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Retirement Answer Man

Roger Whitney, CFP®, CIMA®, RMA, CPWA®

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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 ...
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If you’re 55 and older and thinking about retirement, then this is the only retirement podcast you need. From tax planning to managing your investment portfolio, we cover the issues you should be thinking about as you develop your financial plan for retirement. Your host, Ryan Morrissey, is a Fee-Only CERTIFIED FINANCIAL PLANNER TM who lives and breathes retirement planning. He’ll be bringing you stories and real life examples of how to set yourself up for a successful retirement.
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Take Back Retirement

Stephanie McCullough & Kevin Gaines

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You’re a woman on the cusp of “retirement” naturally feeling some anxiety. We are two financial planners who take this subject seriously (but ourselves less so). We will help you feel more confident about your choices by cutting through the myths and mysteries. Through conversations and interviews with both subject-experts and women who have gone through what you are approaching, you will have the correct information and motivation to be in control of your future.
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How can you protect your data and personal information from IRS scammers and criminals? Everyone is afraid of being audited by the IRS. Maybe you’re scared you may have filed your taxes incorrectly. Criminals take advantage of that fear to perpetuate their scams. But there are some simple things you can do to avoid falling victim to these scams. I’…
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We would all love to have that magic number–the exact amount we need to retire. However, since there are so many unknowns it is impossible to attain an exact number. This is why the big question of retirement is a complex one. In this episode, I’ll walk a listener through the process of how she can learn how much she really needs to retire. Make su…
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“Every single thing in my life that has ever terrorized me and terrified me, and I avoided like nobody's business, when I finally either had no place else to run, or I chose to turn around and face it, it has never been as bad as I thought it would be. It has never been as shameful as continuing to avoid.” Our hosts Stephanie McCullough of Sofia Fi…
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Do you usually get a tax refund? What do you typically do with your tax refund? Do you have it earmarked for a specific purpose? As we’re inching closer to the tax filing deadline, I thought it would be interesting to share some ways you can wisely invest your tax refund. I’ll cover 9 ideas you can consider to make good use of your money. You will …
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Have you been wondering what retirement is like for real retirees out in the wild? With the success of our Retirement Plan Live series, we decided to try mini-case studies to learn more about what retirees like you are doing to rock retirement. In this episode, you’ll hear some feedback from Sarah who asked a question on the show about a year and a…
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Do you own stock in the company that you work for in your 401K? Net unrealized appreciation could potentially save you a significant amount of money on your taxes when you start making withdrawals. I’ll share how to take advantage of the process as well as mistakes to avoid making in this episode of Retire with Ryan. You will want to hear this epis…
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Michael 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 h…
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“It's not a line that you are either academic or creative, or you are either scientific or creative, or you are either mathematical…They're not separate.” -Claire Waite Brown Ever felt like your creative spark got lost in the shuffle of life? Our hosts Stephanie McCullough of Sofia Financial and Kevin Gaines of American Financial Management Group s…
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The Federal Reserve Met on 3/20/24 to discuss monetary policy and whether or not to raise or lower interest rates. They announced that they won’t make any changes. Most experts believe that they’ll lower interest rates in June. So should you start selling your money market funds and short-term bond funds? When should you do it? Should you move the …
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Have you ever wondered why it is so hard for you to spend your money? Even now after all these years of saving you know you have enough, but it’s hard to let go and untie those purse strings. Today, my friend and renowned author, Michael Easter joins me to discuss overcoming frugality from a different perspective. Click play to hear about the evolu…
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As we get closer to the tax filing deadline (April 15th), I wanted to talk about contributing to a Roth IRA or traditional IRA. In this episode, I’ll cover contribution and deduction limits, spousal IRAs, and non-deductible IRA contributions (and why you’d want to consider them). You will want to hear this episode if you are interested in... [1:16]…
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For the past ten years, we have been exploring how to do retirement right so that you can get down to the business of living a great life. This is why this month we have had a series of special guests. Today’s guest is behavioral investment expert and author Dan Crosby. Together we explore why it is so hard to overcome your money mindset and how yo…
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“I first ask this question: What is the number to make you feel successful? You and no one else. It might be a scary number. There’s nothing wrong with fear.” -Ella Glasgow Ever felt the anxiety-inducing pressure of pinning a price tag on your brainchild? Our hosts Stephanie McCullough and Kevin Gaines break that down with guest Ella Glasgow, who's…
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What is Indexed Universal Life Insurance? Is it something you should consider investing in? Are the rumors you’ve heard about it true? In this episode, Andy Panko (of Tenon Financial) and I dispel 7 myths that are circulating about UILs and we cover what you need to know to make an informed decision about the insurance product. You will want to hea…
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Retirement planning has changed over the years, but has the industry evolved to keep up? Your retirement needs are much different from those of your parents' generation. This is why it is important to focus on retirement planning in a holistic way rather than from solely a financial perspective. Morningstar’s Christine Benz joins me today on this e…
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On December 23rd, 2022, congress passed the SECURE 2.0 Act. Among the many changes, one of them had to do with 529 plans. You can now make tax-free and penalty-free rollovers from a 529 plan to a Roth IRA. This became effective 1/1/2024. Before this, if you wanted to take a non-qualified withdrawal from a 529 plan (using the money for something out…
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This month we celebrate the Retirement Answer Man’s 10th anniversary milestone with several guests throughout the month. Today we welcome Professor Rick Nason, author of It’s Not Complicated, to discuss complicated vs complex thinking. If that discussion didn’t Stick around for the listener questions with Tanya Nichols and Bring It On with Dr. Bobb…
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“If they're only worried about that current year, then that's what they're going to focus on. Let your accountant know, ‘I'm interested in what my tax bill's going to be three, five years down the road. So, if there's something we need to be doing, let's have a conversation.’” Tax season is among us. Or as Kevin would sing, “It’s the most wonderful…
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What are some overlooked benefits of investing for retirement in a brokerage account? Why would you want to invest in a brokerage account in addition to a 401k or other retirement account? Shaun Jones—the President of Jones Fiduciary Wealth Management and author of “Unbrainwashed Investing”—shares 7 reasons to invest in a taxable brokerage account …
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Those who have FIREd like Keven Sebesta are choosing to rock life each day. In this final episode on the FIRE movement, we’ll explore what we can learn from them. Join Kevin and me to discover how you can do what FIRE is doing right. What can you learn from FIRE? Traditional retirement planning is all about achieving the end goal. Climbing the moun…
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Are you aware of how your biases—both conscious and unconscious—impact your investment decisions? Brie Williams of State Street Global Advisors joins me in this conversation to talk not only about the impact of biases on decision-making but how to cultivate an awareness of your biases to change your behavior, ultimately leading to better decisions.…
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Over these past few weeks, we have been discussing the FIRE movement with Kevin Sebesta, a coach in the RRC who achieved FIRE some time ago and has been rocking retirement ever since. This week Kevin helps me explore the challenges that retiring early can bring. Listen in to hear if these are similar to the issues you face in retirement. OUTLINE OF…
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“If you're looking at the costs of medical expenses over time, they've actually historically grown faster than regular inflation. Healthcare is expensive, and it goes up faster than the rest of your spending; don’t overlook it.” Listen in as our hosts, Stephanie McCullough of Sofia Financial, and Kevin Gaines of American Financial Management Group …
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Last year’s Super Bowl set the record as the most-watched TV event in Nielsen rating history at over 150 million viewers. It’s hypothesized that this year’s Super Bowl is going to set a record for something completely different: The most amount of money bet on a Super Bowl. Why? Because sports betting is now legal in 38 states. So if you’re one of …
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Now that we know what FIRE is, let’s learn the benefits. In this episode of Retirement Answer Man, Kevin Sebesta joins me to discuss the benefits of FIRE. Afterward, Mark Ross comes aboard to noodle on why creativity is important in retirement. And finally, Taylor Schulte from the Stay Wealthy podcast helps me answer some listener questions. Don’t …
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Before you think about when you’re going to retire there’s another question that should be addressed: Are you going to retire? It’s assumed that when you turn 62 or 65, you’re going to retire. And many people do count the days until they retire. But many others love the careers they’re in and can’t imagine stopping. Their concern is that they’ll ge…
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Have you heard of the FIRE movement? It’s become increasingly popular in the past few years. Even if you are technically too old to retire early, there is something we can all learn from FIRE seekers. In this episode, Kevin Sebesta, a real live FIREer joins me to discuss what FIRE is, how he achieved it, and what people who retire early do with the…
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As you enter retirement, tax planning is something that must be prioritized. A Qualified Charitable Distribution (QCD) can be a great tool in your arsenal to help you minimize the taxes you have to pay. So what is a Qualified Charitable Distribution (QCD)? How can it actually help you lower your taxes? In this episode, I’m going to cover what a QCD…
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How do you manage a joint cash flow with separate assets? In addition to discussing Mark and Mary’s situation, today I chat with Kay about how she and her husband handled finances with their late in life marriage. Kay gives us some insight on how to manage finances in a financially unbalanced relationship. You’ll appreciate her perspective on how t…
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“If you know about a certain scam, you're 80% less likely to engage with it. So, please tell everybody you know.” -Kathy Stokes Could your loved ones be vulnerable to a $9 billion wave of deception? Kathy Stokes from AARP joins our hosts Stephanie McCullough and Kevin Gaines to unravel the complexities of fraud that's sweeping the nation, hitting o…
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We’re back with Retirement Plan Live to explore how two adults who married later in life can share their resources as they age. Last week we looked at their goals both individually and together and today we’ll do the same with their resources. Listen in to hear the different ways that older adults who come together later in life can pool their reso…
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The SEC recently and historically approved 11 Bitcoin spot ETFs on January 10th. This is big news because now you can invest in Bitcoin through a brokerage account. On this episode, I’m discussing what this means for you, how you can invest in Bitcoin ETFs, and what to look out for if you're going to take that plunge. You will want to hear this epi…
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With every new year comes a list of resolutions to make this one the best yet. However, a lack of planning leaves most of these goals unfinished. On this episode, I’m sharing five financial resolutions to help you grow your money in 2024 and the follow-through steps to help make them possible. You will want to hear this episode if you are intereste…
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Do you like lemonade? If so, you won’t want to miss out on the lemonade I make on today’s episode. We’re discussing goals on this episode of the Retirement Plan Live series and we get to catch up with Lori from the 2017 Retirement Plan Live. Find out what she is up to and how to work through shared and separate goals in retirement. OUTLINE OF THIS …
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“People tend to underestimate both how long they'll live and how long they'll spend in retirement. That's something that we really need to be realistic about.” - Heather Schreiber Have you ever wondered how the labyrinth of Social Security intricacies might be uniquely affecting your retirement plan? Our hosts Stephanie McCullough and Kevin Gaines …
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Now that 2023 is officially in the history books, let’s review my 2023 market predictions to see how close I got! On this episode, we’ll be reviewing last year’s market predictions as well as making new ones for the year ahead. You will want to hear this episode if you are interested in... Reviewing Ryan’s 2023 market predictions [2:38] Looking ahe…
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If you’re married, do you have retirement planning meetings? If you’re single do you plan a time to meet with yourself to plan your retirement? What or whom do you use as a sounding board? In this Retirement Plan Live, we’re getting to know Mark and Mary–two lovely people who have found each other later in life. This mature newlywed couple is tryin…
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Today you’ll meet Mark–half of our newest case study for Retirement Plan Live. Mark and Mary are a year and a half into their new marriage and are trying to figure out how to plan the rest of their lives. On this episode, you’ll learn about Mark and his aspirations and concerns for their life together. In the next episode, you’ll meet Mary, in week…
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Are you a small business owner struggling to choose a retirement plan? Then this episode is for you! Join me as we look at the specifics of SEP IRAs and Solo 401(k)s, the pros and cons of each, and the easiest way to get your small business or self-employed retirement plan set up today. You will want to hear this episode if you are interested in...…
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Ever feel like you're wading through murky waters when it comes to retirement planning? You're not alone. Stephanie McCullough and Kevin Gaines of Sofia Financial and American Financial Management Group illuminate the path with their expertise, debunking pervasive myths that cloud the judgment of many investors. They kick things off by setting the …
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Have you ever accidentally put post-tax money in with pre-tax when rolling over a traditional IRA? On this episode, I’m answering a listener's question about fixing this easy-to-make but frustrating mistake. We’ll look at the definition of a rollover, why you should separate pre-tax and post-tax money, and how to correct this situation if it occurs…
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One of our listeners actually has a better mortgage rate than me! However, as they begin to test their retirement budget they have found that the mortgage payment leaves that budget a bit tight. So they are wondering if they should pay off their mortgage early by withdrawing from their IRA. What would you do? Listen in to hear my response in additi…
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It seems like no matter how much we save we always have that nagging worry about whether it is truly enough. One of our listeners is looking for ways to reduce the chances of running out of money in retirement. My response to his question may surprise you. Listen in to hear what I have to say about improving his retirement trajectory. OUTLINE OF TH…
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Did you inherit an IRA from a non-spouse on January 1, 2020 or later? Well a big change happened this summer that you should be aware of that could impact your 2023 tax season. On this episode, I’m unpacking the passing of and subsequent changes to the SECURE Act, how to best manage an inherited IRA in light of these changes, and how you can leave …
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“You'll start seeing some things that are really helping you in life and some that are hurting you. And when you don't have an outlet or a way to review these things, we stay to our consistent habits just like with our diet.” Dive into the world of financial therapy with our guest, Erika Wasserman. Fully 81% of Americans were taught not to talk abo…
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We talk so much about the financial aspects of retirement that it’s important to address the mental and emotional shift this season can bring. On this episode, I sit down with life coach Craig Colvett to discuss getting ready for the retirement transition. We talk about the benefits of life coaching for retirees as well as the importance of maintai…
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Have you ever wondered how the subjects from our Retirement Plan Live series are doing now? Did everything turn out okay for them? Find out how Emma (from 2019 RPL) is doing on this episode of Retirement Answer Man. In the listener questions segment you’ll learn about the Rule of 55, donor-advised funds, and contributing to a teen’s Roth IRA. Press…
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Are you approaching retirement with tons of questions about Social Security? Then don’t miss this episode! I’m going over the seven most frequently asked questions about Social Security benefits from clients and listeners alike. Hit play for the tips and tricks you have to know before you start collecting. You will want to hear this episode if you …
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The way does not exist–there is no one correct way to do things. We are all finding our own ways in life and retirement. Working with an agile structure will help give you the scaffolding to create a retirement plan in an organized way. On this episode, you’ll hear how drafting your agile retirement plan can help you discover your unique way to roc…
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"You have a choice about everything, and not choosing is still a choice. Prioritize yourself and ask for what you need." - Emi Kirschner What if you were told that self-care isn't just an indulgence, but a key player in achieving personal and professional success? Our hosts Stephanie McCullough and Kevin Gaines chat with Emi Kirschner, a seasoned i…
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