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Retire Well

Josh Bretl

Our weekly radio show dedicated to giving you the confidence to make retirement the best part of your life. We're on the air every Saturday and Sunday from 7-8 am CST on WLS 890AM Chicago!

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Avg 51 min
English

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#103
Yesterday · 52 min
103: Dino Nuggets, National Debt, and Navigating Your Retirement Tax Shock
Football season is back in the Bretl house, complete with team Dino Nuggets. But on this episode, Josh Bretl and Mark Elliott tackle a bigger opponent: the 40 trillion dollar national debt and what it means for your retirement taxes. Learn how required minimum distributions can trigger an unexpected tax shock, how the three tax buckets work, and why laddering Roth conversions might save you money down the road. Plus, Josh answers listener mailbag questions on Medicare, spousal timing, and business sales. Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with a Wellment advisor.
#102
September 19 · 52 min
102: How to Turn Your 401(k) Into Lifetime Retirement Income
Is your 401(k) actually ready to fund your retirement? On this episode of Retire Well, Josh Bretl and Mark Elliott break down how to replace traditional pensions with a reliable lifetime income plan. Learn how to manage debt, navigate inherited IRAs under the 10-year rule, handle money in second marriages, and evaluate private equity risks. Josh also shares his simple two-lane strategy to balance safe income with market growth. Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with a Wellment advisor.
#101
September 12 · 52 min
101: Why People Without Kids Feel Less Confident About Retirement
Did you know people without kids report lower retirement confidence than parents? On this episode of Retire Well, Josh Bretl breaks down why this gap exists and how a written plan changes the game. From managing market downturns and longevity to finding your true purpose in retirement, Josh shares practical tips and a few fun stories along the way. Learn how smart withdrawal strategies and tax planning keep your retirement on track. Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with a Wellment advisor.
#100
September 5 · 52 min
100: How to Shift From Saving to Spending in Retirement
Why is it so hard to spend money after saving it your whole life? In our 100th episode of Retire Well, Josh Bretl explores the emotional shift from saving to spending and explains why your nest egg is a tool to be enjoyed, not just artwork to look at. Josh also recaps a fun family river tour in Chicago, breaks down how national debt could impact your future taxes, and answers mailbag questions about RMDs and family loans. Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with a Wellment advisor.
#99
August 29 · 52 min
099: Is a Million Dollars Enough, and What Happens if You Un-Retire?
Can you retire on one million dollars? In this episode of Retire Well, Josh Bretl breaks down the truth about retirement numbers, tax diversification, and income blending. Learn how managing your traditional IRA, Roth IRA, and taxable accounts can help protect your savings. Plus, Josh answers real questions from the mailbag about paying off low interest mortgages, evaluating Roth conversions, and what to consider if you get bored and decide to un-retire. Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with a Wellment advisor.
#98
August 22 · 52 min
098: Medicare Part D Changes and Smart Strategies for Market Volatility
Big changes are coming to Medicare Part D in 2026. In this episode, Josh Bretl and Mark Elliott break down what shifting drug costs mean for your retirement cash flow. Plus, learn how to handle market volatility with a smart plan that balances safety and growth. Josh also shares a fun trip back to 1996 to show why your financial strategy needs to prepare for 30 years of change. Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with a Wellment advisor.
#97
August 15 · 52 min
097: Movie Myths, Money Secrets, and Portfolio Checkups: Navigating Your Retirement Journey
Are you on track for the retirement you want? This week on Retire Well, host Josh Bretl shares a fun movie trip with his son, Alex, and breaks down why mid-year financial checkups matter. Learn how to rebalance your portfolio, turn savings into steady income, and handle big choices like pension lump sums versus monthly payouts. Josh also explains how to balance required expenses with fun goals. Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with a Wellment advisor.
#96
August 8 · 52 min
096: From Pearl Harbor to Portfolios: Smart Ways to Manage Your 401(k)
This week on Retire Well, host Josh Bretl shares personal reflections from a family trip to Pearl Harbor and connects those lessons of perspective and preparation directly to retirement planning. Josh and Mark Elliott discuss whether you should move an old employer 401(k) account and how timing plays a major role in your choice. Josh also answers listener mailbag questions about business succession planning, setting a travel budget, prenuptial agreements in estate planning, and strategies to guard your portfolio against early market downturns. Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with a Wellment advisor.
#95
July 18 · 52 min
095: Why the Federal Reserve Should Not Dictate Your Retirement Success
Economic shifts and Federal Reserve changes can create confusion, but your financial plan should keep you secure regardless of market trends. In this episode, Josh Bretl and Mark Elliott discuss how to assess your true portfolio risk using a clear scoring system rather than vague labels. Josh also shares his new book, personal stories about facing anxiety, and how to navigate the emotional side of leaving the workforce. Retirement is about more than just money: it's about your identity. Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with a Wellment advisor.
#94
July 11 · 52 min
094: From the Balcony to the Front Row: Navigating Social Security and Mid-Year Checkups
What happens when a concert ticket mix up turns into a front row upgrade? On this episode of Retire Well, Josh Bretl shares a funny story from a recent family outing that perfectly sets the stage for today's discussion: turning stressful situations into major financial wins. Josh and Mark Elliott break down the latest headlines about the Social Security trust fund and explain why fear-based, emotional decisions can permanently damage your long-term plan. They also share an essential mid year financial checklist to help you catch small issues before they turn into big problems. From portfolio risk drift and proactive tax strategies to avoiding costly withdrawal mistakes, this episode is packed with plainspoken advice to help you build a confident path forward. Ready to talk? Call (630) 478-9599 to schedule your introductory 15-minute call with a Wellment advisor.
#93
July 4 · 52 min
093: Navigating Life Transitions and the Reality of Market Hype
Major life milestones, like dropping a child off at summer camp or watching twins head to college, bring an undeniable wave of emotional change. Retirement is no different, representing one of the most pivotal life transitions you will ever navigate. In this episode, Josh Bretl and Mark Elliott discuss how to manage the emotional weight of these milestones while keeping your financial strategy on track. They look closely at the reality of market hype, specifically examining the headlines surrounding the SpaceX initial public offering and the dangers of letting the fear of missing out drive your long term investment decisions. Josh breaks down why retirement success relies on steady cash flow planning rather than chasing volatile media trends. You will also learn practical steps for right-sizing your emergency fund, avoiding tax drag, and preparing for unexpected variables like single tax brackets and long term care expenses. Ready to talk? Call (630) 478-9599 to schedule your initial 15-minute call with a Wellment advisor.
#92
June 27 · 52 min
092: From Sleepaway Camp to SpaceX: Navigating Major Retirement Transitions
Retirement is one of the most significant life transitions you will ever face, bringing a unique mix of excitement and uncertainty. In this episode, Josh Bretl compares preparing for retirement to dropping his daughter off at sleepaway camp, showing how deliberate preparation is what makes any new chapter successful. We look at recent financial headlines, including the intense media hype surrounding the SpaceX initial public offering, and explain why chasing popular stocks out of a fear of missing out can disrupt a long term strategy. We also address the real numbers behind rising healthcare expenses, highlighting that a healthy couple may need around $340,000 for medical costs in retirement. Josh explains how Medicare brackets work, explores proactive long term care options, and answers listener questions about unwinding concentrated stock positions and organizing finances after a personal loss. Ready to talk? Ready to talk? Call (630) 478-9599 to schedule your 15-minute call with a Wellment advisor.
#91
June 20 · 52 min
091: Donut Runs, Top Gun, and the Hidden Tax Traps in Retirement
What do old school donut shops, the movie Top Gun, and your estate plan have in common? They're all on the table in this episode of Retire Well! Hosts Josh Bretl and Mark Elliott share stories about family traditions before diving into some critical retirement realities. A recent study reveals that nearly 60% of people retire earlier than they planned, often due to layoffs or health changes. Josh explains the vital steps to take if your timeline shifts unexpectedly. They also tackle legacy planning, highlighting why an outdated will or an uncompleted trust can leave a massive mess for your family. From the hidden tax adjustments that hit surviving spouses to the simple steps of updating your beneficiaries, this episode delivers clear, simple strategies that could help protect your hard-earned assets. Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with a Wellment advisor.
#90
June 13 · 52 min
090: What a Theme Park Dinner Teaches Us About Retirement Planning
Welcome to Retire Well with Josh Bretl and Mark Elliott. This week, Josh shares a story from a recent family trip to Universal Studios, illustrating how exceptional personal care changes your perspective. That same level of dedication is exactly what you should expect from your retirement team. Josh and Mark break down the critical shift from saving a pile of money to generating a reliable monthly income stream. They discuss the major risks facing retirees today, including inflation, market volatility, and tax traps like required distributions. Josh outlines the fiscal house strategy, a practical framework that uses distinct buckets to balance growth and protection. Finally, the team answers listener questions on unexpected job loss at 61, choosing Medicare policies, planning for cognitive decline, and handling a spouse who loves chasing investment trends. Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with a Wellment advisor.
#89
May 30 · 51 min
089: Why Your Retirement Magic Number Might Be a Total Myth
What is your retirement magic number? In this episode of Retire Well, Josh Bretl and Mark Elliott break down why relying on a single savings target might be a myth. True financial security is not just about the size of your nest egg, it's about how much you spend in relation to what you have. Josh shares insights on navigating major life transitions and explains the core pillars of the Wellment Way. You'll learn the mechanics of strategic Roth conversions, including a unique tax advantage specifically for Illinois residents. We also dive into how to protect your Social Security from tax traps and manage Medicare premium surcharges. Finally, we discuss the habits of the quietly wealthy and how to align your retirement spending with what brings you true peace of mind. Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with a Wellment advisor.
#88
May 23 · 52 min
088: The Two Lane Highway Strategy for a Confident Retirement
A recent report shows that most Americans fear outliving their savings more than death itself. It makes sense. For decades, you knew exactly how much money was coming in from your paycheck. In retirement, that predictable income disappears, and the responsibility shifts entirely to you. This week, Josh Bretl breaks down how to transition from a saving mindset to an income mindset. He shares a simple two lane highway strategy designed to protect your short term needs while keeping your long term wealth growing. Plus, Josh answers listener questions about evaluating early retirement packages, managing taxes after selling a family business, deciding whether to file taxes jointly or separately, and protecting an inheritance for a child who struggles with money. Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with a Wellment advisor.
#87
May 16 · 52 min
087: Sweating the Small Stuff: Lessons from an 85 Degree Seminar
Josh Bretl begins this episode with a story from a recent Social Security workshop in Wheaton where the room hit 85 degrees, the fans sounded like a hurricane, and his laptop died mid-presentation. While it felt like a disaster, sitting down with the audience led to a profound connection with a recent widow who felt lost in the complexity of retirement. We explore why confidence in retirement is plummeting for 39% of American workers. Josh breaks down the truth about Social Security cuts and Medicare surcharges, explaining why your tax strategy is just as important as your investment strategy. We also dive into the Wellment Way, a holistic approach that covers income, assets, taxes, healthcare, and legacy planning. Learn how to separate your must haves from your nice to haves to ensure you never outlive your money. 📞 Ready to talk? Call (630) 478-9599 to schedule your complimentary 15 minute call with a Wellment advisor.
#86
May 9 · 52 min
086: Beyond the Pension: Building Your Own Retirement Paycheck
In this episode of Retire Well, Josh Bretl and Mark Elliott discuss the fundamental shift in retirement planning over the last few decades. With traditional pensions largely a thing of the past, today’s retirees must act as their own pension managers. Josh breaks down the recent Federal Reserve Beige Report and explains why emotional reactions to global uncertainty often lead to costly mistakes. We dive deep into the Wellment Way, specifically the strategy of income blending across different tax buckets to minimize your lifetime tax liability. You will learn about the three tax buckets (Tax Me Now, Tax Me Later, and Tax Free) and how a written strategy can provide the clarity you deserve. Whether you are ten years out or already retired, this conversation offers a clear path toward financial freedom. 📞 Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with a Wellment advisor.
#85
May 2 · 52 min
085: Unexpected Visitors and the Most Dangerous Decade
Life has a way of surprising us when we least expect it. This week, Josh Bretl shares a story about an unwelcome visitor in his car that serves as a perfect metaphor for the unexpected challenges of retirement. Whether it is a mechanical failure at home or a sudden shift in the stock market, being prepared is the key to maintaining your peace of mind. Josh and Mark Elliott dive deep into what experts call the most dangerous 10 year period of your financial life: the five years before and the five years after you retire. They discuss why this window is so critical for your long-term success and how the sequence of returns risk can impact your lifestyle. The conversation also covers the four big questions every retiree eventually faces, ranging from the size of your nest egg to the security of your loved ones. We explain why retirement is less about a math problem and more about the freedom to live life on your terms. 📞 Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with a Wellment advisor.
#84
April 25 · 52 min
084: The Parmesan Reset and the Women’s Retirement Marathon
In this episode of Retire Well, Josh Bretl and Mark Elliott discuss how to find clarity when you are feeling out of sorts due to market volatility or headline driven anxiety. Josh shares a personal story about a family dinner reset involving a tableside Parmesan cheese wheel that turned a lethargic Sunday into a great start to the week . We then dive into the unique challenges of the retirement marathon for women, focusing on the specific financial whammies that hit when transitioning from a married to a single filer. From a last minute office wedding that saved a couple eighty thousand dollars in taxes to timeless wisdom from Ben Franklin on plugging financial leaks, this conversation is all about making retirement the best part of your life . We simplify the complex so you can focus on what truly matters most. 📞 Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with a Wellment advisor.

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