HeyJaredWinning 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…
- Indexed episodes, last 90 days
- 12
- Latest publication
- Sep 22, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 7, 2026
Latest episodes
Stop Watching the Market: How Often Should Retirees Check Their Investments? (opens the original)
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How often should you really check your retirement accounts? In this episode of Winning Retirement , Greg and Kristen explain why watching your portfolio every day can fuel anxiety and lead to emotional decisions. They discuss what retirees should actually look for during portfolio reviews, why your risk tolerance matters, and how a purposeful retirement strategy can help you stay focused on long term goals instead of short term headlines. Plus, learn how a three bucket approach to growth, depend
Can You Really Afford to Retire? Turning Retirement Math Into a Real Plan (opens the original)
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Being told you’re “97% likely” to have enough money for retirement may sound reassuring, but retirement is more than a probability on a spreadsheet. In this episode of Winning Retirement , Greg and Kristen explain how to determine whether you’re truly ready to retire by looking at reliable income, Social Security and pensions, lifestyle expenses, income gaps, inflation, and market risk. They also discuss why the transition from saving money to withdrawing it requires a different strategy and how
Finding Purpose After Retirement: How to Get Your Spark Back (opens the original)
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Retirement may solve the work question, but it can create an unexpected one: What gives my life purpose now? In this episode of Winning Retirement , Greg and Kristen explore why some retirees struggle with boredom, a sense of lost identity, and a lack of direction after leaving their careers. They share real-life examples of retirees who found renewed purpose through travel, volunteering, stronger relationships, physical activity, faith, and simply having something meaningful to look forward to.
Retirement Rules You Don’t Have to Follow (opens the original)
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Should you retire at 65, pay off your mortgage, move your investments to safety, or claim Social Security because that’s what everyone else seems to do? Not necessarily. In this episode of Winning Retirement , Greg and Kristen explain why some of the most common retirement decisions shouldn’t be made simply because they’re considered “normal.” They discuss retiring before Medicare eligibility, balancing investment risk and income, deciding whether to pay off a mortgage, and choosing the right ti
Do You Really Need a Written Retirement Plan? (opens the original)
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What happens when retirement throws you something you didn’t plan for? In this episode of Winning Retirement, Greg and Kristen explain why preparing for retirement is a lot like preparing for a big game—you may have great players and plenty of savings, but you still need a strategy. They discuss why the transition from saving for retirement to living on your savings changes the game, how a written retirement plan can help prepare for market volatility and unexpected challenges, and when working
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