10 Most Inspiring Books

Yesterday a friend on Facebook challenged me to post a list of the 10 most inspiring books I’ve read.  “Inspiring” is defined fairly broadly.

This has provoked 24 hours of introspection; I’ve read a lot of books in my lifetime, many of which have affected me in one way or another.

But here goes with my list, grouped into a few (hopefully) useful categories.


Business books:

Crossing the Chasm.  Everyone who works in technology needs to read this book, as it challenges the conventional wisdom on how tech marketing works. In my experience, it’s spot-on.

The Leader’s Voice. By far the best book I’ve ever read on business communication. This has been my bible for several years, and it works remarkably well. And it applies beyond business communication as well.

The Visual Display of Quantitative Information.  I wish I could cheat and add all of Tufte’s books as one item in the list. Tufte’s exploration of data visualization, the good, the bad, the ugly and the beautiful, are classics for anyone who needs to explain things.


Books that  expanded my world view:

The Children’s Story. The shortest book in the list. I won’t expand further on why this is on the list, so as not to ruin the reading experience for anyone.

Generation X.  Every generation has a writer who powerfully interprets its place in the world order. For my generation, it’s Douglas Coupland.

Suburban Nation. On the surface, it’s a book about the history of American suburban neighborhoods. At a deeper level, it’s a treatise on how our environment shapes us.


Books that changed my view of storytelling and made me want to be a writer:

The Princess Bride.  The movie is wonderful.  The book is wonderful-er.

The Diamond Age. This book broke new ground in how to talk about technology in fiction without turning it into hard SF, and without sacrificing the storytelling.

Lamb. Staggeringly ambitious, and delivers. Funny, poignant, rich, risky, irreverent.

Player Piano.  I love me some Vonnegut. I could easily have cross-listed this under “Business books.”  Profound (and yet simple) social commentary on technology’s role in society. Every Apple and Google fanboy should read this.


Ok, I’m going cheat a bit, and list some runners-up that I considered for the list:


Ender’s Game.

The Bridges of Madison County.

The Design of Everyday Things.

Value Migration.


Teaching as a Subversive Activity.


The Mythical Man-Month.




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