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!

 

Time Magazine named the &ldquo;Architects of AI&rdquo; its 2025 Person of the Year&mdash;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&mdash;while uncomfortable&mdash;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&mdash;financial, emotional, and social&mdash;and explains why being &ldquo;ready&rdquo; 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.
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🗂️ Get Organized. Get Confident. Get Your <a href="https://www.legacyretirementgroup.com/podcast-request">FREE Retirement Kit</a> from Legacy!
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🎙️ 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.