Retirement Answer Man

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.

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

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

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

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?