Stay Wealthy Retirement Podcast

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™

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. *** 📆 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™

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. *** 📆 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™

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. *** 📆 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™

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. *** 📆 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™

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 → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

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 market history to answer a question most retirement plans don't spend enough time on: "How much does your exact retirement date shape the outcome of your plan?" Here's what you'll learn: → Why retirement timing may matter more than your withdrawal rate or asset allocation  → Why a larger nest egg at retirement has historically led to worse outcomes → A 3-part playbook, in priority order, for protecting your plan when the starting point looks unfavorable Most retirement strategies focus on what happens after you retire. But this research suggests the year you walk away from work may deserve a much bigger seat at the planning table. *** 📆 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™

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 Fidelity that helps explain why having "enough" so often still doesn't feel like enough. I'm also sharing the four things I consistently see in retirees who feel genuinely secure.  Here's what you'll learn: → The retirement planning factor that more than doubles confidence → A cognitive concept that explains why retirement anxiety has very little to do with your account balance → The question many well-prepared retirees still can't answer — and why ignoring it can be so costly Not one of the four pillars has anything to do with the size of your portfolio. Which raises the real question: what's actually keeping wealthy retirees up at night? *** 📆 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™

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 expensive decision than it looks. In this episode, I'm turning the mic over to Josh Rendler — a partner at our firm — who walks through a case study of a 62-year-old woman with a $1.5 million IRA and the question most retirees are wrestling with. Here's what you'll learn: → The reframe that makes "wait until 70" fall apart for retirees with healthy pre-tax balances → How Social Security timing and Roth conversions compete for the same bracket space (and why claiming earlier can actually EXPAND your conversion runway) → The planning window that opens at 61, and what gets harder to fix once it closes The biggest claiming-age check isn't always the biggest after-tax outcome. And a well-built plan shouldn't make you choose between doing the math right and actually enjoying the retirement you spent 35 years earning. *** 📆 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™

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. In this episode, I sit down with Josh Rendler, CFP®, a partner at our firm and someone who spends his days deep inside client tax returns. Together, we're answering some of the biggest questions we're hearing from retirees right now. Here's what you'll learn: → The 3 numbers on last year's return that reveal your biggest 2026 planning opportunities → How to know if charitable giving belongs in your plan (plus the QCD detail that keeps it "invisible" to the IRS) → A fresh, counterintuitive take on Social Security timing While last year's return is still on your desk: what's hiding in there that could make 2026 better? 🤔 *** 📆 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™