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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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.

***

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

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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

***

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

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At 63, David has $4 million saved.

Two advisors have told him he's ready to retire, and every Monte Carlo simulation agrees... but he still can't bring himself to do it.

"I'm no longer being smart," he admits. "I'm just scared to pull the trigger."

The uncomfortable part is that no number may fix this, because what's holding David back was never on the spreadsheet.

In this episode, I'm joined by Daniel Crosby, Ph.D. — a psychologist and behavioral finance expert — to answer listener questions about the part of retirement the math can't solve.

You'll learn:

→ How to spend in retirement so the enjoyment doesn't wear off so fast

→ A 3-part framework for putting your money where it creates the most happiness

→ When changing your plan is wise, and when it's just reacting to noise

→ The 2 questions to ask when you're financially ready but still can't pull the trigger

→ What actually moves the 40% of your happiness that's within your control

By the end, you'll have a clearer way to separate a plan that works on paper from a retirement you actually feel ready to live.

***

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

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Imagine I hand you two mutual funds and ask how you'd split your money.

Same holdings. Same cost. Line by line, they're the exact same fund.

The only difference?

One has a name you recognize and the the other is generic.

Financially, there's no reason to prefer one over the other.

But when researchers ran this experiment, investors didn't split their money evenly.

In this episode, I break down new research on the hidden cost of making investment decisions based on familiarity.

Here's what you'll learn:

→ Why a familiar fund name changes how investors judge risk, return, and safety

→ What the "trust premium" reveals about how investors value familiarity

→ How famous fund families have performed against their benchmarks

→ The questions to ask before choosing a fund or accepting an advisor's recommendation

By the end, you'll have a more disciplined and informed way to judge whether confidence is being earned or merely assumed.

***

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

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You spend 30 or 40 years protecting your future self.

Then you finally retire... and the person you were saving for never quite arrives.

There's always an older version down the road who still feels like they need protecting.

So you keep saving for tomorrow while postponing the life you could enjoy today.

But more money for "future you" isn't what makes retirement better.

In this episode, Hal Hershfield, Ph.D. — a UCLA professor of Behavioral Decision Making and author of Your Future Self — joins me to explain why.

Here's what you'll learn:

→ Why your brain treats your future self like a stranger (and how that shapes every money decision)

→ How "projection bias" distorts irreversible choices like when to retire or claim Social Security

→ The "denominator problem" that stops retirees from spending + a simple reframe to help

The distance we feel from our future selves is real and well-documented.

It is also, with the right perspective, something we can learn to close.

***

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

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When inflation makes headlines, it can feel like one of those retirement risks you just have to endure.

Saving, investing, tax planning, income strategy... those are levers you can pull.

Rising prices feel different. They feel like something that happens to you.

But the inflation number you see in the news is rarely the number that matters most for your retirement plan.

Two retirees can live through the same inflation environment and face very different risk — and the gap between them often comes down to a few things they can actually control.

In this episode, I'm simplifying how retirement savers should think about inflation.

You'll learn:

→ The 3 questions that reveal your true inflation risk

→ Why headline inflation can mislead retirees in both directions

→ How to protect your income, spending power, and retirement confidence

A strong retirement plan doesn't require a perfect inflation forecast.

It just needs to be built for the reality that uncomfortable periods will happen, and prepared for them before they arrive.

***

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

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Umbrella insurance isn't usually the first thing people think about when they picture retirement planning.

Most conversations focus on saving enough, investing well, reducing taxes, and creating income.

But in retirement, one unintentional accident can create a very different kind of risk.

Not just a temporary setback, but a threat to savings you may no longer have decades to rebuild.

In this episode, I'm simplifying how umbrella insurance works for retirement savers.

Specifically, I'm sharing:

→ Why liability risk doesn't necessarily disappear after your working years

→ What umbrella insurance does and doesn't cover

→ 5 common mistakes people make when buying or reviewing a policy

→ A simple 4-part formula for estimating how much coverage you actually need

You'll also learn why the common "match coverage to net worth" rule can be misleading + why coverage may still make sense even when the math says you don't technically need it.

***

📆 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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