Stay Wealthy Retirement Podcast

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 fea...

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...

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 p...

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 D...

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 n...

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 Hers...

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 throu...

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 epis...

Two retirees. Same $1 million portfolio. Same 60/40 allocation. Same 4% withdrawal rate. Same 30-year retirement. The only difference? One retired in 1973. The other retired in 1975.  Fast forward 30 years: one finished with about $280,000 and the other finished with over $3 million. Same plan. Just two years apart. In this episode, I'm breaking down new research that analyzes nearly a century of...

Many retirement savers assume the anxiety will lift once they hit a certain number. Maybe it's $1 million. Maybe $2 million. Maybe $5 million or more. And then the account crosses the line, the headlines turn ugly, and the worry is still there. A recent Wall Street Journal headline put it bluntly: "Even Rich Retirees Fear Outliving Their Money." In this episode, I'm sharing new research from Fidel...

The math behind "wait until 70" for Social Security is real. Hold off claiming from 62 to 70 and your monthly benefit climbs by roughly 77%. So why would anyone walk away from a number that big? The short answer is that the standard break-even analysis only measures one variable.  And for retirees with healthy pre-tax savings, there are other factors at play that can make "waiting" a more expensiv...

Tax season is finally over. The returns are filed, the stress is behind you, and the last thing you probably want to do is think about taxes again. But the weeks right after tax season are one of the most valuable windows you have all year. Every number from last year is fresh, every missed opportunity is still visible, and every mistake you just uncovered is a clue about what to fix going forward...

One of the biggest decisions you'll make in your 70s and 80s has nothing to do with your portfolio. It's not about Social Security timing. And it's not about Roth conversions. It's about where you'll live and, more importantly, how care will be delivered, coordinated, and paid for if your health changes later on. Most people think of this as a lifestyle decision. But in reality, it's a housing-and...

According to the FBI, Americans lost nearly $21 billion to cyber-enabled fraud last year—a 26% increase from the year before. And the single largest category? Investment-related fraud, with more than $8.6 billion in losses. But what's most unsettling isn't the scale... it's how simple some of these scams really are. A retired couple recently lost thousands of dollars from their IRA after a scammer...

A viral claim keeps making the rounds: that a 1% advisory fee will drain hundreds of thousands of dollars from your retirement savings. The math looks alarming... and that's exactly the point. But as with most things in finance (and life!), the truth is more nuanced than a headline or social media post makes it seem. In this episode, I break down research from Derek Tharp, Ph. D., CFP®, that puts...

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 esp...

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...

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 wro...

📝 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 *** 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 av...

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 wai...

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 an...

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...

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...

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 uninte...

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 m...