How to Fail at Almost Everything and Still Win Big

This was given to me as a gift, and originally I dropped out about halfway through. That was before Scott Adams was thoroughly and rightfully canceled for being a paranoid racist, though—an event that rekindled my interest in the book.

While it initially styles itself somewhat as an autobiography, it falls squarely in the self-help category. And in a sense, this is as good as self-help gets. It's written by someone with an interesting life who makes his money writing funny comic strips, so at the very least, it's a competent and entertaining read. And Adams actually presents a handful of useful mental models on life and success and shares some outrageous stories. But most of the chapters either give off major pick up artist vibes or boil down to “sleep well, exercise and eat your veggies.”

Seeing how Scott Adams' own life has turned out, it's safe to say that all the “tactics” and “systems” in here–the ones he literally wrote the book on–didn't really help him in the end. So, in a way, Adams' behavior has inadvertently and retroactively transformed this book into a profound take-down of the self-help genre, I guess?

On a side note, if you have read this and still were surprised to find out Adams is a douchebag, I ... don't think we've read the same book? He's really not hiding it.

Finally, since seeing one of his videos for the first time was one of the cringier experiences of my life, I'd like to quote Adams' complete YouTube channel description. Because it's really all you need to know about him and the tone of the book:

“Scott Adams (famous for creating Dilbert) is a trained hypnotist, and is widely recognized as an expert on persuasion. Adams has emerged as one of the most influential observers of politics in the United States. His bestselling book, “Win Bigly,” teaches persuasion, and his bestselling book “How to Lose Almost Every Time and Still Win Big” is widely considered the best book ever written on developing systems for success. His most recent book is Loserthink, which teaches you how to avoid it. If you enjoy learning how to be more effective in life while catching up with the interesting news, this is the channel for you.”

My favorite part is that he seems to get the title of his own book wrong? What a loser.