Retirement Answer Man

Latest Episodes:

Direct Indexing vs. Mutual Fund or ETFs Aug 20, 2025

Show notes

💬 Show Notes

In this episode, Roger explores how naming and recognizing the different phases of life can bring clarity to the retirement journey. A listener’s question about inherited money sparks a conversation about direct indexing—what it is, when it makes sense, and what to watch out for. He also shares how to navigate calm, choppy, and rough waters in retirement planning so listeners can move forward with more confidence and control.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) Today we will talk about direct indexing and answer some more of your questions.
(01:04) Roger talks about acknowledging and naming things in life.
(04:19) There are four levels that Roger wants to acknowledge with clients- calm waters, choppy waters, rough waters, and change of course.

ROCKIN RETIREMENT IN THE WILD

(08:55) Brian says he focuses on spending time with family in retirement.
(09:20) Don says electric bikes are game changers.

PRACTICAL PLANNING SEGMENT

(10:30) John asks a question about direct indexing.
(13:17) Direct indexing is when you buy the individual stocks of an index in your own account instead of a fund, allowing for tax benefits and customization but with more complexity.
(16:32) Should you do this if you are concerned about taxes? What are the benefits? The drawbacks?
(20:38) Roger says exchanging traded funds has some advantages over indexing.

LISTENER QUESTIONS

(21:20) Scott has a follow up question about getting a mortgage in retirement.
(28:45) An anonymous listener says it's too late for long term care and wants a recommendation for a low risk investment.
(35:40) Our next question comes from John related to being an executor for an estate.
(39:17) Dan asks a question about rebalancing.

SMART SPRINT

(43:46) In the next seven days, take a small step by naming the season of life you’re in—calm, choppy, rough, or changing direction—so you can better focus your energy on where to lean in right now.

UP NEXT

(44:40) Next week Roger chats with Tanya Nichols on the show and answers some of your questions.

REFERENCES

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Elder Care Options for Singles Aug 13, 2025

Show notes

💬 Show Notes

In this episode, Roger Whitney welcomes elder law expert Kathy McNair to discuss the often-overlooked but crucial topic of elder care, especially for those retiring solo. They explore what elder law really means, how it differs from traditional estate planning, and why having the right legal documents—like healthcare proxies and powers of attorney—is vital for protecting your future and legacy. Alongside practical insights on guardianships and conservatorships, Roger shares a fresh perspective on gratitude and contentment as essential mindsets for a meaningful retirement. Plus, he answers listener questions and wraps up with a special personal announcement.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) Today on the show, we are going to start exploring elder care with an expert in the area, Kathy McNair.
(01:06) Let’s talk about gratitude and contentment.

ROCKIN RETIREMENT IN THE WILD

(04:40) Roger and Kimberly are embracing retirement as an opportunity to live fully and give back and reconnect with things that matter most.

INTERVIEW WITH KATHY MCNAIR

(06:26) Roger introduces Kathy, an elder attorney and founder of seniorsolutionsinfo.com and SoloAllies.com
(08:16) Kathy explains elder law and talks about her background.
(10:20) What is the difference between a guardianship and a conservatorship?
(12:00) Roger says one of his clients has a question about his aging mother and how to approach the situation.
(17:26) Is a power of attorney enough when someone is not cognitively capable?
(21:33) Kathy talks about starting SoloAllies.com.
(25:35) For seniors who are aging without close family, the key is to start building your team while you’re still healthy and capable.
(31:30) The hardest role to solve sometimes is the healthcare proxy role.

LISTENER QUESTIONS

(33:07) Submit questions on AskRoger.me.
(35:45) Joe asks a question about the interview with Charles Ellis.
(42:30) Joe asks “Can you explain some comments in Charles Ellis book?”
(45:00) Brian says he’s thinking of doing an NUA with company stock.

SMART SPRINT

(49:13) In the next seven days, pick an activity and don’t listen to music or a podcast or anything. Be Present.

BONUS

(49:00) Roger explains that Agile Retirement Management has merged with Align Financial.

REFERENCES

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How to Choose a Retirement Coach Aug 06, 2025

Show notes

💬 Show Notes

In this episode, Roger Whitney returns after a month off, ready to help you rock your retirement! He answers listener questions on a range of topics, including the benefits of choosing between Fidelity and Vanguard, the Rule of 55 for 401(k) withdrawals, and inherited IRA distributions. Roger also chats with discusses the importance of finding the right retirement coach. Join us for practical advice and insights to help you navigate your retirement journey!

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) Roger Whitney answers your retirement questions on today's show

ROCKIN’ RETIREMENT IN THE WILD

(01:08) Brian says he and his wife are playing pickleball during retirement.

CHAT WITH KEVIN LYLES

(03:30) Roger talks to Kevin Lyles about a financial advisor versus a retirement coach
(06:29) How does someone determine if they need an advisor or a coach?
(10:15) Define what you are looking for before finding a coach.
(12:44) A good coach will listen and have good intuition about what is really going on.

LISTENER QUESTIONS

(14:47) Barb says she was thinking of moving her Fidelity assets to Vanguard.
(21:44) Mark has a question about the Rule of 55.
(25:53) Craig asks a question about an inherited IRA
(27:54) Scott says he has discovered something about TSP withdrawals.
(30:53) An audio question about my Switzerland interview with Scott from a few weeks back

SMART SPRINT

(32:05) In the next seven days, define something you would like to do and find one person who has done this thing.

BONUS

(35:00) Roger reflects on how he is going to spend the next 5 weeks.

REFERENCES

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Replay: How to Manage Your Scarcity Brain Jul 30, 2025

Show notes

In this episode, Roger Whitney welcomes Michael Easter, New York Times bestselling author of 'The Comfort Crisis' and 'Scarcity Brain.' They delve into the concept of overcoming frugality and the evolutionary mismatches that affect our resource management in retirement. Discover how short-term discomfort can lead to long-term growth, the importance of taking the stairs in life, and the psychological implications of our modern abundance. Tune in for insights that can help you not just survive retirement, but thrive in it!

*Episode originally aired March 27, 2024

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

[01:04] Today we have Michael Easter, author of Scarcity Brain, on the show.

PRACTICAL PLANNING SEGMENT WITH MICHAEL EASTER

[02:20] Roger introduces Michael Easter to the show
[03:14] The Comfort Crisis falls into the Energy Pillar- building energy so you can show up for your life.
[04:30] Roger asks Michael what his objective was in exploring the Comfort Crisis
[09:40] Why is it a bad thing to be comfortable?
[12:40] How do we start being more uncomfortable?
[16:11] The Scarcity Brain falls into the Vision Pillar.
[18:00] Why do we have a constant feeling that we don’t have enough?
[25:25] Quantifying goals is not always the best thing to do.
[29:01] Michael defines what the scarcity loop is.

TODAY’S SMART SPRINT SEGMENT

[33:21] In the next seven days, take the stairs! Do something that most people don't do.

RESOURCES

BOOK - The Comfort Crisis by Michael Easter
BOOK - Scarcity Brain by Michael Easter
Stutz
Rock Retirement Club

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Replay: Overcoming Frugality in Retirement with Dr. Dan Crosby Jul 23, 2025

Show notes

In this enlightening episode, we tackle the often overlooked mental shift required in retirement: transitioning from a saver to a spender. Join us as we revisit a compelling conversation with Dr. Daniel Crosby, Chief Behavioral Officer at Orion Advisory Services. We'll explore the psychological barriers many face in letting go of frugality and how to embrace the resources they've accumulated to enhance their lives. Discover practical strategies to gain confidence in spending, overcome the fear of uncertainty, and ultimately, live a fulfilling retirement without the regret of dying with too much money. Tune in for insights that could transform your approach to retirement!

*This episode originally aired March 20, 2024

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

[00:30] Overcoming frugality is a major crisis for many in retirement

INTERVIEW WITH DAN CROSBY

[01:19] Roger introduces Daniel Crosby.
[02:50] How do we overcome frugality?
[04:30] There are a lot of behavioral things that change when you leave full-time work.
[09:45] How to gain confidence in the midst of uncertainty.
[17:22] People are wired to avoid regret.
[18:01] What are some basic things people can do to overcome frugality?
[22:16] You can't undo 40 years of programming in 4 minutes- experiment with behavior and small commitments.

TODAY’S SMART SPRINT SEGMENT

[25:15] In the next seven days, I challenge you to examine your retirement plan and ask yourself- is there something else I should add that’s important to my life?

RESOURCES

BOOK - The Soul of Wealth by Dan Crosby
BOOK - The Top 5 Regrets of the Dying by Bronnie Ware
BOOK - Die with Nothing by Bill Perkins
Rock Retirement Club

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Replay: My Experience Moving to a Retirement Community Jul 16, 2025

Show notes

In this episode, we explore the journey of retirement through the eyes of Brad, a member of the Rock Retirement Club. Brad shares his experience of moving to The Villages in Florida, detailing his decision-making process, the community's offerings, and how it has transformed his retirement lifestyle. Join us as we uncover valuable insights and tips for anyone considering retirement living, all while enjoying the vibrant atmosphere of this unique community.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

A MINI CASE STUDY

[01:30] Roger introduces Brad and asks how he discovered The Villages Retirement Community in Florida.
[09:30] Roger asks Brad what led them to explore 55+ communities.
[11:35] Brad explains how The Villages community is organized.
[19:14] Roger asks Brad what advice he would give to someone exploring places to retire.

TODAY’S SMART SPRINT SEGMENT

[22:09] In the next seven days, think about where you are going to live in retirement.

RESOURCES

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Replay: The State of Retirement Planning with Michael Kitces Jul 09, 2025

Show notes

All of July we will be replaying some of our popular past episodes. In this episode, we engage with retirement planning expert Michael Kitces as we explore the evolving landscape of retirement planning. Discover the importance of flexibility in retirement spending and how to select the right retirement planner for your needs. We also discuss the implications of dying with too much money and the critical questions you should ask when interviewing potential advisors. Tune in for insights that will empower you to not just survive, but truly rock your retirement!

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(0:00) The key to finding a retirement planner is to find someone that puts YOU and not your money in the center of everything.
(00:45) Today we have a replay of last year's interview with Michael Kitces.

INTERVIEW WITH MICHAEL KITCES

(02:11) Roger introduces Michael Kitces and chats about flexibility.
(13:30) Michael says as a professional, he does not want to have a client fail on his watch.
(19:21) Roger says the quote that comes to mind when he thinks about retirement planning is: “You’re never going to be exonerated from uncertainty, pain, or the need to do work” Stutz
(24:00) Most people understand that change is to be expected.
(29:05) Michael talks about risk tolerance.
(32:55) Michael reflects on the question “How do we help clients actually make better decisions?”
(33:51) Tips on how to choose a retirement planner.

SMART SPRINT

(45:55) In the next seven days, evaluate the quality of your process for making decisions in retirement.

RESOURCES

BOOK - Die with Zero by Bill Perkins
BOOK - It’s Not Complicated by Rick Nason
Kitces.com
BOOK - Rock Retirement by Roger Whitney
Roger’s Retirement Learning Center

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Replay: How to Retire with Christine Benz Jul 02, 2025

Show notes

All July long, we’re featuring a special replay series of standout episodes—and this week is no exception.

Join us for a special episode as we welcome Christine Benz to discuss her book, "How to Retire." In a captivating conversation in the Rock Retirement Club, we dive into topics like long-term care, the 4% rule, investing strategies, and simplification. Featuring insights from Fritz Gilbert, a member of the club and contributor to Christine's book, this episode offers a holistic view of retirement planning. Discover how to balance financial and non-financial aspects for a fulfilling retirement journey.

*Episode Originally Aired December 4, 2024*

OUTLINE OF THIS EPISODE OF RETIREMENT ANSWER MAN

(00:55) We are going to play some past impactful episodes for the whole month of July

INTERVIEW WITH CHRISTINE BENZ

(01:28) Today we start off the month with a replay of our interview with Christine Benz.
(03:17) Roger asks about the goal for the readers of this book.
(04:48) Christine: The goal was to cover retirement in a really holistic way and include as much non-financial as financial information on retirement planning.
(06:10) Roger thinks the interview style of the book helped make it more approachable.
(08:13) Roger asks Christine about any big, unexpected insights that came up when she was writing her book.
(11:12) Fritz Gilbert says I give Christine serious kudos for the approach she took and the amount of homework she did.
(12:35) Christine tells Fritz that she loves his methodical approach to dealing with the years leading up to retirement.
(14:16) Marla asks Christine if she would change anything if she was writing this book today to accommodate the 2024 election results and also asks about managing portfolios on Morningstar.
(18:15) Roger says when it comes to portfolio construction, it's easy to overcomplicate things
(21:14) Larry asks Christine what challenges her or confounds her most about her own retirement planning.
(23:35) Larry asks “Are you concerned that we may not find people to provide long term care?”
(31:08) Kevin Lyles asks Christine about asset allocation in retirement.
(37:55) Laura asks: When talking about high quality bond portfolios, do bond funds work?
(42:00) Roger asks about indexes and broad diversification.
(44:37) Roger says someone had a comment related to some of the research on small cap value and asks Christine her view on having a more diversified small cap value tilt?
(48:19) Eric asks “what is the argument for using TIPS (Treasury Inflation-Protected Securities) for retirees?”
(51:28) Roger asks Fritz if he has been simplifying his portfolio or working more on optimization since retiring in 2018.
(53:52) Roger says the optimization part of retirement sometimes dominates the conversation.
(54:44) Roger asks Christine: Have you found in your own life a balance between making sure you don’t get too complicated in investments?
(57:55) Brianna asks Christine what question she has been reflecting on after the 20 interviews?
(58:45) Christine she’s been thinking more about whether the concept of retirement is flawed.

BONUS

(01:01:26) Roger reads an excerpt from his grandfather's WWII journal

Resources Mentioned In This Episode

Wade Pfau

Morningstar

The Retirement Manifest- Fritz Gilbert

Daughterhood.org

Christine Benz

Six Shot Saturday

BOOKS

How to Retire: 20 Lessons for a Happy, Successful, and Wealthy Retirement - Christine Benz

Being Mortal: Medicine and What Matters in the End - Atul Gawande

Keys to a Successful Retirement: Staying Happy, Active, and Productive in Your Retired Years - Fritz Gilbert

Rock Retirement: A Simple Guide to Help You Take Control and Be More Optimistic About the Future - Roger Whitney

I Just Lost My Job. Can I Retire Now? Jun 25, 2025

Show notes

💬 Show Notes

This week on the Retirement Answer Man show, we kick things off with a couple of Rockin’ Retirement in the Wild stories from listeners living out their retirement dreams. Then we dive into a mini case study from a listener recently laid off who’s wondering if early retirement is on the table, we’ll walk through the numbers and stress test his plan. We wrap up our month of travel talk with a fun chat with Chris and Cathy about their retirement adventures and how they’re making the most of their freedom to explore.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) In this episode, we wrap up our travel reflections and explore a listener's question about the pros and cons of retiring at age 59.
(01:40) Looking ahead, July will feature 'Best of' episodes of the Retirement Answer Man podcast and August will focus on listener questions.

ROCKIN’ RETIREMENT IN THE WILD

(02:50) Rock Retirement Club member, Pete, has a podcast called Retiring with Enough and that podcast just hit episode 150.
(04:04) Listener, Adrianne, sent in a letter about rocking retirement.

LISTENER CASE STUDY

(04:45) An anonymous listener reached out to share that he’s considering early retirement after a job loss caused by the downturn in the automotive industry. Today, we explore whether he can make it work.
(09:20) A breakdown of the listener’s financial situation.
(13:35) We have to make some assumptions about investment and will use software to simulate different scenarios.
(17:00) Let’s look at the results- a feasible plan is not necessarily resilient.
(19:40) Let’s do some basic stress testing to see how your plan holds up when life throws curveballs.

TRAVEL STORIES WITH CHRIS AND CATHY

(24:52) Two recent retirees, Chris and Cathy, have focused on domestic travel now that work is out of the way.
(29:10) Roger: What was one moment that stood out from your entire trip that stands out for each of you?
(31:45) Roger: Do you two talk when you're on road trips or do you audiobook or something?
(32:23) Chris and Cathy said they retired together and knew they wanted to go back to Jersey.
(33:21) Roger: How did you adjust to being together 24/7?
(34:55) Chris and Cathy discuss how they will approach travel in retirement.
(36:17) Roger: Over a twelve month period, what percentage of time do you travel? And what is the pull to travel so much?
(39:36) Roger: Do you think this three months a year travel cycle is a season or do you think this is a new identity as explorers?
(42:05) Roger: What tips or suggestions would you give to others who have never traveled internationally or have never planned a big road trip?
(46:55) Roger: What is it internally that travel you feel adds to your life?

SMART SPRINT

(48:19) In the next 7 days, confirm that you have at least two years of safe assets, cash or short-term reserves, to cover your lifestyle expenses not covered by income. Even if your plan looks feasible on paper, test its resiliency. Would it hold up if the market took a hit tomorrow?

BONUS

(48:55) Now that we’ve finished my grandfather’s journal, to end the show I will share things I’m geeking out on. Today: electric bikes.

REFERENCES

TRAVEL WEBSITES

Free Range Fun Hogs- Travel Blog

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How to Quality Check Your Retirement Plan Jun 18, 2025

Show notes

💬 Show Notes

In this episode, we tackle the intricacies of retirement planning and the importance of trusting your financial projections. Join us as we explore the concept of 'productive paranoia' and how it can help you avoid costly errors in your retirement strategy. We'll also hear a heartfelt travel story from Scott, who shares how he embraced international travel after a significant life change. Don't miss this enlightening discussion that will empower you to take charge of your retirement journey!

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) This show is dedicated to helping you have the confidence to rock retirement.
(01:15) How do you have confidence in your retirement plan?
(04:44) How do you quality check your plan?
(05:07) Let’s start by talking about the concept of productive paranoia from Jim Collins’ Great by Choice—a mindset of staying hyper-aware, building buffers, and zooming out for perspective to strengthen your retirement plan even when things seem to be going well.
(07:09) Quality checking a retirement plan means making sure the inputs and results align with your goals.
(08:33) What are the most common unforced errors?
(12:21) What are some of the obstacles to quality checking your plan?
(13:30) How do we quality check a retirement plan using metacognition?
(19:30) What is the benefit of reading your goals out loud?
(22:45) Another tactic is running your plan through another system.

INTERVIEW WITH SCOTT

(24:40) Roger continues talking about traveling in retirement.
(26:20) Roger reads an email from his client Larry, an avid RV traveler.
(28:30) Roger introduces Scott for a conversation about international travel.
(34:30) Scott shares thoughts about both solo and group travel.
(39:30) Scott talks about traveling after his wife of 30 years passed away.
(41:25) Some people feel intimidated being the third wheel even when they're invited
(43:50) Roger says he is really interested in the micro communities of people who are comfortable enough to travel together.
(47:55) Roger asks Scott what advice he would give to people to embrace single traveling.
(50:30) Roger reflects on how we often overlook the beauty of our own surroundings and asks Scott what deeper meaning travel holds for him in retirement.

SMART SPRINT