This book, wow...
I think it's a matter of timing, but The Cliff Walk changed my life.
I think I picked it up around 1997, after reading Phillip Greenspun talk about it. If I remember correctly, Greenspun read it, realized academics doesn't have to consume your entire life, dropped everything and went on to cross the country and back.
So the amazing thing about this book is that it's the story of a guy that is really ambitious about academics, does everything he can to excel and ends up somewhere like Harvard or Darthmouth (I forget the exact ivy league-ish school) teaching english. A few years pass, he publishes a ton and teaches and devotes every waking moment to it but in the end doesn't get tenure and has to find a position somewhere else. He looks for other high profile schools and doesn't find any slots, and refuses to look for work at smaller universities.
It doesn't take long before he's run out of money, his wife hates him and his kids barely know him from being ignored for the job. In a pinch, he takes a job as a carpenter and after a few years of struggling starts doing really well and turns his life around. In the end, he realizes Work is not Life and Family is much more important.
I can't say for sure if this really is an amazing or well-written book, but it was the perfect thing at the perfect time of my life. I was fresh out of academics and working a crappy job I hated, wishing I had the nerve to drop everything and my previous 8 years of schooling to do this new web thing I loved so much.
This book inspired me to search for my first web job and when I got it, I dove into that job and worked my ass off, teaching myself everything I needed to know for a new career. This book is what got me to where I am today. If you spent a life in academics and are thinking of moving on with your life, this is the greatest book ever written.
