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The Playground Phase

March 9, 2026 | Career Transitions, Leadership, Reflection & Purpose

AI.

If you’re a curious leader, like I certainly tend to be, this can be both magical and mildly hazardous to your productivity.

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Because suddenly you’re surrounded by tools that can:

You can prototype something in an afternoon that used to take six months.

It’s like someone handed a room full of adults the keys to the world’s most advanced playground. And if you’re like me, you start thinking:

“Let me just try one thing.”

Two hours later you’ve:

Was it productive? Debatable.

Was it fascinating? Every single time, YAY.


The Slightly Guilty Joy of Playing

Eventually, that responsible voice shows up.

You know the one. “Shouldn’t you be doing real work?”

I have one that has occupied my head, rent-free, for years. I believed that voice. But here’s something I’ve come to understand:

Playing with ideas is real work.

Imagination is simply the earliest stage of strategy.

Before there’s a plan, there’s exploration.
Before there’s execution, there’s curiosity.
You may even have to wander on purpose for awhile.

And wandering — while uncomfortable for people who like certainty — is often where the next meaningful thing begins. We’re living in a moment where the tools to stretch imagination are everywhere. Which means the real risk right now isn’t playing too much.

It’s stopping yourself from playing at all.


So here’s the question I’m sitting with this week:

What have you done lately to stretch your imagination

?

The ReflectionPoint Advisor is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

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