Retirement Answer Man

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Roger Whitney, CFP®, CIMA®, RMA, CPWA®

622 episodes

1 day ago

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 softer side of retirement. It will teach you how to retire with confidence. Two-time PLUTUS winner for best retirement podcast / blog and the 2019 winner for best financial planner blog. This retirement podcast covers how to create a paycheck, medicare, healthcare, Social Security, tax management in retirement as well as retirement travel and other non-financial issues you'll need to address to rock retirement. Retirement isn’t an age OR a financial number. It’s finding that balance between living well today and feeling confident about your retirement. It’s about gaining more freedom to pursue the life you want. Join the rock retirement community at www.rogerwhitney.com

All content for Retirement Answer Man is the property of Roger Whitney, CFP®, CIMA®, RMA, CPWA® and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

Episodes (20/622)

Retirement Answer Man

The 10 R's for a Joyful Retirement with Cesar Aguirre

💬 SHOW NOTES

In this episode, Roger Whitney explores the art of retirement goal setting with his signature blend of practical advice and thoughtful reflection. He sits down with Cesar Aguirre, who shares how leaving a corporate career led to a purposeful and fulfilling retirement, the evolution of his book, and the importance of aligning goals with personal values rather than just chasing big achievements. Roger also addresses listener questions on planning, discretionary spending, and shifting mindsets around money, offering actionable insights to help create a retirement that’s intentional, joyful, and aligned with personal values.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) This show is dedicated to helping you not just survive retirement, but rock it
(01:07) The cost-of-living adjustment for Social Security was announced.

ROCKIN’ RETIREMENT IN THE WILD WITH CESAR AGUIRRE

(02:05) Roger talks with Cesar about his book and how he is rockin’ retirement.
(02:41) Roger introduces Cesar Aguirre, author of Retirement with Purpose: The 10 R's for a Joyful Retirement.
(05:55) At 65, Cesar realized many people approached retirement without a plan, inspiring him to document his process so others could find structure and clarity in their own journey.
(08:35) The pandemic slowed Caesar’s busy career, prompting him to shift from focusing on leaving work to discovering what he was retiring to.
(11:35) Caesar shares how a five-year assignment abroad led to a permanent move to the U.S. in the early ’90s, marking a pivotal shift in his life and career.
(12:25) Caesar reflects on cultural views of retirement, blending Mexico’s family-centered “jubilación” with the U.S. ideal of independence to create a more balanced, proactive approach to this new season of life.
(14:51) There are 10 R’s in the book, starting with Review.
(17:25) Roger asks Cesar how to answer the question, “What do I want?”
(20:17) Caesar explains that creating his book with a service, not business, purpose removed pressure, letting him focus on making it useful, reach a broader audience, and now develop a Spanish edition.
(21:56) Caesar encourages newly retired listeners to create structure, revisit plans, and embrace retirement as a journey with purpose.

LISTENER QUESTIONS

(24:18) In an audio question, Gary, who will retire in 2026, shares how managing “old” retirement savings feels different from spending a paycheck and asks for guidance on navigating this shift in mindset.
(33:56) A listener, who chose to remain anonymous, asks how to distinguish between the essentials of a “base great life” and the discretionary spending that falls into the “wants” category.’
(35:55) A listener praised Roger’s shift from chasing big goals to focusing on values and creating conditions to explore life personally and meaningfully.
(38:20) Dennis asks about the Retirement Podcast Network, and Roger explains that while it’s still active, he and Taylor Schulte decided to prioritize other projects and let this one remain on the back burner.

SMART SPRINT

(40:01) In the next seven days, reflect on the phrase, “you can’t take it with you.”

BONUS

(41:03) In this wrap-up, Roger addresses listener feedback from a past episode on organic food.

REFERENCES

1 week ago

46 minutes

Retirement Answer Man

Retirement Goal Case Study

💬 Show Notes

In this episode, Roger Whitney wraps up our four-week series on smarter retirement goal setting. He dives into the ideas of buoyancy and Maslow’s hierarchy of needs, showing how they play a role in planning a retirement that actually works for you. Using two relatable avatars – the Grinder and the Dreamer – Roger shares practical, real-world strategies to help navigate the twists and turns of retirement planning. Tune in for insights that will help you make your retirement not just secure, but truly rock!

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) This is the last of a four-week series on better retirement goal setting

PRACTICAL PLANNING SEGMENT

(01:58) The first concept for today is the concept of buoyancy.
(04:50) Roger talks about Maslow’s hierarchy of needs.
(07:50) A look inside the Advice Lab Roger runs with his work team.

AVATAR CASE STUDY- THE GRINDER AND THE DREAMER

(10:10) Introduction of two avatars created by the team — the Grinder and the Dreamer.
(10:58) First, Roger breaks down the Grinder.
(14:27) What are triggers that might help a grinder reevaluate retirement planning?
(16:57) What do Grinders crave?
(18:50) How do you navigate as a Grinder or as someone in a relationship with a Grinder?
(21:50) The pillars of retirement are a helpful framework when it comes to Grinders.
(27:00) Next, Roger breaks down the avatar of the Dreamer.
(29:30) What are the triggers that a Dreamer faces?
(32:30) Roger breaks down the retirement pillars for Dreamers.
(37:00) Roger reflects on how his partnership with Tanya mirrors the Dreamer and Grinder archetypes, showing how balancing vision and execution can lead to better communication and more effective retirement goals.

LISTENER QUESTIONS

(38:14) You can submit questions at AskRoger.me
(38:40) Barbara shares thoughts on a recent episode.
(42:04) Roger shares an audio clip from Tom.
(44:27) One listener shares that drawing down the accounts is a mental challenge.
(45:49) Rod asks what portion of a 71-year-old’s $5–6M retirement portfolio could go into low-risk private credit.

SMART SPRINT

(48:38) In the next seven days, reflect on where you fall between Dreamer and Grinder and consider that when setting or refreshing your retirement goals, so you can better balance your approach.

REFERENCES

2 weeks ago

51 minutes

Retirement Answer Man

How to Navigate Goals as Life Unfolds

💬 Show Notes

In this episode, we continue our four-week series on better retirement goal setting with Roger Whitney. This week, we delve into the dynamics of navigating retirement goals as life unfolds and the concept of opportunity cost. In the second half, Roger has enlightening discussion with Dr. Bobby, where he explores the pros and cons of organic food and its relevance to our health and finances. Discover how to align your retirement goals with your evolving self and make informed choices about your lifestyle. Tune in for practical insights that can help you rock your retirement!

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) This is week three of a four-week series on better retirement goal setting, plus Roger chats with Dr. Bobby about the cost-benefit of buying organic.
(02:55) Roger encourages registration for his next live meetup at livewithroger.com.

PRACTICAL PLANNING SEGMENT

(03:40) Roger reflects on setting goals that will align with the current version of you and also who you are becoming.
(05:44) Roger explores how goals evolve over time, the barriers that make it hard to recognize and adapt to those changes, and a simple protocol to help ensure your goals stay aligned with what matters most.
(07:15) Priorities shift over time as what once mattered may lose importance and new values emerge.
(10:27) Life events like health changes, family needs, or loss can rapidly reorder goals.
(12:41) Common barriers to noticing change include inattention, sunk cost fallacy, and social pressure.
(16:01) Regular reflection helps keep goals aligned with what’s truly important.
(20:05) Review spending regularly to ensure it reflects your current priorities.

CHAT WITH DR. BOBBY

(23:20) Roger introduces Dr. Bobby to talk about organic foods.
(25:52) What are organic foods?
(29:03) Dr. Bobby breaks down the cost of organic food.
(33:00) What are the benefits of organic food? Is it worth the cost?
(38:15) Roger acknowledges that some people feel strongly about buying organic as a way to take control of their health.
(40:57) 80% of the US population doesn't get enough fruits and vegetables.
(42:16) Dr. Bobby breaks down the ROI on buying organic.
(48:23) If you do buy organic, which products should you buy?
(52:20) Bobby talks about his podcast and the power of positive thinking when dealing with illness.

SMART SPRINT

(53:13) In the next seven days, pull out your retirement plan of record and review your goals.

REFERENCES

3 weeks ago

55 minutes

Retirement Answer Man

Building Agile Retirement Goals

In this episode, Roger Whitney continues his four-week series on retirement goal setting, focusing on the importance of building agile retirement goals. He emphasizes creating the right conditions for discovering what you truly want in retirement, rather than fixating on specific desires. Roger shares insights on self-discovery, the anatomy of goals, and the significance of establishing a solid foundation for a fulfilling retirement. Tune in to learn how to navigate your retirement journey with confidence and purpose!

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) This week Roger talks about building agile retirement goals.

PRACTICAL PLANNING SEGMENT

(03:10) The intent is to build goals that are more meaningful to you so you can rock retirement.
(07:00) How do you set goals that are meaningful to you in an agile way?
(07:39) You want to start with self-discovery and establishing or revisiting your values.
(09:53) Focus on creating conditions to explore your values and build a life where fulfillment naturally follows.
(13:43) You have to experiment to determine what is right for you.
(18:30) Roger talks about the anatomy of a goal, specifically low stakes goals that maximize optionality in retirement planning.
(21:08) Roger talks about high stakes goals.
(25:04) Low-stakes goals help you experiment, make confident decisions, and discover what truly supports a fulfilling retirement.

LISTENER QUESTIONS

(27:30) Roger answers Melissa’s questions about rolling over an IRA without penalty and whether to trust a flat-fee fiduciary firm that offers to manage her accounts.
(33:06) Greg asks Roger to revisit healthcare before Medicare.
(34:17) Rob asks about deferring Social Security to age 70 and whether he still receives COLA increases in addition to the 8% delayed retirement credit.
(36:03) Chris asks about using only a total world stock and bond index for his portfolio.
(40:20) Roger advises keeping a local contingency fund so you always have accessible cash and don’t feel “cash poor.”

SMART SPRINT

(43:20) Go back to your retirement goals and the plan you’ve put together. Look at them through the lens of our recent discussion

RESOURCES

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1 month ago

45 minutes

Retirement Answer Man

Setting Retirement Goals: The Paradox of Knowing What You Want

💬 Show Notes

In this episode, Roger Whitney kicks off a four-week series on retirement goal setting, tackling the paradox of knowing what you want in retirement. He discusses the challenges of articulating desires for a life stage that many have never experienced, emphasizing the importance of not oversimplifying retirement goals. Tune in to explore how to set the right conditions for a fulfilling retirement and avoid the pitfalls of external scripts and societal expectations.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

PRACTICAL PLANNING

(01:32) We are starting a four week series on retirement goal setting.
(02:44) Why “What do you want to spend in retirement?” isn’t the right question.
(05:54) Next week, we'll talk about how to be more nuanced when setting retirement goals.
(09:40) The problem with following other people’s scripts
(13:14) The problem of getting too detailed

LISTENER QUESTIONS

(16:36) Am I required to keep an Inherited IRA separate from my other IRA's or can it be combined with an existing IRA for simplicity?
(19:11) Richard wants to noodle on the retirement distribution order.
(23:40) I’m 3-5 years from retirement. Is now the right time to join Rock Retirement Club?
(26:29) Estate preparation hint from Jane on the three passwords a family needs

SMART SPRINT

(28:19) In the next seven days, revisit your retirement goals.

EXTRA

(29:11) Shauna and I are celebrating our 35th wedding anniversary this week!

REFERENCES

1 month ago

32 minutes

Retirement Answer Man

Simple Isn't Easy: Carl Richards on Life and Retirement

SHOW NOTES

In this episode, Roger Whitney sits down with Carl Richards, a financial advisor-turned-artist, to talk about keeping retirement planning simple and meaningful. They dive into the idea of “elegant simplicity,” the importance of knowing your goals, and making decisions that actually work for you. Plus, hear inspiring stories from club members to help you rock your retirement!

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) The ultimate goal in building a retirement plan of record is elegant simplicity

CHAT WITH CARL RICHARDS

(02:00) Roger introduces Carl Richards.
(03:50) Carl started sketching to help explain complex financial concepts.
(07:33) Roger asks Carl about his new book coming out in October.
(11:00) Roger and Carl talk about the differences between simplistic and elegant simplicity in retirement planning.
(17:55) How do you decide when you have enough information to make a decision?
(22:19) There are many different types of decisions that need to be made- Decisions where you need a lot of research versus decisions where you already have all of the information.
(26:58) Writing makes decisions tangible versus rehashing them in your brain
(28:19) Carl talks about mimetic desire and figuring out what it is that you really want.
(39:45) Carl says he loves the idea of experiment design.
(41:40) Carl talks about living a life of meaning.
(46:50) There is a deep source of identity and purpose that comes from work. When you remove that, what do you replace it with?
(52:58) Carl talks about competing values.
(55:00) Roger talks about the Retirement Life Lab in the Rock Retirement Club

SMART SPRINT

(56:43) In the next seven days, review your retirement plan and look for ways to simplify it so it’s easier to manage.

CONCLUSION

(57:37) Roger says that what stuck out to him from the conversation is how difficult it can be to truly know what we want and how easy it is to just grab someone else’s goals, when what we really need is to slow down and take the time to define our own so we don’t end up living a life that doesn’t fit us.

REFERENCES

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1 month ago

59 minutes

Retirement Answer Man

The Difference Between an IRS Late Payment Penalty and Interest

SHOW NOTES

In this episode, we tackle the often-overlooked topic of taxes in retirement with expert Erin Coe, an enrolled agent. Discover how to avoid unexpected penalties and interest on your IRA distributions and Roth conversions. We also share an inspiring retirement success story from Lottie, reminding us of the importance of clarity and simplicity in planning. Tune in for practical advice that will help you rock your retirement!

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) Today Erin Coe joins Roger to talk through penalties and interest during retirement, what those things are.

ROCKIN’ RETIREMENT IN THE WILD

(01:30) Lottie says she got caught up in ideas about the perfect retirement and it was getting in her way.

PRACTICAL PLANNING SEGMENT WITH ERIN COE

(03:31) Today we're going to talk about penalties and interest when it comes to taxes.
(04:52) Erin explains the difference between a tax penalty and interest.
(11:14) Roger asked Erin how to calculate an estimated quarterly tax if not doing safe harbor?
(13:55) Erin shares her tips on tax returns.
(16:08) Being prepared is always better than being taken by surprise when it comes to taxes.

LISTENER QUESTIONS

(16:40) Roger makes a correction on a past statement.
(17:25) Jeff asks a question about the pie-cake explainer video.
(20:30) Dave asks a question about helping his elderly mother with her finances.
(26:11) Robert asks about getting two mortgages near retirement.

SMART SPRINT

(32:15) Over the next seven days, download the 1040 form and review how it applies to your retirement income. Decide whether you’ll handle taxes through estimated payments, safe harbor payments, or automatic withholdings from distributions.

REFERENCES

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1 month ago

35 minutes

Retirement Answer Man

How to Read Your Social Security Statement

💬 SHOW NOTES

In this episode, we focus on empowering you to navigate retirement with confidence. We break down the process of reading a Social Security statement, examining each section and its significance. Additionally, we tackle listener questions regarding retirement strategies, second mortgages, and Roth conversions. Join us for practical insights that will help you make informed decisions as you approach this new chapter in life.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) Today on the show we are going to walk through how to read a social security statement.
(01:10) Roger talks about doing extensive blood work every year and the similarities between the protocol of blood tests and retirement planning.

PRACTICAL PLANNING SEGMENT

(09:52) Sign up for the Noodle to watch a video of Roger walking through the Social Security statement.
(10:30) Roger breaks down the Social Security statement section by section- go to SSA.gov to get a pdf version of your statement.
(17:07) Roger reads through a few of the Important Things to Know bullet points on page two of the statement.

LISTENER QUESTIONS

(21:21) Jeff asks if there is any difference in retirement strategy if he decides to delay retirement until age 70.
(25:22) Mary says she is going through a divorce at age 63 and recently started listening to the podcast to educate herself on retirement and asks for advice for finding a retirement planner.
(29:36) Julie says her husband is looking at sudden retirement at age 59 ½. She wants to know if there are any episodes or resources Roger can direct him to to get a great overview of retirement.
(32:48) Joy has a question about ROTH conversions.

SMART SPRINT

(34:18) In the next seven days, make sure you have your most recent Social Security statement.

REFERENCES

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1 month ago

38 minutes

Retirement Answer Man

Don't Get Cute with Your Retirement Investments

💬 Show Notes

In this episode of the Retirement Answer Man, Roger Whitney sits down with Peter Lazaroff, Chief Investment Officer at Plancorp, for a thoughtful conversation on the power of simplicity in retirement planning. Together, they unpack the common traps of overcomplicating investments and the cognitive biases that often lead us astray. Peter also offers valuable insights into private equity and other complex investment strategies—highlighting when they might help, and when they might hurt. Don’t miss this episode if you're looking to build a retirement plan rooted in clarity, confidence, and peace of mind.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) Today Roger chats with Peter Lazaroff about bringing simplicity to retirement planning strategies.
(02:44) We tend to overcomplicate everything when it comes to retirement planning.
(04:09) Complexity makes us think something is better or more sophisticated.
(05:35) “Anything one needs to market heavily is either an inferior product or an evil one.”- Nassim Taleb

ROCKIN’ RETIREMENT IN THE WILD

(06:22) Todd shares reflections on why he travels in retirement.

INTERVIEW WITH PETER LAZAROFF

(10:16) Think of your assets that you need to rock retirement in their own bucket, if you have excess- put it in its own bucket.
(11:05) Complex investments are just active managers in a different wrapper.
(11:45) Peter Lazaroff joins Roger to discuss retirement investing and private equity.
(12:25) Peter discusses his books and announces that he has a new one coming out in 2026.
(15:00) The core intent of retirement planning is to have core confidence that you can live the life you want now, but also when you're ninety.
(15:51) Ultimately the goal in retirement planning is elegant simplicity.
(20:00) Peter reflects on the business of investing.
(23:02) Investing creates an illusion of control.
(26:38) Peter discusses the benefit of simplicity and how it helps living heirs when it is time to settle an estate.
(28:33) Roger chats about an executive order paving the way for private equity to become part of 401ks.
(30:08) Peter talks about the steps of the probabilistic decision framework.
(35:48) From 2020 to present, private equity has not added return over public equity.
(38:30) If the yield is high and you can’t find the risk, it doesn’t mean it's not there.
(42:08) Private investments are not inherently good or bad, but they are not necessary and can add complications.
(42:50) Peter shares an example of complexity that he would be more welcome to.
(47:25) If you don’t believe in traditional active management- you should be out on private investments.

SMART SPRINT

(48:00) In the next seven days, choose one area—retirement planning, investments, or any aspect of life you want to improve. Before adding anything new, ask: What can I remove or simplify first?

REFERENCES

BOOKS

Scarcity Brain- Michael Easter
Antifragile: Things That Gain from Disorder- Nassim Nicholas Taleb
Making Money Simple: The Complete Guide to Getting Your Financial House in Order and Keeping It That Way Forever- Peter Lazaroff

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2 months ago

49 minutes

Retirement Answer Man

Navigating Medicare in 2025

💬 Show Notes

In this episode, we explore the intricacies of navigating Medicare in 2025 with Medicare expert Danielle Roberts from Boomer Benefits. Discover the recent changes in Medicare Advantage and Part D plans that could impact your healthcare decisions. We also share inspiring stories of individuals embracing life in retirement and discuss the importance of reviewing your Medicare options annually. Tune in for valuable insights and practical tips to ensure you make the best choices for your health coverage!

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) Today on the show, we are going to explore how to navigate Medicare in 2025

ROCKIN’ RETIREMENT IN THE WILD

(01:30) Roger shares a story from a listener who was “jolted” into action.
(03:00) Jamie says she plays mahjong with a group of retired ladies and started a book club.

PRACTICAL PLANNING SEGMENT

(04:55) Roger introduces Danielle with Boomer Benefits to chat about Medicare
(05:25) What is the state of Medicare right now?
(10:25) How important is it to pay attention to the annual notice of change?
(12:15) What are the key things to pay attention to when they get these notices?
(17:41) Medicare Advantage is heavily marketed and people have strong opinions about Medicare Advantage versus original Medicare.
(25:05) Roger talks about the company- Boomer Benefits.
(26:40) What is the service level of Boomer Benefits? What kind of support do you get after you enroll?

LISTENER QUESTIONS

(31:26) Visit Askroger.me to submit questions.
(31:46) Terri asks for reputable sources for buying health insurance after retirement.
(35:40) Beth asks a question about the Affordable Care Act and putting contributions into an HSA account without an employer deduction.

SMART SPRINT

(38:36) In the next seven days, put a date on your calendar for October to review your healthcare coverage

BONUS

(39:30) Roger shares about what he has been doing in Colorado for the last three weeks.

REFERENCES

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2 months ago

41 minutes

Retirement Answer Man

Should I Do a "Free" Retirement Analysis?

💬 SHOW NOTES

In this episode, we explore the implications of the saying 'nothing is for free' in the context of retirement planning. Join Roger Whitney, a seasoned retirement planner, as he shares a heartfelt story from a listener, David, who exemplifies the spirit of 'rocking retirement.' Additionally, Roger tackles the critical question of whether to accept a free retirement analysis from brokers, discussing the potential costs and consequences involved. Tune in for insightful advice on navigating your retirement journey with confidence!

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) Roger Whitney: This podcast is dedicated to helping you rock your retirement

ROCKIN’ RETIREMENT IN THE WILD

(01:06) David emailed in saying he and his wife are leaning into rocking retirement.

PRACTICAL PLANNING SEGMENT

(03:00) Our title question today came from Phil- he wants to know if it is worth going through free retirement analysis.
(07:15) What are some of the cautions or things you want to understand about free retirement analysis?

LISTENER QUESTIONS

(13:37) Doug shares feedback about my Smart Sprint on being present.
(15:11) Rick says he'd like to simplify portfolio.
(19:30) Cliff sent in a question about stress testing your retirement plan.
(27:09) Dave has a question about moving a 401k to an independent advisor upon retirement.
(32:55) Bob asks which retirement plan should you use first: Social Security or savings.

SMART SPRINT

(38:10) In the next seven days, pay attention to “free” offers—whether it’s a retirement analysis, discount, or credit card perk—and notice the hidden costs or unintended consequences that may come with them.

REFERENCES

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2 months ago

40 minutes

Retirement Answer Man

Direct Indexing vs. Mutual Fund or ETFs

💬 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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2 months ago

45 minutes

Retirement Answer Man

Elder Care Options for Singles

💬 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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3 months ago

51 minutes

Retirement Answer Man

How to Choose a Retirement Coach

💬 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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3 months ago

36 minutes

Retirement Answer Man

Replay: How to Manage Your Scarcity Brain

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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3 months ago

35 minutes

Retirement Answer Man

Replay: Overcoming Frugality in Retirement with Dr. Dan Crosby

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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3 months ago

28 minutes

Retirement Answer Man

Replay: My Experience Moving to a Retirement Community

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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4 months ago

24 minutes

Retirement Answer Man

Replay: The State of Retirement Planning with Michael Kitces

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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4 months ago

48 minutes

Retirement Answer Man

Replay: How to Retire with Christine Benz

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

4 months ago

1 hour 2 minutes

Retirement Answer Man

I Just Lost My Job. Can I Retire Now?

💬 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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4 months ago

51 minutes