Winning Retirement Radio

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 segmenting assets for income, growth, and liquidity can help create a more purposeful retirement plan. Because the real question isn’t simply, “Do I have enough to retire?” It’s “Do I have a plan that lets me live the retirement I want with confidence?”See omnystudio.com/listener for privacy information.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

More Americans are finding themselves caring for aging parents while preparing for their own retirement. In this episode, Greg and Kristen discuss the emotional and financial realities of caregiving, share personal and client stories, and offer practical strategies to help families protect both their loved ones and their retirement. From budgeting and legal planning to long-term care and having difficult family conversations, they explain why planning ahead can make all the difference.   🔍 Gain clarity and confidence—book your no-cost retirement review today!See omnystudio.com/listener for privacy information.

A new report warns that Social Security's trust fund could run short of reserves by 2032, potentially leading to benefit reductions if lawmakers fail to act. In this episode of Winning Retirement, Greg and Kristen break down what that could mean for retirees and whether claiming benefits early is the right move. They explore possible solutions Congress may consider—including higher payroll taxes, raising the retirement age, and adjusting cost-of-living increases—and discuss why Social Security should be viewed as a foundation of retirement income, not the entire plan. You'll also hear why maximizing Social Security isn't always the same as maximizing your retirement, and why having a comprehensive income strategy may be more important than ever.   🕒 Don’t leave retirement to chance—claim your FREE consultation now.  See omnystudio.com/listener for privacy information.

Greg and Kristen discuss why nearly 6 in 10 retirees leave the workforce earlier than expected. From layoffs and workplace burnout to health challenges and family caregiving responsibilities, they explore the real-life reasons retirement plans often change. You'll learn why building flexibility into your retirement strategy is critical, how to prepare for life's unexpected "what ifs," and ways to create a reliable income while preserving assets for future opportunities and challenges.    🤔 Feeling stuck with your retirement planning? Download a FREE copy of Legacy’s My Retirement Kit to help become better organized. See omnystudio.com/listener for privacy information.

Greg and Kristen discuss summer travel, family vacations, and the rising cost of living. Then, using the latest Social Security COLA projections as a starting point, they explore why inflation remains one of the biggest threats to a successful retirement. You'll learn how inflation compounds over time, why budgeting is critical regardless of your net worth, and how a written retirement income plan can help ensure your money keeps pace with rising expenses throughout retirement. 👉 Ready to take the guesswork out of retirement? Get your FREE copy of Legacy’s My Retirement Kit today—your step-by-step guide to getting organized and staying on track! See omnystudio.com/listener for privacy information.

In this episode of Winning Retirement, Greg and Kristen discuss the question many retirees are asking: “Have we done enough?” They explain why retirement planning is about more than building wealth—it’s about creating reliable income, managing taxes, and maintaining your lifestyle. You’ll also hear insights on diversification, Roth conversion strategies, and why the real goal of retirement planning is having the confidence to enjoy life without worrying about running out of money.   ✍️ Ready to design your ideal retirement? Schedule a FREE consultation by completing this brief form.  See omnystudio.com/listener for privacy information.

In this heartfelt episode of Winning Retirement, Greg and Kristen discuss how quickly retirement plans can change when unexpected health challenges arise. Inspired by the ALS diagnoses of close friends and clients, they explore the emotional and financial impact serious illness can have on retirees and their families. Greg shares the story of a client whose retirement changed dramatically just months after leaving work, and why having a flexible plan in place helped provide peace of mind during a difficult time. They also break down the three major retirement risks—market volatility, taxes, and healthcare costs—and explain why true retirement planning goes far beyond investments alone. You’ll also hear why flexibility matters, the importance of family conversations, and how a comprehensive plan can help protect both your finances and your loved ones when life takes an unexpected turn.   🗂️ Get Organized. Get Confident. Get Your FREE Retirement Kit from Legacy!  See omnystudio.com/listener for privacy information.

Greg and Kristin explore an important retirement question: Is the goal to become wealthy—or simply make sure you never run out of money? Greg shares a personal story about losing everything in a childhood house fire and how it shaped his views on financial security. They also break down the difference between harmful debt and strategic debt in retirement, including when it may make sense to keep a mortgage rather than pay it off. They discuss cash flow, taxes, home equity lines of credit, and why retirement planning should fit your comfort level—not someone else’s definition of success.   📄 Snag your FREE copy of Legacy's My Retirement Kit to help you get organized today! See omnystudio.com/listener for privacy information.

In this episode of Winning Retirement, Greg and Kristen start with some fun family stories before tackling a challenge many families face today. With rising housing costs and more young adults living at home, parents are helping more than ever—but how much is too much? They break down the difference between support and dependency, share real client scenarios, and explain why your retirement comes first. If you’re wondering how to help your kids without putting your own future at risk, this episode is for you. 🔎 Feeling confident—or just want to be sure—you’re on the right path to your version of a Winning Retirement? Take a moment to complete a short form and schedule your complimentary consultation. See omnystudio.com/listener for privacy information.