Juggernaut

In 2023, I stepped in to lead the product engineering teams of WordPress.com. The role was bigger than anything I’d done previously, but after talking to a friend, I figured I could commit to anything for a year.

A few months in, Matt Mullenweg pinged me for a Zoom. A funny detail that I remember is that he was calling from a plane and he could hear me, but I couldn’t hear anything he said. We got by with him typing and me talking.

The subject of the call was a project that the leadership team was concerned about. Matt told me that he thought people were being overly cautious. “Be the Juggernaut,” he said. Break through the walls and push it forward.

I hung up and started moving. I told the Dotcom leadership team we were doing this. Then I worked across functions to push the project to the end. Sometimes this meant working with marketing or legal to not tone down a message too much. Sometimes it meant deploying or reviewing code.

We shipped the project. In the end, it didn’t have the kind of impact that we wanted. But, that was fine. We committed and took the swing.

A while later, I was talking with my coach about that moment. About what it felt like to be the juggernaut, to do whatever it took to make the project ship.

He listened, and then asked a simple question:

“What keeps you from being the juggernaut for yourself?”

That stung. It was a simple but heavy question. I didn’t need permission to push that hard for the things I was convicted about.