Stay Wealthy Retirement Podcast

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™

Every January, we go through the same routine. Limits adjust, brackets shift, and most years it's just a quick refresh. But 2026 is different. Sweeping tax legislation passed last summer is introducing some of the biggest changes we've seen in a while. And buried inside those updates are two new rules that have already caused widespread confusion (even among experts). In this bonus episode, I walk through the most important tax updates for 2026 and explain why they matter for your retirement plan. I also also break down those two unique rules, sharing how they work, who they apply to, and why they matter. So even if you feel up to speed on the 2026 changes, I'm confident you'll walk away with at least one new and useful insight. *** 📆 BOOK A CALL: For nearly 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: → Download the 2026 Tax Cheat Sheet → Grab the Episode Show Notes → Learn About the Total Retirement System™

After decades of saving and doing the right things, most people expect retirement to feel clear. But for many, it doesn't. Not necessarily because they didn't save enough, but because key financial decisions were made in isolation. In this episode, I walk through the seven questions every retirement saver should be able to answer. I also share the exact planning framework my team and I use to make sure those questions are addressed in a thoughtful, coordinated way. By the end of today's episode, you'll have a clearer framework for evaluating your retirement decisions. And more importantly, you'll understand what it actually takes to feel confident about the years ahead. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly 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 Here to Learn More *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™

It's that time of year again—time to step back from the complex tax strategies, Roth conversion debates, and retirement planning deep dives… and have a little fun. 😊 In this annual "surprising stats" episode, I'm sharing 7 counterintuitive facts about the markets and investing. Some are counterintuitive. A few might make you question things you've believed for years. And at least one involves math that should make anyone considering complex insurance products hit the pause button. By the end of today's episode, you'll walk away feeling more confident in the proven (sometimes boring!) academic approach to investing that we talk about so often here on the show. And if nothing else, you'll have a few holiday-dinner stats to drop between bites of pie. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly 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 Here to Learn More *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™ → Download the 2026 Tax Cheat Sheet

💥 Download the freshly updated 2026 Tax Planning Cheat Sheet (PDF): www.youstaywealthy.com/cheatsheet *** Most year-end tax advice is generic... max out your 401(k), bunch your deductions, donate to charity. But for diligent retirement savers with healthy nest eggs, the real opportunities are more nuanced. In this episode, I break down three tax strategies that can help you avoid overpaying the IRS and reduce your lifetime tax bill. You'll learn how to evaluate whether each move makes sense for your situation, so you're making informed decisions rather than chasing aimless deductions. If you're nearing retirement or already there, this episode will help you close out the year with a clearer tax picture and a smarter plan for the years ahead. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly 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 Here to Schedule a Call *** EPISODE RESOURCES: → Download the 2026 Tax Cheat Sheet → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™ → Careers at Define Financial

The Oracle of Omaha is officially "going quiet." In a rare and deeply personal announcement, Warren Buffett published what appears to be his final press release to shareholders. This episode isn't about taxes, investing, or the latest market headlines. It's about how one of the most successful investors of all time is thinking about money, family, aging, and what actually matters when the scoreboard stops moving. In this Thanksgiving special, I break down: ▶ Why he chose to say this now (at age 95!) ▶ What retirement savers and investors can learn from his message ▶ How his parting wisdom can change the way you use your time and wealth If you've ever wondered what your future self might wish you'd paid more attention to today, this conversation is for you. Tune in for the deeper meaning behind Buffett's Thanksgiving sign-off ("yes, even the jerks") and what it reveals about redefining success in the second half of life. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly 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 Here to Schedule Your FREE Strategy Session *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™

"Just buy the index." It's the simple advice that built your wealth and got you to the finish line. But here's what often gets overlooked: The strategy that got you to retirement won't necessarily keep you there. When you switch from saving to spending, the math changes. Suddenly, relying on a "simple" S&P 500 strategy exposes you to risks that didn't matter when you had a paycheck. In this episode, we cover: ▶ The Simplicity Trap: Why "decision fatigue" lures smart retirees into risky, overly concentrated portfolios. ▶ S&P 500 Reality Check: Why the "safe" default option is actually dangerous for your retirement income. ▶ The "Flatline" Defense: How to build a retirement portfolio that protects your purchasing power during downturns. ▶ Beyond Investing: How to align your investments, taxes, and legacy for true peace of mind. If you are approaching retirement and wondering if your "set it and forget it" strategy is enough to last a lifetime this episode is for you. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, my team and I 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 Here to Schedule Your FREE Strategy Session *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™

Everyone fears running out of money in retirement—even millionaires. What most people don't realize is that research shows most retirees rarely spend down their savings. In fact, many actually see their wealth grow throughout retirement, even during some of the toughest markets in history. In this episode, we unpack: ▶ Why that happens ▶ What the data really says about retirement spending ▶ How to find the right balance between confidence and caution By the end, you'll see why most retirees worry far more than they need to, and how to feel confident spending your own money. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, my team and I 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 Here to Schedule Your FREE Strategy Session *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™

Sales of "traditional" long-term care insurance have fallen 92% since 2002. Meanwhile, hybrid policies have surged to over 500,000 sales a year. But which option actually makes sense for your situation? In this episode, I break down everything you need to know before buying long-term care insurance, including: ▶ The optimal age to purchase ▶ Traditional vs. hybrid policies (the real pros and cons beyond the sales pitch) ▶ The actual costs of proper coverage I'm also sharing three critical implementation details that can make or break your coverage when you need it most. If you're approaching retirement and wondering how to protect yourself from potentially catastrophic long-term care costs, this episode will give you the clarity you need to make an informed decision. *** SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule Your FREE Strategy Session *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™

You've heard it before—70% of Americans over 65 will need long-term care. While that number is technically true, it's also misleading. Because here's what many people don't realize: the vast majority of retirees will never face a catastrophic, six-figure care event. In fact, nearly two-thirds will spend ZERO out of pocket during their lifetime! 🤯 So how do you prepare responsibly without overpaying for protection you may never use? In this episode, I walk you through a simple 5-step process to decide if you can safely "self-fund" your long-term care needs, while still protecting your retirement plan and peace of mind. *** SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Strategy Session *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™

Americans lost a record $16 billion to scams in 2024—nearly 40% from investment fraud alone. The trend is moving in the wrong direction. In this episode, I share the story of a small-town financial advisor who built trust over decades, until that trust unraveled into one of the most devastating scams they'd ever seen. More importantly, I break down 8 red flags that experts say could indicate you're being conned. Because here's the truth: falling for a scam doesn't mean you're careless or foolish—it means you're human. And understanding the psychology behind deception is the best way to protect yourself. If you think you're immune, that confidence might be exactly what scammers are counting on. *** SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Strategy Session *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™

Most experts say the smartest Social Security move is to wait until age 70 to claim. On paper, the logic seems simple—delay claiming, and you'll lock in a larger monthly check for life. But here's what's interesting: only about 10% of Americans actually wait that long. 🤯 Nearly one-third claim Social Security at 62, and the majority file before full retirement age. So are millions of retirees making a huge mistake… or is the conventional wisdom missing something? In today's episode, I'm sharing findings from a new research paper showing why delaying until 70 isn't always the clear-cut, no-brainer strategy it's made out to be. *** SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Strategy Session *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™

We've been told our whole lives that retirement happens at 65—maybe 62 if you're lucky. But in my experience, that traditional timeline isn't always the reality. In fact, for many people, retirement may be much closer than they realize. After nearly 20 years of building retirement plans, I've noticed a recurring theme: Most people overestimate how much they think they need and underestimate how ready they already are. That's why in this episode, I'm breaking down 7 signs that could mean you're closer to early retirement than you realize. These aren't about chasing some arbitrary savings target—they're practical, real-world markers that can help you rethink your timeline and gain confidence in your next chapter. If even a few of these resonate with you, it may change the way you think about retirement and the life you've worked so hard to create. *** SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Strategy Session *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™

Even if you're not on Medicare right now, chances are someone you love is—and sooner or later, you'll face those decisions yourself. That's why it's worth paying attention to an important letter that arrives every September: the Annual Notice of Change. Most people glance at it, toss it aside, and never think twice. But with big shifts coming in 2026, ignoring it could be a costly mistake. And that letter is just the beginning. There are three other Medicare traps that cost people thousands each year and, in some cases, wreck entire retirement plans. In this episode, I'll walk you through the 2026 changes you (and your loved ones!) need to prepare for, plus the three mistakes to avoid no matter what year it is. By the end, you'll know exactly what to watch for and how to feel confident about Medicare—whether you're enrolled now, preparing for it soon, or helping someone you care about. *** SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Strategy Session *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™

Despite making insurance decisions almost daily, many retirement savers don't truly understand what they're buying or why they need it. In today's episode, I'm breaking down life insurance into simple, actionable terms. Specifically, I'm sharing: ‣ The 3 essential steps to managing insurable risks ‣ The key differences between term and permanent life insurance ‣ The exact questions to ask yourself before buying (or hanging onto) any policy I'm also sharing a few little-known facts and tips to help you properly evaluate options you may be considering. Even if you think you know everything about life insurance as it relates to your retirement plan, today's episode will provide valuable and important reminders as you continue managing your ongoing insurance needs. *** SCHEDULE A RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Strategy Session *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Schedule Your Free Retirement Strategy Session

Retirement is about so much more than money—it's a complete life transition. In this episode, I'm sharing my recent conversation with Adam Cmejla, where we explore the often-overlooked aspects of retirement planning. We discuss: ‣ Why retirement can feel like a grieving process—and how to navigate it ‣ The surprising role responsibility and community play in long-term happiness ‣ Smarter ways to approach Monte Carlo simulations, taxes, and cash management We also share our favorite retirement and investing charts that reinforce the principles essential to keeping financial plans grounded. Whether you're 10 years out from retirement or already there, this conversation challenges common assumptions and offers a helpful perspective on this stage of life. *** SCHEDULE YOUR FREE DISCOVERY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Discovery Meeting *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Get Your FREE Retirement & Tax Analysis!

Required Minimum Distributions (RMDs) could force you to withdraw as much as 15% of your retirement account balance in a single year. But do RMDs really put you at risk of outliving your money? Why does the IRS expect you to live so much longer than the Social Security Administration does? And what proactive steps can you take before age 73 to avoid giving the IRS more than its fair share? In this episode, I'm unpacking: ‣ How RMDs are actually calculated ‣ Why the IRS tables are more conservative than most people realize ‣ The pros and cons of using RMDs to build a dynamic withdrawal strategy I'm also sharing tax planning tips and strategies for navigating your RMDs. If you're concerned about how RMDs might impact your retirement plan—or you're looking to optimize your tax situation before they kick in—this episode is for you. *** SCHEDULE YOUR FREE DISCOVERY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Discovery Meeting *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Get Your FREE Retirement & Tax Analysis!

Is retiring in your 50s actually realistic for everyday Americans? According to a recent NerdWallet survey, the average target retirement age for households earning $100,000+ isn't 65—it's 58. And these aren't tech moguls or lottery winners. They're teachers, small business owners, and dual-income couples who've steadily built their nest eggs and now want to enjoy their healthy, active years while they can. But retiring in your 50s requires a very different kind of plan. One that accounts for early withdrawal penalties, health insurance gaps, and delayed Social Security. These obstacles are the "triple threats" of early retirement. In today's episode, I'll share how to combat them and provide a simple 5-step process for turning your retirement vision into a reality. *** SCHEDULE A COMPLIMENTARY DISCOVERY CALL: Looking to hire a retirement and tax planning expert? We help 100+ families across the country navigate retirement, optimize investments, and reduce taxes. 🗓️ Schedule a Complimentary Discovery Meeting to Learn More. *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Get Your FREE Retirement & Tax Analysis!

What if everything you've learned about money completely changes once you cross the $1 million mark? Many people think a healthy 7-figure nest egg means the hardest part is done, but ironically, that's when the biggest financial challenges start. Today, Nick Maggiulli returns to share his latest retirement research, which inspired his new book, "The Wealth Ladder." In this conversation, we explore: ▸ Why retirement savers with $1-10 million often feel "stuck" ▸ The surprising reason wealthy retirees are more likely to LOSE wealth than those with less money ▸ Why your investment portfolio becomes more important than your income at this stage ▸ The academic research showing good health is worth $400,000 per year If you're nearing retirement (or already there), you'll learn why crossing the million-dollar mark isn't the finish line—it's when the game changes entirely. *** SCHEDULE A COMPLIMENTARY DISCOVERY CALL: Looking to hire a retirement and tax planning expert? We help 100+ families across the country navigate retirement, optimize investments, and reduce taxes. 🗓️ Schedule a Complimentary Discovery Meeting to Learn More. *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Get Your FREE Retirement & Tax Analysis!

A recent study reported that 76% of retirees regret not saving more money. But after working with hundreds of successful retirees and analyzing thousands of survey responses, I've discovered something interesting: Their deepest regrets actually have little to do with financial shortfalls. Instead, they revolve around critical aspects of financial planning that significantly impact purpose, independence, and fulfillment in your golden years. In this episode, I'm revealing three (3) retirement regrets that many people don't consider until it's too late. I'm also sharing how to avoid the same mistakes so YOUR retirement is fulfilling instead of filled with regret. *** SCHEDULE A COMPLIMENTARY DISCOVERY CALL: Looking to hire a retirement and tax planning expert? We help 100+ families across the country navigate retirement, optimize investments, and reduce taxes. 🗓️ Learn more and schedule a Discovery Meeting with us. *** EPISODE RESOURCES: ✏️ Grab the Episode Show Notes 📫 Join the Stay Wealthy Retirement Newsletter 📊 Get Your FREE Retirement & Tax Analysis!

Wondering how the new 'One Big Beautiful Bill Act' affects you and your retirement plan? Don't want to read 870 pages of Congressional jargon? I've got you covered! In this episode, I'm breaking it all down and sharing the 5 biggest things retirement savers need to know. I'm also addressing several broader provisions in the bill and clarifying some common misconceptions. This giant (and confusing!) economic package touches nearly every aspect of your financial life. So, pour yourself some coffee—or something stronger if you need it—and hit play. *** SCHEDULE A COMPLIMENTARY DISCOVERY CALL: Looking to hire a retirement and tax planning expert? We help 100+ families in 40 states across the country navigate retirement, optimize investments, and reduce taxes. 🗓️ Learn more and schedule a Discovery Meeting with us. *** EPISODE RESOURCES: ✏️ Grab the Episode Show Notes 📫 Join the Stay Wealthy Retirement Newsletter 📊 Get Your FREE Retirement & Tax Analysis!

Think you need millions of dollars to retire comfortably? Think again. Most people believe they're "behind" on retirement savings because they're measuring against arbitrary benchmarks that don't reflect their unique situation. But what if retiring at 62 is actually more achievable than you've been led to believe? In this episode, I'm sharing: ► Why you should ignore popular savings benchmarks ► Why delaying Social Security isn't always the right move (and how taking it early might preserve MORE wealth) ► A simple 4-step process to build your personalized early retirement plan If you're tired of feeling behind and want to discover how early retirement might be within reach right now, this episode is for you. *** SCHEDULE A COMPLIMENTARY DISCOVERY CALL: Need retirement & tax planning guidance? We help 100+ families across the country navigate retirement, optimize investments, and reduce taxes. 🗓️ Learn more and schedule a Discovery Meeting with us. *** EPISODE RESOURCES: 📊 Get Your FREE Retirement & Tax Analysis! ✏️ Grab the Episode Show Notes 📫 Join the Stay Wealthy Retirement Newsletter

"I planned for 30 years of expenses—but zero years of purpose." This was a recent client's confession, and she's not alone. In fact, nearly 40% of retirees say they wish they had waited longer to retire (and it's not about money). In this episode, I'm revealing why even the most financially prepared retirees fall into identity crises and regret. I'm also sharing my 5-step "Bridge Strategy" to help you retire with clarity and purpose, not just a seven-figure portfolio. If you're planning FOR retirement but haven't considered what you're retiring TO, this episode is for you. *** SCHEDULE A COMPLIMENTARY DISCOVERY CALL: Need professional retirement & tax planning help? We help 100+ families across the country navigate retirement, optimize investments, and reduce taxes. 🗓️ Learn more and schedule a Discovery Meeting with us. *** EPISODE RESOURCES: 📊 Get Your FREE Retirement & Tax Analysis! ✏️ Grab the Episode Show Notes 📫 Join the Stay Wealthy Retirement Newsletter

"Cash is king" has guided investors since the 1987 market crash. But what if this so-called "king" is actually putting your retirement plan at risk? Millions of retirees are lured by today's enticing cash yields, confusing safety nets for sound investment strategies. In this episode, I'm revealing why cash (even at 4-5%) is a deceptive long-term investment. I'm also sharing details about a critical investment performance metric to help you make more informed portfolio decisions. If you're wondering how to balance safety and growth in today's uncertain market, this episode is for you. *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive my recently updated 2025 Tax Cheatsheet (PDF). You'll also receive weekly retirement and investing tips from yours truly. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📊 Get Your FREE Retirement & Tax Analysis! ✏️ Grab the Episode Show Notes

You've finally made it to retirement! But what if some of the choices you're making right now are quietly pulling you back to work? Every year, countless retirees are forced back into the workplace. Not because they were reckless, but because they followed advice that sounded smart and safe. In this episode, I'm sharing 7 of the most common retirement pitfalls that can derail even the best-laid plans. I'm also sharing our Total Retirement System™—a comprehensive framework to ensure you retire once and never look back. If you're approaching retirement (or already there) and want to avoid mistakes that force people back to work, this episode is for you. *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive my recently updated 2025 Tax Cheatsheet (PDF). You'll also receive weekly retirement and investing tips from yours truly. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📊 Get Your FREE Retirement & Tax Analysis! ✏️ Grab the Episode Show Notes

"I'll just work a few more years." It's the retirement safety net millions of Americans often count on. In large part because the financial industry has convinced everyone that retiring later is the most sensible backup plan if your savings fall short. But what if this common advice is actually setting you up for one of the most costly mistakes of your life? In this episode, I'm sharing why the real danger may not be running out of money in retirement, but rather working too long. I'm also sharing why choosing the right withdrawal strategy may help you retire sooner AND give you more confidence to spend in retirement. *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive my recently updated 2025 Tax Cheatsheet (PDF). You'll also receive weekly retirement and investing tips from yours truly. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📊 Get Your FREE Retirement & Tax Analysis! ✏️ Grab the Episode Show Notes

Today I'm diving into the tariff-induced market mania that has been dominating every news headline. Specifically, I'm joined by Cullen Roche, monetary economics expert and founder of Discipline Funds, to discuss three important things: ► How tariffs actually work and why economists across the political spectrum overwhelmingly agree they are bad ► What the recent tariff proposal means for the economy (and American consumers) ► What yesterday's "90-day pause" means for the markets going forward We also discuss how retirement investors should approach their portfolios during this period of economic uncertainty + what changes are prudent to make. *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive my recently updated 2025 Tax Cheatsheet (PDF). You'll also receive weekly retirement and investing tips from yours truly. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📊 Get Your FREE Retirement & Tax Analysis! ✏️ Grab the Episode Show Notes

ESG investing is exploding in popularity—but it's also a giant, confusing mess. Over $35 trillion in global assets now follow ESG guidelines. 🤯 But despite the rapid growth, most retirement investors still don't fully understand ESG investing... ...or how to spot legitimate ESG strategies from clever marketing hype. To help break through the confusion, Liz Simmie joins me to discuss: ➤ What ESG investing is and how it differs from Socially Responsible Investing (SRI) ➤ How retirement savers should evaluate ESG funds, particularly in terms of cost and performance ➤ The #1 data point Liz screens for when evaluating an ESG investment We also explore how investors can cut through ESG marketing hype to find genuinely responsible investment solutions. *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive my recently updated 2025 Tax Cheatsheet (PDF). You'll also receive weekly retirement and investing tips from yours truly. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📊 Get Your FREE Retirement & Tax Analysis! ✏️ View the Episode Show Notes

Morningstar recently published its annual "State of Retirement Income" research report. This year's report finds the highest 30-year safe withdrawal rate for retirees is... 3.7% 🤯 In this episode, you'll learn: ► How researchers arrive at different recommended withdrawal rates ► Why popular withdrawal strategies are (likely) too conservative ► 3 proven strategies for boosting retirement income And since there is no one-size-fits-all, you'll also learn the pros and cons of each retirement income strategy discussed! *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive my recently updated 2025 Tax Cheatsheet (PDF). You'll also receive weekly retirement and investing tips from yours truly. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📊 Get Your FREE Retirement & Tax Analysis! ✏️ Grab the Episode Show Notes 📘 Subscribe to "The Go-Go" Retirement Newsletter

Today I'm discussing the biggest retirement investment risk. As Morgan Housel put it, "It's the hardest risk for people to understand... ...and it's the only one that really matters." In this episode, you'll learn: ► What the three sides of risk are ► Why tail risk is all that matters ► How to mitigate this risk in your retirement plan You'll also learn why most investors should (probably) stay away from investment products promising you lots of upside with limited downside. *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive my recently updated 2025 Tax Cheatsheet (PDF). You'll also receive weekly retirement and investing tips from yours truly. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📊 Get Your FREE Retirement & Tax Analysis! ✏️ Grab the Episode Show Notes 📘 Check Out the Retirement Podcast Network

Worried about Medicare IRMAA eating into your retirement savings? Whether you're 10+ years away from Medicare or already enrolled, this episode will help you navigate this pesky surcharge and protect your retirement savings. Key topics covered: ► Updated 2025 IRMAA brackets ► Answers to common planning questions ► 3 strategies to minimize (or avoid) IRMAA You'll also learn how to project future IRMAA brackets for better planning. If you want a clear roadmap for making informed decisions about your future healthcare costs, you'll enjoy today's episode. *** RETIREMENT & TAX PLANNING: Looking to hire a financial planner with retirement & tax planning expertise? My team and I only have a few more openings for Discovery Meetings with new clients. If you're seeking professional help, we would love to have a conversation! 👉 Learn more about our process and grab one of the remaining slots. *** EPISODE RESOURCES: 📊 Get Your FREE Retirement & Tax Analysis! ✏️ Grab the Episode Show Notes 📘 Check Out the Retirement Podcast Network

Markets tend to operate in cycles—yesterday's winners often become tomorrow's losers (and vice versa). The most unloved asset classes can quietly become the best performers, while the most popular ones frequently disappoint. Yet, many investors fall into the trap of assuming recent trends will continue indefinitely. But markets don't work that way. No asset class outperforms or underperforms forever. To help you avoid falling into this trap (and make more informed portfolio decisions), I'm sharing key takeaways from Vanguard's 2025 Market & Economic Report in this episode. I'm also sharing 5 actions retirement savers can take right now to prepare for success over the next decade and beyond. *** Looking to hire a financial planner with retirement & tax planning expertise? My team and I only have a few more openings for Discovery Meetings with new clients. If you're seeking professional help, we would love to have a conversation! 👉 Learn more about our process and grab one of the remaining slots. *** EPISODE RESOURCES: 📊 Get Your FREE Retirement & Tax Analysis! ✏️ Grab the Episode Show Notes 📘 Check Out the Retirement Podcast Network

Looking to hire a financial planner with retirement & tax planning expertise? My team and I have availability for 25 Discovery Meetings over the next 8 weeks. If you're seeking professional retirement planning help, we would love to have a conversation! 👉 Learn more about our process and grab one of the 25 meeting slots. We intentionally limit the number of new clients we take on each year. This ensures we can provide each family with highly customized investment, retirement, and tax planning services. Once these 25 meetings are scheduled, we will not have availability to meet with new clients until later this year. Schedule your Discovery Meeting. *** Today I'm sharing the essential steps for evaluating and selecting the right financial advisor for your unique situation. Specifically, I cover 5 important things: ► How to identify and document your financial challenges, needs, and goals before starting your search ► Critical questions to ask yourself about the type of professional you want ► Guidance for conducting background checks ► Non-obvious questions to ask potential advisors ► The importance of a well-defined evaluation process (and why you shouldn't rush your decision) You'll learn how to navigate through the sea of 300,000+ financial advisors to find the right one for you. Whether you want a short-term or long-term engagement, this episode provides actionable steps to help you make the right choice. *** EPISODE RESOURCES: 📊 Get Your FREE Retirement & Tax Analysis! ✏️ Grab the Episode Show Notes 📘 Check Out the Retirement Podcast Network