Podcast
Retire Today
Hosted by Jeremy Keil · EN
In the Retire Today podcast, Jeremy Keil, CFP®, CFA® shows you how to turn your retirement savings into retirement income. Listen in as Jeremy and his guests guide you towards making smarter retirement, investment, and tax planning decisions. Get free resources and learn how to have Jeremy and his team develop your own Retire Today income plan at 5stepRetirementPlan.com. For important disclosures, see www.keilfp.com/disclosures Keil Financial Partners may utilize third-party websites, including social media websites, blogs, and other interactive content. We consider all interactions with clients, prospective clients, and the general public on these sites to be advertisements under the securities regulations. As such, we generally retain copies of information that we or third parties may contribute to such sites. This information is subject to review and inspection by
43episodes
Episodes
Newest firstAll episodes
The Retirement Tax Mistake That Could Cost You Thousands
2d ago00:15:59Tap to summarizeRetirement tax planning isn't simply about following IRS rules or minimizing what you owe this year. Jeremy Keil answers three listener questions that demonstrate why focusing on one tax return at a time can lead retirees to miss opportunities to manage their taxes over the course of retirement. Jeremy breaks down two different five-year rules that can apply to Roth IRAs, including what happens when you complete a Roth conversion after having an existing Roth IRA for years. He then explains why taking only the required minimum distribution from an inherited IRA isn't automatically the best strategy under the 10-year rule, and how qualified charitable distributions may be available from inherited IRAs for eligible account owners. For disclosures and conflicts visit keilfp.com/disclosures.
Transcribe →How Much Money Is Enough to Retire?
1w ago00:07:34Tap to summarizeHow much money do you actually need to retire? Many people approach retirement with a specific number in mind—$1 million, $2 million, or another target they believe will finally make them feel financially ready. But Jeremy Keil has seen how easily that finish line can move, even when the retirement plan already shows someone has enough. Rather than choosing an arbitrary retirement number, Jeremy challenges prospective retirees to determine what their lifestyle actually requires and test that against a retirement calculation. Knowing what "enough" means for your retirement may help you recognize when you've already reached it. For disclosures and conflicts visit keilfp.com/disclosures.
Transcribe →Social Security Questions Married Couples Ask Before Retirement
2w ago00:19:09Tap to summarizeChoosing when to claim Social Security can have a lasting impact on your retirement income, but many retirees make this decision without fully understanding how the rules work. In this Q&A episode, Jeremy Keil answers three listener questions that uncover some of the most common Social Security misconceptions facing married couples. Jeremy explains why your retirement date and your Social Security claiming date are two separate decisions, how poor health should factor into your planning, and why survivor benefits often deserve more attention than the higher earner's own benefit. He also clarifies common confusion around spousal benefits, outdated claiming strategies, and the way delayed retirement credits are actually applied after full retirement age. Whether you're approaching retirement or helping a spouse make these important decisions, this conversation offers practical guidance to help you coordinate your retirement plan and make more informed Social Security choices. For disclosures and conflicts visit keilfp.com/disclosures.
Transcribe →300th Episode Special: The Biggest Retirement Lessons I’ve Learned Featuring Nicole Gebhardt
3w ago00:32:16Tap to summarizeThree hundred episodes into the Retire Today podcast, the microphone is turned around as author and business strategist Nicole Gebhardt interviews Jeremy Keil about the journey that shaped his retirement philosophy and the framework behind his book, Retire Today: Create Your Retirement Master Plan in 5 Simple Steps. Rather than focusing on a single retirement topic, Jeremy shares the evolution of his business, the development of the "Mr. Retirement" brand, and the mindset shifts that matter most for people approaching retirement. He explains why so many successful savers struggle to become confident spenders, why retirement planning is as much about psychology as it is about numbers, and how learning the math behind retirement decisions creates confidence to retire on your own terms. As the Retire Today podcast celebrates its 300th episode, Jeremy reflects on lessons learned from working with thousands of retirees and explains why thoughtful planning isn't about predicting the future—it's about creating the flexibility to enjoy it. For disclosures and conflicts visit keilfp.com/disclosures.
Transcribe →Is the Healthcare System Working Against You? With Dr. Jordan Grumet
Jul 1400:43:50Tap to summarizeHealthcare is one of the biggest expenses retirees face, yet few people understand how the system behind their care actually works. Jeremy Keil welcomes physician, hospice doctor, and author Dr. Jordan Grumet to discuss the ideas behind his new book, The Healthcare Heist. Discover how financial incentives have reshaped modern healthcare, the growing influence of private equity, and why patients and providers often feel caught in a system that prioritizes business interests over care. Dr. Grumet explains the differences between physician-owned practices and corporate healthcare systems, discusses direct primary care and concierge medicine, shares his perspective on Medicare Advantage versus traditional Medicare with supplemental coverage, and offers guidance for becoming a more informed healthcare consumer. Healthcare aside, hear why Dr. Grumet rejects the traditional definition of retirement and what he's learned since beginning the decumulation phase of his own financial life. For disclosures and conflicts visit keilfp.com/disclosures.
Transcribe →What Changes When a Retirement Expert Finally Retires? With David Conti
Jun 3000:46:38Tap to summarizeDavid Conti has spent decades writing about retirement, Social Security, Medicare, and personal finance. After helping others prepare for retirement throughout his career—including his time at Fidelity Investments—he reached an important milestone himself: turning 65. That experience gave him a new perspective on what retirement looks and feels like when the advice you've shared for years becomes your own reality. Jeremy and David explore the lessons that surprised him most, including why retirement is about more than financial independence, the importance of keeping your investment strategy simple, navigating Medicare after enrolling for the first time, preparing emotionally for retirement, creating multiple streams of income, and finding greater purpose through charitable giving. David also shares why he believes everyone should "practice retirement" before leaving work and why taking time to reset may be one of the smartest retirement decisions you can make. Whether you're five years from retirement or already making the transition, this conversation offers practical lessons from someone who has spent a career studying retirement—and is now living it himself. For disclosures and conflicts visit keilfp.com/disclosures.
Transcribe →IRMAA: Why Your Medicare Costs are Higher Than You Expected (and What You Can Do About It)
Jun 2300:25:22Tap to summarizeMany retirees are surprised to learn that Medicare isn't always a fixed cost. If your income exceeds certain thresholds, Medicare can charge significantly higher premiums through a little-known rule called IRMAA (Income-Related Monthly Adjustment Amount). Even more surprising, those higher costs are often based on income from two years ago rather than what you're earning today. In this episode, Jeremy Keil (Mr. Retirement) explains how IRMAA works, why Medicare uses prior-year tax returns to calculate premiums, and what retirees need to know when planning Roth conversions, managing retirement income, and preparing for required minimum distributions. He also shares real-world examples of retirees who successfully appealed their Medicare surcharges after retirement reduced their income. If you've received an IRMAA notice—or want to avoid being surprised by one in the future—this episode will help you understand your options and how Medicare costs fit into a broader retirement tax strategy. For disclosures and conflicts visit keilfp.com/disclosures.
Transcribe →Retirement Planning Needs More Than a Financial Plan with Toni Petrillo
Jun 1600:33:50Tap to summarizeMost people spend decades preparing financially for retirement. They contribute to retirement accounts, pay down debt, evaluate Social Security strategies, and work with advisors to make sure their savings can support the next chapter of life. By the time retirement arrives, many have a well-developed financial plan that answers the most important question: "Can I afford to retire?" This week I spoke with retirement lifestyle coach Toni Petrillo about a different question—one that often surfaces only after retirement begins: "Now what?" Learn about what Toni calls the “in-between chapter” and how to navigate from a meaningful career to a purposeful retirement in this week’s episode of “Retire Today.” For disclosures and conflicts visit keilfp.com/disclosures.
Transcribe →Flood Coverage: The Insurance Gap That Could Wash Away Your Retirement Plan
Jun 900:18:59Tap to summarizeWhen evaluating flood insurance, many people focus on a single question: Do I need it? I think there's a better question. If your home suffered significant flood damage tomorrow, where would the money come from? This week I spent some time looking at flood insurance, flood risk, and what retirees should consider when deciding whether they need coverage. Watch the full episode on the Mr. Retirement YouTube channel: Do I Need Flood Insurance in Retirement? https://youtu.be/XRZKfiY1jGg For disclosures and conflicts visit keilfp.com/disclosures.
Transcribe →Retire Against the Norm with Norman Calvo – A True Retirement Story
Jun 200:30:03Tap to summarizeNorman Calvo explains how he found a third act in retirement by going against the norm and choosing adventure instead of a typical retirement. https://youtu.be/81atmTUjBWE One of the questions I ask people as they approach retirement is deceptively simple: What are you retiring to? Most retirement planning conversations focus on finances. That’s understandable. People want to know if they’ve saved enough, whether their investments are positioned correctly, how Social Security fits into the picture, and what taxes might look like in retirement. Those are important questions, and they’re exactly the kinds of issues my team helps clients navigate. But once the financial pieces are in place, another challenge emerges—one that often receives far less attention. What will make retirement meaningful? Norman Calvo and I dug deeper into how he was able to find meaning in retirement after decades as a successful business owner in this week’s episode of the Retire Today podcast. Norman discovered an entirely new chapter of life after work. His true retirement story illustrates a lesson I’ve seen repeatedly among retirees: financial independence creates freedom, but it doesn’t automatically create purpose. The Risk Nobody Plans For Most people spend years preparing for the financial risks of retirement. They plan for market volatility.They prepare for inflation.They consider healthcare costs.They evaluate longevity risk. Yet many people never prepare for a different risk altogether: drift. Drift rarely happens intentionally. In fact, most retirees who experience it worked incredibly hard to earn the freedom they now possess. The challenge is that work provides structure. It creates goals, deadlines, responsibilities, relationships, and a sense of progress. For decades, many professionals wake up knowing exactly what needs to be accomplished that day. Then retirement arrives. The calendar empties. The obligations disappear. The structure that guided daily life for years suddenly vanishes. For some retirees, that freedom feels exhilarating. For others, it becomes surprisingly disorienting. Why Purpose Doesn’t Automatically Appear Norman explained how many people gradually lose touch with the activities that once excited them. Careers expand, family responsibilities increase, and life’s demands naturally push hobbies and interests to the side. By the time retirement arrives, some people have forgotten what they enjoyed doing before work consumed most of their attention. As a result, retirement can unintentionally become a period of maintenance rather than growth. Days become predictable. Weeks begin to blend together. And while there’s nothing wrong with relaxation, most people don’t spend decades saving and investing simply to become passive observers in their own lives. The Power of One New Decision Norman’s transformation didn’t begin with a grand retirement vision. It started with a single decision. A coworker encouraged him to train for a half marathon. At the time, he weighed 247 pounds, worked long hours, and had never been a runner. He wasn’t looking for a new identity. He simply agreed to try something different. That one decision led to another. Running led to additional races, including the New York City Marathon. Along the way, he discovered interests and opportunities he never would have anticipated. He joined a choir, performed in cabaret productions, taught English overseas, and even began learning handstands in his seventies. What stands out isn’t the specific activities. It’s the willingness to remain curious. Too often we assume retirement is a time to narrow our world. Norman’s experience suggests the opposite may be true. Retirement can be a time to expand it. Create a Plan for Your Life Throughout our working years, we create plans for almost everything. Businesses have strategic plans.Families have financial plans.Organizations establish goals and objectives. Yet many retirees never develop a plan for how they want to spend the freedom they’ve worked so hard to create. That doesn’t mean every hour needs to be scheduled. It does mean thinking intentionally about questions such as: What experiences would I regret never having? What skills would I like to develop? What interests have I neglected? What challenges would energize me? What relationships deserve more of my attention? These questions may seem less urgent than investment allocation or tax planning, but they often determine whether retirement feels fulfilling. Retirement Is More Than Financial Independence Many successful retirees continue to grow long after they stop working. They volunteer.They mentor.They travel.They learn.They teach.They pursue interests that were postponed for decades. Not because they have to. Because they can. Financial independence gives people options. The real challenge is deciding how to use those options in a way that creates a life that remains engaging and meaningful. The Bottom Line When people think about retirement, they often focus on what they’re leaving behind. Work.Commutes.Deadlines.Stress. But retirement is ultimately less about what you’re leaving and more about what you’re building next. The financial plan creates the opportunity. The life you create afterward is what gives that opportunity meaning. As Norman’s story demonstrates, some of the most rewarding experiences in life may not happen before retirement. They may happen because of it. Don’t forget to leave a rating for the “Retire Today” podcast if you’ve been enjoying these episodes! Subscribe to Retire Today to get new episodes every Wednesday. Apple Podcasts: https://podcasts.apple.com/us/podcast/retire-today/id1488769337  Spotify Podcasts: https://bit.ly/RetireTodaySpotify About the Author: Jeremy Keil, CFP®, CFA is a retirement financial advisor with Keil Financial Partners, author of Retire Today: Create Your Retirement Income Plan in 5 Simple Steps, and host of the Retirement Today blog and podcast, as well as the Mr. Retirement YouTube channel. Jeremy is a contributor to Kiplinger and is frequently cited in publications like the Wall Street Journal and New York Times. Additional Links: Buy Jeremy’s book – Retire Today: Create Your Retirement Master Plan in 5 Simple Steps Norman Calvo’s Substack “Against t...
Transcribe →