Stay Wealthy Retirement Podcast

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