Winning Retirement Radio

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.   🕒 Don’t leave retirement to chance—claim your FREE consultation now.  See omnystudio.com/listener for privacy information.

Time Magazine named the “Architects of AI” its 2025 Person of the Year—and that sparks a wide-ranging conversation about how fast technology has changed everything from writing papers to planning our futures. Greg and Kristen reflect on tech evolution (from typewriters and flip phones to ChatGPT), the pros and cons of AI, and why change—while uncomfortable—is unavoidable. From there, the discussion shifts to a much bigger life transition: retirement. Should couples retire at the same time, or separately? Greg breaks down the three pillars of true retirement readiness—financial, emotional, and social—and explains why being “ready” goes far beyond the numbers. They explore identity after work, the loss (and replacement) of daily purpose, and how finding something bigger than yourself can lead to a truly fulfilling retirement. This episode is a reminder that just like technology, retirement works best when you evolve with intention.   🗂️ Get Organized. Get Confident. Get Your FREE Retirement Kit from Legacy!  See omnystudio.com/listener for privacy information.

A $3M widow, a $50K income gap, and a plan that finally made sense—this is what real retirement clarity sounds like. Kevin McCallister’s Plaza Hotel spree is a fun throwback—until you compare what it would cost today and realize how fast prices (and big life goals) have changed. From NYC “experience” trips to an Investopedia breakdown suggesting millions are needed to fund the modern American dream, the conversation turns to the real issue: most people nearing retirement don’t actually know what they can afford to risk. Greg and Kristen unpack why “water cooler” investing advice—especially among high earners—can be misleading when nobody knows each other’s full financial picture, timeline, or true retirement needs. Then they share a powerful client story: a widowed woman with roughly $3 million saved who needed $50,000 a year on top of Social Security and a pension—and finally got a plan aligned with her comfort level (including protected income, protected growth, and long-term growth). The result? Confidence—and tears of relief.   🔎 Feeling confident—or just want to be sure—you’re on the right path to your version of a Winning Retirement? Complete a short form and schedule your FREE complimentary consultation. See omnystudio.com/listener for privacy information.

The “Great Wealth Transfer” may not look the way we expected — and the stories might surprise you. After embracing the holiday season, we discuss how the “Great Wealth Transfer” is happening — but not exactly how the headlines predicted. Greg and Kristen unpack a new Charles Schwab study showing that many high-net-worth Baby Boomers are choosing to enjoy their money now rather than pass it all down. They explain why the real key isn’t whether you leave money behind — it’s knowing what you actually spend, planning for the lifestyle you want, and creating enough protected income to support the life you choose. Whether you want to give, save, or spend it all, a solid income plan brings the confidence to enjoy retirement on your terms.   📂 Need a little help getting organized? Download a FREE copy of Legacy’s My Retirement Kit: https://www.legacyretirementgroup.com/podcast-request   🔎 Keywords: retirement income planning, great wealth transfer, baby boomer spending, inheritance planning, generational wealth, giving while living, retirement lifestyle budget, Columbus Ohio financial advisor, protected income in retirement, retirement expenses, spending in retirement, retirement planning podcast, legacy planning strategies, Adventures by Disney trip retirement, how much do retirees really spend, outliving your money    See omnystudio.com/listener for privacy information.

If market dips shake you up, your portfolio may be built for someone else—not you. The markets may be hovering near all-time highs, but that doesn’t mean investors feel calm. In this episode, Greg and Kristen tackle one of the biggest issues in retirement investing: emotional risk. They discuss why market swings feel so personal, how over-concentration can create unnecessary stress, and why the real question isn’t “Am I aggressive or conservative?”—it’s “How much am I truly comfortable losing?” If market volatility keeps you up at night, this episode can help you understand the root cause and build an investment strategy that lets you finally sleep well.   📆 Make sure your retirement is on track—grab your FREE consultation today.   🔎 Keywords: market volatility, emotional investing, diversification, risk tolerance, investment risk, asset allocation, long-term investing, retirement planning, portfolio stress, concentration risk, investor psychology, portfolio X-ray, risk score, conservative investing, aggressive investing, market highs, market dips, retirement income planning, financial comfort zone, behavioral finance, stock market risk, investment strategy  See omnystudio.com/listener for privacy information.