meant to serve.

ON THE BOOKSHELF

(1:01:12) Nichole recommends The Gales of November: The Untold Story of the Edmund Fitzgerald by John U. Bacon, and Roger shares his thoughts on Animal Farm by George Orwell.

REFERENCES

Your Social Security Playbook: Building Your Strategy- Married Filers Sep 30, 2026

Show notes

Roger Whitney closes out his five-week Social Security series with a practical framework for married couples deciding when to claim. He explains how to coordinate benefits, avoid common mistakes, and make a decision that fits the household rather than relying on a single calculator or searching for a perfect answer.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN PODCAST

(00:00) Roger Whitney closes out his five-week Social Security series with a guide to building a claiming strategy for married couples. He shares a practical framework for coordinating benefits, avoiding common mistakes, and making a decision that fits the household.

PRACTICAL PLANNING

(06:54) Roger shares a framework for coordinating benefits, weighing household priorities, and testing claiming strategies against a retirement plan of record.

LISTENER QUESTIONS

(36:55) Dominic: Do cost-of-living adjustments apply before claiming?
(39:17) Joe: Should he wait until age 70 to claim while his wife claims at 62?
(41:31) Jason: Should the opportunity cost of delaying be compared with the potential return of an aggressive investment portfolio?
(45:05) Ann: What if both spouses have similar, moderate-to-high benefits?
(46:20) Stacy: Is it reasonable for a lower-earning husband to claim at 62 while his higher-earning wife waits until 70?

SMART SPRINT

(49:08) Put time for your Social Security decision on the calendar.

ON THE BOOKSHELF

(50:38) Roger and Nichole share books they’re reading, and Roger previews next week’s conversation with Peter Lazaroff about The Perfect Portfolio.

REFERENCES

ON THE BOOKSHELF

Your Social Security Playbook: Building Your Strategy- Single Filers Sep 23, 2026

Show notes

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 complicated

PRACTICAL 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.

REFERENCES

Your Social Security Playbook: The Levers You Control Sep 16, 2026

Show notes

Roger Whitney explains six levers that can influence Social Security benefits: reviewing your earnings record, choosing when to claim, managing retirement income, reconsidering an early claim, considering where you live, and coordinating spousal or survivor benefits. The episode emphasizes that the best claiming strategy depends on each person’s priorities, resources, and desired outcome.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN PODCAST

(00:00) Roger introduces the Social Security series and explains that this episode focuses on the factors individuals can control.

PRACTICAL PLANNING SEGMENT

(02:52) Roger walks through the six Social Security levers, including earnings history, claiming age, retirement income, application withdrawal, state taxation, and spousal coordination.

LISTENER QUESTIONS

(31:08) Planning for Social Security uncertainty: Roger responds to Turner, who asks how to model future benefits given uncertainty about possible changes to Social Security.
(36:25) Coordinating benefits for spouses with different earnings: Roger examines whether a higher earner should delay benefits while the lower earner claims earlier.
(45:27) Claiming benefits when retirement assets are growing: Roger discusses a listener’s decision to claim Social Security before age 70 because withdrawals from pre-tax accounts would otherwise be needed and how a spouse’s early claiming decision could affect future spousal and survivor benefits.

SMART SPRINT

(49:14) Review your retirement plan, identify the Social Security levers you control, and compare alternative claiming strategies with a “what-if” scenario.

CLOSING THOUGHTS

(50:15) Roger shares a personal story about his daughter and a listener’s positive experience with her work.

REFERENCES

Social Security Administration — Social Security Statement and earnings record
Social Security Administration — Social Security Benefits Calculators
Dinkytown — Social Security Benefits Taxation Calculator
AARP — State Taxation Of Social Security Benefits
Rock Retirement with Roger Whitney — YouTube channel
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Your Social Security Playbook: How Your Benefit is Calculated Sep 09, 2026

Show notes

How is your Social Security benefit actually calculated? In this episode, Roger explains how you qualify for retirement benefits, how your earnings history determines your benefit, and why the age you claim matters. Understanding these basics will help you recognize the areas where you have agency as you build your Social Security claiming strategy.

Roger also answers listener questions about survivor benefits, estimating taxes in retirement, and coordinating spousal benefits.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

[00:00] Understanding the context behind your Social Security benefit

PRACTICAL PLANNING: SOCIAL SECURITY PLAYBOOK

[01:33] How you qualify for Social Security and how benefits are calculated
[11:08] Reviewing your Social Security statement and understanding cost-of-living adjustments
[15:30] Understanding your Social Security claiming age options

LISTENER QUESTIONS

[22:11] What Social Security resources are available for widows and widowers?
[24:18] How to categorize income and expenses for tax planning
[30:43] Can my husband switch from his own benefit to a spousal benefit?

SMART SPRINT

[33:39] Review your Social Security statement

CLOSING THOUGHTS

[34:40] Reconsidering the words “should,” “must,” and “need to”

REFERENCES

Your Social Security Playbook: How the System Works Sep 02, 2026

Show notes

Social Security is one of the most important pieces of a retirement plan, but how does the system work, and will it remain financially viable for future retirees? Roger begins a five-week series on building your Social Security playbook by exploring the program’s history, funding structure, and current financial outlook. He also discusses potential paths to solvency, how he accounts for Social Security in retirement planning, and why building a resilient plan remains essential.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

[00:00] Roger introduces a new five-week series designed to help you build your Social Security playbook.
[01:37] The Retirement Answer Man YouTube channel is relaunching with weekly videos that complement the podcast.

PRACTICAL PLANNING SEGMENT

[02:35] Roger outlines the five-week Social Security series and explains what you need to understand to build your own playbook.
[05:02] A brief history of Social Security provides context for how the program and its purpose have evolved.
[08:18] Roger explains how today’s workers fund benefits for today’s retirees through payroll taxes.
[11:58] Demographic changes and longer lifespans have caused benefit payments to exceed incoming payroll-tax revenue.
[15:45] The 2026 Trustees Report projects what could happen in 2032 if Congress does not address Social Security’s funding shortfall.
[21:50] Roger explores possible paths to solvency and explains how he accounts for Social Security when building a resilient retirement plan.

LISTENER QUESTIONS

[37:40] Will claiming a reduced benefit at age 62 also reduce a spouse’s future survivor benefit?
[39:08] Should the decision to claim Social Security early account for the assets that can remain invested?
[43:17] Is OpenSocialSecurity.com a useful tool for choosing a claiming strategy, and how can you respond to someone who wants to claim early because they fear Social Security will run out of money?

SMART SPRINT

[46:42] Claim your personal Social Security account at SSA.gov and consider contacting your federal representatives about addressing the program’s solvency.

CLOSING THOUGHTS

[48:28] A listener demonstrates how small, consistent efforts can compound into meaningful progress over time.
[52:50] Allison reviews The Calamity Club by Kathryn Stockett, and Roger shares his current book recommendation.

REFERENCES

Summer Reruns: Learn What to Ignore with Dr. Daniel Crosby Aug 26, 2026

Show notes

In this summer replay, Roger talks with Dr. Daniel Crosby about learning what to ignore in an age of information overload. They explore how to filter financial advice, align decisions with your values, and focus your attention on what truly matters to your finances and your life.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

[00:00] Roger introduces this summer replay with Dr. Daniel Crosby and talks about his upcoming Social Security series.

SUMMER REPLAY WITH DR DANIEL CROSBY

[02:21] Roger revisits his conversation with Dr. Daniel Crosby about filtering out the noise competing for our attention.
[09:18] Daniel explains how our spending can reveal whether our choices truly align with our stated values.
[14:03] Roger and Daniel share four questions that can help determine whether information deserves our attention.

CLOSING THOUGHTS

[31:46] Roger looks ahead to the upcoming five-week Social Security series.

REFERENCES

Summer Reruns: Gabbing with Gretchen Rubin- Your Personality and How it Plays into Your Retirement Planning Aug 19, 2026

Show notes

This Summer Replay revisits Roger’s 2018 conversation with Gretchen Rubin about the Four Tendencies and how understanding your personality can help you create a retirement plan and daily life that truly fit who you are.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) Roger introduces this Summer Replay conversation with Gretchen Rubin about creating a retirement plan that fits your personality.

SUMMER REPLAY: CONVERSATION WITH GRETCHEN RUBIN

(01:32) Gretchen explains the Four Tendencies and how each responds to expectations.
(08:25) Learn how working with your natural tendency can help you achieve your goals.
(09:39) Discover how the Four Tendencies can shape your transition into retirement.
(16:53) Understanding the tendencies of your spouse, family members, and coworkers can improve communication and reduce conflict.

CLOSING THOUGHTS

(19:40) Roger shares his thoughts on relaunching YouTube in a way that fits him and the show.

REFERENCES

Summer Reruns: Keep Investments Simple with Peter Lazaroff Aug 12, 2026

Show notes

As part of Roger’s summer replay series, he revisits a conversation with Peter Lazaroff about the value of elegant simplicity in retirement investing. They discuss why more sophisticated strategies are not necessarily better, how added complexity can create unexpected risks, and why the money supporting your retirement should remain separate from any “play money” used to explore alternative investments.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:01) Roger introduces the benefits of simplifying your investments rather than continually adding new strategies.

RERUN: KEEPING INVESTMENTS SIMPLE WITH PETER LAZAROFF

(01:56) Roger and Peter discuss elegant simplicity, private investments, and why adding complexity to your portfolio may create more risk and work without meaningfully improving your retirement.
(20:18) As private investments become more widely available, Peter shares a framework for deciding whether an investment truly belongs in your portfolio.
(32:02) Roger and Peter discuss when added complexity may serve a purpose and why private investments should not be a core part of the strategy securing your retirement.

CLOSING THOUGHTS