Back to Class: Why Every Leader Needs a Fresh Notebook

There's a specific smell to the fall season. Sure – caramel apple and pumpkin spice get all the attention. But for me, it’s freshly sharpened pencils, new backpacks, and that crisp, unmarked notebook with 150 blank pages just waiting to be filled.

I'll admit it, I love school supply shopping. Every year I find myself wandering the aisles, picking up notebooks I don't need and testing pens like I'm buying a car. There's something almost sacred about a blank page and a pen that glides just right. It's silly, maybe, but it's genuinely one of my favorite parts of the year. 

For a long time, I chalked that feeling up to nostalgia. This year I started to think it's something more useful – a reminder of what it feels like to give yourself permission to be a beginner again.

Somewhere along the way, most of us stop being students.

It happens quietly. We get comfortable in our roles – we build expertise, earn trust, and get recognized for what we know. The more of that we accumulate, the harder it becomes to admit there's still something we haven't figured out.

Whether you're leading a team, managing a project, or just settling into a new role, there's a quiet pressure to already have the answers instead of still being the one asking the questions.

The people I admire most, at every level of an organization, tend to share a kind of quiet humility. They're comfortable saying "I don't know yet." And they often notice the question underneath the question – the one nobody else realized was worth asking until they asked it. They treat not-knowing as a starting point worth sitting with, rather than something to hide.

That’s exactly the kind of beginner I want to be again. So, this fall, I’m giving myself a syllabus rooted in beginner mindset leadership.

Nothing formal – just one question I'm committing to sit with for a week at a time. A personal course load, minus the grades, and minus the pressure of pretending I already have it figured out.

Here's how it works, if you'd like to try it too:

The One-Question Journal

• Pick one thing you genuinely want to understand about yourself – or your leadership – better this month. It doesn't need to sound impressive, just something real, like "Why do I avoid certain conversations with my team?" or "What question have I been holding back in meetings that could actually move things forward?"

  
  

• Write that question at the top of a page. This is your syllabus entry for the week.

  
  

• Each day, spend five minutes jotting down one small observation connected to that question, without trying to resolve it yet.

  
  

• At the end of the week, read back through what you wrote and notice what surprised you.

That's the whole exercise. No homework, no deadlines – just five minutes a day and a willingness to admit you're still figuring something out.

What am I putting on my syllabus?

My question this month is simple: "Where am I mistaking busy for productive?" I don't have the answer yet, and that's the point. If I already knew, it wouldn't be worth a week of my attention.

An invitation - not an assignment:

I'm not asking you to overhaul how you work this fall. I'm encouraging you to treat yourself to a new notebook – or a fresh note on your phone – and use it to practice a bit of beginner mindset leadership by sitting with one meaningful question for a week.

Because the people who grow the most aren't the ones with all the answers. They're the ones still willing to raise their hand.

So, what's your one question this fall?