Retirement Answer Man

By Roger Whitney, CFP®, CIMA®, RMA, CPWA®Business Education Self-Improvement Investing

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Retirement Answer Man episodes

October 28How to Interview a Retirement Planner
In this episode, Roger shares how to find the right retirement planner, what to look for when interviewing advisors, and how to evaluate the value they bring. Tanya Nichols joins him to answer listener questions about financial advisors, retirement income, investment accounts, and Social Security.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN
(00:00) Roger shares his concerns about heart health after several friends experience cardiac issues and explains how consulting a specialist helped him determine the appropriate next steps. He connects the experience to the importance of finding a retirement planner who specializes in your needs.
RETIREMENT TOOLKIT: HOW TO CHOOSE A RETIREMENT PLANNER
(05:30) Roger explains why working with a retirement planning specialist matters and how to evaluate potential advisors based on connection, competence, consistency, qualifications, and the value they provide.
(14:41) Roger discusses what to look for when evaluating potential retirement planners, including their fee structure, planning process, and focus on clients’ life goals.
(18:40) Roger shares questions to ask when interviewing potential retirement planners to assess their approach, experience, and fit for your needs.
LISTENER QUESTIONS
(26:24) Kurt asks how to begin developing a retirement strategy, including deciding whether and how to hire a financial advisor.
(32:44) Mike asks how to bridge the years between early retirement, Medicare, and Social Security while making tax-efficient financial decisions.
(38:24) A listener asks whether to continue working with an advisor who manages individual stocks, Roth conversions, cash reserves, and tax planning or switch to a flat-fee planner.
(43:12) Greg asks whether keeping retirement accounts at both Vanguard and Fidelity provides worthwhile protection or whether consolidating would simplify things.
(45:20) Todd asks how Social Security benefit estimates account for inflation and COLAs, and whether the estimates reflect today's dollars.
(49:40) Andrew asks about spousal Social Security benefits for a wife without her own earnings record and whether delaying his benefits until age 70 increases her benefit.
SMART SPRINT
(52:18) Download the How to Choose a Retirement Planner worksheet and use it to evaluate your current advisor, review your own retirement plan, or interview potential planners.
ON THE BOOKSHELF
(54:06) Kevin Lyles reviews Thinking, Fast and Slow by Daniel Kahneman and explores how recognizing biases can improve decision-making.
REFERENCES
Retirement Answer Man FREE Resource Page
Roger Whitney on YouTube
Submit a Question for Roger
Rock Retirement Club
Sign up for the Noodle!
Thinking, Fast and Slow by Daniel Kahneman
56 min
October 21Medicare Update with Danielle Roberts
Roger welcomes Danielle Roberts, co-founder of Boomer Benefits, to discuss Medicare in 2026, including rising Part D premiums, Medicare Advantage versus Medigap, and what to review during open enrollment. Then, Roger shares a Rock Retirement Club case study about building an income reserve before retirement and finding peace of mind by focusing on what matters most.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN
00:00 – Roger introduces the importance of time and attention and previews today's episode.
MEDICARE UPDATE WITH DANIELLE ROBERTS
01:25 – Navigating Medicare in 2026: Part D changes, Medicare Advantage, and Medigap.
25:15 – What to review during Medicare open enrollment and when to make changes.
RETIREMENT TOOLKIT- MINI CASE STUDY
33:55 – A retirement case study on rebalancing investments, creating an income reserve, and reducing anxiety before retirement.
SMART SPRINT
44:56 – Identify one challenge you're facing and ask someone who can offer a fresh perspective to help you see it differently.
CLOSING THOUGHTS
45:35- Roger reflects on getting back into routines, making space for deeper thinking, and the relaunched Rock Retirement with Roger Whitney YouTube channel.
RESOURCES
Medicare.gov
Boomer Benefits
Rock Retirement with Roger Whitney on YouTube
Submit a Question for Roger
Rock Retirement Club

The opinions expressed in this podcast are for general informational purposes only and are not intended as specific advice or recommendations for any individual.
48 min
October 14Year-End Planning Checklist for Retirees
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
Rock Retirement with Roger Whitney — YouTube channel
Submit a Question for Roger
Rock Retirement Club
Dinkytown tax estimator
Boomer Benefits Medicare guidance
Healthcare.gov -- ACA open enrollment
44 min
October 07The Perfect Portfolio with Peter Lazaroff
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
The Perfect Portfolio by Peter Lazaroff
Social Security Administration
Rock Retirement with Roger Whitney — YouTube channel
Submit a Question for Roger
Rock Retirement Club
The Gales of November: The Untold Story of the Edmund Fitzgerald by John U. Bacon
Animal Farm by George Orwell
1 hr 4 min
September 30Your Social Security Playbook: Building Your Strategy- Married Filers
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
Social Security Administration
Live Year-End Planning Session
Sign up for the Noodle!
Rock Retirement with Roger Whitney — YouTube channel
Submit a Question for Roger
ON THE BOOKSHELF
Remarkably Bright Creatures by Shelby Van Pelt
In a Sunburned Country by Bill Bryson
53 min
September 23Your Social Security Playbook: Building Your Strategy- Single Filers
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
Social Security Administration
Live 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 McConaghy
Rock Retirement with Roger Whitney — YouTube channel
Submit a Question for Roger
YouTube video: When Should a Single Person Claim Social Security?
51 min
September 16Your Social Security Playbook: The Levers You Control
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
Submit a Question for Roger
Sign up for The Noodle
53 min
September 09Your Social Security Playbook: How Your Benefit is Calculated
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
Social Security Administration
Open Social Security
Maximize My Social Security
Dinkytown 1040 Tax Calculator
Submit a Question for Roger
Sign up for The Noodle
Rock Retirement with Roger Whitney on YouTube: How to Read Your Social Security Statement
38 min
September 02Your Social Security Playbook: How the System Works
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
Social Security Administration
Open Social Security
Submit a Question for Roger
Sign up for The Noodle
Retirement Answer Man on YouTube
The Calamity Club by Kathryn Stockett
The Way of Excellence by Brad Stulberg
55 min
August 26Summer Reruns: Learn What to Ignore with Dr. Daniel Crosby
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
The Soul of Wealth by Dr. Daniel Crosby
Deep Work by Cal Newport
The Rational Optimist by Matt Ridley
Submit a Question for Roger
Sign up for The Noodle
33 min

About Retirement Answer Man

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A top retirement podcast. Roger Whitney, CFP®, CIMA®, CPWA®, RMA, guides you on how to actually do retirement well financially and personally. This retirement podcast isn't afraid to talk about the…