
I knocked around a lot of different titles for this rule before I settled on this particular wording. Originally, this rule was “Be an asshole for the right reasons” and in some ways, that title was closer to the spirit of this rule.
However, after many revisions, I wanted the rule to land closer to the inspiration of this particular rule: my old boss. After all, “Release the Kraken” was his way of telling us to be the asshole in the situation.
When I first started working for this guy, I couldn’t tell if he was the worst boss I ever had or the best. He was unlike any boss I had before. There was no hand holding, no sugar coating, and no bullsh!t. He expected his team to operate far outside their comfort zone and expected results. That being said, once you proved to be an asset to his team, you were untouchable. He was a bully, but one that believed in his team, treated them like royalty, and fought hard on behalf of them.
I remember seeing a graph online somwhere in the past describing the perfect boss. The y-axis indicated “how much they care about people,” and the x-axis indicated “how much of an asshole they are.” According to this article, leaders that landed in the top right quadrant (assholes that care about people) make the best bosses. This guy was the embodiment of this principle.
That’s the kind of boss I want to be: One that releases the Kraken for the right reasons.
This story is part of an ongoing series diving into the origins of each of rules outlined in Octavo (My eight-fold principles of life and work). Click here to see the full set of rules and to download and print your own copy of the rules and Zine.

Octavo (8vo) is both a format and a philosophy; it is a sheet of paper folded into 8 equal sections to form a book, and it is a philosophy folded into eight principles to form the architecture of how we work and live. Keep these principles posted wherever your work is done and refer to them often. Keep the zine in your back pocket at all times and refer to it when tempted to stray. Both the principles and the zine are provided here for free and can be printed from any monochrome printer that accepts legal-sized paper. Distribute as you see fit to your friends, family, and colleagues (but do not modify).

