What In-N-Out Burger, retirement goals, and purpose after work all have in common.

The conversation starts with a hot topic—In‑N‑Out Burger finally making its way east of the Mississippi—and quickly turns into something much deeper: What does it actually mean to be ready for retirement?

A simple conversation with a nurse sparks a powerful realization—many people don’t know whether their retirement goal should be an age, a dollar amount, or something else entirely. Greg breaks retirement readiness into four critical areas: being financially ready, emotionally ready, socially connected, and having a real sense of purpose once the paychecks stop.

The episode explores why retirement planning isn’t just about assets and accounts—it’s about dependable income, confidence through life’s “what-ifs,” and knowing who you are when your job title disappears. From early retirees living the lake-house dream to stories that highlight the importance of belonging and purpose, this episode challenges listeners to think beyond money and start planning for a retirement that’s actually fulfilling.

📄 Snag your FREE copy of Legacy's My Retirement Kit to help you get organized today! https://www.legacyretirementgroup.com/podcast-request

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A $3M widow, a $50K income gap, and a plan that finally made sense—this is what real retirement clarity sounds like.

Kevin McCallister’s Plaza Hotel spree is a fun throwback—until you compare what it would cost today and realize how fast prices (and big life goals) have changed. From NYC “experience” trips to an Investopedia breakdown suggesting millions are needed to fund the modern American dream, the conversation turns to the real issue: most people nearing retirement don’t actually know what they can afford to risk.

Greg and Kristen unpack why “water cooler” investing advice—especially among high earners—can be misleading when nobody knows each other’s full financial picture, timeline, or true retirement needs. Then they share a powerful client story: a widowed woman with roughly $3 million saved who needed $50,000 a year on top of Social Security and a pension—and finally got a plan aligned with her comfort level (including protected income, protected growth, and long-term growth). The result? Confidence—and tears of relief.

🔎 Feeling confident—or just want to be sure—you’re on the right path to your version of a Winning Retirement? Complete a short form and schedule your FREE complimentary consultation.

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Tech tools are everywhere — but when it comes to retirement, can an algorithm really replace a trusted advisor?

Managing money looks nothing like it did for our parents, especially with pennies slowly going away. With digital wallets, chip cards, and AI-powered investing tools, it’s easy to wonder: Is technology phasing out the traditional retirement advisor? Greg and Kristen explain why the answer is a firm no—especially for retirees.

They break down the difference between investment guidance from a robo-advisor and true holistic retirement planning, which includes income planning, inflation strategy, tax efficiency, healthcare, and legacy planning.

This episode highlights the emotional, human side of retirement planning—the back-and-forth conversations, the guidance through life changes, and the peace that comes from working with someone who genuinely cares. Technology is a great tool… but it can’t replace a relationship.

💭 Unsure if you’re on track for retirement? Fill out this short form for a free consultation.

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The “Great Wealth Transfer” may not look the way we expected — and the stories might surprise you.

After embracing the holiday season, we discuss how the “Great Wealth Transfer” is happening — but not exactly how the headlines predicted. Greg and Kristen unpack a new Charles Schwab study showing that many high-net-worth Baby Boomers are choosing to enjoy their money now rather than pass it all down. They explain why the real key isn’t whether you leave money behind — it’s knowing what you actually spend, planning for the lifestyle you want, and creating enough protected income to support the life you choose. Whether you want to give, save, or spend it all, a solid income plan brings the confidence to enjoy retirement on your terms.

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

🔎 Keywords: retirement income planning, great wealth transfer, baby boomer spending, inheritance planning, generational wealth, giving while living, retirement lifestyle budget, Columbus Ohio financial advisor, protected income in retirement, retirement expenses, spending in retirement, retirement planning podcast, legacy planning strategies, Adventures by Disney trip retirement, how much do retirees really spend, outliving your money

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When it comes to managing your money, should you trust family — or is a fresh set of eyes the smarter move?

From parents who jokingly say they’ll “move in” if their advisor-son loses the money, to widows who struggle to trust anyone new, the Taylors explore the emotional, practical, and financial challenges of working with someone who shares your last name. They discuss why trust can’t be assumed — it must be earned — and why experience, objectivity, and the ability to have tough conversations matter more than familiarity. Whether you’re considering hiring a family member or wondering if it's time to step outside your comfort zone, this episode will help you think more clearly about trust, transparency, and choosing the right guide for your retirement journey.

💬 Ready for your own “financial check-up”? Schedule a call with us to get started. https://www.legacyretirementgroup.com/schedule-an-appointment

🔎 Keywords: financial advisor family member, should family manage money, trusting a financial advisor, retirement planning Columbus Ohio, Legacy Retirement Group, choosing a financial advisor, financial trust issues, retirement income planning, advisor experience vs. family, money and family boundaries, why hire an outside advisor, retirement decisions, financial transparency, Winning Retirement podcast

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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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