We tend to notice dramatic risks, but what happens when the paycheck stops? Greg and Kristin discuss why market downturns can feel different in retirement, how withdrawals can compound losses, and why inflation, taxes, healthcare costs, and longevity all deserve a place in a written retirement plan.

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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.

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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 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.

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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.

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!

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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 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?”

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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, dependable income, and liquid savings can help create greater confidence through changing markets and economic conditions.

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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

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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!

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