Revisiting the “rules” we grew up with—and the financial ones that could be hurting your retirement.

We all remember the rules our parents swore by—don’t sit too close to the TV, wear your coat, turn off that car light! Greg and Kristen share a few laughs about those old sayings, then connect them to the outdated financial “rules” many retirees still follow.

They break down why classics like the 4% rule, the Rule of 100, and “never touch your principal” may no longer make sense—and explain the new mindset smart retirees are using today. Plus, they highlight the real retirement ages that matter: the Rule of 55, 59½, 65, and 73.

If you want to retire confidently, it’s time to know which rules to keep, which to toss, and the one rule Greg lives by: protect your income, grow the rest!

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Honesty isn’t just good for your health—it’s vital for your wealth.

A new study finds that up to 80% of adults admit to lying to their doctors about their lifestyle habits—usually to avoid judgment or bad news. Greg and Kristen open up about how this same fear can show up in retirement planning, too. From family stories about Kristen’s late father-in-law (and his famous iron-skillet cake) to the emotional side of discussing spending habits and savings goals, they reveal why honesty—especially when it’s uncomfortable—is the key to a healthier life and a stronger financial future. Greg also shares how a “functional medicine” approach to health inspired the way he helps families uncover the root causes of financial stress.

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Learn how to keep more of your money in retirement with smart income and tax strategies!

Most people picture Social Security or a 401(k) when they think about retirement income — but that’s just the beginning. In this episode of Winning Retirement, Greg and Kristen explain how to coordinate multiple income streams, from pensions and IRAs to RMDs, dividends, and rental income, while keeping taxes as low as possible. Learn how to identify your real retirement income need, create a comfortable spending plan, and discover why a 10–20% cushion can make all the difference.

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From the $550 calculator watches of the 1970s to today’s free online tools, we’ve always relied on numbers to help us make decisions. But when it comes to retirement, not every “calculator” gives you the full picture. In this episode, Greg and Kristen share why online tools—and even AI—can be misleading, how one client discovered that firsthand, and why professional guidance matters when the stakes are high. Plus, they compare finding the “right” retirement age to playing a tricky hole on the golf course: everyone starts from a similar place, but the path you take can look very different depending on the clubs in your bag.

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When kids leave home, they don’t just move away—they tug on their parents’ hearts, too. Greg and Kristen share the laughs (and frustrations) of watching their son head to college—828 miles away—with a questionable dorm-room haircut to prove his independence. From daily check-ins (or lack thereof) to mom’s Life360 “stalking,” this episode blends family stories with financial wisdom. The Taylors also dive into the dangers of lump-sum payouts, why some pensions and sweepstakes winners run out of money, and how careful planning can help protect both your nest egg and your peace of mind.

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Getting married later in life? Things can get… awkward. From “lady friends” to prenups, Greg and Kristen unpack the not-so-romantic side of love after 50—like protecting your retirement, keeping kids’ inheritances fair, and why Medicaid doesn’t care about your prenup. It’s funny, a little uncomfortable, but super important.

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It turns out that fewer young adults are reaching traditional milestones, such as moving out, getting married, and starting families. After Greg and Kristen share how that contrasts with their own family’s journey, the conversation turns to retirees and how they are prime targets for marketing — and how to filter through the noise. They share practical advice for spotting red flags, verifying sources, and making sure financial products and lifestyle purchases align with your overall plan. Whether you’re considering a senior living community, a travel package, or even gold and Bitcoin ads, this episode helps you focus on what you really need and avoid blowing your budget on shiny objects.

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Greg and Kristen share their own family screen-time confessions along with America's, and how neighbors are turning movie nights into community fun! Then, they shift gears to retirement: When does a Roth conversion really make sense, and how can it protect your lifestyle and legacy? From screen habits to financial habits, this episode is all about finding balance in the digital age—and in your retirement planning.

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