The Whack-a-Mole Problem

This was the very first cartoon I shared—the moment I decided to be a bit brave and infuse more fun into the serious work of strategy and leadership.

I realized that if we’re serious all the time, the challenges of mission-forward work become too heavy to carry. I started playing with cartoons to simplify the big ideas I was sharing with my coaching and strategic advisory clients.

The Problem: We treat our to-do lists like a game of Whack-a-Mole. Every time we “solve” one issue, three more pop up.

The Reflection: Looking back at this first sketch, it reminds me that leadership isn’t about how fast you can swing the mallet; it’s about whether you’re willing to step back and look at the machine itself.