It happened in our school’s Learning Commons, an open, echoey space where every cough, chuckle, and awkward silence feels like it’s amplified on a stadium speaker.

I was midway through explaining an activity at a staff meeting when I felt that unmistakable shift in energy.

I noticed a few eyes glazing over.

One person glanced discreetly at the clock.

I heard myself talking faster, words tumbling out, and realized my lesson wasn’t landing.

I knew I was losing them.

But instead of pausing, checking my notes, and getting clear on my message, I continued to rush on, dropping details, trying to outrun my own confusion.

It felt like juggling too many balls and watching them hit the floor in slow motion.

The activity was a simple one: reflect on our vision of the “ideal” learner.

“What would your best version of a learner look like?”

“What would we see them doing?”

I’d given each group a chart with columns for student, teacher, and leader.

We were only working on the column for students, but I hinted that the fully completed chart might serve as a kind of “menu board” for professional growth.

As I circulated through the room, I noticed something surprising.

They were doing the work.

Talking. Wondering. Jotting ideas. Debating.

They were in it.

I felt a small wave of relief and gratitude.

They weren’t disengaged; they were in the pit, that messy, uncomfortable place James Nottingham calls “The Learning Pit.”

Where answers aren’t obvious.

Where being wrong is part of the process.

Where we’re not sure if we’ve got it “right” yet.

Later that week, during a job interview, a prospective Education Assistant asked me a question that drove the point home:

“What attributes do you think make an EA successful?”

I loved that she was asking me questions during an interview!

It also reminded me that every adult in a school is a learner too.

Sometimes we’re in the pit because a lesson flops.

Sometimes we’re there because we’re pushing into new territory.

Either way, it’s a good place to be.

We’re solving problems, making connections, growing.

So here’s my takeaway:

When we teach, lead, or learn at our highest levels, the pit isn’t something to avoid.

It’s a place to enter together.

It’s uncomfortable.

It’s uncertain.

It’s messy.

And it’s where the real work happens.

If you’re ready to tackle the awkward, terrifying, brilliant stuff of leadership together, come join a community of leaders who get it.

This week, try a reflection activity with your team (or even just yourself):

Ask yourself:

Here’s the twist.

Don’t just answer these questions.

Turn them into a menu.

Imagine each idea as a possible item on a professional development “choice board.”

Which of these would you order for yourself or your team right now?

Which would help bring your vision of a thriving learner to life?

You don’t have to fill in every box today.

Spend some time in the pit.

The clarity comes after the discomfort.