Podcast
Retirement Answer Man
Hosted by Roger Whitney, CFP®, CIMA®, RMA, CPWA® · EN
A top retirement podcast. Roger Whitney, CFP®, CIMA®, CPWA®, RMA, guides you on how to actually do retirement well financially and personally. This retirement podcast isn't afraid to talk about the softer side of retirement. It will teach you how to retire with confidence. Two-time PLUTUS winner for best retirement podcast / blog and the 2019 winner for best financial planner blog. This retirement podcast covers how to create a paycheck, medicare, healthcare, Social Security, tax management in retirement as well as retirement travel and other non-financial issues you'll need to address to rock retirement. Retirement isn’t an age OR a financial number. It’s finding that balance between living well today and feeling confident about your retirement. It’s about gaining more freedom to pursue the life you want. Join the rock retirement community at www.rogerwhitney.com
39episodes
Episodes
Newest firstAll episodes
Retire on Fire- Rocking an Early Retirement: Henry and Lucy's FIRE Goals
Jan 1400:53:53Tap to summarizeAs the Retirement Plan Live case study continues, Roger Whitney helps Henry and Lucy articulate what they want their FIRE retirement to actually look like—starting with values, dreaming without constraint, and then translating that vision into concrete goals. Along the way, Roger shares wisdom from older retirees about purpose, productivity, and flexibility, invites listeners to reflect on their own “magic,” and closes with a Smart Sprint and listener-submitted words for the year.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) This show is dedicated to helping you not just survive retirement, but to have the confidence and clarity to lean in and rock it.(00:23) Roger previews today’s focus: Henry and Lucy’s retirement goals, advice from seasoned retirees, a Smart Sprint, and listener words for the year.(01:00) Roger explains why retirement planning should begin with dreaming big—starting with “everything” before testing feasibility.RETIREMENT PLAN LIVE(03:25) Henry and Lucy walk through their core values and how those values shape their vision for retirement.(05:55) Roger reviews and discusses Lucy’s top ten values.(09:29) Henry talks about his top values.(11:40) Roger reflects on whether retiring early means “burying” one’s gifts, and considers how purpose and contribution can take many forms beyond traditional work.(13:44) Roger talks through Henry and Lucy’s goals for retirement and their budget for a great base life.(19:47) Lucy breaks down her thought process on her great base life budget.(23:00) Henry weighs in with his thoughts on their great base life.(24:05) They review discretionary goals such as travel, a camper van, hobbies, and future family commitments.(27:55) Lucy and Henry talk about aspirational wishes.(35:00) Lucy talks about how they react during uncertain times.WISDOM FROM RETIREES FURTHER ALONG(41:41) Listener Mike shares why he chose “FILE” (Financially Independent, Living Early) instead of full FIRE, emphasizing purpose and reduced stress.(45:10) Listener Renee offers perspective on flexibility, one spouse stepping away from work, and how lower stress improved family life.SMART SPRINT(48:08) Roger encourages listeners to separately write down their own “magic” retirement goals—without self-editing—then share and discuss them with their partner.WORD FOR THE YEAR(50:07) Roger shares listener words for the year.CLOSING THOUGHTS(53:17) Roger previews next week’s episode, where Henry and Lucy’s assets and resources will be evaluated to see what is feasible.REFERENCESSign up for our next webinar!Submit a Question for RogerSign up for The NoodleThe Retirement Answer Man
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Retire on FIRE- Rocking an Early Retirement: Meet Henry and Lucy
Jan 700:49:56Tap to summarizeAs the new year begins, Roger Whitney launches a new Retirement Plan Live case study, introducing Henry and Lucy, a couple in their mid-40s pursuing Financial Independence and Retire Early (FIRE). Roger revisits the 4% rule as a planning heuristic, explains when it can be helpful, and sets the stage for a live community analysis later this month. The episode closes with a Smart Sprint focused on updating your net worth statement and a listener’s word for 2026.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) This show is dedicated to helping you not just survive retirement, but to have the confidence to lean in and rock it.(00:30) Roger introduces a new Retirement Plan Live case study series and previews the upcoming live community meetup on January 29.RETIREMENT TOOLKIT(01:58) Roger revisits the 4% rule, explaining what it is, where it came from, and why it is often misunderstood.(04:55) Roger talks about the 25x rule commonly used in the FIRE community.(06:38) He discusses the drawbacks of using these heuristics and who they are best used for.(11:05) Roger shares how the 4% rule can help overfunded retirees move beyond scarcity and spend more intentionally.(13:55) A breakdown of FIRE- Financial Independence, Retire Early.RETIREMENT PLAN LIVE(17:41) Roger introduces Henry and Lucy.(20:01) They share how they discovered FIRE and what it means to them.(23:10) Lucy reflects on spending habits, saving, and budgeting(25:30) Henry talks about the start of their relationship.(28:12) Henry and Lucy discuss how saving impacted their lifestyle.(31:20) They discuss what drives their desire to retire early.(32:55) Roger reflects on his first impression of the FIRE Movement.(34:15) What are the obstacles of retiring so early?(38:45) Roger talks about the difference between a complicated problem and a complex problem.(40:35) Roger asks if they think about landmines that could pop up with such a long retirement.(43:57) Roger invites listeners further along the retirement path to share perspective and advice for their 40-something selves.SMART SPRINT(45:20) Roger encourages listeners to update their end-of-year net worth statement and identify trends for the year ahead.WORD OF THE YEAR(47:31) Listener Lindsay shares her word for 2026: Listen, and Roger reflects on the value of deep listening.REFERENCESSubmit a Question for RogerSign up for The NoodleThe Retirement Answer ManLivewithroger.comThe Millionaire Next Door: The Surprising Secrets of America's Wealthy- Thomas J Stanley, Ph.D.
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Year-End Planning: Estimated Tax Payments
Dec 31Tap to summarizeAs the year comes to a close, Roger Whitney reflects on the power of words, walks through an important year-end tax planning reminder for retirees, shares listener stories and perspectives, and invites listeners to choose a guiding word for 2026 as a way to approach retirement with greater intention and clarity.OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(00:00) This show is dedicated to helping you not just survive retirement, but have the confidence and clarity to lean in and rock it.(00:45) Roger reflects on slowing down, reclaiming meaning in familiar words, and recommitting to clearing the battlefield as we head into a new year.RETIREMENT TOOLKIT(03:22) Roger explains why estimated quarterly tax payments matter in retirement and how they can help prevent unwelcome tax surprises.(05:44) He outlines safe harbor rules and practical best practices for withholding taxes from Social Security, IRA distributions, and pensions.RETIREMENT LIFE LAB(13:33) Roger shares listener responses about corporate words and phrases people are eager to retire when they leave the workforce.ROCKING RETIREMENT IN THE WILD(19:33) Mick and Patty share reflections on fitness, travel, and meaning in retirement, including experiences shaped by history and family.FOCUSING FORWARD: A WORD FOR 2026(21:10) Roger discusses the practice of choosing a single word to define the coming year and reads listener-submitted words for 2026.(28:40) Roger reveals his own word for 2026.SMART SPRINT(34:07) Roger encourages listeners to reflect on the season they are entering and consider choosing a word to help guide decisions in 2026.CLOSING THOUGHTS(34:55) Roger responds to listener feedback on charitable giving and enjoying retirement, emphasizing balance, generosity, and intentional living as the year ends.REFERENCESSubmit a Question for RogerSign up for The NoodleThe Retirement Answer ManFinancial Calculators from Dinkytown.net
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Replay: The State of Retirement Planning with Michael Kitces
Jul 9, 2025Tap to summarizeAll of July we will be replaying some of our popular past episodes. In this episode, we engage with retirement planning expert Michael Kitces as we explore the evolving landscape of retirement planning. Discover the importance of flexibility in retirement spending and how to select the right retirement planner for your needs. We also discuss the implications of dying with too much money and the critical questions you should ask when interviewing potential advisors. Tune in for insights that will empower you to not just survive, but truly rock your retirement!OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN(0:00) The key to finding a retirement planner is to find someone that puts YOU and not your money in the center of everything.(00:45) Today we have a replay of last year's interview with Michael Kitces.INTERVIEW WITH MICHAEL KITCES(02:11) Roger introduces Michael Kitces and chats about flexibility.(13:30) Michael says as a professional, he does not want to have a client fail on his watch.(19:21) Roger says the quote that comes to mind when he thinks about retirement planning is: “You’re never going to be exonerated from uncertainty, pain, or the need to do work” Stutz(24:00) Most people understand that change is to be expected.(29:05) Michael talks about risk tolerance.(32:55) Michael reflects on the question “How do we help clients actually make better decisions?”(33:51) Tips on how to choose a retirement planner.SMART SPRINT (45:55) In the next seven days, evaluate the quality of your process for making decisions in retirement.RESOURCESBOOK - Die with Zero by Bill PerkinsBOOK - It’s Not Complicated by Rick NasonKitces.comBOOK - Rock Retirement by Roger WhitneyRoger’s Retirement Learning CenterFOLLOW US ON SOCIALSFollow Us on Facebook!Follow Us on Instagram
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The State of Retirement Planning with Michael Kitces
Apr 3, 2024Tap to summarizeMichael Kitces is one of the innovators in the retirement planning and financial services space. His blog and ecosystem of resources help retirees and financial advisors gain the base knowledge needed to rock retirement.On this episode of Retirement Answer Man, Michael joins me to discuss the state of retirement planning, how it has changed, and how you can live your retirement to its fullest. Listen to this interview with one of the great minds in retirement planning. OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN PRACTICAL PLANNING SEGMENT WITH MICHAEL KITCES [5:20] Trends in retirement planning[22:40] How to avoid dying with too much money [36:51] How to choose a retirement planner[43:38] How does someone choose a retirement planning firmTODAY’S SMART SPRINT SEGMENT [49:04] Evaluate the quality of your process for making decisions in retirementResources Mentioned In This Episode BOOK - Die with Zero by Bill PerkinsBOOK - It’s Not Complicated by Rick NasonKitces.comRock Retirement ClubRoger’s YouTube Channel - Roger ThatBOOK - Rock Retirement by Roger WhitneyRoger’s Retirement Learning Center
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What Is a Retirement Plan of Record?
Dec 8, 2021Tap to summarizeYou have probably heard me refer to a retirement plan of record in the past few episodes, but you may be wondering what exactly this is. I have had several listeners reach out and ask me to define this term, so in addition to hearing listener questions, today you’ll learn exactly what a retirement plan of record is and how it can help you plan your retirement. Press play to check it out. What is a plan of record? The retirement plan of record is something that I work on with my clients and I am in the process of developing a template that will be available in the Rock Retirement Club masterclass. This plan of record will help you create a current representation of your decision-making framework so that you can walk through a decision-making process in an organized way. Why is it important to have a plan of record There is so much to consider in retirement planning--asset allocations, withdrawal rates, Roth conversions, IRMAA, taxes, not to mention who your friends will be and what you’re going to do all day. With all of these considerations, it is easy to become overwhelmed by the choices if you don’t have an organized way to make decisions. Without a clear direction, your decision-making process could have you bouncing around like crazy. The 3 pillars of the agile process When creating a retirement plan of record, it is important to organize your financial goals into 3 pillars so that your plan can remain agile. First, develop a feasible plan, then, make it resilient, and lastly, optimize your plan. If you can arrange your decisions under these 3 pillars, then you can think through the process in an organized way. A retirement plan of record can ensure that your decisions reflect your values and goals. You’ll be able to create feasible spending goals based on your resources. Your plan needs to be resilient so that you can manage risks. Once you have your plan of record in place then you can work through each decision while referring to your plan. You’ll be able to see the changes you are considering within your organized process and create a what-if scenario by making a copy of your plan of record and adjust accordingly. This way you’ll be able to flush out the implications of this new variable so that you can examine the decision in a thoughtful way. The plan of record is a useful tool to accomplish organized thinking that you can execute in a consistent rhythm so that you can stay agile and make the most of your life regardless of what happens. Your plan of record allows you to focus on what you can control. OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN WHAT DOES THAT MEAN? [3:50] What is a plan of record?OUR SPONSOR [12:22] Check out LTCI Partners for your long-term care insurance needsLISTENER QUESTIONS [13:31] Lee is worried about inflation--should she work longer?[22:05] Thinking about Social Security claiming strategies[28:18] How IRMAA surcharges work each year[33:26] How to deal with switching from an HSA to Medicare[35:32] Filling up tax bracket bucketsTODAY’S SMART SPRINT SEGMENT [39:03] Review your retirement contributions to make sure you are hitting the numbers you wantResources Mentioned In This Episode Episode 385 - The 4% RuleEpisode 395 - Retirement Risk BasicsCheck out LTCI Partners for your long-term care insurance needsRock Retirement ClubRoger’s YouTube Channel - Roger ThatBOOK - Rock Retirement by Roger WhitneyWork with RogerRoger’s Retirement Learning Center
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Retirement Withdrawal Strategies: Matching Your Assets to Your Spending
Jul 21, 2021Tap to summarizeWhen it comes to creating your retirement withdrawal strategy there is no one-size-fits-all solution. You have to determine what is right for you. That’s why we have been exploring different withdrawal strategies this month on the Retirement Answer Man show. If you missed the last couple of episodes go back and listen to learn about the safety-first strategy and safe withdrawal rates. On this episode, we are digging into asset-liability matching. Press play to learn more about this hybrid approach to withdrawing your assets in retirement. What is asset-liability matching? Asset liability matching is a term that is used in the pension planning world, but you can use it to describe your own assets and liabilities. Your liabilities are your spending or the debts that you need to cover. Your assets are your financial capital. If you prefer, you can also think of your 401K as deferred income rather than as your investment assets if that helps you come to terms with spending it. Basically, asset-liability matching is when you match up your deferred assets with your consumption to make sure that you have your spending covered in retirement. Where does this strategy fall among the retirement withdrawal strategies? On one end of the spectrum, the safe withdrawal rate strategy skims along the top of your investments. It only dips into them as needed. On the other side of the coin, the safety-first approach prefunds all or the majority of your retirement journey. Asset liability matching falls somewhere in between these two extremes. I may be biased towards this approach since I use this structure coupled with agile retirement management with my own clients. Since I value flexibility in retirement, this withdrawal strategy fits my ideology. Start thinking about which way you lean on this spectrum, so you can begin to build your retirement withdrawal strategy framework in the next episode. What's your baseline? To execute the asset-liability matching strategy, you’ll first need to establish a contingency fund or a standard emergency fund as a buffer. The next step is to plan your spending over the first 5 years of retirement including your tax estimates. Once you isolate how much you’ll need from your financial capital, then you can build an income floor. The rest of your assets can then go into a core, growth-based investment portfolio. With this strategy, you’ll get a mix of protection against sequence of return risks in the near term and a hedge against inflation in the long term. What are the benefits of asset-liability matching? This is a good strategy to use if you value optionality. Since retirement is such a big life change it is nice to have a lot of liquidity early on. Retirement does not simply mean that you stop working. Your entire life changes and it can be difficult to understand how it will change when you are in the planning stage. Having this liquidity in the income floor can give you confidence and flexibility as you navigate this momentous life change. Another benefit of asset-liability matching is that you mitigate the sequence of return risk. Having an income floor in place can give you many options if the world falls apart early on in retirement. You may want to pivot to a safety-first approach or safe withdrawal rate as you age, but asset-liability matching gives you plenty of room to adjust while you are figuring this whole retirement thing out. I am naturally biased towards matching assets to spending since this is the strategy that I use with my clients, but there is no single best withdrawal strategy to use in retirement. You’ll need to consider what is right for you. Make sure to listen to all 3 Retirement Withdrawal Strategies episodes to consider which strategy fits your needs and come back next week so that you can learn how to create a framework to navigate this crucial piece of retirement planning. OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN WHAT DOES THAT MEAN? [2:30] What is asset-liability matching? PRACTICAL PLANNING SEGMENT [6:39] Where does asset-liability matching fall in line with the other withdrawal strategies? [9:20] What is a baseline? [12:50] How will you find adjustments along the way? [13:43] What are the benefits of this strategy? LISTENER QUESTIONS WITH NICHOLE [19:15] How to calm the worry about retirement [25:21] Do I take the pension or the lump sum? [29:55] What happens if your money management platform gets hacked? TODAY’S SMART SPRINT SEGMENT [35:42] Do you know of a void in your first year of retirement? Resources Mentioned In This Episode Rock Retirement Club Roger’s YouTube Channel - Roger That BOOK - Rock Retirement by Roger Whitney Work with Roger Roger’s Retirement Learning Center
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Retirement Withdrawal Strategies: The Safety First Approach
Jul 14, 2021Tap to summarizeOne of the biggest questions of retirement is how to withdraw your money. You can’t have a successful retirement without first planning how to withdraw your money. That is why we are discussing different retirement withdrawal strategies this month. Last week we covered the infamous 4% rule and today you’ll learn about the safety-first approach. In our next episode, you’ll hear about a hybrid approach and in the last episode of this series, you’ll discover how to build a framework for your own retirement withdrawal strategy. Are you ready to educate yourself on the various ways that you can withdraw your money in retirement? Press play to get started. What is the safety-first strategy? In the previous episode, you learned about a safe withdrawal strategy using the 4% rule. Whereas the 4% rule is a portfolio-based strategy, the safety-first strategy takes the opposite approach. Safety first ignores safe withdrawal rates and asset allocation. Instead, it focuses on creating income sources via various guaranteed income vehicles. The idea behind the safety-first approach is that retirement is too important to have variables like sequence of return risk that could ruin your retirement. How to implement the safety-first approach Since you only get one shot at retirement, the safety-first method secures a base income by using the assets you have. Prioritization is a key component to safety first. The first thing one must do to utilize the safety-first approach is to calculate your base needs over the span of your lifetime. Once you have this number, then you’ll subtract the income from your social capital so that you can see what’s left. With safety-first, you will secure your base needs by utilizing bond ladders or income annuities. After creating your income floor, then you can focus on building your contingency fund to help with life shocks. Once both of these bases are met then you can focus on any other retirement goals you may have. What are the advantages to safety-first? The first advantage that comes to mind with safety-first is peace of mind. By using the safety-first approach you won’t have to worry about the markets because you know that no matter what happens your base needs will be met. Another advantage is that this approach is easy to manage. There is not much to do after you have the plan in place but collect your monthly paycheck which makes this plan ideal for later in life. One more advantage is that since your needs are met you can focus on being more growth-oriented with the rest of your portfolio. The disadvantages of this approach The main disadvantage that I see with this approach is the lack of flexibility. If you have listened to the show before, you know that my methodology is all about staying agile. People change their minds a lot and life can completely change after retirement, so tying up your assets in an annuity can take away the power to change your mind. Another downfall to safety first is increased inflation risk. Most annuities do not adjust for inflation, so if there are any spikes in inflation you could be at risk. Listen in to discover if the safety-first approach is the right one for you. OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN PRACTICAL PLANNING SEGMENT [1:30] What is the safety-first strategy? [4:35] What are secure assets? [8:06] When to implement the safety-first strategy [10:20] Advantages and disadvantages to the safety-first strategy LISTENER QUESTIONS [17:55] How should I incorporate an inherited IRA into my retirement plan? [20:10] Taxes and Roth conversions [23:45] Does the 4% rule take into account social capital? [24:54] How do bonds work? [28:38] A pro-rata question TODAY’S SMART SPRINT SEGMENT [30:40] Do a basic calculation to figure how much of your base needs will be covered by guaranteed income sources THE FEEDBACK BOOTH [32:43] Women run the finances too [34:35] My 3rd attempt to discuss financial planning fees Resources Mentioned In This Episode Wade Pfau BOOK - Safety First Retirement Planning by Wade Pfau Michael Kitces Rock Retirement Club Roger’s YouTube Channel - Roger That BOOK - Rock Retirement by Roger Whitney Work with Roger Roger’s Retirement Learning Center
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You’re Retired! How to Use Your Accounts: Creating a Withdrawal Strategy to Fund Your Retirement
Apr 10, 2019Tap to summarizeYou have been diligently saving in tax-deferred accounts for years and you finally have enough squirreled away to fund your retirement. But we need to discuss the elephant in the room. You have a looming tax burden that if not handled correctly can really mess up your retirement plans. On this episode, I’m going to teach you how to come up with a withdrawal strategy to help you fund your retirement. Are you ready to learn how to withdraw from your retirement accounts without Uncle Sam getting more than his fair share? Then listen to this episode of Retirement Answer Man to help you plan your retirement withdrawal strategy. The looming tax burden Your money has been growing tax-deferred year after year. This is a great way to get you to save for retirement, but now it’s time to pay the piper. Do you know what your tax liability is? If you have $1 million in tax-deferred accounts and you take it all out in one year then you’ll have to pay 30% in taxes. Your million dollars just shrank to less than $700k. The good news is that you can minimize your tax liability in how you withdraw from your accounts. The great thing about retirement is that you have more control than ever in deciding which tax bracket you will fall under. You can manage how much you take out and where that money comes from. You need to be more tax aware than ever before How do we take advantage of the tax system to maximize the amount of money that we put in our pockets? Early on in retirement is when you start to think of spending in big ways. You may want to buy an RV or a vacation home or remodel your current home. Many people spend on these extraordinary expenses with little thought as to how they should withdraw the money for these projects. You want to be aware of the tax brackets when you decide how you withdraw your income. Thinking about tax strategy is not nearly as exciting as when you think about investment strategy. It’s not glossy and sleek, but having the right tax strategy is even more important at this point in your life and having the right strategy to fund your retirement can save you thousands of dollars down the line. What are your income sources in retirement? There are usually 3 sources of income to fund your retirement. There is social capital like pensions and Social Security. Next, you have human capital, which is the income that you may earn in pretirement. Lastly is financial capital or the money you have saved in various accounts. Your financial capital is then broken up into 3 categories. The money you have already paid taxes on, money from tax-deferred assets (401K’s and IRA’s), and tax-free assets (Roth IRA’s). You have to have a strategy on how to manage all of these buckets of differently taxed assets. Having the 3 buckets gives you some flexibility on how to pull money out of these accounts. What can you do to frame your withdrawal strategy to fund your retirement? Retirement tax strategy can get really complicated. That’s why it is so important to have a plan. Follow these steps to help you minimize your tax burden. Know your income sources. Figure out what your social capital, human capital, and financial capital are and identify where you have control. Know your planned spending. This sounds simple but you should understand the sequence of your spending and plan for the lump sum expenses. Decide how you will pay for them. Model how to find tax equilibrium. You need to look at your tax bracket and plan year by year. Think about where to put your investment assets. Think dynamically to stay agile and flexible each year. OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN HOT TOPIC SEGMENT [2:20] That looming tax burden [6:33] Be aware of your tax bracket as you withdraw your income PRACTICAL PLANNING SEGMENT [9:25] A correction from a previous episode [10:53] Have a withdrawal plan [16:45] RMD is waiting for you [19:02] The ACA adds another element of complexity to your withdrawal strategy [23:12] What can you do to frame your withdrawal strategy THE HAPPY LAB SEGMENT [26:02] Human connection is awesome to see TODAY’S SMART SPRINT SEGMENT [28:05] Outline how you will withdraw money in your first 2-3 years of retirement Resources Mentioned In This Episode Rock Retirement Club Roger’s YouTube Channel - Roger That BOOK - Rock Retirement by Roger Whitney Work with Roger Roger’s Retirement Learning Center The Retirement Answer Man Facebook Page
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