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March 11, 2025 69 mins

In this compelling episode, Mike interviews Jean Hale about her experience losing a vice president position at a point in her career when she thought she'd reached the peak. Jean candidly shares the emotional and practical challenges of job hunting after 50, describing the initial shock as "a physical and emotional gut punch" and discussing the isolation many feel during this process. She reveals her journey from devastation to finding meaningful work in higher education fundraising, explaining how she leveraged her network, evaluated organizational culture during interviews, and ultimately found a position that aligns with her values. The conversation offers both practical job search strategies and emotional support while challenging employers to reconsider hiring practices that might overlook experienced professionals.

Key Takeaways:

  • Job loss can feel isolating because people hesitate to discuss it openly, fearing others will assume they did something wrong
  • Well-intentioned comments like "you'll find something" or "take time to pursue your passions" often aren't helpful to someone worried about financial stability
  • When interviewing, ask specific questions about organizational culture to determine if the workplace will be a good fit for your values
  • Both job seekers and employers should challenge their assumptions—experienced professionals bring valuable perspectives even when their career paths aren't linear
  • The experience of job loss can ultimately lead to greater self-awareness, compassion, and finding work better aligned with your values
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