Wise Guy

(Originally published at Notes from the Metaverse)


Disclaimer: This week marks the publication of Guy Kawasaki’s 15th book, Wiseguy: Lessons from a Life. Having read a few of his previous books, including The Art of Social Media and What’s The Plus? (his guide to the soon-to-be-disappeared Google Plus social network), I jumped at the chance to read an advance copy of this part-memoir, part-advice book.

tldr; Wiseguy is entertaining, but the wisdom isn’t very deep.

Chances are you’ve heard of Kawasaki through his long association with Apple or from his extensive participation on Twitter and other social media (see the book I mentioned in the disclaimer). Both of these facets of Kawasaki’s life are on display in Wiseguy, but this isn’t really about either. In the very first paragraph of the preface, he describes his intent: “it is a compilation of the most enlightening stories of my life.”

Yes, Steve Jobs makes multiple appearances, but the hardest hitting comment Kawasaki makes is that “it wasn’t easy to work for him; it was sometimes unpleasant and always scary, but it drove many of us to do the finest work of our careers.”

The most interesting bits of this book are the personal ones: growing up in Hawaii as the son of a politician. How he quit law school during orientation week. His various sporting pursuits: Playing football in high school. Falling in love with hockey (as a fan and player) in his 40s, and then taking up surfing in his 60s after his daughter went crazy for the sport.

The surfing stories also highlight another theme of the book: the amazing luck Kawasaki has had in meeting the right people at the right time. His surfing teachers include some of the most famous surfers ever (not that I would know, but he doesn’t hesitate to tell us).

Among the stories he tells is his accidental ride in a military fighter jet, arranged after a presentation to the Pentagon Mac Users Group. How he got to be a “brand ambassador” for Mercedes-Benz. How he tweeted his way to an evangelist job at Canva.

After each story, Kawasaki offers us the “wisdom” he gained from the story he’s just told. All these stories are meant to explain how he got to be a “wiseguy.”

Now there’s nothing wrong with the advice he shares. There’s some important ideas in here. For me, the problem is that it’s just not unique. If you’ve read even one self-help book in your life, you’ve probably encountered most of these. After reading the stories, Kawasaki doesn’t offer something he learned that seems counter-intuitive. or different.

Wiseguy: Lessons from a Life is a quick, entertaining read. It might inspire you to do great things. I am going to put one more book on my to-read list after Kawasaki recommends it three times in this 236-page book: If You Want to Write by Brenda Ueland. See how that goes.