Scott Adams, of course, is the creator of Dilbert, but that's not all. He's tried (and often failed) at lots and lots and lots of things in his career, ranging from video games to restaurants to frozen burritos. His self-help book How to Fail at Almost Everything and Still Win Big documents them in detail as well as providing a realistic and often amusing approach to self-help.
Scott's a very original thinker. His blog is full of thought experiments and contrarian thinking. Sometimes it attracts "outragists," but luckily for us Scott soldiers on.
Follow him on Twitter @ScottAdamsSays