Retirement Year End Planning: Tax-Loss Harvesting

💬 Show NotesJoin 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 ViennaShow notes created by https://headliner.appRational optimism✍️ Episode ReferencesDr. Daniel Crosbyhttps://www.danielcrosby.com/The Soul of Wealthhttps://harriman.house/books/the-soul-of-wealth/Dr. Bobby Duboishttps://www.drbobbylivelongandwell.com/James Clearhttps://jamesclear.com/Cal Newporthttps://www.calnewport.com/books/deep-work/The Rational Optimist: How Prosperity Evolves- Matt Ridleyhttps://www.amazon.com/Rational-Optimist-Prosperity-Evolves-P-s/dp/0061452068

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 retirementGEAR 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 yearLISTENER 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 stocksSMART SPRINT[38:00] Be aware of your purchases this holiday season - are you buying gear or stuff?Resources Mentioned In This EpisodeMichael EasterCal NewportBooks: The Comfort Crisis and Scarcity Brain by Michael EasterNetflix documentary Buy NowSix-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 StuffBONUS(01:00:30) Roger reads an excerpt from his grandfather's WWII journalREFERENCESWade PfauMorningstar The Retirement Manifest- Fritz GilbertDaughterhood.orgChristine BenzSix Shot SaturdayBOOKSHow to Retire: 20 lessons for a happy, successful, and wealthy retirement- Christine BenzBeing Mortal: Medicine and What Matters in the End- Atul GawandeKeys to a Successful Retirement: Staying Happy, Active, and Productive in Your Retired Years- Fritz GilbertRock Retirement: A Simple Guide to Help You Take Control and Be More Optimistic About the Future- Roger WhitneyShow 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.REFERENCESSimon Sinek- Originator of Humble Pie Quotehttps://simonsinek.com/Red Crosshttps://www.redcross.org/Schwab Donor-Advised Fundhttps://www.schwabcharitable.org/Fidelity Donor-Advised Fundhttps://www.fidelitycharitable.org/Upcoming Podcast Guests:Christine Benzhttps://www.morningstar.com/people/christine-benzMichael Easterhttps://eastermichael.com/Daniel Crosbyhttps://orion.com/thought-leader/daniel-crosbyTanya Nicholshttps://www.align.financial/tanya-nichols/Retirement Podcast Networkhttps://retirementpodcastnetwork.com/Six Shot Saturdayhttps://rogerwhitney.com/six-shot-saturdayShow 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.REFERENCESAsk Rogerhttps://www.rogerwhitney.com/askrogerMichael Easterhttps://twopct.comDinkytown Calculators- specifically the 1040 tax estimatorhttps://dinkytown.netSchwab Required Minimum Distribution Calculatorhttps://www.schwab.com/ira/ira-calculators/inherited-ira-distribution-calculatorSix Shot Saturdayhttps://6shotsaturday.comShow 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 SaturdayRock Retirement ClubRetirement Answer Man- FREE Resource CenterShow 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 sportLISTENER 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 approachSMART 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.netTurbo TaxRetirement Podcast NetworkSix Shot SaturdayRetirement 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 RegistrationBooks:The Great Mental Models- Shane ParrishPodcasts: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.REFERENCESGreat Mental Models-  Rhiannon Beaubien Shane ParrishInto Thin Air- Jon KrakauerLive Long and Well with Dr. BobbyOverseas Adventure TravelThe History Chicks PodcastRoad ScholarsThe 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 inflationINTERVIEW 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 awaySMART 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.RESOURCESDr. Daniel Crosbyhttps://www.danielcrosby.comThe Soul of Wealthhttps://www.amazon.com/Soul-Wealth-reflections-money-meaning/dp/1804090441Six Shot Saturdayhttps://sixshotsaturday.comOrion Advisor Serviceshttps://www.orion.comMartin Seligmanhttps://www.authentichappiness.sas.upenn.edu