Research shows that retirees following traditional withdrawal rules rarely come close to depleting their portfolios.

In fact, many end up leaving behind balances that are surprisingly large.

Which raises an important question: why is it so hard to spend the money you spent decades saving?

Today, I'm revisiting my conversation with Brian Portnoy, Ph.D., CFA to explore the psychology behind the fear of spending and what retirees can do to move through it.

Longtime listeners will also recognize Brian as the source of a quote I've shared many times on the show, and in this episode, he finally shares the story behind it.

In this episode, we discuss:

→ Why retirees with healthy, well-funded plans still struggle to spend

→ The flawed logic behind "If I just had $X, I'd finally feel comfortable"

→ 5 steps to overcome the fear of spending, whether retirement is five years away or already here

→ What "funded contentment" means, and why it may be the real difference between being rich and being wealthy

Because the goal of retirement planning isn't to die with the biggest possible balance... it's to use your money to support a life that feels meaningful to you.

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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:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

Today, we're stepping away from the spreadsheets, tax strategies, and retirement tactics to have a little fun.

I'm sharing six facts that challenge conventional wisdom — including one involving a famous gangster and a reminder that taxes touch almost everything.

A few highlights:

→ The surprising fate of investors who bought the exact top of the dot-com bubble

→ How much a crystal ball that picks winning funds is actually worth

→ What a 50-year backtest reveals about the real role of bonds in your portfolio

→ The one thing the longest-living retirees have that most retirement plans ignore

By the end, I think you'll feel even more confident in the patient, disciplined, evidence-based approach we talk about so often on this show.

And, if nothing else, you'll walk away with a few new stats and stories worth sharing the next time markets come up in conversation.

***

📆 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™

A strong financial plan can tell you whether you can retire, but it may not tell you whether you'll feel ready.

In this Retirement Replay, behavioral finance expert and psychologist Dr. Daniel Crosby explains why retirement is not just a portfolio decision.

He shares the five areas happy retirees tend to prepare for, why purpose and connection matter more than many people realize, and why even people with plenty of money can still struggle to make the leap.

About Retirement Replay: After select guest interviews, we pull together the most replayed moments from the full conversation—the ideas listeners found valuable enough to rewind, revisit, or hear again. It's a quick way to catch the highlights or return to the takeaways that stood out most.

Listen to the full episode: https://www.youstaywealthy.com/289

***

📆 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™