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. 

A $3M widow, a $50K income gap, and a plan that finally made sense&mdash;this is what real retirement clarity sounds like.
Kevin McCallister&rsquo;s Plaza Hotel spree is a fun throwback&mdash;until you compare what it would cost today and realize how fast prices (and big life goals) have changed. From NYC &ldquo;experience&rdquo; 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&rsquo;t actually know what they can afford to risk.
Greg and Kristen unpack why &ldquo;water cooler&rdquo; investing advice&mdash;especially among high earners&mdash;can be misleading when nobody knows each other&rsquo;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&mdash;and finally got a plan aligned with her comfort level (including protected income, protected growth, and long-term growth). The result? Confidence&mdash;and tears of relief.
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🔎 Feeling confident&mdash;or just want to be sure&mdash;you&rsquo;re on the right path to your version of a Winning Retirement? Complete a short form and schedule your <a href="https://www.legacyretirementgroup.com/schedule-an-appointment">FREE complimentary consultation</a>.&nbsp;

🎙️ Greg and Kristen Taylor, along with their co-host Kristen Charles, explore down-to-earth tips and strategies to help pre and current retirees better achieve their goals.

📊 With discussions about everything from balancing risk, to 401(k) rollovers, Roth conversions, pension decisions, withdrawal strategies, taxes in retirement, income planning, Social Security, and most importantly... your lifestyle!

👫 Greg and Kristin's goal is to help you have confidence in your transition into retirement, and for years to come by helping you create a personalized plan for your retirement.

Have specific questions? Schedule a 15-minute call with a team member.

Greg Taylor is an investment adviser representative of Legacy Advisory Network, LLC, a registered investment advisor with the state of Ohio. The firm only conducts business in states where it is properly registered or is excluded from registration requirements. Legacy Advisory Network, LLC, and this radio station are not affiliated. The investment ideas and financial vehicles discussed here should not be considered to be personalized investment advice, nor are these recommendations to buy or sell any particular investment or product. The information should not be considered tax or legal advice. Individuals should first consult with competent tax, legal, accounting, and other professionals regarding the applicability and suitability of any investment ideas. Past performance is not a guarantee of future results. Investments will fluctuate, and when redeemed may be worth more or less than when originally invested. Any comments regarding safe and secure investments and guaranteed income streams refer only to fixed insurance products. They do not refer in any way to securities or investment advisory products. Fixed insurance and annuity product guarantees are subject to the claims-paying ability of the issuing company.

🎙️ Greg and Kristen Taylor, along with their co-host Kristen Charles, explore down-to-earth tips and strategies to help pre and current retirees better achieve their goals.
📊 With discussions about everything from balancing risk, to 401(k) rollovers, Roth conversions, pension decisions, withdrawal strategies, taxes in retirement, income planning, Social Security, and most importantly... your lifestyle!
👫 Greg and Kristin's goal is to help you have confidence in your transition into retirement, and for years to come by helping you create a personalized plan for your retirement.
Have specific questions? <a href="https://www.legacyretirementgroup.com/schedule-an-appointment">Schedule a 15-minute call</a> with a team member.
<hr>
Greg Taylor is an investment adviser representative of Legacy Advisory Network, LLC, a registered investment advisor with the state of Ohio. The firm only conducts business in states where it is properly registered or is excluded from registration requirements. Legacy Advisory Network, LLC, and this radio station are not affiliated. The investment ideas and financial vehicles discussed here should not be considered to be personalized investment advice, nor are these recommendations to buy or sell any particular investment or product. The information should not be considered tax or legal advice. Individuals should first consult with competent tax, legal, accounting, and other professionals regarding the applicability and suitability of any investment ideas. Past performance is not a guarantee of future results. Investments will fluctuate, and when redeemed may be worth more or less than when originally invested. Any comments regarding safe and secure investments and guaranteed income streams refer only to fixed insurance products. They do not refer in any way to securities or investment advisory products. Fixed insurance and annuity product guarantees are subject to the claims-paying ability of the issuing company.

Insight for those near and in retirement.

Winning Retirement Radio

🎙️ Greg and Kristen Taylor, along with their co-host Kristen Charles, explore down-to-earth tips and strategies to help pre and current retirees better achieve their goals.

📊 With discussions about everything from balancing risk, to 401(k) rollovers, Roth conversions, pension decisions, withdrawal strategies, taxes in retirement, income planning, Social Security, and most importantly... your lifestyle!

👫 Greg and Kristin's goal is to help you have confidence in your transition into retirement, and for years to come by helping you create a personalized plan for your retirement.

🎙️ Greg and Kristen Taylor, along with their co-host Kristen Charles, explore down-to-earth tips and strategies to help pre and current retirees better achieve their goals.
📊 With discussions about everything from balancing risk, to 401(k) rollovers, Roth conversions, pension decisions, withdrawal strategies, taxes in retirement, income planning, Social Security, and most importantly... your lifestyle!
👫 Greg and Kristin's goal is to help you have confidence in your transition into retirement, and for years to come by helping you create a personalized plan for your retirement.