This month’s field note reflects on the uncomfortable middle of design and how small actions help move thinking forward.

📓 Field Note: Get comfortable being uncomfortable
📍 Sparked by: LFNTX and creativity cards
💡 Big idea: Thinking develops through doing

Some months, my Field Notes come together quickly. Other months, like this one, I find myself staring at a blank Doc a little longer than I’d like to admit.

At the beginning of April, I had my usual calendar reminders nudging me to get started. And still, nothing felt quite right. I kept thinking, What did I even learn this month?

It wasn’t that nothing had happened. It was that nothing felt clear enough to name, and I wasn’t quite sure where to begin.

Recently, I attended a Learning Forward North Texas affiliate meetup hosted by Dallas ISD’s Professional and Digital Learning team. As part of the session, we used a set of creativity strategy cards. Each card offered a small prompt designed to provoke new ways of thinking.

We each received a deck to take home. That weekend, still feeling stuck, I picked up the deck and started flipping through. “64 creativity strategies to provoke and inspire thinking.”

That felt like exactly what I needed.

As I looked around, I realized I had other prompt-based tools too. Gretchen Rubin’s Muse Machine. A set of intention sticks I had tucked away. Small structures designed to help generate ideas.

And something shifted. Instead of waiting for inspiration, I had something to work with.

That small nudge led me in an unexpected direction. Because I’ve been enjoying experimenting with vibe-coding lately, I wondered if I could create my own digital version of a creativity prompt tool.

So I tried. And somewhere in that small act of making, I felt the energy come back.

And that was enough to get me moving again. It also made me think differently about what that “stuck” feeling actually is.

The work of designing learning often happens in the uncomfortable middle.

It’s the space where ideas aren’t fully formed yet. Where something feels possible, but not clear. Where you’re holding pieces, but they don’t quite fit together.

In many ways, this mirrors what we know about learning itself.

The concept of the zone of proximal development suggests that learning happens in the space between comfort and overwhelm, where a challenge is within reach, but not yet mastered. Susan David describes a similar balance, where we are neither complacent nor overwhelmed, but engaged in work that stretches us.

And yet, when we find ourselves in that space as designers, it’s easy to misinterpret it.

We procrastinate getting started. We tell ourselves we’re stuck. That we need a better idea. That we’re not quite ready to begin. But this kind of productive struggle is often the work.

Design requires us to sit with uncertainty long enough to make something from it.

Research on creativity reinforces this idea. Creativity doesn’t emerge from perfect clarity, but from constraints, prompts, and opportunities to respond to something.

Anne-Laure Le Cunff describes how “intentional imperfection can fuel new thinking.” Amy Burvall and Dan Ryder highlight the role of tinkering and play. And Jennie Magiera reminds us that when we remove struggle entirely, we also remove the opportunity to learn, iterate, and grow.

For designers, this raises an important consideration: 
Not how to avoid the uncomfortable middle, but how to keep moving within it.

When I was sitting in that uncomfortable middle, what helped most wasn’t finding the right idea. It was following a small thread of curiosity.

The creativity cards gave me something to react to. But the real shift happened when I asked a slightly different question: What could I try?

Instead of trying to draft my Field Note right away, I started wondering if I could build a simple digital version of a creativity prompt tool.

It wasn’t polished. It wasn’t planned. It was just a small experiment. But that act of making changed something. It gave me a way back into the work.

As designers, we often think we need clarity before we begin. But in practice, clarity often comes through action, not before it.

Following curiosity, even in small ways, can help us stay in the middle space long enough for ideas to take shape.

In my case, that looked like:

The tool itself isn’t the point. It’s the move.

Creating something to react to. Trying something before it’s fully formed. Letting the work unfold through doing.

If you’re in the middle of designing something right now and feeling a bit stuck, you’re not alone.

That uncomfortable middle shows up in all kinds of work. A presentation that isn’t quite coming together. A report you haven’t started. A session you’re trying to shape.

When that happens, it can help to give yourself something small to react to.

Here are a few prompts you might try:

None of these solve the whole problem. But they can help you start.

If you’re curious, here’s my small “Design Boost” tool that generates prompts like these. It’s a simple way to explore ideas, reframe your thinking, or add a bit of play when things feel stuck.

You’re welcome to try it and see what it sparks for you.

And as you think about the educators you support…

When you find yourself in the middle of designing and things aren’t quite clear yet…

What helps you keep going?

Noting, reflecting, connecting,
Kathryn

PS: If something here sparked an idea, please forward this post to an EduFriend who’s also designing professional learning. ✨

This newsletter is inspired by the idea of self-anthropology from Tiny Experiments by Anne-Laure Le Cunff. Just like field notes help researchers make sense of what they observe, these monthly reflections help me capture ideas, tools, and questions from my own work designing professional learning. I share them here in the spirit of experimentation, connection, and ongoing refinement.

🤖 AI helped polish this post, but the ideas, intention, curation, and care are all mine.