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In leadership, there are moments that stop us cold. Jim Ryan’s recent resignation as the president of the University of Virginia was one of those moments for us.

A renowned educational leader, a former dean of the Harvard Graduate School of Education, and the author of Wait, What? And Life’s Other Essential Questions, Ryan brought grace, clarity, and courage to every role he held. His decision to resign, reportedly to protect the university from politically driven consequences—including the threat of losing federal funding for continuing DEI initiatives left many of us stunned.

This post isn’t just about the resignation. It’s about what it means—and why Ryan matters so deeply to so many of us.

How Wait, What? Changed Our Leadership Practice
Back in 2017, Michael was 10 years into his role as the superintendent of a suburban district outside Seattle when Ryan’s book Wait, What? And Life’s Other Essential Questions crossed his desk. Intrigued by the title, Michael devoured it. He then purchased a copy for every one of his school board members and executive team.

The board and district administrators didn’t just read the book, they studied it. They explored how its questions could reshape conversations and improve engagement with presenters, staff, and one another. Michael and his team printed the following questions onto a poster and hung them in a place where the questions could guide their thinking and remind them of their shared purpose.

• Wait, what?
• I wonder …?
• Couldn’t we at least …?
• How can I help?
• What truly matters?
• Bonus question: And did you get what you wanted out of life, even so?
  

What started as a study quickly became a shift in culture. Presenters felt heard. Board members listened more intentionally. The school community was engaging in meaningful inquiry to ultimately support the students and staff in our district. We were engaging in meaningful inquiry to ultimately support the students and staff in our district. That shift came from Ryan’s book.

The Resignation—and the Questions It Raises
When we learned of Ryan’s resignation in June, we were caught off guard.
Wait, what? Was this really happening?
Then came the next wave of questions—his own questions, echoing back to us in a new context:

• I wonder …? What led to this moment? What happens next—for Ryan, for UVA, for higher education?
• Couldn’t we at least …? Come together to protect the integrity of leadership and learning spaces?
• How can I help? What can we, in our small corner of the education world, do to show our support?

What Truly Matters
After we processed the first four questions, we naturally arrived at how Ryan ended his book:

• What truly matters?
• And did you get what you wanted out of life, even so? (bonus question)

The final question as well as his bonus question are as relevant to moments of transition as they are to leadership and life itself. They help us navigate uncertainty, reconnect with purpose, and reaffirm what we value most.

Jim Ryan’s resignation as president is more than a headline or one nightly news story. It’s a reminder of the fragility and importance of courageous leadership. In a time when educational leaders are being tested in unprecedented ways, his questions remain as vital as ever. They challenge us not just to react, but to reflect. Not just to lead, but to lead with integrity, purpose, and heart. UVA must have ultimately considered the lessons from Ryan’s book because they hired him for a new role where his impact will continue at the university.