Winning Retirement Radio

Greg and Kristen discuss why nearly 6 in 10 retirees leave the workforce earlier than expected. From layoffs and workplace burnout to health challenges and family caregiving responsibilities, they explore the real-life reasons retirement plans often change. You'll learn why building flexibility into your retirement strategy is critical, how to prepare for life's unexpected "what ifs," and ways to create a reliable income while preserving assets for future opportunities and challenges.    🤔 Feeling stuck with your retirement planning? Download a FREE copy of Legacy’s My Retirement Kit to help become better organized. See omnystudio.com/listener for privacy information.

Greg and Kristen discuss summer travel, family vacations, and the rising cost of living. Then, using the latest Social Security COLA projections as a starting point, they explore why inflation remains one of the biggest threats to a successful retirement. You'll learn how inflation compounds over time, why budgeting is critical regardless of your net worth, and how a written retirement income plan can help ensure your money keeps pace with rising expenses throughout retirement. 👉 Ready to take the guesswork out of retirement? Get your FREE copy of Legacy’s My Retirement Kit today—your step-by-step guide to getting organized and staying on track! See omnystudio.com/listener for privacy information.

In this episode of Winning Retirement, Greg and Kristen discuss the question many retirees are asking: “Have we done enough?” They explain why retirement planning is about more than building wealth—it’s about creating reliable income, managing taxes, and maintaining your lifestyle. You’ll also hear insights on diversification, Roth conversion strategies, and why the real goal of retirement planning is having the confidence to enjoy life without worrying about running out of money.   ✍️ Ready to design your ideal retirement? Schedule a FREE consultation by completing this brief form.  See omnystudio.com/listener for privacy information.

In this heartfelt episode of Winning Retirement, Greg and Kristen discuss how quickly retirement plans can change when unexpected health challenges arise. Inspired by the ALS diagnoses of close friends and clients, they explore the emotional and financial impact serious illness can have on retirees and their families. Greg shares the story of a client whose retirement changed dramatically just months after leaving work, and why having a flexible plan in place helped provide peace of mind during a difficult time. They also break down the three major retirement risks—market volatility, taxes, and healthcare costs—and explain why true retirement planning goes far beyond investments alone. You’ll also hear why flexibility matters, the importance of family conversations, and how a comprehensive plan can help protect both your finances and your loved ones when life takes an unexpected turn.   🗂️ Get Organized. Get Confident. Get Your FREE Retirement Kit from Legacy!  See omnystudio.com/listener for privacy information.

Greg and Kristin explore an important retirement question: Is the goal to become wealthy—or simply make sure you never run out of money? Greg shares a personal story about losing everything in a childhood house fire and how it shaped his views on financial security. They also break down the difference between harmful debt and strategic debt in retirement, including when it may make sense to keep a mortgage rather than pay it off. They discuss cash flow, taxes, home equity lines of credit, and why retirement planning should fit your comfort level—not someone else’s definition of success.   📄 Snag your FREE copy of Legacy's My Retirement Kit to help you get organized today! See omnystudio.com/listener for privacy information.

In this episode of Winning Retirement, Greg and Kristen start with some fun family stories before tackling a challenge many families face today. With rising housing costs and more young adults living at home, parents are helping more than ever—but how much is too much? They break down the difference between support and dependency, share real client scenarios, and explain why your retirement comes first. If you’re wondering how to help your kids without putting your own future at risk, this episode is for you. 🔎 Feeling confident—or just want to be sure—you’re on the right path to your version of a Winning Retirement? Take a moment to complete a short form and schedule your complimentary consultation. See omnystudio.com/listener for privacy information.