Now that the One Big Beautiful Bill Act has made the 2017 tax rates permanent, more retirees are taking a fresh look at Roth conversions.

But there's one rule that even reputable sources struggle to explain clearly—and the confusion can lead to costly mistakes.

In this episode, I'm simplifying the Roth conversion 5-year rule and sharing:

→ Why the rule is so confusing (and what most people get wrong)

→ The fastest way to determine how the rule applies to your specific situation

→ 4 real-world scenarios so you can see exactly how it works

If Roth conversions aren't a fit today, I'm also sharing one simple step everyone can take right now to make future conversions much easier.

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📝 GRAB THE ROTH 5-YEAR FLOWCHART (PDF)

Want to apply what you learned in this episode to your unique situation?

Subscribe to the Stay Wealthy Retirement Newsletter and I'll send you my freshly updated Roth 5-Year Flowchart (PDF).

It's a simple guide to help you navigate this tricky rule step by step.

Grab your copy here.

***

📆 BOOK A CALL WITH OUR TEAM:

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.

See how they fit together in one coordinated strategy built around your numbers.

👉 Learn More and Book a Call

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

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📝 Note: The 6.5% withdrawal rate is based on an 80% stock portfolio, a 30-year time horizon, and a 90% "confience score." Thanks for your patience while we update the episode to include that information. ~Taylor

***

Most people spend far less in retirement than they likely could.

In fact, one study found married households age 65+ with more than $100k in savings withdrew just 2.1% per year on average.

And ironically, the traditional 4% rule may be one reason why.

In this episode, I'm breaking down new research on retirement withdrawal strategies—and what it reveals about how retirees may be able to spend more.

Here's what you'll learn:

→ 5 strategies that (safely) support higher retirement income

→ The overlooked key to sustainable and confident retirement spending

→ 3 factors that can push starting withdrawal rates to as high as 6.5%

The goal of retirement planning isn't just making your money last…it's making sure you actually use it.

Which raises an important question: "Could you afford to spend more in retirement than you think?"

***

📆 BOOK A CALL:

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.

See how they fit together in one coordinated strategy built around your numbers.

👉 Learn More and Book a Call

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

Health insurance is keeping millions of Americans stuck in jobs they'd otherwise leave.

In fact, 1 in 5 workers ages 50–64 say they're staying put because of their employer health coverage.

And with recent changes to the ACA, that pressure is only growing.

In this episode, I cover:

→ Why healthcare before Medicare has become a psychological roadblock to early retirement

→ Why the real cost of waiting until 65 may not be what you think

→ The options many people overlook and the tradeoffs worth understanding

Because for most people, the healthcare challenge does have a solution.

And the worst thing you can do is never explore your options at all.

***

📆 BOOK A CALL:

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.

See how they fit together in one coordinated strategy built around your numbers.

👉 Learn More and Book a Call

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

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→ Learn About the Total Retirement System™

For 30 or 40 years, a paycheck simply showed up. Then one day, it stops.

Now you're staring at a portfolio and asking:

"How do I turn this into reliable income for the rest of my life…without overpaying the IRS or outliving my money?"

It's no surprise so many retirees gravitate toward dividends. They feel like a replacement paycheck.

In fact, the majority of investors say they prefer dividends and interest over capital gains to fund retirement.

But retirement income planning isn't just about generating cash flow.

It's about creating sustainable income from a finite pool of capital while coordinating taxes and the rest of your retirement plan.

In this episode, I break down new research on dividend investing and explain why the most popular income strategy may be far less efficient than it appears.

I also share what the evidence suggests about building a portfolio and a plan that actually supports long-term retirement success.

Because when it comes to funding your retirement, small structural decisions compound into very large outcomes.

***

📆 BOOK A CALL:

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.

See how they fit together in one coordinated strategy built around your numbers.

👉 Learn More and Book a Call

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

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Markets move every day. Headlines change every hour.

But the greatest threat to your retirement plan isn't volatility... it's something far less visible.

In this episode, I'm breaking down:

→ The three components of risk most investors focus on (and the one they ignore)

→ Why rare, extreme events have an outsized impact on long-term wealth

→ How to build a retirement plan designed to survive (and even benefit from) uncertainty

I'm also sharing why many "downside-protection" strategies sound compelling in theory, but are risky and difficult to execute in the real world.

***

📆 BOOK A CALL:

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.

See how they fit together in one coordinated strategy built around your numbers.

👉 Learn More and Book a Call

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.

See how they fit together in one coordinated strategy built around your numbers.

👉 Learn More and Book a Call

-----

Strong rallies make people uneasy.

So does the fear that one bad crash could undo decades of careful saving.

Recently, Morningstar published a great article centered around a chart mapping nearly 100 years of U.S. market history.

When you zoom out, several widely accepted beliefs about market crashes and bull markets start to look far less certain.

In this episode, I break down the three common myths the article explores.

I also share what the data actually tells us about bear markets and what's far more likely to derail your retirement than a crash.

Not to predict the future or eliminate risk.

But to help you think more clearly about the environment we're in and how it fits into a disciplined, long-term retirement plan.

-----

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

Annuities are often sold as a simple solution to a complicated retirement problem.

Guaranteed income. Protection from market volatility. Peace of mind that your money won't run out.

But behind those promises is a much more complex set of trade-offs that many investors don't consider.

Because while annuities can play a role in retirement planning, evaluating them in isolation often leads to unintended consequences (higher fees, reduced flexibility, extra taxes).

So in today's episode, I break down how annuities actually work.

We'll walk through the major types of annuities, how "guarantees" are structured, what you're really paying for, and where the risks tend to show up later in retirement.

I'll also explain when annuities may make sense, when they don't, and how to evaluate them as part of a coordinated retirement plan so you can make informed decisions with confidence.

***

📆 BOOK A CALL:

For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning.

The result?

Less stress. Lower taxes. More confidence about the future.

If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation.

👉 Click to Learn More and Schedule

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

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What makes an investment "good?"

It seems like a straightforward question, but the answer is more subjective than most people realize.

Recently, my wife asked why I thought real estate was such a BAD investment when others she knows call it the BEST they've ever made.

Hearing it framed that way struck a different chord.

And rather than quickly defending my position with data and facts, I found myself reconsidering the question entirely.

In today's episode, I share how to evaluate investments in the real world, what separates good investments from bad ones, and why some popular metrics can mislead.

If you've ever wondered why an investment looks great paper but doesn't feel right—or why others swear by strategies you'd never touch—this episode will give you a clearer framework for thinking about your own portfolio.

***

📆 BOOK A CALL:

For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning.

The result?

Less stress. Lower taxes. More confidence about the future.

If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation.

👉 Click to Learn More and Schedule

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™