When I first started as an editorial cartoonist, I was terrified on a daily basis. Filling that hole the next day, knowing that tens of thousands of people were going to expect something funny. There is still that pressure, but you kind of learn how to cope with it a little better.
It's a fun job, but it's stressful because you have to be funny. You have to have punch lines and captions. Be funny now! And if you're not inspired, they don't care - be funny now! They have to fill that hole the next day.
Chess is a thinking person's game. But you don't have to be smart to know what's funny! Lots of check, mate!