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May 28, 2025 32 mins
Ryan Gray is joined by Charity Anne Caldwell, Classroom Technology Supervisor for the University of Illinois College of Medicine. In this lively conversation, they explore the unique culture of working in a medical school environment, the tension between tradition and innovation in higher ed, and how personal idealism can shape leadership.

Charity shares insights about navigating institutional politics, the evolving role of IT in education, and how staying mission-driven sustains long-term fulfillment. From boundaries and burnout to community-driven strategies for survival, this episode captures the spirit of building meaningful careers — on purpose, not by accident.


  • Life inside a College of Medicine AV department
  • Differences between Gen Ed and Med Ed tech support
  • Growing influence in higher education institutions
  • Centralization vs. local autonomy in IT
  • Staying idealistic in long-term roles
  • Balancing management and leadership
  • Why cross-institutional collaboration is no longer optional

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Voiceovers by Chris Dechter:

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