Retire Today

Saving for retirement is a skill that most people spend decades developing. But once retirement begins, the challenge changes completely. Instead of accumulating wealth, retirees must learn how to confidently spend it—and for many, that's much harder than expected.

In this episode, Jeremy explores why so many retirees struggle to spend the money they've worked so hard to save. Learn about the psychology behind "fear of running out," why many retirees underspend despite having more than enough assets, and how changing your mindset from "saver" to "planner" can transform the retirement experience. Jeremy also shares practical strategies for creating retirement income that feels like a paycheck and discusses how to spend with purpose while minimizing future regret.

If you've ever hesitated to enjoy your retirement because you're worried about spending too much, this episode offers a practical framework for turning your savings into the meaningful retirement you've spent a lifetime building.

For disclosures and conflicts visit keilfp.com/disclosures.

David 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.

Many 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.

Most 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.

When 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.