A new report warns that Social Security's trust fund could run short of reserves by 2032, potentially leading to benefit reductions if lawmakers fail to act. In this episode of Winning Retirement, Greg and Kristen break down what that could mean for retirees and whether claiming benefits early is the right move.

They explore possible solutions Congress may consider—including higher payroll taxes, raising the retirement age, and adjusting cost-of-living increases—and discuss why Social Security should be viewed as a foundation of retirement income, not the entire plan. You'll also hear why maximizing Social Security isn't always the same as maximizing your retirement, and why having a comprehensive income strategy may be more important than ever.

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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.

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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.

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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.

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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.

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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!

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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.

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This week, it’s all about this powerful statistic: nearly 70% of family wealth is lost by the second generation, and 90% by the third. So why does that happen? Greg and Kristin break down the biggest reasons families lose wealth over time, including a lack of communication, a lack of financial education, and failing to pass down values along with money. You’ll also hear real-life stories about clients—both the successes and the struggles of wealth transfer—and learn how open conversations, proper planning, and intentional legacy-building can make all the difference. Because in the end, your legacy isn’t just about the money you leave behind—it’s about the impact you make while you’re here.

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