💬 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

• Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man
• Thinking, Fast and Slow- Daniel Kahneman
  
  

💬 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

• Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man
• Retirement With Purpose: The 10 R's for a Joyful Retirement: A practical and thoughtful guide to rediscovering yourself and flourishing in the retirement stage.- Cesar Aguirre

💬 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

• Sign up for our next Webinar!
• Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man
• Maslow's Hierarchy of Needs
  
  

💬 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

• Live Long and Well with Dr. Bobby- podcast
• Sign up for our next Webinar!
• Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man
  
  

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

• Sign up for our next Webinar!
• Scarcity Brain: Fix Your Craving Mindset and Rewire Your Habits to Thrive with Enough- Michael Easter
• Submit a Question for Roger
• Sign up for The Noodle

FOLLOW US ON SOCIALS

• Follow Us on Facebook!
• Follow Us on Instagram
  
  

💬 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

• Submit a Question for Roger
• Sign up for The Noodle

FOLLOW US ON SOCIALS

• Follow Us on Facebook!
• Follow Us on Instagram

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

• Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man
• BehaviorGap.com- Carl Richards

FOLLOW US ON SOCIALS!

• Follow Us on Facebook!
• Follow Us on Instagram
  
  

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

• 
  Submit a Question for Roger
• Sign up for The Noodle
• The Retirement Answer Man
• IRS.gov Forms
  
  

FOLLOW US ON SOCIALS!

• 
  Follow Us on Facebook!
• Follow Us on Instagram