Retire Today

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