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. You’ll also hear why preparing emotionally for retirement can be just as important as preparing financially, and how having a clear retirement income and financial plan can provide the confidence to enjoy what comes next. Because retirement isn’t the finish line. It’s a new journey, and having purpose, connection, and a plan can make that journey a whole lot more fulfilling!See omnystudio.com/listener for privacy information.
Sep 8
10 min
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 time to claim Social Security. The takeaway: There’s no universal roadmap for retirement. The right strategy is the one built around your income needs, goals, taxes, lifestyle, and the future you actually want.See omnystudio.com/listener for privacy information.
Sep 1
11 min
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 with a financial advisor may become more important. If you’re wondering whether you really need a written retirement plan—or if your savings alone are enough—this episode offers practical insights for preparing for the “what ifs” ahead.See omnystudio.com/listener for privacy information.
Aug 25
11 min
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 designed to provide reliable income through changing markets and economic conditions. They explore retirement income planning, taxes, healthcare costs, market risk, and how to enjoy the money you've worked hard to save without constantly worrying about whether it will last. The goal isn't simply to survive retirement—it's to build a strategy that helps you thrive throughout it!See omnystudio.com/listener for privacy information.
Aug 18
7 min
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 organizing important documents and identifying valuable assets to giving meaningful possessions to loved ones while you're still here, they explore practical ways to make things easier for your family. Most importantly, they explain why your true legacy isn't simply the wealth or possessions you leave behind—it's the memories, values, lessons, and love you leave inside the people who matter most.See omnystudio.com/listener for privacy information.
Aug 11
11 min
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 financial world. They discuss why guaranteed pensions have become rare, how longer life expectancies have changed retirement planning, and why creating reliable retirement income is more important than ever. You'll also learn why taxes, healthcare planning, investments, and legacy planning must work together to create lasting financial confidence. If you're wondering how to replace a pension, avoid running out of money, or build a retirement plan that fits today's realities, this episode offers practical guidance to help you retire with greater peace of mind.See omnystudio.com/listener for privacy information.
Aug 4
12 min
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 discuss the limitations of the 4% withdrawal rule, why market timing can make or break a retirement plan, and how unexpected expenses like healthcare, home repairs, and vehicle replacements can quickly change your financial picture. You'll also learn why focusing on your retirement income gap—instead of an arbitrary savings goal—can provide greater confidence and long-term financial security. Whether you're approaching retirement or already retired, this episode explains how personalized income planning, liquidity for life's surprises, and strategies for long-term growth can help create a more resilient retirement plan. Topics covered: Do you really need $1 million to retire? Why the 4% withdrawal rule isn't one-size-fits-all How market volatility affects retirement income Planning for unexpected retirement expenses The importance of guaranteed income and liquidity Why retirement planning should be based on your lifestyle—not national averages See omnystudio.com/listener for privacy information.
Jul 28
10 min
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 the most valuable inheritance is often character, faith, and family values. They also explain practical estate planning strategies, including wills vs. trusts, beneficiary designations, financial and healthcare powers of attorney, and how Roth conversions can potentially create a larger tax-free inheritance for your children. If your goal is to leave your loved ones—not the IRS—the biggest benefit, this episode offers valuable retirement and estate planning insights. 💬 Ready for your own “financial check-up”? Schedule a call with us to get started. See omnystudio.com/listener for privacy information.
Jul 21
10 min
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 is no one-size-fits-all retirement number. They discuss the 4% withdrawal rule, Social Security, guaranteed income, income annuities, market volatility, taxes, and strategies for creating reliable, tax-efficient retirement income. Whether you're planning for retirement or already retired, you'll learn how to determine the retirement savings you need based on your income goals—not just your nest egg. ✅ Your retirement deserves a plan—grab your FREE complimentary consultation. See omnystudio.com/listener for privacy information.
Jul 14
10 min
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 conversations are essential before saying "I do" again. ✅ Your retirement deserves a plan—grab your complimentary consultation. See omnystudio.com/listener for privacy information.
Jul 7
12 min
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