Stay Wealthy Retirement Podcast

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!