Book Review: How to Fail at Everything and Still Win Big…

Ugh – This is a hard review to write, so I’ll keep it short.


First of all, the book is written by the guy that writes the cartoon about cubicle life that used to be funny.  I’m purposefully not linking to his book, to his website, anything. Not even using his name here. Why? Because he has very strange political/social beliefs. Very controversial, if not downright scary.  And the people that gravitate in those circles are quite vocal and militant. I don’t wish to bring that on myself, but I did feel like it was necessary to address this book, as in my searches on Systems vs Goals, it comes up a lot.

I thought this book was going to give information about systems, etc…and while there is some detail of such, it’s mostly a weird love letter to himself.  It’s both arrogant and self-deprecating.  Like some of his most outrageous claims about  him not getting promoted because he’s a white male, literally follow him explaining how he was terrible at his job.  Massive lack of self-awareness going on.

Several times I became so angry at the book I stopped listening.  The information about his hand issue, etc…might prove useful to others going through the same medical concern, but ultimately if you are looking for a good book on systems vs goals, this is not it. Skip it, and skip giving money to someone who supports some pretty disturbing theories. I asked Audible for a refund.

Very disappointing.