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“What would you be willing to do for the rest of your life?”

That is the seminal thought in a great little book my brother sent me awhile back, and I thought I’d do a short review of it on the site tonight. The book is “The Monk and the Riddle” by Randy Komisar. It is, on one hand, a narrative representation of Randy’s experience with countless numbers of Silicon Valley hopefuls who came to him seeking advice and financial backing for their big ideas. Randy embodies the hopes, fears, strengths, and weaknesses of these collective entrepreneurs in the form of Lenny, an entrepreneur with a big idea to revolutionize the funeral industry. On the other hand, the book is also a statement about how to measure personal success in entrepreneurial endeavors, as Randy’s protagonist learns that entrepreneuring by doing something one really loves is much more likely to be successful at bringing one happiness than entrepreneuring in order to one day be able to do what one loves.

Randy’s personal experience and main point with the book seems to be to remind us that happiness comes not so much through the acquisition of resources, but by engaging in an endeavor to which we feel personally committed and interested. He shows the folly of sacrificing our devotion and personal passions today and spending our time and energy working only on seemingly hyper-lucrative pursuits in the hopes that we will strike it rich and then be able to spend the remainder of our lives doing nothing but pursuing our dreams. Of the myriad problems inherent in such an approach, Randy addresses a few, including the minute likelihood that any particular entrepreneur is actually going to be fortunate enough to actually find the payoff they have been looking for, and the fact that even among those who make it, they have often so deeply ingrained in themselves the notion of working for money, that they have lost the capacity to work on their dreams. Randy’s personal moment of enlightenment came as he stared down a hallway and could see his whole career and life’s ambitions, being confined to that narrow corridor and the context within which it functioned. He realized that, although that career path would bring him financial success, that success would be hollow because he could not love what he was doing.

The Monk and the Riddle is a very interesting and entertaining book, and a very quick read because of its easy, narrative style and compelling principles. I think somehow we all know instinctively that the world would be a better place if everyone dedicated themselves professionally to the things they love most and were most interested (and hence educated) in, instead of dreading their job, boss or both as they grudgingly trudge off to work every day. The Monk and the Riddle is great not just because of the insights Randy gives by sharing his life view, but also because of the way it naturally leads one to look internally and ask those same questions about one’s own professional activities. Not only do I strongly believe that we will be more likely to become leaders in our industries if we dare to do things we love, I think we also will have less risk in our professional lives in the long run, because we will be willing and able to dedicate ourselves fully to our pursuit, instead of begrudging our employer and always looking around for greener pastures. I highly recommend giving “The Monk and the Riddle” a read.