Setting Retirement Goals: The Paradox of Knowing What You Want

In this episode, Roger Whitney continues his four-week series on retirement goal setting, focusing on the importance of building agile retirement goals. He emphasizes creating the right conditions for discovering what you truly want in retirement, rather than fixating on specific desires. Roger shares insights on self-discovery, the anatomy of goals, and the significance of establishing a solid foundation for a fulfilling retirement. Tune in to learn how to navigate your retirement journey with confidence and purpose!OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) This week Roger talks about building agile retirement goals.PRACTICAL PLANNING SEGMENT(03:10) The intent is to build goals that are more meaningful to you so you can rock retirement.(07:00) How do you set goals that are meaningful to you in an agile way?(07:39) You want to start with self-discovery and establishing or revisiting your values.(09:53) Focus on creating conditions to explore your values and build a life where fulfillment naturally follows. (13:43) You have to experiment to determine what is right for you.(18:30) Roger talks about the anatomy of a goal, specifically low stakes goals that maximize optionality in retirement planning.(21:08) Roger talks about high stakes goals.(25:04) Low-stakes goals help you experiment, make confident decisions, and discover what truly supports a fulfilling retirement. LISTENER QUESTIONS(27:30) Roger answers Melissa’s questions about rolling over an IRA without penalty and whether to trust a flat-fee fiduciary firm that offers to manage her accounts. (33:06) Greg asks Roger to revisit healthcare before Medicare. (34:17) Rob asks about deferring Social Security to age 70 and whether he still receives COLA increases in addition to the 8% delayed retirement credit.(36:03) Chris asks about using only a total world stock and bond index for his portfolio.(40:20) Roger advises keeping a local contingency fund so you always have accessible cash and don’t feel “cash poor.”SMART SPRINT(43:20) Go back to your retirement goals and the plan you’ve put together. Look at them through the lens of our recent discussionRESOURCESSign up for our next Webinar!Scarcity Brain: Fix Your Craving Mindset and Rewire Your Habits to Thrive with Enough- Michael EasterSubmit a Question for RogerSign up for The NoodleFOLLOW US ON SOCIALSFollow Us on Facebook!Follow Us on Instagram

💬 Show NotesIn this episode, Roger Whitney kicks off a four-week series on retirement goal setting, tackling the paradox of knowing what you want in retirement. He discusses the challenges of articulating desires for a life stage that many have never experienced, emphasizing the importance of not oversimplifying retirement goals. Tune in to explore how to set the right conditions for a fulfilling retirement and avoid the pitfalls of external scripts and societal expectations.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MANPRACTICAL PLANNING(01:32) We are starting a four week series on retirement goal setting.(02:44) Why “What do you want to spend in retirement?” isn’t the right question.(05:54) Next week, we'll talk about how to be more nuanced when setting retirement goals.(09:40) The problem with following other people’s scripts(13:14) The problem of getting too detailedLISTENER QUESTIONS(16:36) Am I required to keep an Inherited IRA separate from my other IRA's or can it be combined with an existing IRA for simplicity?(19:11) Richard wants to noodle on the retirement distribution order.(23:40) I’m 3-5 years from retirement. Is now the right time to join Rock Retirement Club?(26:29) Estate preparation hint from Jane on the three passwords a family needsSMART SPRINT(28:19) In the next seven days, revisit your retirement goals.EXTRA(29:11) Shauna and I are celebrating our 35th wedding anniversary this week!REFERENCESSubmit a Question for RogerSign up for The NoodleFOLLOW US ON SOCIALSFollow Us on Facebook!Follow Us on Instagram

SHOW NOTESIn this episode, Roger Whitney sits down with Carl Richards, a financial advisor-turned-artist, to talk about keeping retirement planning simple and meaningful. They dive into the idea of “elegant simplicity,” the importance of knowing your goals, and making decisions that actually work for you. Plus, hear inspiring stories from club members to help you rock your retirement!OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) The ultimate goal in building a retirement plan of record is elegant simplicityCHAT WITH CARL RICHARDS(02:00) Roger introduces Carl Richards.(03:50) Carl started sketching to help explain complex financial concepts.(07:33) Roger asks Carl about his new book coming out in October.(11:00) Roger and Carl talk about the differences between simplistic and elegant simplicity in retirement planning.(17:55) How do you decide when you have enough information to make a decision?(22:19) There are many different types of decisions that need to be made- Decisions where you need a lot of research versus decisions where you already have all of the information.(26:58) Writing makes decisions tangible versus rehashing them in your brain(28:19) Carl talks about mimetic desire and figuring out what it is that you really want.(39:45) Carl says he loves the idea of experiment design.(41:40) Carl talks about living a life of meaning.(46:50) There is a deep source of identity and purpose that comes from work. When you remove that, what do you replace it with?(52:58) Carl talks about competing values.(55:00) Roger talks about the Retirement Life Lab in the Rock Retirement ClubSMART SPRINT(56:43) In the next seven days, review your retirement plan and look for ways to simplify it so it’s easier to manage.CONCLUSION(57:37) Roger says that what stuck out to him from the conversation is how difficult it can be to truly know what we want and how easy it is to just grab someone else’s goals, when what we really need is to slow down and take the time to define our own so we don’t end up living a life that doesn’t fit us.REFERENCESSubmit a Question for RogerSign up for The NoodleThe Retirement Answer ManBehaviorGap.com- Carl RichardsFOLLOW US ON SOCIALS!Follow Us on Facebook!Follow Us on Instagram

SHOW NOTESIn this episode, we tackle the often-overlooked topic of taxes in retirement with expert Erin Coe, an enrolled agent. Discover how to avoid unexpected penalties and interest on your IRA distributions and Roth conversions. We also share an inspiring retirement success story from Lottie, reminding us of the importance of clarity and simplicity in planning. Tune in for practical advice that will help you rock your retirement!OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) Today Erin Coe joins Roger to talk through penalties and interest during retirement, what those things are.ROCKIN’ RETIREMENT IN THE WILD(01:30) Lottie says she got caught up in ideas about the perfect retirement and it was getting in her way.PRACTICAL PLANNING SEGMENT WITH ERIN COE(03:31) Today we're going to talk about penalties and interest when it comes to taxes.(04:52) Erin explains the difference between a tax penalty and interest.(11:14) Roger asked Erin how to calculate an estimated quarterly tax if not doing safe harbor?(13:55) Erin shares her tips on tax returns.(16:08) Being prepared is always better than being taken by surprise when it comes to taxes.LISTENER QUESTIONS(16:40) Roger makes a correction on a past statement.(17:25) Jeff asks a question about the pie-cake explainer video.(20:30) Dave asks a question about helping his elderly mother with her finances.(26:11) Robert asks about getting two mortgages near retirement.SMART SPRINT(32:15) Over the next seven days, download the 1040 form and review how it applies to your retirement income. Decide whether you’ll handle taxes through estimated payments, safe harbor payments, or automatic withholdings from distributions.REFERENCESSubmit a Question for RogerSign up for The NoodleThe Retirement Answer ManIRS.gov FormsFOLLOW US ON SOCIALS!Follow Us on Facebook!Follow Us on Instagram

💬 SHOW NOTESIn this episode, we focus on empowering you to navigate retirement with confidence. We break down the process of reading a Social Security statement, examining each section and its significance. Additionally, we tackle listener questions regarding retirement strategies, second mortgages, and Roth conversions. Join us for practical insights that will help you make informed decisions as you approach this new chapter in life.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) Today on the show we are going to walk through how to read a social security statement.(01:10) Roger talks about doing extensive blood work every year and the similarities between the protocol of blood tests and retirement planning.PRACTICAL PLANNING SEGMENT(09:52) Sign up for the Noodle to watch a video of Roger walking through the Social Security statement.(10:30) Roger breaks down the Social Security statement section by section- go to SSA.gov to get a pdf version of your statement.(17:07) Roger reads through a few of the Important Things to Know bullet points on page two of the statement.LISTENER QUESTIONS(21:21) Jeff asks if there is any difference in retirement strategy if he decides to delay retirement until age 70.(25:22) Mary says she is going through a divorce at age 63 and recently started listening to the podcast to educate herself on retirement and asks for advice for finding a retirement planner.(29:36) Julie says her husband is looking at sudden retirement at age 59 ½. She wants to know if there are any episodes or resources Roger can direct him to to get a great overview of retirement. (32:48) Joy has a question about ROTH conversions.SMART SPRINT(34:18) In the next seven days, make sure you have your most recent Social Security statement.REFERENCES Submit a Question for RogerSign up for The NoodleThe Retirement Answer ManSocial Security AdministrationFOLLOW US ON SOCIALS!Follow Us on Facebook!Follow Us on Instagram

💬 Show NotesIn this episode of the Retirement Answer Man, Roger Whitney sits down with Peter Lazaroff, Chief Investment Officer at Plancorp, for a thoughtful conversation on the power of simplicity in retirement planning. Together, they unpack the common traps of overcomplicating investments and the cognitive biases that often lead us astray. Peter also offers valuable insights into private equity and other complex investment strategies—highlighting when they might help, and when they might hurt. Don’t miss this episode if you're looking to build a retirement plan rooted in clarity, confidence, and peace of mind.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) Today Roger chats with Peter Lazaroff about bringing simplicity to retirement planning strategies.(02:44) We tend to overcomplicate everything when it comes to retirement planning.(04:09) Complexity makes us think something is better or more sophisticated.(05:35) “Anything one needs to market heavily is either an inferior product or an evil one.”- Nassim TalebROCKIN’ RETIREMENT IN THE WILD(06:22) Todd shares reflections on why he travels in retirement.INTERVIEW WITH PETER LAZAROFF(10:16) Think of your assets that you need to rock retirement in their own bucket, if you have excess- put it in its own bucket.(11:05) Complex investments are just active managers in a different wrapper.(11:45) Peter Lazaroff joins Roger to discuss retirement investing and private equity.(12:25) Peter discusses his books and announces that he has a new one coming out in 2026.(15:00) The core intent of retirement planning is to have core confidence that you can live the life you want now, but also when you're ninety.(15:51) Ultimately the goal in retirement planning is elegant simplicity. (20:00) Peter reflects on the business of investing.(23:02) Investing creates an illusion of control.(26:38) Peter discusses the benefit of simplicity and how it helps living heirs when it is time to settle an estate.(28:33) Roger chats about an executive order paving the way for private equity to become part of 401ks.(30:08) Peter talks about the steps of the probabilistic decision framework.(35:48) From 2020 to present, private equity has not added return over public equity.(38:30) If the yield is high and you can’t find the risk, it doesn’t mean it's not there.(42:08) Private investments are not inherently good or bad, but they are not necessary and can add complications.(42:50) Peter shares an example of complexity that he would be more welcome to.(47:25) If you don’t believe in traditional active management- you should be out on private investments.SMART SPRINT(48:00) In the next seven days, choose one area—retirement planning, investments, or any aspect of life you want to improve. Before adding anything new, ask: What can I remove or simplify first?REFERENCESPlancorp- Your Financial Life AdvocatePeterLazaroff.com: Free BookBOOKSScarcity Brain- Michael EasterAntifragile: Things That Gain from Disorder- Nassim Nicholas TalebMaking Money Simple: The Complete Guide to Getting Your Financial House in Order and Keeping It That Way Forever- Peter LazaroffFOLLOW US ON SOCIALS!Follow Us on FacebookFollow Us on Instagram

💬 Show NotesIn this episode, we explore the intricacies of navigating Medicare in 2025 with Medicare expert Danielle Roberts from Boomer Benefits. Discover the recent changes in Medicare Advantage and Part D plans that could impact your healthcare decisions. We also share inspiring stories of individuals embracing life in retirement and discuss the importance of reviewing your Medicare options annually. Tune in for valuable insights and practical tips to ensure you make the best choices for your health coverage!OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) Today on the show, we are going to explore how to navigate Medicare in 2025ROCKIN’ RETIREMENT IN THE WILD(01:30) Roger shares a story from a listener who was “jolted” into action.(03:00) Jamie says she plays mahjong with a group of retired ladies and started a book club.PRACTICAL PLANNING SEGMENT(04:55) Roger introduces Danielle with Boomer Benefits to chat about Medicare(05:25) What is the state of Medicare right now?(10:25) How important is it to pay attention to the annual notice of change?(12:15) What are the key things to pay attention to when they get these notices?(17:41) Medicare Advantage is heavily marketed and people have strong opinions about Medicare Advantage versus original Medicare.(25:05) Roger talks about the company- Boomer Benefits.(26:40) What is the service level of Boomer Benefits? What kind of support do you get after you enroll?LISTENER QUESTIONS(31:26) Visit Askroger.me to submit questions.(31:46) Terri asks for reputable sources for buying health insurance after retirement.(35:40) Beth asks a question about the Affordable Care Act and putting contributions into an HSA account without an employer deduction. SMART SPRINT(38:36) In the next seven days, put a date on your calendar for October to review your healthcare coverageBONUS(39:30) Roger shares about what he has been doing in Colorado for the last three weeks.REFERENCESSubmit a Question for RogerSign up for The NoodleThe Retirement Answer ManBoomer BenefitsMedicare.govInflation Reduction ActHealthcare.govFOLLOW US ON SOCIALS!Follow Us on Facebook!Follow Us on Instagram

💬 SHOW NOTESIn this episode, we explore the implications of the saying 'nothing is for free' in the context of retirement planning. Join Roger Whitney, a seasoned retirement planner, as he shares a heartfelt story from a listener, David, who exemplifies the spirit of 'rocking retirement.' Additionally, Roger tackles the critical question of whether to accept a free retirement analysis from brokers, discussing the potential costs and consequences involved. Tune in for insightful advice on navigating your retirement journey with confidence!OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) Roger Whitney: This podcast is dedicated to helping you rock your retirementROCKIN’ RETIREMENT IN THE WILD(01:06) David emailed in saying he and his wife are leaning into rocking retirement.PRACTICAL PLANNING SEGMENT(03:00) Our title question today came from Phil- he wants to know if it is worth going through free retirement analysis.(07:15) What are some of the cautions or things you want to understand about free retirement analysis?LISTENER QUESTIONS(13:37) Doug shares feedback about my Smart Sprint on being present.(15:11) Rick says he'd like to simplify portfolio.(19:30) Cliff sent in a question about stress testing your retirement plan.(27:09) Dave has a question about moving a 401k to an independent advisor upon retirement.(32:55) Bob asks which retirement plan should you use first: Social Security or savings.SMART SPRINT(38:10) In the next seven days, pay attention to “free” offers—whether it’s a retirement analysis, discount, or credit card perk—and notice the hidden costs or unintended consequences that may come with them.REFERENCESSubmit a Question for RogerSign up for The NoodleThe Retirement Answer ManFOLLOW US ON SOCIALS!Follow Us on Facebook!Follow Us on Instagram

💬 Show NotesIn this episode, Roger explores how naming and recognizing the different phases of life can bring clarity to the retirement journey. A listener’s question about inherited money sparks a conversation about direct indexing—what it is, when it makes sense, and what to watch out for. He also shares how to navigate calm, choppy, and rough waters in retirement planning so listeners can move forward with more confidence and control.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) Today we will talk about direct indexing and answer some more of your questions.(01:04) Roger talks about acknowledging and naming things in life.(04:19) There are four levels that Roger wants to acknowledge with clients- calm waters, choppy waters, rough waters, and change of course.ROCKIN RETIREMENT IN THE WILD(08:55) Brian says he focuses on spending time with family in retirement.(09:20) Don says electric bikes are game changers.PRACTICAL PLANNING SEGMENT(10:30) John asks a question about direct indexing.(13:17) Direct indexing is when you buy the individual stocks of an index in your own account instead of a fund, allowing for tax benefits and customization but with more complexity.(16:32) Should you do this if you are concerned about taxes? What are the benefits? The drawbacks?(20:38) Roger says exchanging traded funds has some advantages over indexing.LISTENER QUESTIONS(21:20) Scott has a follow up question about getting a mortgage in retirement.(28:45) An anonymous listener says it's too late for long term care and wants a recommendation for a low risk investment.(35:40) Our next question comes from John related to being an executor for an estate.(39:17) Dan asks a question about rebalancing.SMART SPRINT(43:46) In the next seven days, take a small step by naming the season of life you’re in—calm, choppy, rough, or changing direction—so you can better focus your energy on where to lean in right now.UP NEXT(44:40) Next week Roger chats with Tanya Nichols on the show and answers some of your questions.REFERENCES Submit a Question for RogerSign up for The NoodleThe Retirement Answer ManFOLLOW US ON SOCIALS!Follow Us on Facebook!Follow Us on Instagram

💬 Show NotesIn this episode, Roger Whitney welcomes elder law expert Kathy McNair to discuss the often-overlooked but crucial topic of elder care, especially for those retiring solo. They explore what elder law really means, how it differs from traditional estate planning, and why having the right legal documents—like healthcare proxies and powers of attorney—is vital for protecting your future and legacy. Alongside practical insights on guardianships and conservatorships, Roger shares a fresh perspective on gratitude and contentment as essential mindsets for a meaningful retirement. Plus, he answers listener questions and wraps up with a special personal announcement.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) Today on the show, we are going to start exploring elder care with an expert in the area, Kathy McNair.(01:06) Let’s talk about gratitude and contentment.ROCKIN RETIREMENT IN THE WILD(04:40) Roger and Kimberly are embracing retirement as an opportunity to live fully and give back and reconnect with things that matter most.INTERVIEW WITH KATHY MCNAIR(06:26) Roger introduces Kathy, an elder attorney and founder of seniorsolutionsinfo.com and SoloAllies.com(08:16) Kathy explains elder law and talks about her background.(10:20) What is the difference between a guardianship and a conservatorship? (12:00) Roger says one of his clients has a question about his aging mother and how to approach the situation.(17:26) Is a power of attorney enough when someone is not cognitively capable?(21:33) Kathy talks about starting SoloAllies.com.(25:35) For seniors who are aging without close family, the key is to start building your team while you’re still healthy and capable. (31:30) The hardest role to solve sometimes is the healthcare proxy role.LISTENER QUESTIONS(33:07) Submit questions on AskRoger.me.(35:45) Joe asks a question about the interview with Charles Ellis.(42:30) Joe asks “Can you explain some comments in Charles Ellis book?”(45:00) Brian says he’s thinking of doing an NUA with company stock.SMART SPRINT(49:13) In the next seven days, pick an activity and don’t listen to music or a podcast or anything. Be Present.BONUS(49:00) Roger explains that Agile Retirement Management has merged with Align Financial.REFERENCESSoloAllies.comKathy McNair- SeniorSolutions.comSubmit a Question for RogerSign up for The NoodleThe Retirement Answer ManFOLLOW US ON SOCIALS!Follow Us on Facebook!Follow Us on Instagram