Advertise on podcast: Stay Wealthy Retirement Podcast

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-care decision, and it's one most retirement plans barely address. In this episode, I'm breaking down the later-life housing choices most retirement savers haven't fully thought through. Here's what you'll learn: → The four main housing options later in life—and how they differ in cost, care, and flexibility → What Continuing Care Retirement Communities (CCRCs) actually are (+ a little-known tax planning tip) → The four types of risk every housing decision really involves → When this decision usually needs to be made, and what can happen if you wait too long Because "we'll just stay in the house" isn't a plan...it's an assumption. And assumptions tend to get tested at the worst possible moment. *** 📆 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™

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 tricked them into sharing a single six-digit verification code over the phone. No hacking. No stolen password. Just one text message and one phone call. In this episode, I'm breaking down how "account takeover" scams work, why they're so effective, and the specific steps you can take to close the security gap. Here's what you'll learn: → The 3-step pattern behind most account takeover scams  → Why your personal information may already be compromised (and what that means for your account security) → What to do—and what not to do—when a financial institution contacts you about suspicious activity → 3 simple upgrades to better protect your accounts that most people overlook In a world where scammers only need a few seconds to strike, your ability to slow down and take back control of the moment may be the most valuable layer of protection you have. *** 📆 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 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 this widely shared math to the test and reveals where it falls apart.  Here's what you'll learn: → The misleading assumptions behind the popular "1% fee" calculation  → How alternative fee models can be 3x more expensive using the same math → What academic research says about quantifying the value of a good advisor → A smarter way to evaluate whether hiring an advisor makes sense for your specific situation This episode isn't about defending any particular fee model. It's about making sure you have the right information to evaluate the cost, the value, and the role financial advice may play in your retirement planning.  *** 📆 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™

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™

📝 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 average. And ironically, the traditional 4% rule may be one reason why. In this episode, I'm breaking down new research on retirement withdrawal strategies—and what it reveals about how retirees may be able to spend more. Here's what you'll learn: → 5 strategies that (safely) support higher retirement income → The overlooked key to sustainable and confident retirement spending → 3 factors that can push starting withdrawal rates to as high as 6.5%  The goal of retirement planning isn't just making your money last…it's making sure you actually use it. Which raises an important question: "Could you afford to spend more in retirement than you think?" *** 📆 BOOK A CALL: 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™

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 waiting until 65 may not be what you think  → The options many people overlook and the tradeoffs worth understanding Because for most people, the healthcare challenge does have a solution. And the worst thing you can do is never explore your options at all. *** 📆 BOOK A CALL: 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™

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 and interest over capital gains to fund retirement. But retirement income planning isn't just about generating cash flow. It's about creating sustainable income from a finite pool of capital while coordinating taxes and the rest of your retirement plan. In this episode, I break down new research on dividend investing and explain why the most popular income strategy may be far less efficient than it appears. I also share what the evidence suggests about building a portfolio and a plan that actually supports long-term retirement success. Because when it comes to funding your retirement, small structural decisions compound into very large outcomes. *** 📆 BOOK A CALL: 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™

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 even benefit from) uncertainty I'm also sharing why many "downside-protection" strategies sound compelling in theory, but are risky and difficult to execute in the real world. *** 📆 BOOK A CALL: 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™

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 around a chart mapping nearly 100 years of U.S. market history. When you zoom out, several widely accepted beliefs about market crashes and bull markets start to look far less certain. In this episode, I break down the three common myths the article explores. I also share what the data actually tells us about bear markets and what's far more likely to derail your retirement than a crash. Not to predict the future or eliminate risk. But to help you think more clearly about the environment we're in and how it fits into a disciplined, long-term retirement plan. ----- EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

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 unintended consequences (higher fees, reduced flexibility, extra taxes).  So in today's episode, I break down how annuities actually work. We'll walk through the major types of annuities, how "guarantees" are structured, what you're really paying for, and where the risks tend to show up later in retirement. I'll also explain when annuities may make sense, when they don't, and how to evaluate them as part of a coordinated retirement plan so you can make informed decisions with confidence. *** 📆 BOOK A CALL: For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click to Learn More and Schedule *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

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 myself reconsidering the question entirely. In today's episode, I share how to evaluate investments in the real world, what separates good investments from bad ones, and why some popular metrics can mislead. If you've ever wondered why an investment looks great paper but doesn't feel right—or why others swear by strategies you'd never touch—this episode will give you a clearer framework for thinking about your own portfolio. *** 📆 BOOK A CALL: For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click to Learn More and Schedule *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

After decades of filing taxes together, most couples assume their retirement plan will continue largely unchanged if one spouse passes away. But for many surviving spouses, the first surprise is a higher tax bill, even when income hasn't changed much. In this episode, I explain how a feature of the tax code can increase taxes after the loss of a spouse. Using a real-world example, I show why tax brackets shrink, why retirement income often doesn't, and how that mismatch can quietly drive taxes higher over time. More importantly, I share a planning framework couples can use while both spouses are still alive. We'll cover common mistakes, why the "married window" matters, and how small, intentional decisions made years in advance can meaningfully protect the surviving spouse. This isn't about fear or worst-case scenarios—it's about avoiding unnecessary surprises and making thoughtful, proactive decisions that support confidence throughout retirement. *** 📆 BOOK A CALL: For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click to Learn More and Schedule *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

Every year, Wall Street rolls out its market predictions. Targets get published, expectations get set, and the headlines make it sound like the future is just a spreadsheet away. But markets have a long history of humbling even the most confident forecasts, and that creates a real problem for retirement savers. Because, while short-term forecasts are usually noise, ignoring market expectations altogether isn't the answer either.  So in today's episode, I break down how to think about market outlooks the right way. We'll cover why forecasts so often miss the mark, when long-term assumptions actually matter, and how market research can be used as a planning tool (not a prediction engine). I also share key themes from Vanguard's Economic and Market Outlook for 2026, focusing on growth, inflation, and expected returns—and why all of that matters for your portfolio and retirement plan. *** 📆 BOOK A CALL: For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click to Learn More and Schedule *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™