Finding Purpose After Retirement: How to Get Your Spark Back

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 …

Retirement Rules You Don’t Have to Follow

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 ma…

Do You Really Need a Written Retirement Plan?

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 w…

Will Your Money Last as Long as You Do?

One of the biggest fears in retirement is running out of money. In fact, one survey found that 67% of Americans worry more about outliving their savings than dying. In this episode of Winning Retirement, Greg and Kristin discuss how to turn retirement uncertainty into confidence with a plan designe…

What Will You Leave Behind? Building a Legacy Beyond Money

What does it really mean to leave a legacy? In this episode of Winning Retirement, Greg and Kristin share the treasured keepsakes and family memories that mean more than money—and discuss why planning what happens to your belongings can be an important part of retirement and estate planning. From o…

How Retirement Planning Has Changed: What Still Works—and What Doesn't Anymore

Retirement planning has evolved just as dramatically as the shift from manual transmissions to today's high-tech vehicles. In this episode of Winning Retirement, Greg and Kristen Taylor explore which retirement principles have stood the test of time—and which strategies no longer work in today's fi…

Do You Really Need $1 Million to Retire? The Truth About Retirement Income?

Do you really need $1 million—or more—to retire comfortably? In this episode of Winning Retirement, Greg and Kristen break down a recent Investopedia study estimating that the average American couple needs $1.16 million for retirement and explain why there's no universal retirement number. They di…

The Legacy You Leave: Estate Planning, Roth Conversions & Passing Down More Than Money

What will your family remember—and inherit—when you're gone? In this heartfelt episode of Winning Retirement, Greg and Kristen Taylor explore the difference between leaving behind possessions, wealth, and a lasting legacy. Inspired by estate sales and treasured family heirlooms, they discuss why th…

How Much Do You Need to Retire on $100,000 a Year?

How much money do you need to retire comfortably in the United States? Is $1 million enough? And how much savings does it take to generate $100,000 a year in retirement income? In this episode of Winning Retirement, Greg and Kristen answer common retirement-planning questions and explain why there …

Love, Retirement & Second Chances: The Money Talk Every Couple Needs

Greg and Kristin share stories from their own relationship before diving into the unique financial challenges of dating and remarriage later in life. From blending finances and protecting assets to estate planning, prenups, family dynamics, and retirement strategies, they explain why honest money c…