If market dips shake you up, your portfolio may be built for someone else—not you.

The markets may be hovering near all-time highs, but that doesn’t mean investors feel calm. In this episode, Greg and Kristen tackle one of the biggest issues in retirement investing: emotional risk.

They discuss why market swings feel so personal, how over-concentration can create unnecessary stress, and why the real question isn’t “Am I aggressive or conservative?”—it’s “How much am I truly comfortable losing?” If market volatility keeps you up at night, this episode can help you understand the root cause and build an investment strategy that lets you finally sleep well.

 

📆 Make sure your retirement is on track—grab your FREE consultation today.

 

🔎 Keywords: market volatility, emotional investing, diversification, risk tolerance, investment risk, asset allocation, long-term investing, retirement planning, portfolio stress, concentration risk, investor psychology, portfolio X-ray, risk score, conservative investing, aggressive investing, market highs, market dips, retirement income planning, financial comfort zone, behavioral finance, stock market risk, investment strategy

 

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What would you do if your job were suddenly outsourced in your 60s? Greg and Kristen talk about how to prepare—financially and emotionally—for a retirement that may come sooner than expected.

 

A woman in her early 60s called the team worried that her position might be outsourced—a fear that’s becoming more common as companies evolve and technology reshapes the workplace. Greg and Kristen explore what to do if you’re facing a possible forced retirement: from taking an honest look at your spending and savings (401(k), IRA, pension, etc), to building a flexible income plan that can adapt when life changes. They also share stories from families who’ve discovered the freedom that comes from simply knowing they’re ready—plus, the importance of working with an advisor who builds a plan around you, not a product.

 

✅ Your retirement deserves a plan—grab your complimentary consultation.

 

🔑 Keywords: forced retirement planning, early retirement at 60, retirement after job loss, preparing for early retirement, retirement income planning, flexible income plan, retirement readiness, financial planning after layoff, 401(k) IRA pension, retirement planning for women over 60, Greg and Kristen Taylor, Legacy Retirement Group, Winning Retirement podcast, retirement advisor, financial freedom in retirement, job outsourcing and retirement

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An ad claims you can skip Roth conversions and avoid taxes. We reveal what’s real—and what’s just marketing.

When a Facebook ad promises you can “eliminate taxes on your retirement accounts—no Roth conversion required,” it’s hard not to click. But is it too good to be true?

Greg and Kristen dive into the buzz around “tax-free retirement” webinars and explain why eliminating taxes completely isn’t realistic—but reducing them absolutely is. Greg shows how different strategies—like timing Roth conversions, managing required minimum distributions, and planning around Medicare and income brackets—can save hundreds of thousands in taxes over a lifetime.

They also unpack why some advisors discourage Roth conversions (and when that advice might actually be right), plus one simple truth every retiree should remember: there’s no one-size-fits-all plan.

 

🔍 Gain clarity and confidence—book your no-cost retirement review today!

🔑 Keywords: retirement planning, Roth conversion, retirement taxes, IRA, 401(k), 403(b), tax strategies, required minimum distributions, financial planning, retirement income, Legacy Retirement Group, Winning Retirement Radio

 

 

 

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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!

🕒 Don’t leave retirement to chance—claim your FREE consultation now.

 

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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.

💬 Ready for your own “financial check-up”? Schedule a call with us to get started!

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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.

✅ Need a little help getting organized? Download a FREE copy of Legacy’s My Retirement Kit: https://www.legacyretirementgroup.com/podcast-request

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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.

 

Wondering if you’re on track for retirement? Fill out this short form for a FREE consultation.

 

 

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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.

 

📆 Make sure your retirement is on track—grab your FREE consultation today.

 

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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.

🤔 Feeling stuck with your retirement planning? Download a FREE copy of Legacy’s My Retirement Kit to help become better organized: 

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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.

✍️ Ready to design your ideal retirement? Schedule a FREE consultation by completing this brief form.  

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