Saving for retirement is one challenge.

Feeling comfortable (and confident) enough to actually enjoy it is another.

Even when the numbers say you're okay, uncertainty about the future can make it hard to use money for the things that matter most.

Today, I'm revisiting a conversation with Dr. Daniel Crosby where we talk about money, happiness, and why spending is often harder than saving.

It's especially relevant for me as my family currently navigates some big financial decisions... and a birthday trip for my oldest son that almost didn't happen. 🫣

In this episode, we discuss:

→ What the research gets wrong about the link between money and happiness

→ Why certain types of spending leave a bigger impact than others

→ A simple mindset shift that can make spending feel safer in retirement

→ What people near the end of life rarely regret—and what they wish they had done more of

This conversation is a good reminder that money is a tool, and the goal is to use it to support the life you truly value.

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If you're in or near retirement, one bad investment decision can have lasting consequences.

And new research shows just how risky stock picking can be:

Over the last 100 years, nearly 60% of all U.S. stocks underperformed Treasury bills—one of the safest investments you can own.

Even more surprising, fewer than 4% of companies created all of the stock market's net wealth.

In other words, the odds of consistently picking the right stocks are far lower than most people realize.

In this episode, I'm breaking down this eye-opening research and what it means for protecting your portfolio and retirement plan.

Here's what you'll learn:

→ Why owning a handful of well-known, familiar stocks can be far riskier than it feels

→ What the research reveals about where long-term market returns actually come from

→ The 3 actions you can take to better position and optimize your portfolio for the years ahead

Because in retirement, successful investing isn't about hitting home runs—it's about avoiding unnecessary mistakes and stacking the odds in your favor.

***

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

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***

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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:

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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% "confidence score." Thanks for your patience while we update the episode to include that information. ~Taylor

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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?"

***

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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.

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***

EPISODE RESOURCES:

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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.

***

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

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***

EPISODE RESOURCES:

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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.

***

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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.

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***

EPISODE RESOURCES:

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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

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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.

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EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™