Retirement Answer Man

Latest Episodes:

Should I do a Roth Conversion This Year? Nov 11, 2026

Show notes

Year-end planning brings plenty of decisions to work through, and Roth conversions are one of them. Should you convert in 2026, or is it better to wait? This week, Roger walks through a practical framework for evaluating Roth conversions, including the factors to consider, potential tax implications, and how to make a decision that fits your retirement plan. He also answers listener questions about simplifying investment portfolios, IRMAA surcharges, Roth conversion strategies, and asset location for early retirees.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) Introduction and why it's time to close the loop on Roth conversion decisions for 2026

PRACTICAL PLANNING SEGMENT

(01:05) Roger walks through a framework for deciding whether a Roth conversion makes sense in 2026. He covers the factors to weigh, including current and future tax brackets, required minimum distributions, tax implications, and potential impacts on healthcare costs. The goal is to evaluate your options, make an informed judgment call, and close the loop before year-end.

LISTENER QUESTIONS

(25:55) How can you simplify an investment portfolio with multiple mutual funds while managing capital gains and tax consequences?
(35:39) What types of income are included when calculating IRMAA Medicare surcharges?
(37:06) Should you be more aggressive with Roth conversions when you have substantial retirement assets and future inheritance?
(39:56) Should early retirees prioritize keeping bonds in their brokerage bridge account rather than following traditional asset location strategies?

SMART SPRINT

(43:52) If you're considering a Roth conversion for 2026, set aside time to review your retirement plan, complete a tax estimate, weigh the factors for and against converting, and make a decision.

ROCKIN’ RETIREMENT IN THE WILD

(44:29) Christine discovers her passion for nature and wildlife photography after years of exploring different interests. Her story is a reminder that finding your lane in retirement can take time, experimentation, and a willingness to keep trying.

REFERENCES

How to Rebalance Before Retirement Nov 04, 2026

Show notes

In this episode, Roger explains how to rebalance your portfolio before retirement and why it's important to align your investments with the changing purpose of your money. He discusses how guaranteed income, your retirement plan's fundedness, and your comfort with market volatility influence your approach. Roger also shares a practical framework for organizing your assets into three layers to provide financial flexibility, fund your retirement paycheck, and support long-term growth. Plus, he answers listener questions about finding a retirement planner and preparing for the nonfinancial aspects of retirement.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) Roger introduces the episode and discusses why rebalancing your portfolio before retirement is important, particularly as the purpose of your money changes. He previews the discussion on retirement portfolio allocation, listener questions, and a Rockin' Retirement in the Wild story.

RETIREMENT TOOLKIT: HOW TO REBALANCE YOUR PORTFOLIO BEFORE RETIREMENT

(01:29) Roger explains why having enough liquidity is essential to enjoying retirement without allowing market downturns to force you to defer your life. He discusses three factors that influence how important rebalancing is: guaranteed income, how funded your retirement plan is, and your psychological comfort with volatility.
(08:55) Roger walks through his practical approach to rebalancing, starting with creating a retirement plan of record and defining your base great life and discretionary spending. He explains how to assign every dollar a job through three layers: a contingency fund for unexpected expenses, an income reserve to fund your retirement paycheck, and a long-term portfolio for future growth. He also discusses how to determine appropriate reserves and execute the rebalancing strategy.

LISTENER QUESTIONS

(20:25) William asks how to find a retirement planner who can validate his DIY retirement plan, prepare tax returns, and serve as a trusted financial resource for his wife if he passes away.
(25:12) An anonymous listener asks whether conventional retirement planning focuses too much on accumulating wealth and not enough on preparing for the loss of purpose, mission, structure, and identity that can come with leaving work.

ROCKIN' RETIREMENT IN THE WILD

(27:45) Rebecca shares how listening to the podcast helped her discover Social Security survivor benefits after her husband's passing and find her path to retirement. Now retired since 2024, she shares how she's living her best life.

SMART SPRINT

(29:30) Evaluate whether your current asset allocation is doing the job it's supposed to do for the stage of life you're in or approaching. Consider whether strong market returns have made you hesitant to make adjustments that better serve your future needs.

ON THE BOOKSHELF

(30:37) Kevin Lyle reviews Better with Age: The Psychology of Successful Aging by Alan Castel, exploring how attitude, adaptation, curiosity, and finding personal meaning can contribute to successful aging.

REFERENCES

How to Interview a Retirement Planner Oct 28, 2026

Show notes

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

Medicare Update with Danielle Roberts Oct 21, 2026

Show notes

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

The opinions expressed in this podcast are for general informational purposes only and are not intended as specific advice or recommendations for any individual.

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
Submit a Question for Roger
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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