Even if you’re not on Medicare right now, chances are someone you love is—and sooner or later, you’ll face those decisions yourself.

That’s why it’s worth paying attention to an important letter that arrives every September: the Annual Notice of Change.

Most people glance at it, toss it aside, and never think twice.

But with big shifts coming in 2026, ignoring it could be a costly mistake.

And that letter is just the beginning.

There are three other Medicare traps that cost people thousands each year and, in some cases, wreck entire retirement plans.

In this episode, I’ll walk you through the 2026 changes you (and your loved ones!) need to prepare for, plus the three mistakes to avoid no matter what year it is.

By the end, you’ll know exactly what to watch for and how to feel confident about Medicare—whether you’re enrolled now, preparing for it soon, or helping someone you care about.

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SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING:

My team and I have guided hundreds of families across the U.S. through retirement’s biggest challenges over the last two decades.

The result?

Smarter tax strategies, better investment decisions, and a more confident retirement.

If you’re seeking clarity and a proven retirement planning process, we’d be honored to help.

👉 Schedule a Complimentary Strategy Session

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

Despite making insurance decisions almost daily, many retirement savers don't truly understand what they’re buying or why they need it.

In today's episode, I'm breaking down life insurance into simple, actionable terms.

Specifically, I’m sharing:

‣ The 3 essential steps to managing insurable risks

‣ The key differences between term and permanent life insurance

‣ The exact questions to ask yourself before buying (or hanging onto) any policy

I’m also sharing a few little-known facts and tips to help you properly evaluate options you may be considering.

Even if you think you know everything about life insurance as it relates to your retirement plan, today’s episode will provide valuable and important reminders as you continue managing your ongoing insurance needs.

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SCHEDULE A RETIREMENT STRATEGY MEETING:

My team and I have guided hundreds of families across the U.S. through retirement’s biggest challenges over the last two decades.

The result?

Smarter tax strategies, better investment decisions, and a more confident retirement.

If you’re seeking clarity and a proven retirement planning process, we’d be honored to help.

👉 Schedule a Complimentary Strategy Session

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Schedule Your Free Retirement Strategy Session

Retirement is about so much more than money—it's a complete life transition.

In this episode, I'm sharing my recent conversation with Adam Cmejla, where we explore the often-overlooked aspects of retirement planning.

We discuss:

‣ Why retirement can feel like a grieving process—and how to navigate it

‣ The surprising role responsibility and community play in long-term happiness

‣ Smarter ways to approach Monte Carlo simulations, taxes, and cash management

We also share our favorite retirement and investing charts that reinforce the principles essential to keeping financial plans grounded.

Whether you’re 10 years out from retirement or already there, this conversation challenges common assumptions and offers a helpful perspective on this stage of life.

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SCHEDULE YOUR FREE DISCOVERY MEETING:

My team and I have guided hundreds of families across the U.S. through retirement’s biggest challenges over the last two decades.

The result?

Smarter tax strategies, better investment decisions, and a more confident retirement.

If you’re seeking clarity and a proven retirement planning process, we’d be honored to help.

👉 Schedule a Complimentary Discovery Meeting

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Get Your FREE Retirement & Tax Analysis!