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  • In this special Christmas Day episode, we explore the art of reflection as we approach the end of 2024. Join us as we dive into Tanya Nichols' year-end reflection protocol and challenge ourselves to look back on our successes, failures, and lessons learned. We'll also answer listener questions on topics ranging from Roth contributions to mortgage strategies. Plus, get a sneak peek into 2025 with upcoming episodes focused on retiring single and live case studies. Don't miss this opportunity to glean wisdom and set intentions for the new year.

    PRACTICAL PLANNING SEGMENT

    (00:45) It is a good time of year to reflect on 2024

    (03:00) Today we are going to work through Tanya Nichol’s end of year 2024 worksheet.

    (03:47) What are some successes you achieved this year, professionally and personally?

    (06:15) What are some failures this year that you're not proud of?

    (06:56) What are some things you wish you had done in 2024?

    (07:27) What are things that you thought were really critical last year that are meaningless now?

    (08:03) The next category for 2024 reflection is what made me truly happy in 2024?

    (09:10) What made you deeply sad this last year?

    (10:00) Next category. Something new I discovered about myself this year

    (10:50) What did you love in 2024?

    (11:12) When you reflect on 2024, what seasons are ending for you?

    (12:15) What new seasons are coming?

    (14:20) My theme for 2025 is outdoors. I want to be outdoors more next year.

    (15:00) Our team word for 2025 is HONE.

    LISTENER QUESTIONS

    (15:51) Bob asks about Roth contribution limits as a low earned income household for 2024

    (18:11) Listener Brian has found a way to keep his brain active by attending college courses to work on his Mindset nonfinancial pillar.

    (21:01) Our next question comes from Jim related to paying down a mortgage

    (26:50) Nancy just wanted to share her gratitude as a long time listener of the show.

    SMART SPRINT

    (27:17) Grab the intention worksheet that we're going to share on Six Shot Saturday and reflect on your 2024

    BONUS

    (28:06) Roger shares the next entry from his grandfather's WWII journal

    Show notes created by https://headliner.app

  • 💬 Show Notes

    Join us in this episode as we delve into the complexities of retirement planning with Dr. Daniel Crosby, author of The Soul of Wealth. Discover the importance of learning what to ignore and how to trust your inner voice amidst the noise. We also explore the nuances of health management with Dr. Bobby Dubois, discussing how to tailor your health journey to your unique style. Plus, get a sneak peek into the upcoming Retirement Plan Live case study and exciting changes for the show in 2025.

    (00:30) Today we are going to talk to Doctor Daniel Crosby and Doctor Bobby Dubois

    (04:20) Retirement Plan Live starts in January. We will have two subjects this go round, both are retiring single, with no children.

    (05:30) In 2025, the show will be more focused on retirement.

    INTERVIEW WITH DANIEL CROSBY

    (06:20) Welcome Doctor Daniel Crosby to the show.

    (07:00) We are going to focus on a chapter in The Soul of Wealth, Learning What to Ignore.

    (08:15) Daniel: I feel like our attention is being pulled in negative ways...We live in a world where we are utterly unprepared for the amount of information coming our way.

    (10:35) Daniel: Going back to the top of your funnel and figuring out what you want can be deeply obscured by focusing on the wrong thing.

    (12:35) Daniel: The reason that we are at the top of the food chain is our ability to work cooperatively together and part of working together is benchmarking with each other.

    (13:20) Roger: Whatever your vision is should be a reflection of your values.

    (17:55) Roger: We have to know what to pay attention to when it comes to practical planning so we don't spend too much time focusing on the wrong thing. What are those filtering questions?

    (19:05) Question 1: Do you have a reason to believe the accuracy of this information?

    (21:31) Question 2: What is the motivation of the person giving forecast or information?

    (26:20) Daniel: That which we obtain too easily, we esteem too lightly.

    (27:15) Question 3: Will I care about this in the next 5 years?

    (29:29) Daniel: “Given the state of everything,” is kind of how everyone feels all the time.

    (30:30) Last question: Does this matter to my finances or my soul?

    (33:40) Daniel: When people look back on their lives, they don’t care about work and money all that much.

    INTERVIEW WITH DR BOBBY DUBOIS

    (35:50) Dr. Bobby Dubois joins us to talk about energy and retirement.

    (36:41) Today we are going to talk about HOW we approach our health.

    (38:06) Bobby: One size fits all doesn't reflect our personality types. How things motivate us are not the same from one person to another.

    (40:02) Roger: Quote from Neal Stephenson might apply to today's longevity discussion. Most of us are too busy living our lives to think about longevity.

    (41:35) Bobby: There are five different health types and there's a quiz to identify them

    (42:11) Bobby: The first type is the holistic health hacker, wellness is front and center.

    (43:52) Bobby: Next is single minded achievers, they focus on one or two things and can get tunnel vision.

    (45:55) Bobby: Purposeful path planners are folks who are motivated about their health but can get overwhelmed by information.

    (47:39) Bobby: Contentment creators have mastered the art of enjoying life. Life is front and center and health is secondary.

    (49:40) The last type is the smallest in my database, hopeful health seekers. They keep at it and don’t give up but they haven’t found the way toward health.

    (51:17) Bobby talks about Roger being a purposeful path planner.

    (55:36) Roger: There's a difference between deciding, indecisive, and undecided

    (59:40) Your health type may change over time.

    SMART SPRINT

    (01:05:42) IN the next seven days, I challenge you to use Dr Crosby’s focusing questions to strengthen the muscle around what you should pay attention to and what you should ignore.

    BONUS

    (01:06:23) All right, mission number seven and eight, July 8, 1944. Ship number 188, sortie 5th Vienna

    Show notes created by https://headliner.app

    Rational optimism

    ✍ Episode References

    Dr. Daniel Crosby

    https://www.danielcrosby.com/

    The Soul of Wealth

    https://harriman.house/books/the-soul-of-wealth/

    Dr. Bobby Dubois

    https://www.drbobbylivelongandwell.com/

    James Clear

    https://jamesclear.com/

    Cal Newport

    https://www.calnewport.com/books/deep-work/

    The Rational Optimist: How Prosperity Evolves- Matt Ridley

    https://www.amazon.com/Rational-Optimist-Prosperity-Evolves-P-s/dp/0061452068

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  • In this episode, Roger discusses the impact of our relationship with "stuff" on our retirement journey. With the holiday season upon us, we're all about giving and receiving, but how does this accumulation affect us long-term? Michael Easter, author of The Comfort Crisis and Scarcity Brain, joins the conversation and shares insights on distinguishing between gear and stuff. Michael shares insights on the psychological and societal influences driving consumption and offers practical tips for making more mindful purchasing decisions. We also address listener questions on topics like the tax implications of campaign promises and master limited partnerships. Tune in for a thought-provoking discussion that might just change the way you view your possessions and retirement planning.

    OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

    [01:00] Our relationship with stuff can have second and third order consequences in retirement[01:50] How watching the Buy Now documentary inspired Roger to think about possessions[03:10] The impact of clutter on retirement

    GEAR VS. STUFF CHAT WITH MICHAEL EASTER

    [05:40] How the amount of items in the average home has changed over time and why[07:36] Michael Easter defines gear and stuff [09:39] Humans evolved to get as much information as possible[12:00] Managing gear vs. stuff in holiday shopping[12:45] How ecommerce platforms have taken features from casinos to help speed purchases[14:25] Strategies to reduce needless purchases[19:50] Roger’s plan for gifts this year

    LISTENER QUESTIONS

    [23:45] David’s comment on verse and versus[24:55] Mary on how to ask better questions[26:26] Armand asks why we aren’t discussing potential elimination of income tax on Social Security[30:41] Todd has a question about master limited partnership stocks

    SMART SPRINT

    [38:00] Be aware of your purchases this holiday season - are you buying gear or stuff?


    Resources Mentioned In This Episode

    Michael Easter

    Cal Newport

    Books: The Comfort Crisis and Scarcity Brain by Michael Easter

    Netflix documentary Buy Now

    Six-Shot Saturday

  • Join us for a special episode as we welcome Christine Benz to discuss her new book, "How to Retire." In a captivating conversation at 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.

    INTERVIEW WITH CHRISTINE BENZ

    (01:26) Rock Retirement Club welcomes Christine Benz to chat about her new book, How to Retire

    (02:40) Roger asks about the goal for the readers of this book.

    (04:00) Christine: The goal was to cover retirement in a really holistic way and include as much non-financial as financial information on retirement planning.

    (05:09) Roger: I was surprised that you did the book in the interview style, I think it helped make the book more approachable.

    (07:24) Roger: Did you have any big insights that were unexpected?

    (10:18) Fritz: I give Christine serious kudos for the approach she took and the amount of homework she did.

    (11:47) Christine to Fritz: I love your methodical approach to dealing with the years leading up to retirement

    (13:19) 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.

    (17:28) Roger: When it comes to portfolio construction, it's easy to overcomplicate things

    (20:30) Larry asks Christine what challenges her or confounds her most about her own retirement planning.

    (22:53) Larry asks “Are you concerned that we may not find people to provide long term care?”

    (30:11) Kevin Lyles asks about asset allocation when you retire

    (30:47) Christine: My chapter on asset allocation addresses the bucket approach, which I do find very customizable.

    (36:56) Laura asks: When you talk about high quality bond portfolios, do bond funds work?

    (41:06) One question I have when we're talking about indexes is about broad diversification.

    (43:42) Roger: Now someone had a comment related to some of the research on small cap value. Do you have any view on that research on having a more diversified small cap value tilt?

    (47:19) Eric asks “what is the argument for using tips for retirees?”

    (50:24) Roger asks Fritz if he has been simplifying his portfolio or working more on optimization since retiring in 2018.

    (52:50) Roger: The optimization part sometimes dominates the conversation.

    (53:38) Roger asks Christine: Have you found, even in your own life, a balance between making sure you don’t get too complicated in investments?

    (56:45) Biranna asks after 20 interviews, what question now rests in your mind?

    (57:40) Christine: I've been thinking more about whether the concept of retirement is flawed

    (58:59) We're going to share a link with members offering a discount to Morningstar.

    (59:55) Next week on the show, we're going to chat about with Michael Easter about Gear vs Stuff

    BONUS

    (01:00:30) Roger reads an excerpt from his grandfather's WWII journal

    REFERENCES

    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

    Show notes created by https://headliner.app

  • Welcome to another episode dedicated to enhancing your retirement journey! Today, we wrap up our series on year-end action items with a focus on charitable and family giving. Discover how strategic charitable contributions can optimize your tax plan and learn about family giving opportunities that can make a difference. We also address your questions and share essential updates, including a correction on HSA contribution limits and an exciting upcoming live case study. Plus, get ready for a December packed with insightful guests like Christine Benz and Michael Easter. Dive in and explore ways to rock your retirement with confidence!

    PRACTICAL PLANNING SEGMENT

    (00:30) Today we are going to talk about charitable and family giving.

    (00:53) I misquoted the HSA contribution limits in episode 565

    (02:40) In January we are doing another Retirement Plan Live series.

    03:50 In December we will have several great guests on the podcast including Christine Benz, Daniel Crosby, Michael Easter, and Tanya Nichols.

    (04:21) Today we're going to talk about charitable and family giving

    (05:30) There's no real impact from a tax perspective on charitable giving unless you itemize your tax return.

    (07:41)What are ways of giving to a charitable organization?

    (12:00) You can batch your charitable contributions into one year in order to have a significant impact on the tax you pay in reduction.

    (14:42) Let’s talk about family giving. You can give up to $18,000 a year in family giving.

    (16:44) You can pay family educational expenses and medical expenses without limit as long as you are paying directly to the institution.

    LISTENER QUESTIONS

    (18:00) I had a discussion with a member of the Rock Retirement Club yesterday about moving to a warmer state in retirement and helped analyze the feasibility of their plan in the different states.

    (25:14) One question related to the upside portfolio, do I have to build a whole asset allocation?

    (28:45) Our next question is an audio question related to rebalancing. “Hi, Roger. I have a question about the process of rebalancing your pie cake
 what process should I use to refill layer two of my pie cake to continually fund the next five years of my life?”

    SMART SPRINT

    (37:55) In the next seven days review your charitable and family giving.

    BONUS

    (38:15) Roger shares another excerpt from his grandfather's WWII journal.

    REFERENCES

    Simon Sinek- Originator of Humble Pie Quote
    https://simonsinek.com/

    Red Cross
    https://www.redcross.org/

    Schwab Donor-Advised Fund
    https://www.schwabcharitable.org/

    Fidelity Donor-Advised Fund
    https://www.fidelitycharitable.org/

    Upcoming Podcast Guests:

    Christine Benz
    https://www.morningstar.com/people/christine-benz

    Michael Easter
    https://eastermichael.com/

    Daniel Crosby
    https://orion.com/thought-leader/daniel-crosby

    Tanya Nichols
    https://www.align.financial/tanya-nichols/

    Retirement Podcast Network
    https://retirementpodcastnetwork.com/

    Six Shot Saturday
    https://rogerwhitney.com/six-shot-saturday

    Show notes created by https://headliner.app

  • Join us in this insightful episode as we continue our series on year-end action items, focusing on optimizing your retirement planning. Today, we delve into the intricacies of withdrawing assets, discussing everything from flexible spending accounts to inherited IRAs. We also explore the concept of "gear, not stuff" with insights from Michael Easter, and how making thoughtful purchasing decisions can impact your financial health and the environment. Don't miss our deep dive into tax strategies and the importance of building a resilient retirement plan. Plus, we answer listener questions about decumulation, working with financial advisors, and more. Tune in to take actionable steps toward a secure and fulfilling retirement!

    PRACTICAL PLANNING SEGMENT

    (00:00) This week we continue to discuss year end action items to optimize your retirement planning

    (00:50) We are gearing up for a retirement plan live case study for January. This time we will be focusing on someone who is single with no children.

    (02:10) Roger shares an anecdote about having his kitchen cabinets painted and discusses gear versus stuff.

    (05:00) Roger discusses the importance of buying high quality items that last.

    (07:25) Today we're going to talk about accounts we should consider withdrawing money from before the end of the year. First up are FSA accounts.

    (08:14) The next accounts we are going to talk about are inherited pre-tax accounts.

    (09:30) If you inherited an IRA prior to January 1, 2020, your required minimum distribution is required to be taken out by the end of this year.

    (10:48) What happens if you inherited an IRA after 2020?

    (12:25) Since the Secure Act 2.0 started in 2023, the penalty for not taking the required minimum distribution is 25% of what you should have taken.

    (13:35) The next type of required minimum distributions we are going to talk about are those that are age related for original IRA owners.

    (15:03) Proactively taking qualified distributions can lower your overall tax rate in retirement.

    LISTENER QUESTIONS

    (20:44) Next Month, we'll focus on answering some of your questions on AskRoger.

    (21:12) The first question comes from Scott about principal versus interest and decumulation.

    (28:59) Next, Joy says she needs help with retirement planning and decumulation of assets.

    (32:45) Mike asks about decumulation and resilience. How should pre-retirees position retirement assets as they reach the last five years or so before retirement?

    (39:11) Tom asks about the five year rule for Roth 401k conversions.

    SMART SPRINT

    (41:08) Take a look at the items that we talked about in terms of withdrawing assets.

    BONUS

    (41:45) Roger reads another excerpt from his grandfather's war journal.

    REFERENCES

    Ask Roger

    https://www.rogerwhitney.com/askroger

    Michael Easter
    https://twopct.com

    Dinkytown Calculators- specifically the 1040 tax estimator
    https://dinkytown.net

    Schwab Required Minimum Distribution Calculator
    https://www.schwab.com/ira/ira-calculators/inherited-ira-distribution-calculator

    Six Shot Saturday
    https://6shotsaturday.com

    Show notes created by https://headliner.app

  • Join us as we dive into year-end financial planning strategies to optimize your retirement plan. This episode unpacks the essentials of contributing to various accounts like 401(k)s, IRAs, Roth IRAs, HSAs, and donor-advised funds before the year ends. We also discuss Roth conversions and answer listener questions about IRMAA brackets and required minimum distributions. Plus, hear a special tribute to veterans, featuring the first mission of Roger’s grandfather, a WWII bomber pilot. Don’t miss this comprehensive guide to maximizing your retirement savings and honoring those who served!

    SMART PLANNING SEGMENT

    (01:01) Rock Retirement Club is having its last open enrollment for the year.

    (02:26) This month the theme has been to look at year end planning items in order to optimize your plan of record.

    (03:40) This week we focus on contributing to assets between now and the end of the year. We will start off by discussing contributing to your 401K account.

    (05:30) The second thing we want to look at is contributing to an IRA or Roth IRA.

    (08:37) The next account you might consider contributing to is your health savings account.

    (10:07) Another thing you might consider contributing to is a donor advised fund or any type of charity.

    (15:03) The next one I’ll talk about today is 529 education plans.

    (17:00) Another account you might want to contribute to is your after tax investment account.

    LISTENER QUESTIONS

    (20:00) Roger talks about 51 missions that his grandfather flew during World War II in honor of Veterans Day.

    (21:10) Reid is concerned about IRMAA in 2026 regarding Roth conversions.

    (24:35) David asks a question about projected required minimum distributions for Roth conversions.

    (28:30) Joe asks about tax brackets and Roth conversions.

    (31:13) Denise says the more she reads about Roth conversions, the more confused she gets.

    SMART SPRINT

    (35:00) If you want to try to do some optimization, grab the worksheets from Six Shot Saturday and go through the lists.

    IN HONOR OF VETERANS DAY

    (35:54) In honor of Veterans Day, I'm going to share some missions from my grandfather to thank all of our veterans.

    REFERENCES

    Six Shot Saturday

    Rock Retirement Club

    Retirement Answer Man- FREE Resource Center

    Show notes created by https://headliner.app

  • Welcome to a transformative episode where we delve into year-end financial strategies to optimize your retirement planning. Join us as we discuss tax-loss harvesting with Erin Coe, a seasoned planner and tax expert. Learn how to strategically sell capital assets at a loss to reduce your tax burden and explore the nuances of capital gains, wash-sale rules, and more. Plus, we answer listener questions about Roth conversions and annuities. Don't miss this insightful guide to maximizing your financial health!

    PRACTICAL PLANNING SEGMENT

    (00:25) Today on the show we begin to explore year-end action items.

    (02:23) So now that we're into tax season, we're going to do a primer on tax-loss harvesting with Erin Coe.

    (03:59) Tax-loss harvesting is the act of intentionally selling capital assets at a loss

    (05:25) Defining what a capital loss is

    (08:42)The intent is to reduce taxable income and reduce taxable liability

    (10:12) How do you gauge the impact of this?

    (13:34) Leave some buffer room to be careful on tax cliffs

    (15:35) The wash-sale rule means you can't sell a capital asset and claim that loss and then repurchase it within 30 days

    (21:27) What are some gotchas that we need to watch out for when evaluating portfolios?

    (22:24) Another problem is those carry forwards, you need to track it every year whether you are using it or not.

    (25:38) Tax loss harvesting is not just a December activity, it’s a year-round sport

    LISTENER QUESTIONS

    (28:05) Greg asks a question about Roth conversions for his older relative

    (34:24) Stanley says his wife has a taxable MYGA, multi year guaranteed annuity, and wants to know if he should take the lump sum or roll it into something else.

    (40:28) Jay asks about the pie or bucket approach

    SMART SPRINT

    (46:50) Review your after-tax accounts looking for unrealized losses and examine whether you can use them productively

    Join our live event on Roth conversions at livewithroger.com or sign up for the replay at sixshotsaturday.com.

    REFERENCES

    Dinkytown.net

    Turbo Tax

    Retirement Podcast Network
    Six Shot Saturday

    Retirement Answer Man

  • Welcome to our latest episode, where we focus on empowering your retirement journey with clarity and energy. Today, we delve into two powerful mental models, Occam's Razor and Hanlon's Razor, to simplify your retirement planning and decision-making processes. We also welcome back Dr. Bobby Dubois in our Rock Life segment, where he shares insights on living longer and more energetically. Don't miss our discussion on practical steps to enhance your life and retirement.

    PRACTICAL PLANNING SEGMENT

    (00:55) Roger will host a live online meetup on November 7 to discuss ROTH Conversions

    (02:30) Today we are going to talk about Occam’s Razor and Hanlon’s Razor

    (04:20) Occam’s Razor talks about when confronted with multiple options, the simplest is the best. Don’t overcomplicate things.

    (05:20) How to apply Occam's Razor in retirement planning

    (10:43) Hanlon's razor says never attribute to malice that which can be adequately explained by incompetence or ignorance

    (12:15) Humans are messy and are usually not trying to harm or cause problems

    (12:50) How do you apply Hanlon’s Razor to retirement planning?

    INTERVIEW WITH DR. BOBBY

    (15:53) Today we are going to focus on building energy and discuss four different studies about inflammation.

    (17:00) The first study talks about how sleep impacts inflammation.

    (21:45) The next study discusses measures of inflammation that can be tested in the blood and what they suggest.

    (26:05) Third study shows exercise can improve our sleep and reduce inflammation

    (28:20) One study looked at five characteristics of an 80 year old to determine who was more likely to live to 100.

    (30:54) The takeaways are, there are things we can do that can really help us live long and well. Sleep, exercise, and diet can really make a difference in longevity.

    SMART SPRINT

    (32:40) I want you to look for an opportunity to practice Occam’s or Hanlon’s Razor in the next seven days.

    Six Shot Saturday Email

    Retirement Answer Man Webinar Registration

    Books:

    The Great Mental Models- Shane Parrish

    Podcasts:

    Live Long and Well with Dr. Bobby- Episode 3: Sleep

  • In this episode, we delve into the concept of the Circle of Competence, a key principle in the mental mindset arsenal. We also feature Karen's inspiring story of transitioning from accumulation to decumulation, redefining her retirement journey. Join us as we explore the importance of deep knowledge versus surface understanding, and how you can apply these insights to your life. Also, don't miss our upcoming live online meetup on November 7, where we'll discuss Roth conversions and introduce the Rock Retirement Club. Sign up at livewithroger.com and take the first step towards rocking your retirement!

    PRACTICAL PLANNING SEGMENT

    (00:00) This week we will talk about the Circle of Competence and decumulation

    (01:05) Live online meet up 11/ 7 at 7pm central about Roth conversions and RRC Open House

    (04:33) The internet creates false competence and internet experts

    (07:05) Circle of competence says individuals should focus their efforts within areas where they have a deep understanding or expertise

    (07:32) Warren Buffett is a master at staying within the Circle of Competence

    (12:10) Your competence in retirement is informed by your experience and research

    (14:00) How do you know who is competent at some level in retirement planning?

    (15:10) As competence goes up, sometimes confidence can diminish

    (18:40) If you’re not in your Circle of Competence, what should you do?

    (21:30) How do you gauge someone's Circle of Competence?

    INTERVIEW WITH KAREN ABOUT DECUMULATION

    (24:27) Karen shares her story and journey to understanding decumulation

    (25:20) Karen became a widow five years before she retired from pediatrics at age 62

    (26:50) Karen learned from the RRC about the concept of decumulation

    (29:30) Second Order consequence of not touching principal

    (33:00) Karen talked about a degenerative issue from a vision standpoint in your family

    (35:56) I asked RRC members for recommendations on where to go, what to do

    (38:00) Karen recaps her travels as a single elderly lady traveling alone and with groups

    (40:29) So I'm thinking of you in decumulation, that change in conception and seeing in detail that it’s okay to spend x amount of money on various things.

    SMART SPRINT

    (43:11) In the next seven days, I want you to think about the distinction between accumulation and decumulation.

    REFERENCES

    Great Mental Models- Rhiannon Beaubien Shane Parrish

    Into Thin Air- Jon Krakauer

    Live Long and Well with Dr. Bobby

    Overseas Adventure Travel

    The History Chicks Podcast

    Road Scholars

    The Soul of Wealth- Dr. Daniel Crosby

  • Join us in this insightful episode as we explore the concept of 'The Map vs. The Territory' in retirement planning. Discover how mental models can enhance decision-making and lead to a more fulfilling retirement. Our special guest, Dr. Daniel Crosby, discusses his latest book, "The Soul of Wealth," offering profound insights into achieving soulful wealth beyond mere numbers. Learn how to balance maps and reality, and the importance of feedback loops in financial planning. Plus, get practical advice on adapting to the unpredictable nature of life and finances. Don't miss this engaging conversation on rocking retirement with agility and purpose!


    PRACTICAL PLANNING SEGMENT

    (00:30) Talking about the map versus the territory and how it applies to retirement

    (2:00) Personal anecdote about GPS maps

    (4:00) Maps are a good abstraction to help us navigate things but understand maps are not reality

    (5:15) Practical example using map versus territory

    (07:25) Maps can be very useful in retirement planning, but they can also have limitations

    (9:00) If we view map as reality, it’s easy to create static rules and can reduce our ability to adapt

    (10:00) In the context of retirement planning, the map is the plan and comes with a lot of limitations.

    (12:31) There are multiple ways to deal with variability of inflation

    INTERVIEW WITH AUTHOR DR. DANIEL CROSBY

    (16:22) Dr. Daniel Crosby is the author of the newly released book The Soul of Wealth

    (18:25) Use a phrase called soulful wealth to describe what makes life rich

    (20:00) Retirement is not a spreadsheet

    (22:48) Martin Seligman is the father of positive psychology and the PERMA Model

    (29:37) You have to get very specific in what it means to have meaning in life

    (31:00) The Three B’s of having purpose in life- Believing, Belonging, Becoming

    (35:26) What is it, especially around retirement, that creates this crisis of confidence with people?

    (39:25) Identify when you are lying to yourself and it becomes harder to be complacent

    (40:45) Have a purpose for your money

    (44:55) One of the most fulfilling ways to spend money is giving it away

    SMART SPRINT

    (48:32) In the next seven days, evaluate whatever retirement plan you have in place and identify specifically what is the feedback loop to improve that plan.

    RESOURCES

    Dr. Daniel Crosby
    https://www.danielcrosby.com

    The Soul of Wealth
    https://www.amazon.com/Soul-Wealth-reflections-money-meaning/dp/1804090441

    Six Shot Saturday
    https://sixshotsaturday.com

    Orion Advisor Services
    https://www.orion.com

    Martin Seligman
    https://www.authentichappiness.sas.upenn.edu

  • Welcome to the second week of our series on improving decision-making skills with mental models to help you rock retirement! This week, we delve into the concept of second order thinking, also known as the law of unintended consequences. Learn how to think beyond immediate outcomes and explore the long-term impacts of your decisions, whether it's buying a new car or helping your child with a down payment. We'll also share insightful stories from RRC retirees who have navigated the transition to retirement, offering wisdom on what they were excited about, what they worried about, and how their perspectives have changed. Plus, we answer your questions and discuss practical applications of second order thinking in retirement planning. Join us for an episode packed with valuable insights and tips to enhance your retirement journey!

    PRACTICAL PLANNING SEGMENT

    (00:00) This week's show focuses on improving decision making skills ahead of retirement

    (01:15) Revisiting inversion thinking with listener feedback

    (03:18) Shoutout to RRC Member Kevin

    (5:00) Starting our second mental model: Second order thinking or the law of unintended consequence

    (9:00) Reflecting on giving money productively to children using second order thinking

    (12:58) Second order consequence thinking can help you tease out downstream consequences of retirement planning

    (13:40) Building a retirement plan of record thinking in second order consequence thinking.

    RRC RETIREE INTERVIEWS

    (15:20) Talking to our own Kevin Sebesta about retirement

    (18:09) What is a fun bucket?

    (23:00) Talking with two-year retiree, Bob, about what his concerns were before retirement and what he was most looking forward to.

    (27:54) Bob talks about making indulgent purchases in retirement.

    (30:46) Asking Bob what advice he would have given his younger self.

    (33:01) Talking to five-year retiree, Becky, about her concerns prior to retirement.

    (36:06) When you retired, would you say you were overfunded or very constrained?

    (38:00) How were you comfortable with the unknown going into retirement?

    (39:30) How important is it to have friends who are on a similar journey?

    (44:57) Talking to four-year retiree, Jack, about his concerns two years prior to retirement.

    (48:35) Jack talks about volunteering at food pantries and food banks.

    (50:46) How do you avoid getting bored in retirement?

    (52:04) What would you have done differently when it comes to transitioning to retirement?

    (53:15) Talking with five-year retiree, Chip, about transitioning from professional to retiree.

    (55:55) A year or two before retirement, what were your biggest concerns?

    (56:50) “Getting laid off was probably the best thing that ever happened to me.”

    (59:17) It's been a journey after retirement figuring out how to manage your time

    (01:03:10) Looking back, is there anything you would’ve done differently?

    LISTENER QUESTIONS

    (01:05:14) Mikey asks about withdrawing social security before seventy.

    (01:09:23) Mike and Bonnie ask about using debt for tax management purposes

    (01:16:21) Dirk asks about principle protected, structured ETFs

    (01:17:25) What is principal protection structured ETF?

    (01:23:59) Tim asks about investing based on newsletters.

    SMART SPRINT

    (01:28:59) Use second order thinking to help you make low-stakes decisions

    REFERENCES

    Rock Retirement Club
    https://rockretirementclub.com


    Six Shot Saturday
    https://sixshotsaturday.com


    Roger Whitney
    https://rogerwhitney.com

    Catching Up to FI Podcast
    https://catchinguptofi.com

    Fooled by Randomness: The Hidden Role of Chance in Life and in the Markets by Nassim Nicholas Taleb
    https://www.amazon.com/Fooled-Randomness-Hidden-Markets-Incerto/dp/0812975219

  • Welcome to another insightful episode where we kick off a month-long series on improving your decision-making abilities. This week, we delve into the concept of inversion, a powerful mental model that can significantly enhance your retirement planning. Learn how to avoid common unforced errors and make better decisions to ensure a successful retirement. Plus, get answers to listener questions about HSAs, security issues, and investment strategies. Don't miss this episode packed with practical advice and useful tips!

    PRACTICAL PLANNING SEGEMENT

    (00:30) This week starts a month-long series on improving your decision-making abilities

    (04:38) First mental model- Inversion

    (10:30) Inversion in investing

    (12:20) Combining inversion with the vision pillar to determine what you want your life to be

    (15:00) Using things you don’t want to help build goals of what you DO want

    (15:54) Inversion with energy pillar. What do I need to AVOID to get more energy?

    LISTENER QUESTIONS

    (17:55) Jay asks about HSA and transferring funds

    (21:55) Questions from Connie about password website, onepassword.com, and about securing social security account.

    (24:55) Question about financial advisors and Dimensional Funds

    (30:12) Linda asks about asset allocation and optimization.

    BRING IT ON SEGMENT

    (33:33) Kevin Lyles comes on to talk about identity

    (37:15) Identity after retirement and losing your work identity

    (43:07) Identify what you got from your career identity-wise that you want to continue in retirement

    SMART SPRINT

    (52:55) In the next 7 days when faced with a decision, think about inverting the question.

    RESOURCES

    Rock Retirement Club
    https://rockretirementclub.com

    Six Shot Saturday
    https://sixshotsaturday.com

    Roger Whitney
    https://rogerwhitney.com

    Vanguard
    https://vanguard.com

    Charles Ellis, Winning the Loser's Game
    https://www.amazon.com/Winning-Losers-Game-Strategy-Investing/dp/1264257697

    Bronnie Ware, The Top Five Regrets of the Dying
    https://www.amazon.com/Top-Five-Regrets-Dying-Transformed/dp/140194065X

    One Password
    https://1password.com

    LastPass
    https://lastpass.com

    Login.gov
    https://login.gov

    ID.me
    https://id.me

    Dimensional Fund Advisors
    https://us.dimensional.com

    Avantis Investors
    https://www.avantisinvestors.com

    The Retirement Collective- Shared Wisdom from Top Retirement Coaches
    https://www.amazon.com/Retirement-Collective-Shared-Wisdom-Coaches/dp/1951915186

  • In this episode of the Retirement Answer Man, Roger Whitney wraps up his series on the eight pillars of a great retirement plan by diving into the last two non-financial pillars: passion and relationships. Discover how your hobbies, curiosities, and social connections can significantly impact your retirement happiness. Roger also shares personal stories and practical tips on maintaining energy, fostering a growth mindset, and building a fulfilling post-retirement life. Tune in for insights and strategies to help you rock your retirement!

    PRACTICAL PLANNING SEGMENT

    (00:26) Eight pillars are needed as a foundation for having a great retirement plan

    (02:50) Importance of showing up and doing the work

    (04:12) Having projects is a core component of living an enriching, full life

    (04:49) Passion is our next nonfinancial pillar, find projects you’re passionate about

    (07:19) What are the obstacles to pursuing passion and projects outside of retirement

    (08:50) Roger’s personal anecdote about digital obstacles

    (10:30) Plan for developing passions

    (11:52) Last of the four non-financial pillars is relationships

    (15:17) What are the obstacles of building relationships?

    LISTENER QUESTIONS

    (18:50) Mark asks about spousal IRA

    (20:09) Question from Beth: Should I keep 401k or roll over to an individual IRA?

    (24:28) Fund choices can be a determinant of your 401K success

    (27:07) Simplification and consolidating your assets into an IRA

    (30:21) Listener feedback on losing a spouse

    (34:50) It only takes one account or property to force probate

    SMART SPRINT

    (37:20) Identify one thing that you are curious about and pull that thread

  • This week, we continue our journey through the eight pillars of rocking retirement, shifting our focus to the non-financial realm. We delve into the first two non-financial pillars: Energy and Mindset. These pillars are crucial for showing up fully in life and maintaining a growth-oriented perspective. We'll explore how to overcome obstacles like stress, injuries, bad habits, and the impacts of aging, and discuss actionable plans to boost your energy and cultivate a growth mindset. Additionally, we’ll answer your pressing questions about Roth IRA contributions, tax planning, Social Security spousal benefits, and CD investments. Join us as we build a holistic retirement plan that goes beyond finances to truly rock your retirement!

    PRACTICAL PLANNING SEGMENT

    [00:33] Focus on the non-financial aspects of your retirement planning

    [01:35] Sign up for Six Shot Saturday

    [03:20] The first pillar that we want to talk about is energy

    [04:15] Obstacles that we face in having energy in our life

    [06:05] Plan when it comes to energy

    [08:43] Pillar number two is mindset

    [09:53] Obstacles to maintaining and growing a growth mindset

    [12:45] What is your plan for a growth mindset?

    [14:17] Reflecting on my father-in-law’s mindset

    LISTENER QUESTIONS

    [16:56] Roger answers your questions on how to rock retirement

    [17:35] Beth: audio question about Roth contributions

    [20:30] Jim talks about managing taxes in retirement

    [24:38] Our next question comes from Patrick on Social Security spousal benefits

    [27:12] Daniel: I was wondering what your thoughts were on CD investments

    BRING IT ON SEGMENT

    [31:14] Mark Ross talks about mindset

    [33:30] I changed my self-talk and it changed the outcome

    [37:18] Tools to change to an abundance mindset

    SMART SPRINT

    [38:55] When you find yourself saying “I can’t,” add the word yet. “I can’t do that YET.”

    RESOURCES

    Agile Retirement Management

    https://www.agileretirementmanagement.com

    Rock Retirement Club
    https://www.rockretirementclub.com

    Six Shot Saturday
    https://www.sixshotsaturday.com

    Younger Next Year
    [https://www.youngernextyear.com

    Limitless Mind by Jo Boaler

    https://www.amazon.com/Limitless-Mind-Learn-Lead-Live/dp/0062851748

    Spartan Race
    https://www.spartan.com

  • This month, we're revisiting the eight pillars of rocking retirement. Today, we focus on the second two financial pillars: having a resilient plan of record and optimizing the plan to enhance the journey. Many people are good at setting goals and determining feasibility, but often overlook the importance of resilience in their retirement plan. We delve into how to stress test your plan for various risks like bear markets, health care shocks, and premature death, and how to build redundancies to make your plan more robust. We also discuss optimizing your plan with tax strategies, investment implementation, and legacy planning.

    PRACTICAL PLANNING SEGMENT

    -[00:35] - Introduction to the eight pillars of rocking retirement

    - [04:55] Building a Resilient Retirement Plan

    - [10:30] Building a funding strategy for the first five years of retirement

    - [14:38] The fourth pillar: Optimization

    LISTENER QUESTIONS

    - [18:55] Mark asks about estimating Social Security benefits

    - [20:32] Mary inquires about investing in Real Estate Investment Trusts versus private crowdfunding platforms

    - [27:20] John seeks advice on choosing a retirement planner

    - [31:58] Tammy's question on whether to sell a high-value home for liquidity

    BRING IT ON SEGMENT

    - [36:37] Building relationships and the importance of micro roles

    SMART SPRINT SEGMENT

    - [42:50] Assess the resilience of your retirement plan

    Resources Mentioned In This Episode

    Six Shot Saturday
    https://sixshotsaturday.com

    Jeremy Siegel's "Stocks for the Long Run"
    https://www.amazon.com/Stocks-Long-Run-Definitive-Investment/dp/0071800514

    Roger's YouTube Channel - Roger That

    BOOK - Rock Retirement by Roger Whitney

    Roger’s Retirement Learning Center

  • This September, we're doing something a bit different. We're revisiting the basics with a refresher on the eight pillars of rocking retirement—four financial and four non-financial pillars that form the foundation for a great life. Too often, retirement planning gets bogged down with too many details and the pressure to get everything right. But in my experience, focusing on the most important things gets you 90% of the way there. This month, we’ll air classic episodes to revisit these pillars, starting today with the first two financial pillars: Vision and Feasibility.

    The first financial pillar we are going to discuss is VISION. How do you start to figure out your vision in retirement? We would suggest reconnecting with who you actually are outside of your identity as an employee and identifying your core values. The second pillar in the financial realm is having a FEASIBLE plan. The objective is to establish a foundation of a safe path that is feasible given the resources and the choices that you are willing to make.

    OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

    PRACTICAL PLANNING SEGMENT

    - 00:28 September will focus on the eight pillars of rocking retirement

    - 08:00 First two pillars of rock retirement are vision and feasibility

    - 08:14 Vision: What do you want when you retire?

    - 13:28 What are some of the obstacles to creating a vision in retirement?

    - 17:44 The next pillar in the financial realm is having a feasible plan

    LISTENER QUESTIONS

    - 24:10 Listener Scott has a tip about going from two to one

    - 26:13 Bill discusses piecake

    - 27:44 Our next question is from Steve related to asset allocation in retirement

    - 33:53 Another listener, Steve, wants to know if a stable value fund is a good investment

    BRING IT ON

    - 38:33 Kevin Lyles talks passion in work and volunteering in retirement

    SMART SPRINT

    - 45:55 Think about your life as a clean slate

    ✍ Episode References

    Six Shot Saturday
    https://sixshotsaturday.com

    The Top Five Regrets of the Dying- Bronnie Ware
    https://bronnieware.com/regrets-of-the-dying/

    The Retirement Manifesto- Fritz Gilbert
    https://www.theretirementmanifesto.com/

    Stocks for the Long Run- Jeremy Siegel
    https://www.amazon.com/Stocks-Long-Run-Definitive-Investment/dp/0071800514

  • If you are exploring a unique retirement, it is important to do your research. The best way to research something is to talk to someone who has walked the walk. That’s why, on this episode of Retirement Answer Man, I chat with people who are living their own unique retirements.

    Press play to hear these unique stories. OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN TODAY’S SMART SPRINT SEGMENT

    [6:02] Identify what type of community has served you well in life

    STORIES FROM AN EXPAT

    [8:22] Meet Doug living the expat life in Thailand[15:03] How to maintain a US address[21:35] How to handle buying land in other countries[26:41] How does estate planning work?

    STORIES FROM A PARENT OF A DISABLED CHILD

    [29:53] Navigating retirement with children with special needs[31:11] How our retirement focus is different from other retirees[38:08] How Special Sitters coordinates care in Omaha, Nebraska[44:35] How they are making sure that their children are cared for[49:49] What else you should remember

    STORIES FROM A HUB AND SPOKE TYPE OF RETIREMENT

    [50:35] What Rhoda and Rob are doing in retirement [54:38] How they travel in retirement[1:04:44] How they managed their finances

    Resources Mentioned In This Episode
    Special Sitters
    Rock Retirement Club
    Roger’s YouTube Channel - Roger That
    BOOK - Rock Retirement by Roger Whitney
    Roger’s Retirement Learning Center

  • Have you ever thought about retiring abroad? It seems like a fun adventure, but how do you begin?

    On this episode of Retirement Answer Man, expat expert, Jane Mepham from Elgon Financial Advisors, joins me to discuss the financial and nonfinancial considerations of moving abroad in retirement. Press play to learn whether retiring abroad would be right for you. OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN RETIRING AS AN EXPAT

    [3:46] What is the attraction of retiring to another country?[6:18] How to explore whether retiring abroad is right for you[12:01] Should you buy or rent?[14:54] How do you navigate your finances?[22:04] What other considerations should you think about?

    LISTENER QUESTIONS

    [37:09] Is it worth selling investments and incurring significant taxes to change firms to reduce fees?[46:03] How to plan retirement without using the 4% rule [52:25] Where to put your contingency fund

    TODAY’S SMART SPRINT SEGMENT

    [58:08] Examine the advice you’re getting and your process

    Resources Mentioned In This Episode
    Elgon Financial Advisors
    Rock Retirement Club
    Roger’s YouTube Channel - Roger That
    BOOK - Rock Retirement by Roger Whitney
    Roger’s Retirement Learning Center

  • If you have a special needs child, you know that your retirement plan will need to include plans for their future. How do you create a great retirement while honoring and caring for your child with special needs who will most likely live beyond your years? That’s what we’ll be learning today.

    In this episode, Matt from Haystack Financial Planning joins me to explore this question. His practice specializes in serving the disabled community and he offers years of experience in this area. Press play to learn what you can do to take care of your children while making the most of your retirement. OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN RETIREMENT PLANNING WHEN YOU HAVE A SPECIAL NEEDS CHILD

    [2:30] Why Matt chose this path[4:25] How to plan for your child’s needs[7:40] How to determine the costs needed[12:02] What other tools do these children have available to them?[14:38] What is an ABLE account[20:07] How to approach guardianship[22:42] Resources to help

    LISTENER QUESTIONS WITH NICHOLE

    [24:42] How Nichole has been doing[25:25] Maggie’s backdoor Roth conversion question[29:38] On the order of withdrawals in retirement[33:33] How much will I need to self-insure for long-term care?[40:46] How to handle finances as a newly married couple[45:55] My plans with Michael Easter

    TODAY’S SMART SPRINT SEGMENT

    [47:39] Limit your exposure to mainstream media related to the election

    Resources Mentioned In This Episode
    Haystack Financial Planning
    ABLE 529 account
    BOOK - The Special Needs Planning Guide by John Nadworny
    BOOK - Retire Secure for Parents of a Child with a Disability by James Lange
    Rock Retirement Club
    Roger’s YouTube Channel - Roger That
    BOOK - Rock Retirement by Roger Whitney
    Roger’s Retirement Learning Center