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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 using projected future tax rates. For disclosures and conflicts visit keilfp.com/disclosures.

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 considerations. For disclosures and conflicts visit keilfp.com/disclosures.

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 costs, building dependable retirement income, and enjoying time with family and community. For disclosures and conflicts visit keilfp.com/disclosures.

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, and direction. For disclosures and conflicts visit keilfp.com/disclosures.

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 company issuing the contract. Plus, Jeremiah highlights the 4 major types of annuities and what typical use cases they apply in. For disclosures and conflicts visit keilfp.com/disclosures.

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 suspicious communications, while unique passwords, password managers, two-factor authentication, and updated devices can create additional barriers for criminals. The goal isn't to assume you're too smart to be scammed. It's to build habits that make it harder for a scammer to get through. For disclosures and conflicts visit keilfp.com/disclosures.

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 whether professional advice is worthwhile, start by identifying the problems you need help solving. Once you know what you need from an advisor, you can make a much better decision about whether—and what kind of—financial planner is right for you. For disclosures and conflicts visit keilfp.com/disclosures.

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 approaching the process from different angles, both emphasize an important point: your investments should serve your retirement plan—not become the plan itself. For disclosures and conflicts visit keilfp.com/disclosures.

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 retirement investing is that many questions are answered more clearly by re-focusing on when you'll need the money and what you need it to accomplish, rather than predictions about what markets, interest rates, or individual investments will do next. For disclosures and conflicts visit keilfp.com/disclosures.

Retirement can change how you approach life insurance, mortgages, income, and investments. Jeremy Keil answers three financial questions retirees may not expect to face.

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.

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.

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.

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 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.