Description:

That quiet Sunday-night dread isn’t failure—it’s information. In this episode, we break the myth that it’s “too late” and explore five powerful, strategic pivots you can make at any stage of life.

Episode Summary:

You’ve worked hard, built success, and checked the boxes—so why does something still feel off? That feeling of misalignment isn’t a weakness; it’s often the clearest signal that you’re ready for a strategic reinvention.

In this episode, we reframe late-stage career change as an advantage, not a liability. Drawing on research, lived experience, and real-world examples, we explore how accumulated wisdom—what Chip Conley calls “experience metabolized”—becomes your greatest asset.

We walk through five meaningful pivot paths, from purpose-driven burnout recovery and entrepreneurship later in life, to digital reinvention, portfolio careers, and deeply fulfilling encore careers. You’ll also learn a simple, realistic roadmap for navigating change without blowing up your life—or your finances.

If you’ve ever wondered, “Is this really it?” this conversation offers clarity, courage, and a grounded way forward.

Show Notes

• Why it’s never “too late” to pivot
• Turning decades of experience into strategic advantage
• Reframing burnout as actionable data
• Skills-based futures over age-based limitations
• Designing work that fits who you are now

Time Stamps:

00:00 – 06:30
Recognizing misalignment & why it’s never too late to pivot

06:30 – 17:40
Pivot 1: Burnout → purpose & Pivot 2: Entrepreneurship later in life

17:40 – 31:50
Pivot 3: Digital reinvention & Pivot 4: Portfolio careers

31:50 – 42:50
Pivot 5: Encore careers & blending income with impact

42:50 – 51:30
5-stage reinvention roadmap & choosing courage over comfort

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