Retire Well

Josh Bretl
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  • Investing

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!

  1. Jul 18

    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.

  2. Jul 11

    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.

  3. Jul 4

    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.

  4. Jun 27

    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.

  5. Jun 20

    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.

  6. Jun 13

    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.

  7. May 30

    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.

  8. May 23

    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.

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About

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!

Information

  • Creator
    Josh Bretl
  • Years Active
    2025 - 2026
  • Episodes
    96
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Josh Bretl
  • Show Website
    Retire Well