Create interesting things. Seems like fairly obvious advice, but it’s easy for a designer to find themselves over-analyzing how a shape is viewed or a couple of letters are kerned. But my mom doesn’t care about kerning. Neither does your grandma. And the last time you cared about shapes was when you tried on those skinny jeans. Sometimes you have to shove the overly dramatic rationale into the passenger seat and tell it to shut up and hold on.
That’s where I started with this project, trying to find something that would make other people curious about this guy and what he does for a living. Build character, create a story, give somebody a reason to talk about him. You might argue that this guy was open-minded enough to have some fun. Guess what, everyone is. If you don’t think so, I’d like to be around when you go tell your grandma that she isn’t fun.