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.

***

📆 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

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

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.

***

📆 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

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

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.

***

📝 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

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™