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June 4, 2025 33 mins
We’re back for a brand-new second conversation with Charity Anne Caldwell — and this time we’re keeping it fun, insightful, and future-focused! Charity and Ryan swap stories about running for school board, building more inclusive spaces in tech, and why conferences like InfoComm are about so much more than just the gear. Charity also shares her sci-fi favorites, what makes great leadership in higher ed, and why asking “Why are we doing this?” is always a good place to start.
If you’re packing for InfoComm, tuning in on the road, or just thinking about growing your career — this one’s for you! And remember… you’re going to do great.


  • The real experience of running for school board
  • Why representation in leadership matters — in schools and in tech
  • First impressions of InfoComm and the AV industry’s diversity challenges
  • The higher ed advantage in leadership representation
  • Why building community at local events is key
  • How sci-fi helps us process the world around us (and why Octavia Butler feels prophetic)
  • Dune, Hitchhiker’s Guide, and the irresistible pull of a good fictional universe
  • The “why” question higher ed teams should ask more often
  • The importance of building space for others to lead
  • Charity’s advice for anyone facing self-doubt: “You’re going to do great.”


Connect with Charity:
LinkedIn: https://www.linkedin.com/in/charityannecaldwell/

Connect with Ryan:
https://twitter.com/Ryan_A_Gray
https://www.linkedin.com/in/ryanagray/
ryan@higheredav.com

Follow the Show:
http://higheredav.com/ryangray

Voiceovers by Chris Dechter:
https://twitter.com/cdechter
https://www.linkedin.com/in/cdechter/

Please rate and review the show wherever you get your podcasts!
Feedback is very welcome — we look forward to hearing from you!
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