Every new release of WordPress is named after a jazz musician. That’s not random; WordPress’ co-founder and my boss, Matt, is a jazz musician.

What really blew my mind was when a colleague pointed out that our company, Automattic, also runs a bit like a jazz band. Ever since learning this, I’ve gradually found it easier to work within our company.

Most corporate environments — if I want to stick with the music imagery — want to be run like classical orchestras. There’s a clear score, the conductor is in charge, everyone knows what they should and shouldn’t do, and there’s occasionally a star that takes on the biggest challenge.

If you’re into sports, this is probably more alike to how American football functions with clear set pieces, and predefined running lines.

Automattic runs like jazz. There’s a lot of freedom to explore new ways, and everyone at the company is skilled enough to embrace that new tune, that new direction. It can feel like chaos at times, and sometimes the notes and instruments when headed in a new exploration feel like they are war with each other. But jazz is jazz because somehow the musicians find each other again. The chaos is not at odds with jazz, it’s an integral part of its beauty. The chaos is also not the goal at the same time. It feels like a process to go through, but jazz also has many moments where the musicians find each other again and the whole feels symphonic.

In jazz, it’s also not consistently the same person who takes the lead. Most jazz ensembles will have a star who takes the majority of that weight, but true jazz beauty also happens when that person occasionally steps back to let others have the spotlight. In sports, it’s much more like football (soccer) where watching the ball is only a tiny part of the enjoyment, it’s seeing how the team moves around it and positions themselves based on decisions both team members and opponents make.

Working at Automattic at times feels chaotic, but it’s also a space where I don’t have to tell anyone the specifics about their work. It’s a place where there’s enough freedom to stir the pot and go into a novel direction, even if it feels at odds with our current one. It’s a space where many people in my wider team will have a great idea and start building it without feeling the need to get my approval first. It’s an environment where I will head into a certain direction and people who report to me will push back. We can have gone in a certain direction for months, and then someone decides it’s not the right one and we all have the skills to — in play — decide if that person is right, and join along with them. It’s a lot like jazz.

There are brilliant classical musicians who are lost in jazz. The best NFL players would be dominated by a lower tier football player. And people who function amazingly at corporate environments with more clarity may struggly at Automattic. I don’t think the question here is “do you get jazz”, but does this freedom to improvise, and learn to improvise with others around you, energises or exhausts you. Which one resonates with how you want to work?