Episodes

What if you finally retire, have enough money, and still feel too busy to enjoy your life? Jeremy Keil welcomes returning guest Bruce Fear, author of Unhurried Abundance, to explore why retirement doesn't automatically create a slower, more fulfilling life. After experiencing a stroke in 2024, Bruce reconsidered how he spent his time and why creating margin in everyday life matters. For disclosures and conflicts visit keilfp.com/disclosures.

Most people think tax planning means finding ways to pay less in taxes this year. But reducing today's tax bill doesn't necessarily mean you'll be better off in retirement. Jeremy Keil talks with Freeman Linde, author of Tax Savings Strategies, about how couples over 50 can think more strategically about taxes before and during retirement. Explore the difference between tax preparation and tax planning, why deferring taxes isn't always the best choice, and how Roth conversions can be evaluated ...

Turning 65 doesn't mean Medicare works the same way for everyone. Some people are enrolled automatically, others need to sign up, and those who are still working may have additional decisions to make. Jeremy Keil walks through five common Medicare mistakes that can create confusion, unexpected costs, or coverage problems. He explains why employer coverage isn't always enough to delay Medicare, how Parts A, B, C, and D fit together, and why Medicare Advantage and Medigap require different consid...

What does a successful retirement actually look like? Is it having $1 million, $2 million, or even $10 million saved? Is it having enough retirement income to cover your expenses, minimizing taxes, or simply having the freedom to spend your time however you choose? Jeremy Keil shares responses from four retired listeners who define retirement success in very different ways. Their stories touch on setting savings goals, spending money you've worked decades to accumulate, managing Medicare IRMAA ...

Retirement planning often begins with a financial question: Will I have enough money? But once the paycheck stops and the financial pieces are in place, another question can become just as important: What am I going to do with the rest of my life? Jeremy Keil talks with Arlene Nelson about her own transition into retirement as a single woman. Arlene expected retirement to bring freedom, but after the initial excitement wore off, she found herself struggling with a lack of structure, connection,...

Annuities tend to generate strong opinions. Some people insist they're terrible. Others talk about them as though every retiree should own one. Jeremy Keil and Jeremiah Konger of Annuity Association argue that both approaches miss the more useful question: When does an annuity actually make sense within a retirement plan? Jeremiah and Jeremy discuss common misconceptions about annuities, including fees, access to money, market exposure, guarantees, and the financial strength of the insurance co...

Scammers don’t only hack into a computer to steal from their victims. Increasingly, they're trying to hack the person using it. Jeremy Keil talks with cybersecurity and fraud-prevention expert Robert Siciliano about how modern scams use text messages, artificial intelligence, deepfakes, voice cloning, manufactured urgency, and human psychology to gain trust. Learn practical ways to reduce your vulnerability. Robert’s three-step Analyze, Authenticate, Act protocol provides a simple response to ...

Do you really need a financial advisor in retirement? Jeremy Keil argues that the answer depends on a better question: What do you actually want a financial advisor to do for you? After reading responses from Kiplinger readers about whether they use financial advisors, Jeremy noticed that most people immediately focused on investment management—choosing investments, managing portfolios, or trying to improve returns. Real retirement planning extends well beyond investments. For retirees deciding...

A retirement plan is more than an investment portfolio and a decision about when to claim Social Security. Jeremy Keil is joined by financial advisor Joe Schmitz Jr. to compare the planning processes they use to help clients coordinate the many financial decisions that come together at retirement. Joe explains his five-pillar approach covering tax planning, investments, income, healthcare, and estate planning, while Jeremy compares it with his own five-step Retirement Master Plan. Despite appro...

Some of the most tempting retirement investing mistakes begin with ideas that sound perfectly reasonable: move to cash when the market looks expensive, put everything in CDs while rates are attractive, leave stocks behind once you retire, or rely on dividend stocks for income. The problem is that each approach can allow one concern or prediction to dictate an entire investment strategy. Jeremy Keil answers five listener questions about investing in retirement. The surprising truth about retirem...

3 Retirement Decisions Nobody Prepares You For Retirement can change how you approach life insurance, mortgages, income, and investments. Jeremy Keil answers three financial questions retirees may not expect to face. https://youtu.be/H4WXLWLuHi0 When people think about retirement planning, oftentimes they naturally think about their investment portfolio, Social Security, or taxes. Those are important parts of the plan, but after helping hundreds of people retire, I’ve found that some of the qu...

What does a successful retirement look like? Jeremy Keil explores how financial independence, spending, lifestyle, and personal priorities can shape what it means to win at retirement. https://youtu.be/FVbs7kVxOzw When you picture someone who has “won” at retirement, what do you see? Maybe it’s someone taking beach vacations, belonging to a golf club, buying the boat they’ve always wanted, or finally moving into the house they’ve spent years dreaming about. Those can all be wonderful ways to ...

Retirement tax planning requires more than minimizing this year’s taxes. Learn how Roth conversions, inherited IRAs, and charitable giving can affect your lifetime tax strategy. https://youtu.be/iANLKaHoBqw One of the biggest financial mistakes you make in retirement might have nothing to do with your investments. You could follow the tax rules correctly, file every return on time, avoid penalties, and still end up paying more in taxes than you needed to over the course of your retirement. I...

How much money do you need to retire? Learn why an arbitrary retirement savings target may keep you working longer than necessary—and how to determine what “enough” actually means for your retirement. https://youtu.be/kHyhns6PHnA Over my 23 years as a financial advisor, I’ve heard many people attach their retirement date to a specific dollar amount. “I’ll retire when I get to $2 million.” For someone else, the number might be $500,000, $1 million, or $10 million. The amount varies, but the t...

Choosing 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 wh...

Three 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 mos...

Healthcare 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...

Jeremy Keil explains how putting your cash in the wrong spot could prevent you from earning thousands in interest during your retirement. Many retirees spend a lot of time thinking about how to get better returns on their investments. But very few spend time thinking about the return on their cash. That’s a problem. Because for many retirees, cash isn’t a small side account. It can be a meaningful portion of their overall financial picture—and if it’s sitting in the wrong place, it may be qui...

Author Ethan Lohr shares how the four buckets retirement income strategy helps retirees behavior-proof their retirement. Many retirees face one similar problem that they struggle to name: the emotional shift from saving money to spending it. Retirement typically means going from “decades of saving to decades of retirement where you’re spending,” and that transition creates real anxiety for people who want their money to last. Ethan Lohr’s answer is not just a better spreadsheet. It’s a “behavio...

Jeremy Keil explains 3 smart ways to help your kids with money while avoiding IRS paperwork Early in the year, I received an email from a couple asking a question I hear all the time: “What’s the maximum we can give our kids?” That question usually shows up in December. Parents are trying to get a last-minute gift in before the year ends, and the conversation quickly becomes about tax limits. But that’s the wrong starting point. If you’re thinking about giving money to your kids, the first q...

The retirement mindset mentor George Jerjian explains how a second chance at life inspires him to help coach people into retirement. When George Jerjian was 52 years old, he was diagnosed with a bone tumor and given six months to live. For three weeks, he believed that was it. Then he was told he belonged to what he calls “the 2% club.” The cancer hadn’t spread. He would live. That experience didn’t just save his life. It reframed it. “Too often we just drift,” George said. “Even in retireme...

Jeremy Keil explains the 5 RMD (Required Minimum Distribution) mistakes in Retirement and how to avoid them. A retiree recently called for help. It was their first year taking Required Minimum Distributions. They had delayed their first RMD until April of the following year — which meant taking two distributions in one tax year. That part was allowed. In some cases, it can even be strategic. But when they called their IRA custodian and asked, “How much should I withhold for taxes?” they were g...

Nate Miles joins Jeremy Keil to discuss how the Allspring retirement research reveals trends of concern among retirees and the options they have to address them. Mike and Susan did what many couples do. They saved diligently. They crossed the $1 million mark before retirement. They felt prepared. But when it came time to make actual retirement decisions—when to claim Social Security, how to withdraw from their accounts, how to manage taxes—they realized something uncomfortable: They had spent ...

Jeremy Keil examines how tax law changes might affect Roth conversion strategies for retirees in 2026. A few years ago, Roth conversions felt like one of those rare financial strategies that was almost too obvious to ignore. Taxes were historically low. The Tax Cuts and Jobs Act had put a clear expiration date on those lower brackets. And for many retirees, the logic seemed airtight: pay taxes now at a lower rate so you don’t pay more later. Fast forward to today, and that certainty just isn’t ...