"If your life were to end suddenly and unexpectedly tomorrow, would you be able to say you've been doing what you truly care about today?"

First of all, a big THANK YOU for signing up!  For the second installment Influential Books, I’m introducing The Monk and the Riddle: The Art of Creating a Life While Making a Living by Randy Komisar.

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Brief Summary

The story opens with the author on a motorcycle journey through Miramar, where he meets a monk who poses a riddle:

"Imagine I have an egg and I want to drop this egg three feet without breaking it. How do I do that?"

The author answers the riddle using the anecdote of an overzealous, aspiring entrepreneur trying to quickly launch and sell a tech startup.  Through this story, he poses philosophical questions about finding satisfaction in our work and challenging the conventional thought that we should sacrifice our lives to make a living.

About The Author, Randy Komisar

Randy Komisar is an impressive guy.  Although he holds a JD from Harvard Law School, he was eventually pulled toward business and its potential to bring about positive change.  He was a co-founder of Claris Corporation, a founding Director of TiVo, served as CEO for LucasArts Entertainment and Crystal Dynamics, and acted as a “virtual CEO” for such companies as WebTV, Mirra, and GlobalGiving.

More recently, Komisar joined Kleiner Perkins Caufield and Byers (the venture capital firm behind Google, Groupon, Spotify, and countless other tech companies) as a partner in 2005.  He also co-authored Getting to Plan B in 2009.

Who Should Read This

  • Anyone with the nagging feeling that they were meant to do work that has greater meaning to them.
  • Anyone at a crossroads in their career and looking for guidance or direction.
  • Anyone who at their core believes that finding meaning and fulfillment in one’s work is not an elitist concept.
  • Any entrepreneur or aspiring entrepreneur embarking on a new project (especially an internet startup).
  • Anyone who believes you need to work the majority of life doing something you don’t want to do, so you can eventually retire and then devote your time to your passion.  PLEASE READ THIS, you need it the most.

 Who Shouldn’t Read This

  • Anyone who has achieved a meaningful existence in their work and life.  You already have it figured out.
  • Anyone needing immediate tactical advice on starting or running a business.  This book is more about the why of business, less about the how.
  • Anyone with an aversion to technology and internet startups.  A tech startup is merely used to tell the story, so if this really turns you off you might get disinterested.

How This Resonates With Me

The author’s opinion of the interdependent relationship of work and life is something I believe in wholeheartedly.  Life is brief, and it’s wasteful to spend time doing things that do not align with your passions or gifts.  The brevity of life is a lesson my friend Shannon dealt me firsthand and I try to remind myself of this everyday.

Related to this, the author challenges a societal norm he calls The Deferred Life Plan.  It’s a concept I always had a hard time buying into as well, but feel more comfortable confronting that belief after reading this book.

There’s a point in the book where Komisar mentions that gaining self-knowledge is so important when honing in on your passions and gifts.  This is something that really resonates with me as I travel, learn to follow my intuition, and make decisions based on the options which excite me the most.  The experience of my current trip coupled with the lessons in this book reaffirm my belief that taking a break from working in one’s life to work on it is so important.


This book was originally written in 2000, so the references to TiVo and WebTV feel a little dated.  And given the speed of technology, twelve years is like a century in tech years.  But it’s surprisingly not as archaic as I expected; although the names have changed, the lessons are timeless. Also, the writing isn’t very sophisticated and the way the story ends feels a little Disney-fied.  It’s tough to be too critical of this though because the book delivers its lessons clearly.

 Thirteen Take-Aways

1. Entrepreneurs and immigrants have a lot in common.  Using the example of his own grandparents immigrating to America from Russia and Germany, Komisar identifies an interesting similarity between these two groups:

"I see a common gene among immigrants and entrepreneurs who strike out from the pack to pursue their dreams...some of these risk takers...have a profound impact on what happens in the world. They place bets on the future, often against fantastic odds."

2. Venture capitalists and their role in the startup economy can be demystified.  There are several scenes in the book depicting a discussion between entrepreneur and venture capitalist, and occasionally some passages that look into the mind of a VC.

"Venture Capitalists want to know three basic things when investing in a business. Is it a big market? Can your product or service win over and defend a large share of the market? Can your team do the job?"

3. There should be a deeper purpose driving you to start a business besides money.  A business shouldn’t be started as a means to an end.  A business should be built for the purpose of building it and making a positive impact, not just for the success and reward that may come.  Put another way, “the journey is the reward.”

"There must be something more, a purpose that will sustain you when things look bleakest. Something worthy of the immense time and energy you will spend on this, even if it fails."

4. Business, more so than any other institution, has the potential for creative expression and positive change.

"The rules of business are like the laws of physics, neither inherently good nor evil, to be applied as you may. You decide whether your business is constructive or destructive. I help people understand this and express themselves in what they do, trying to make a difference through business."

5. Most of us have been living life according to the “Deferred Life Plan”. There are two steps in life according to this plan.  Step one: Do what you have to do.  Then, eventually — Step two: Do what you want to do.  This concept implies that we should spend our life working hard doing something uninspiring so we can retire one day and then devote our time to our passion.  The problem is our life’s timeline is unknown.  We may never reach “one day.”

"The Deferred Life Plan also dictates that we divorce who we are and what we care about from what we do in that first step...we hope and suppose that when we get [to the second step], we will be able to resurrect our passions on our own terms. If we get there."

6. There’s a difference between a Big Idea and a Business Model.  Komisar brings this point home by discussing Apple’s tumultuous times under Sculley, where the CEO began operating Apple to a business model rather than a big idea, the way Jobs did (and eventually would re-do).

"Business conditions are forever changing. You need to reconsider your strategies and business models constantly and adjust them when necessary. But the big idea that your company pursues is the touchstone for these refinements."

7. Business is about people.  This is a concept that Chris Guillebeau hammers home in The $100 Startup as well.

"Business...is about nothing if not people. First, the people you serve, your market. Then the team you build,  your employees. Finally, your many business partners and associates. Sever the chain of values between leadership and the people translating strategy into products and services for your customers, and you will destroy your foundation for long-term success."

8. Your Passion is not the same as your Drive.  This is an interesting distinction I had never considered before. In reference to the steps in the Deferred Life Plan, drive is what you experience in the first step, and passion is what you hope to experience after you’ve put in your time.

"Passion pulls you toward something you cannot resist. Drive pushes you toward something you feel compelled or obligated to do."

9. It requires true self-knowledge to understand your passion.

"If you know nothing about yourself, you can't tell the difference [between passion and drive]. Once you gain a modicum of self-knowledge, you can express your passion."

10. If management is a science, leadership is an art.

"[Management]'s purpose is to produce the desired results on time and on budget. It complements and supports but cannot do without leadership, in which character and vision combine to empower someone to venture into uncertainty."
"I found that the art wasn't in getting the numbers to foot, or figuring out a clever way to move something down the assembly line. It was in getting somebody else to do that and to do it better than I could ever do; in encouraging people to exceed their own expectations; in inspiring people to be great; and in getting them to do it all together, in harmony. That was the high art."

11. Personal risks need to be evaluated with just as much scrutiny as business risks. Personal risks include the risk of working with people you don’t respect, the risk of working for a company whose values don’t align with your own, the risk of doing something you don’t care about, or the risk of doing something that does not express who you are.

"And then there is the most dangerous risk of all -- the risk of spending your life not doing what you want on the bet you can buy yourself the freedom to do it later."

12. The value of time > the value of money. By valuing your time more than you value money, you’re able to appreciate each moment and live a more fulfilling existence spending your time doing something worthwhile. The alternative notion is thinking money can buy you the happiness you’ve missed out while you were focused on acquiring things.  The problem is you don’t know when it will be too late.

"Marrying our values and passions to the energy we invest in work...increases the significance of each moment. Consider your budget of time in terms of how much you are willing to allocate to acquiring things versus how much you are willing to devote to people, relationships, family, health, personal growth, and the other essential components of a high-quality life."

13. Can you answer the Monk’s Riddle?  Check out the book to find out.

Interested in reading the this book?  It's available on Amazon: The Monk and the Riddle: The Art of Creating a Life While Making a Living

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