The reason I'm second guessing the humour of "My Financial Career"? I've not found Leacock as funny since.
Sunshine Sketches of a Little Town begins promisingly enough. In his preface, Leacock writes
I was born at Swanmoor, Hants, England, on December 30, 1869. I am not aware that there was any particular conjunction of the planets at the time, but should think it extremely likely. My parents migrated to Canada in 1876, and I decided to go with them.This was certainly enough to make me smile and I was optimistic for the rest of the book to come. Unfortunately, I found the rest somewhat boring. The passage above hints at a theme of Leacock's humour that pervades the rest of the book: the idea that people taking themselves too seriously is funny. And he's right. The Spinal Tap/ Mighty Wind guys have made a career off of that sort of thing. However, I did it wearing a little thin in Sunshine Sketches.
I also thought there was a hint of meanness in some of these stories. Whereas the target in Leacock's preface is himself, the target in the rest of the book is the townspeople of Mariposa. True, Mariposa is a fictional place, but as Leacock himself explains, it's supposed to represent rural Canada, or at the very least, rural Ontario. The message consistently falls somewhere between "country people are idiots" and the kinder, but more patronizing, "aww, isn't it cute when country people think they're doing something important." I'm from a small town, so it would be easy to accuse me of being over sensitive, but really I just prefer equal opportunity offenders. Make fun of the small towns all you want, but save some jokes for the cities.