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 10/40 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