Time Magazine named the “Architects of AI” its 2025 Person of the Year—and that sparks a wide-ranging conversation about how fast technology has changed everything from writing papers to planning our futures. Greg and Kristen reflect on tech evolution (from typewriters and flip phones to ChatGPT), the pros and cons of AI, and why change—while uncomfortable—is unavoidable.

From there, the discussion shifts to a much bigger life transition: retirement. Should couples retire at the same time, or separately? Greg breaks down the three pillars of true retirement readiness—financial, emotional, and social—and explains why being “ready” goes far beyond the numbers. They explore identity after work, the loss (and replacement) of daily purpose, and how finding something bigger than yourself can lead to a truly fulfilling retirement. This episode is a reminder that just like technology, retirement works best when you evolve with intention.

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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.

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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.

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