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:

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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.

***

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:

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→ 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.

***

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:

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Required Minimum Distributions (RMDs) could force you to withdraw as much as 15% of your retirement account balance in a single year.

But do RMDs really put you at risk of outliving your money?

Why does the IRS expect you to live so much longer than the Social Security Administration does?

And what proactive steps can you take before age 73 to avoid giving the IRS more than its fair share?

In this episode, I'm unpacking:

‣ How RMDs are actually calculated

‣ Why the IRS tables are more conservative than most people realize

‣ The pros and cons of using RMDs to build a dynamic withdrawal strategy

I'm also sharing tax planning tips and strategies for navigating your RMDs.

If you're concerned about how RMDs might impact your retirement plan—or you're looking to optimize your tax situation before they kick in—this episode is for you.

***

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

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Is retiring in your 50s actually realistic for everyday Americans?

According to a recent NerdWallet survey, the average target retirement age for households earning $100,000+ isn't 65—it's 58.

And these aren't tech moguls or lottery winners.

They're teachers, small business owners, and dual-income couples who’ve steadily built their nest eggs and now want to enjoy their healthy, active years while they can.

But retiring in your 50s requires a very different kind of plan.

One that accounts for early withdrawal penalties, health insurance gaps, and delayed Social Security.

These obstacles are the "triple threats" of early retirement.

In today’s episode, I’ll share how to combat them and provide a simple 5-step process for turning your retirement vision into a reality.

***

SCHEDULE A COMPLIMENTARY DISCOVERY CALL:

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We help 100+ families across the country navigate retirement, optimize investments, and reduce taxes.

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***

EPISODE RESOURCES:

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What if everything you've learned about money completely changes once you cross the $1 million mark?

Many people think a healthy 7-figure nest egg means the hardest part is done, but ironically, that's when the biggest financial challenges start.

Today, Nick Maggiulli returns to share his latest retirement research, which inspired his new book, "The Wealth Ladder."

In this conversation, we explore:

▸ Why retirement savers with $1-10 million often feel "stuck"

▸ The surprising reason wealthy retirees are more likely to LOSE wealth than those with less money

▸ Why your investment portfolio becomes more important than your income at this stage

▸ The academic research showing good health is worth $400,000 per year

If you're nearing retirement (or already there), you'll learn why crossing the million-dollar mark isn't the finish line—it's when the game changes entirely.

***

SCHEDULE A COMPLIMENTARY DISCOVERY CALL:

Looking to hire a retirement and tax planning expert?

We help 100+ families across the country navigate retirement, optimize investments, and reduce taxes.

🗓️ Schedule a Complimentary Discovery Meeting to Learn More.

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

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A recent study reported that 76% of retirees regret not saving more money.

But after working with hundreds of successful retirees and analyzing thousands of survey responses, I've discovered something interesting:

Their deepest regrets actually have little to do with financial shortfalls.

Instead, they revolve around critical aspects of financial planning that significantly impact purpose, independence, and fulfillment in your golden years.

In this episode, I'm revealing three (3) retirement regrets that many people don't consider until it's too late.

I'm also sharing how to avoid the same mistakes so YOUR retirement is fulfilling instead of filled with regret.

***

SCHEDULE A COMPLIMENTARY DISCOVERY CALL:

Looking to hire a retirement and tax planning expert?

We help 100+ families across the country navigate retirement, optimize investments, and reduce taxes.

🗓️ Learn more and schedule a Discovery Meeting with us.

***

EPISODE RESOURCES:

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Wondering how the new 'One Big Beautiful Bill Act' affects you and your retirement plan?

Don't want to read 870 pages of Congressional jargon?

I've got you covered!

In this episode, I'm breaking it all down and sharing the 5 biggest things retirement savers need to know.

I'm also addressing several broader provisions in the bill and clarifying some common misconceptions.

This giant (and confusing!) economic package touches nearly every aspect of your financial life.

So, pour yourself some coffee—or something stronger if you need it—and hit play.

***

SCHEDULE A COMPLIMENTARY DISCOVERY CALL:

Looking to hire a retirement and tax planning expert?

We help 100+ families in 40 states across the country navigate retirement, optimize investments, and reduce taxes.

🗓️ Learn more and schedule a Discovery Meeting with us.

***

EPISODE RESOURCES:

✏️ Grab the Episode Show Notes

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📊 Get Your FREE Retirement & Tax Analysis!