Retirement Answer Man

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

631 episodes

3 days 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 (20/631)

Retirement Answer Man

Retire on FIRE- Rocking an Early Retirement: Meet Henry and Lucy

As the new year begins, Roger Whitney launches a new Retirement Plan Live case study, introducing Henry and Lucy, a couple in their mid-40s pursuing Financial Independence and Retire Early (FIRE). Roger revisits the 4% rule as a planning heuristic, explains when it can be helpful, and sets the stage for a live community analysis later this month. The episode closes with a Smart Sprint focused on updating your net worth statement and a listener’s word for 2026.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) This show is dedicated to helping you not just survive retirement, but to have the confidence to lean in and rock it.
(00:30) Roger introduces a new Retirement Plan Live case study series and previews the upcoming live community meetup on January 29.

RETIREMENT TOOLKIT

(01:58) Roger revisits the 4% rule, explaining what it is, where it came from, and why it is often misunderstood.
(04:55) Roger talks about the 25x rule commonly used in the FIRE community.
(06:38) He discusses the drawbacks of using these heuristics and who they are best used for.
(11:05) Roger shares how the 4% rule can help overfunded retirees move beyond scarcity and spend more intentionally.
(13:55) A breakdown of FIRE- Financial Independence, Retire Early.

RETIREMENT PLAN LIVE

(17:41) Roger introduces Henry and Lucy.
(20:01) They share how they discovered FIRE and what it means to them.
(23:10) Lucy reflects on spending habits, saving, and budgeting
(25:30) Henry talks about the start of their relationship.
(28:12) Henry and Lucy discuss how saving impacted their lifestyle.
(31:20) They discuss what drives their desire to retire early.
(32:55) Roger reflects on his first impression of the FIRE Movement.
(34:15) What are the obstacles of retiring so early?
(38:45) Roger talks about the difference between a complicated problem and a complex problem.
(40:35) Roger asks if they think about landmines that could pop up with such a long retirement.
(43:57) Roger invites listeners further along the retirement path to share perspective and advice for their 40-something selves.

SMART SPRINT

(45:20) Roger encourages listeners to update their end-of-year net worth statement and identify trends for the year ahead.

WORD OF THE YEAR

(47:31) Listener Lindsay shares her word for 2026: Listen, and Roger reflects on the value of deep listening.

REFERENCES

3 days ago

49 minutes

Retirement Answer Man

Year-End Planning: Estimated Tax Payments

As the year comes to a close, Roger Whitney reflects on the power of words, walks through an important year-end tax planning reminder for retirees, shares listener stories and perspectives, and invites listeners to choose a guiding word for 2026 as a way to approach retirement with greater intention and clarity.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) This show is dedicated to helping you not just survive retirement, but have the confidence and clarity to lean in and rock it.
(00:45) Roger reflects on slowing down, reclaiming meaning in familiar words, and recommitting to clearing the battlefield as we head into a new year.

RETIREMENT TOOLKIT

(03:22) Roger explains why estimated quarterly tax payments matter in retirement and how they can help prevent unwelcome tax surprises.
(05:44) He outlines safe harbor rules and practical best practices for withholding taxes from Social Security, IRA distributions, and pensions.

RETIREMENT LIFE LAB

(13:33) Roger shares listener responses about corporate words and phrases people are eager to retire when they leave the workforce.

ROCKING RETIREMENT IN THE WILD

(19:33) Mick and Patty share reflections on fitness, travel, and meaning in retirement, including experiences shaped by history and family.

FOCUSING FORWARD: A WORD FOR 2026

(21:10) Roger discusses the practice of choosing a single word to define the coming year and reads listener-submitted words for 2026.
(28:40) Roger reveals his own word for 2026.

SMART SPRINT

(34:07) Roger encourages listeners to reflect on the season they are entering and consider choosing a word to help guide decisions in 2026.

CLOSING THOUGHTS

(34:55) Roger responds to listener feedback on charitable giving and enjoying retirement, emphasizing balance, generosity, and intentional living as the year ends.

REFERENCES

1 week ago

37 minutes

Retirement Answer Man

Year-End Planning: The Basics of Charitable Giving

In this Christmas Eve episode, Roger Whitney explores the basics of charitable giving as part of an intentional retirement plan, with a timely focus on year-end decisions. He explains how charitable deductions work, common planning mistakes to avoid, and why generosity is most effective when paired with a resilient financial plan. Roger also shares a Rocking Retirement in the Wild story from a listener who is actively living a purpose-filled retirement, reflects on the corporate language we can leave behind when we retire, and answers listener questions on retirement readiness, gifting inheritance early, and the risks of relying on high-yield bonds for retirement income. He closes the episode with personal reflections on lessons learned, reminding listeners how to keep retirement simple, resilient, and meaningful while making a positive impact on others.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) This show is dedicated to helping you not just survive retirement, but confidently lean in and rock it.
(00:20) Roger introduces a Christmas Eve episode focused on charitable giving, listener stories, answering questions, and reflecting on intentional retirement living.

RETIREMENT TOOLKIT

(03:45) Roger walks through the basics of charitable giving, including qualified charities, documentation requirements, and how deductions work with standard versus itemized returns.
(07:55) Year-end timing rules for checks, credit cards, stock transfers, and donor-advised funds.

ROCKIN’ RETIREMENT IN THE WILD

(09:30) A listener shares how, at 67, he backpacked 121 miles through Maine’s 100-Mile Wilderness, reconnecting with longtime friends and staying physically engaged in retirement.
(12:28) Roger reflects on why rocking retirement doesn’t have to be impressive—only meaningful to the person living it.

RETIREMENT LIFE LAB

(13:03) Roger explores the idea of “retiring” corporate jargon in retirement and how simplifying language can help us reconnect and speak more human again.
(18:21) Listeners are invited to share the words and phrases they are most looking forward to leaving behind.

LISTENER QUESTIONS

(19:50) Don asks why most people enter retirement with relatively little savings and what that reality means for financial and social stability.
(29:25) A listener asks how to give inheritance before death without triggering taxes.
(33:46) James asks whether using high-yield corporate bonds as the foundation for retirement income is a safe strategy.

SMART SPRINT

(42:08) In the next seven days, Roger challenges listeners to choose a single word for 2026 to serve as a guiding focus for the year ahead.

CLOSING THOUGHTS

(43:59) Roger shares final reflections on the lessons of the episode, emphasizing elegant simplicity, financial resilience, and showing up to help others in meaningful ways.

REFERENCES

2 weeks ago

46 minutes

Retirement Answer Man

Year End Planning: RMD Rules for IRAs & Inherited IRAs

In this episode, Roger Whitney walks listeners through the complexities of inherited IRAs, highlighting the impact of the SECURE Act of 2019 and clarifying the distinctions between eligible and non-eligible designated beneficiaries. He explains how these classifications affect withdrawals and tax planning, making the rules easy to understand. Roger also answers listener questions on topics like retirement team selection and funding health insurance with HSA accounts. Beyond the numbers, he shares practical strategies for creating more meaningful holiday conversations, drawing on real-life examples to show how curiosity and intentionality can help you connect more deeply with the people you care about.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) This show is dedicated to helping you rock retirement.
(00:30) In today’s episode, Roger Whitney covers the rules around inherited IRAs, explores ways to foster deeper and more meaningful conversations during the holidays and beyond, and answers listener questions.

RETIREMENT TOOLKIT

(01:00) Today in the Retirement Toolkit we're going to talk about the rules around inherited IRAs.
(02:40) Differences between eligible and non-eligible designated beneficiaries for inherited IRAs are explained.
(14:32) Roger talks about ROTH IRAs and how they work.

RETIREMENT LIFE LAB

(16:04) Roger explains how approaching conversations with curiosity and intentionality, especially with older family members or those with different interests, can create more meaningful and enriching interactions.

LISTENER QUESTIONS

(25:37) Ira asks what to ask a financial advisor’s team to understand their retirement planning services and team longevity.
(37:02) Mary Jane asks if she can use Health Savings Account funds tax-free to pay for private health insurance premiums before Medicare eligibility.

SMART SPRINT

(38:42) In the next week, approach holiday or New Year’s gatherings with curiosity by asking questions and engaging with people you don’t see often to create more meaningful interactions.

REFERENCES

3 weeks ago

40 minutes

Retirement Answer Man

Year-End Planning: Annual Gifting Rules

In this episode, Roger Whitney, a retirement planner with 30 years of experience, breaks down annual gifting limits and year-end planning. He shares practical strategies for giving that make a real impact and create meaningful experiences for loved ones. Roger also answers listener questions, providing clear guidance to help you navigate your retirement with confidence.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) This podcast is dedicated to helping you rock retirement.
(00:57) Today Roger talks about annual gifting limits.

RETIREMENT TOOLKIT

(01:45) In today’s Retirement Toolkit, Roger explores year-end planning by breaking down the 2025 annual gift exclusion.
(04:05) Roger discusses giving money during your lifetime and shares the reasons why it can be beneficial.
(12:05) Roger shares his observations on giving money, noting that gifts can feel most meaningful when attached to a specific purpose rather than given with expectations.
(14:21) Strategies for impactful gifting are explored, including transferring appreciated assets, paying medical expenses, and covering tuition directly, showing ways to help others while maximizing meaning and efficiency.

LISTENER QUESTIONS

(19:00) Mary shares feedback on qualified charitable distributions (QCDs).
(21:27) Lee describes his “shoulder bonus” strategy to spend excess retirement funds while staying within a safe withdrawal rate.
(30:10) John asks when to switch from a general financial advisor to a retirement planner
(34:19) Rick asks about gifting appreciated stocks to adult children.
(35:17) Steve asks about building a resilient retirement plan at age 80.

SMART SPRINT

(38:13) In the next seven days: Do you want to give? Can you? How much and to whom? Can it have a purpose? Even small gifts can make a big impact.

CLOSING THOUGHTS

(40:00) Giving money can bring profound joy, often the greatest gift is the one you give yourself by helping others.

REFERENCES

1 month ago

41 minutes

Retirement Answer Man

Year-End Planning: Tax-Loss Harvesting

💬 Show Notes

In this episode, Roger Whitney kicks off a month-long series on year-end planning for retirement. He shares insights on tax loss harvesting, a technique that can help you minimize capital gains tax. Listen in as Roger explains the basics of capital gains, the importance of proactive planning, and the potential benefits of offsetting gains with losses. Plus, he introduces a smart sprint action item to help you optimize your tax strategy before the year's end!

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) This podcast is dedicated to helping you rock retirement.
(01:07) Roger shares that he recently finished George Orwell’s 1984, his first in a new hobby of collecting classic authors.

RETIREMENT TOOLKIT

(03:43) Roger breaks down the basics of tax loss harvesting, explaining capital gains, the difference between short-term and long-term gains, and how they impact year-end retirement planning.
(09:17) Roger explains how to implement tax loss harvesting by estimating your realized capital gains, identifying losses in your taxable accounts, selling positions to offset gains, and being mindful of the IRS wash sale rule that prevents repurchasing the same security within 61 days.
(16:50) Using losses in taxable accounts strategically can help reduce capital gains taxes.

ROCKIN’ RETIREMENT IN THE WILD

(18:28) Share your story of rocking retirement at askroger.me to inspire others with your confidence and passion.
(19:30) Mark plans to pivot into business consulting after retiring so he can keep learning, adding value, and connecting with people while enjoying more freedom and purpose.

LISTENER QUESTIONS

(21:54) Richard is preparing for retirement at 67 and asks how he should handle his 401(k) and income to make his plan work best.
(25:00) Kathy asked how a new bill will affect those 65+ with year-end tax planning, and Roger said he’ll provide a checklist to guide Noodle subscribers through the changes.
(25:42) Karen pointed out that annuity payments aren’t inflation-adjusted and emphasized balancing them with other investments.
(30:08) Dan asks: “Where should I keep the cash for living expenses and market downturns?”

SMART SPRINT

(33:59) Smart Sprint: In the next seven days, review your after-tax investment accounts, estimate year-end capital gains or losses, and consider selling positions with unrealized losses to offset gains while avoiding the 31-day wash sale rule.

CLOSING THOUGHTS

(35:18) Over Thanksgiving, Roger continued his childhood tradition of watching the Lions lose, ending up jumping in a pool after a bet with his nephew Graham, a devoted Packers fan.

REFERENCES

1 month ago

36 minutes

Retirement Answer Man

Should I Use My Traditional IRA to Fund My Life or Do Roth Conversions?

💬 Show Notes

In this Thanksgiving Eve episode, Roger Whitney encourages listeners to carry gratitude into everyday life, emphasizing the value of recognizing specific moments and taking “mental snapshots” of what matters. He also addresses common retirement questions, including how to think about traditional versus Roth IRAs and whether to use IRA withdrawals or pursue Roth conversions. It’s a clear, practical discussion to help you reflect and make informed planning decisions.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) This show is dedicated to helping you rock retirement
(00:40) Roger reflects on thankfulness and gratitude.

RETIREMENT TOOLKIT

(08:33) Roger gives a quick refresher on the three main types of accounts used in retirement planning and how each is treated for tax purposes.

LISTENER QUESTIONS

(14:16) Roger walks through how to approach the common dilemma of using a traditional IRA for living expenses versus doing Roth conversions.
(26:49) Dominic asks why qualified charitable distributions can’t be used to fund a donor-advised fund, even though the donation is tax-deductible.
(30:31) BB and Shell ask whether contributing to a Roth versus traditional 403(b) and 457 plans makes sense given their high current tax rate and plans to retire and move to a lower- or no-tax state.

SMART SPRINT

(34:35) This week’s Smart Sprint challenges listeners to make thankfulness meaningful by telling someone specifically why they are grateful for them.

CLOSING THOUGHTS

(35:18) Roger shares his gratitude for listeners and feedback, acknowledges the complexity of retirement planning, and emphasizes his commitment to providing actionable advice while reminding everyone it’s okay not to have all the answers.

REFERENCES

1 month ago

38 minutes

Retirement Answer Man

My Advisor Recommended an Annuity. Should I Buy It?

💬 Show Notes

In this episode, Roger Whitney dives into the essentials of required minimum distributions, explaining the age thresholds, how the amounts are calculated using IRS life expectancy tables, and how to manage multiple IRAs and 401(k)s. He also answers listener questions, including whether a flexible premium deferred income annuity might make sense and how to determine how much you can safely give to loved ones or charity now. Packed with practical advice and actionable insights, this episode helps listeners navigate the rules and strategies that can impact their retirement planning.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) This show is dedicated to helping you have the confidence to rock retirement.

THE RETIREMENT TOOLBOX

(01:18) In this Retirement Toolbox segment, we take a timely look at required minimum distributions—what they are and how they work for the accounts you own.
(03:22) A quick breakdown of the current IRS rules for required minimum distributions, outlining the different start ages based on your birth year.
(05:22) How RMDs are calculated using your year-end balance and IRS life expectancy tables.
(08:30) When should you take your money out, and what happens if you don’t?
(10:48) How to handle RMDs across multiple IRAs and 401(k)s and why long-term planning and account consolidation matter.
(14:00) What are some strategies to minimize or mitigate your future required minimum distributions?

LISTENER QUESTIONS

(15:23) Submit your questions through AskRoger.me, and we’ll help you take a baby step toward a rock-solid retirement.
(15:54) Our title question comes from Rich, who asks if a flexible premium deferred income annuity would be a good idea given his retirement savings, Social Security, pension, and minimal debt.
(27:14) A listener asks how to determine how much they can safely give to loved ones or charity now, rather than leaving it as an inheritance later.

SMART SPRINT

(33:22) In the next seven days, estimate your future RMD—even if it’s 10 years away—assuming your IRA or 401(k) grows at a reasonable rate.

CLOSING THOUGHTS

(34:04) An update on the merger of Tanya Nichols’ and Roger’s advisory firms, with a new unified brand—Retire Agile—coming in 2026 and opportunities for client feedback on branding and design.

REFERENCES

1 month ago

35 minutes

Retirement Answer Man

How Do I Build My Initial Cash Cushion for Retirement?

💬 Show Notes

In this episode, Roger Whitney explores the psychology of loss aversion and how it affects financial decision-making. He introduces the new Retirement Toolbox segment, offering practical, actionable tools to help you strengthen your retirement plan. We also cover the benefits of Qualified Charitable Distributions and answer listener questions on retirement planning and asset allocation. Don’t miss this insightful discussion designed to help you confidently navigate and optimize your retirement!

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

PRACTICAL PLANNING SEGMENT

(01:00) Roger breaks down loss aversion and how it relates to retirement.

THE RETIREMENT TOOLBOX

(04:35) Roger launches a new segment on essential financial tools, starting with the Qualified Charitable Distribution, a timely, tax-smart way to give at year-end.

LISTENER QUESTIONS

(11:53) Wes asks how to build retirement reserves before retirement without triggering higher taxes.
(17:12) Roger responds to John’s critique of the “Process Over Panic” episode, clarifying why a retirement plan should be treated as a living, flexible guide rather than a rigid set of rules.
(22:52) Feedback from David highlights why factoring early losses in Monte Carlo simulations can boost confidence despite slight double-counting.
(26:35) Thoughtful listener disagreements are welcomed as a way to deepen understanding and improve retirement planning insights.
(27:43) Thomas has some questions about getting started with a retirement planner.

SMART SPRINT

(36:07) In the next seven days, anyone within three years of retirement should map out their liquidity and consider reallocating assets to protect against market swings in the early years, avoiding unnecessary risk if funds will be needed soon.

CLOSING THOUGHTS

(37:05) I've been building a personal library of classics, including fiction and nonfiction, and welcome book suggestions via The Noodle to help expand the reading list.

REFERENCES

1 month ago

38 minutes

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

2 months 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 months 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

2 months 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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2 months 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

3 months 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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3 months 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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3 months 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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3 months 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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4 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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4 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.