How did you got into characters?

I hope to start a discussion between one who did and who are thinking about transitioning from strictly lettering to also characters. Cartoony, Abstract, Traditional, Realistic doesn't matter.

Where do you see it's standing in street art in general? Where/With/Ehy what did you start? Was at a natural progression for you? When did you incorporate them? Did you learn that it just wasn't your thing? What where some surprises you encountered? What can you recommend on someone that wants to go there?

It feels like something an artist might do, for example lets say I created an amazing pro-feminist poster, I’d upload it somewhere and be cool with others downloading it and putting it up in their town, I wouldn’t be very concerned about relinquishing the rights to it.