For the past few years, I have ended each school year with a list post, one item for every year I’ve worked in education. It’s become a bit of a tradition, a way to pause, reflect and take stock before heading into summer.

In 2022, I wrote about 26 teachers and the 26 lessons they taught me.
In 2023, it was 27 ways schools are better now than when I started.
And in 2024, I shared 28 reasons I still love teaching.

This year marks my 29th in education, and I have found myself in a different space, one filled less with answers and more with questions.

Some are big and philosophical. Others are daily dilemmas. All of them keep me curious, grounded and sometimes even uncomfortable (in the best way).

After nearly three decades in classrooms and schools, I have discovered something unexpected: the more I learn, the more comfortable I am with not knowing.

Where I once rushed to have answers, I now find myself lingering in questions.

Experience has taught me that the best conversations that actually move us forward often begin not with someone declaring what is right, but with someone brave enough to wonder what is possible.

Asking questions keeps me curious, not certain and invites nuance over neat and tidy solutions. They are invitations for dialogue, not assertions disguised as inquiries. In a field where we are constantly pressed to have all the answers for our students, I am learning there is profound wisdom in modeling intellectual humility, in showing that the most important thing we can do is keep asking better questions.

So here they are: 29 questions I am still asking about education.

1. What do students remember ten years after they leave us and how can we build more moments that stay with them ?

2. How do we ensure we are preparing students for their rapidly changing future rather than the education system we experienced?

3. How do we measure success in ways that actually matter to all students, not just those who fit traditional molds?

4. What is the perfect balance between structure and freedom in a school day?

5. How do we make professional learning as engaging as the best classroom lesson?

6. How might we reframe ‘failure’ as a necessary part of learning and innovation in our schools?

7. Can AI make education more human—or will it just keep writing emails  that are more diplomatic than we’d ever be?

8. What is the role of joy in academic achievement?

9. How do we create schools where every adult loves coming to work?

10. Are we brave enough to stop doing things just because we have always done them?

11. What should a report card really tell a parent?

12. How can we build systems that support innovation without burning people out?

13. What happens when students lead the learning?

14. Why do some of our best students struggle after graduation and what can we do about it?

15. What if extracurriculars were seen as essential, not extra?

16. How can we get better at truly listening to students?

17. What would it take to fully integrate physical literacy into our academic priorities?

18. Is grading helping or hurting learning?

19. How do we support staff to be both bold and well and not just surviving on caffeine, calendar invites and good intentions?

20. What do families really want from schools and are we asking enough?

21. What makes a school feel safe emotionally, not just physically?

22. How do we teach digital citizenship without sounding like someone’s uncle trying to explain TikTok?

23. What messages are our systems and structures sending to students, and how do they align with what we say we value?

24. How do we honour our most experienced teachers while still challenging them to grow?

25. How can we make educational leadership less lonely?

26. What does it look like when we build systems where every student regardless of background, cultural identity or learning needs truly belongs and can succeed on their own terms?

27. What is the role of wonder in learning and how do we protect it?

28. When will conference organizers take me up on my suggestion to stop serving meals and just handout $15 gift cards for the local mall food court?

29. How do we keep the humanity at the centre as education evolves through rapid technological and social change?

These questions don’t have easy answers, and that is exactly the point. In a world racing toward efficiency and automation, schools must remain gloriously, stubbornly human.

The questions that matter most aren’t about systems or standards, they’re about the people in front of us, the relationships we build, and the humanity we nurture together.

Here’s to year 30. Let’s keep wondering. Let’s keep being human.

In the creation of this post I used Chat GPT and Claude as work partners – helping refine my ideas and questions.  The image at the top of this post is also created by AI.