The Monk and the Riddle … a call to pursue meaningful work, reject empty careerism, and find fulfilment in the journey, not just the destination.

May 15, 2025

In my first week as a CEO, way back in 2003, I gave my leadership team a book to read (it’s short, you can read it in an evening). It’s a book that had inspired me to think differently – about work, and life – for entrepreneurs, but equally for anyone in business.

“The Monk and the Riddle: The Art of Creating a Life While Making a Living” by Randy Komisar is a short semi-fictional tale, set in Silicon Valley during the frenetic “dotcom” times of the late 1990s.

Komisar is a seasoned entrepreneur, venture capitalist, and Stanford professor. With a Harvard law degree, he was a co-founder of TiVo, was a key player in Apple’s early growth, co-founded and led a series of other companies, then became a leader of VC firm Kleiner Perkins Caufield.

The entrepreneur, and his life plan

The book starts in a meeting with a young entrepreneur named Lenny, who is seeking funding for his startup called Funky Funeral—a company that aims to revolutionise the funeral industry by allowing people to plan their own funerals in fun and quirky ways. Lenny has a well-prepared business plan and is trying to convince Komisar, a venture capitalist and experienced entrepreneur, to back the idea.

Komisar listens politely but senses something off—not in the business model per se, but in Lenny’s motivation. Lenny admits that he doesn’t really care about the funeral business; he’s only doing it because he thinks it will make money quickly, and then he can go do what he really wants with his life. It’s a classic example of what Komisar calls the “Deferred Life Plan.”

The encounter with Lenny is a setup to introduce the book’s central conflict: Should you do what you love now, or delay gratification in hopes of someday living the life you want? Komisar uses the story as a metaphor for a broader conversation about entrepreneurship, life design, and finding fulfillment. He wants the reader to ask “What would you be willing to do even if you knew you might fail?”

As the story unfolds, Lenny begins to confront his own assumptions about success and happiness, ultimately reflecting the core message of the book: that you should design your life around your values, not around an exit strategy.

The monk, and the riddle

So who is “The Monk”?

The monk appears in the book’s prologue as part of a story Komisar tells about traveling in Myanmar (Burma). During a long, dusty ride to a monastery, he meets a Buddhist monk who poses a riddle—not with words, but through presence and perspective. The monk seems to live with deep contentment despite having few possessions and no ambition in the Western sense.

The monk embodies a life of purpose, simplicity, and spiritual clarity, in stark contrast to the Silicon Valley culture of constant striving, planning, and deferred gratification.

And what is “The Riddle”?

The riddle is this: “What would you be willing to do for the rest of your life, even if you knew you would never be financially rewarded for it?” This question is at the heart of the book. It challenges the reader—and Lenny, the fictional entrepreneur Komisar mentors—to think beyond business plans and exit strategies. It asks you to define: What you truly care about, what gives your life meaning, and whether you’re building your life intentionally, or simply following a socially conditioned script.

The monk and his riddle serve as a moral compass for the entire book. As Komisar listens to Lenny pitch his “Funky Funeral” startup, he realizes Lenny is driven by the deferred life plan: make money now, do something meaningful later. Komisar, inspired by his experience with the monk, encourages Lenny to flip the script: do what you love now, and trust that meaning and success will follow—even if they don’t come with a big financial payoff. The riddle becomes a recurring theme, urging both Lenny and the reader to rethink the purpose of work and life.

The monk’s riddle is really Komisar’s way of asking “Are you designing a life or just building a resume?” It’s a call to pursue passion over prestige, purpose over profit, and to avoid the trap of postponing joy and meaning until it’s too late.

What are the takeaways?

Here are my takeaways from the book, relevant to every entrepreneur or business leader:

1. Don’t pursue the “deferred life plan”

“The deferred life plan is when you do what you have to do so you can do what you want to do.”

  • Many people fall into the trap of working a job they dislike now with the hope of eventually doing something meaningful “later.”

  • Instead consider integrating purpose and passion into your work today rather than postponing fulfillment.

2. Passion and purpose matter more than business plans

  • Success in business (and life) isn’t just about clever strategies or perfect business plans—it’s about being passionate about your work.

  • If you don’t care deeply about the venture, you’ll burn out before it pays off.

  • Investors look for people who are committed, not just ideas.

3. Create a life, not just a career

  • The central theme is about aligning your personal values with your professional pursuits.

  • Build a life that is meaningful and fulfilling—not just financially lucrative or impressive on paper.

4. The journey is the reward

“The experience of the journey has to be enough, because the outcome is never guaranteed.”

  • The path for any entrepreneur or business leader is uncertain, so your motivation must come from enjoying the process, not just chasing a pot of gold at the end.

  • If you don’t love the journey itself, the risks may not be worth it.

5. Integrity and authenticity build trust

  • In both life and business, being true to yourself, honest with others, and consistent in your values builds the trust you need for success—especially in startups and leadership.

6. Leaders pursue meaning, not just money

  • Many of the best entrepreneurs and business leaders are purpose-driven, they seek meaning as well as money from what they do.

  • They build companies to solve real problems or make a positive impact, not just to flip them or make a quick return.

7. Luck favours the prepared and passionate

  • While chance plays a role in success, those who are truly invested and persistent are more likely to capitalize on opportunities.

  • Passion fuels resilience and attracts talent, investors, and momentum.

8. Riddles over resumes

  • The “monk” in the title symbolizes mystery and purpose; the “riddle” reflects the ambiguity of life’s choices.

  • Embrace the unknown and explore deeper questions about why we do what we do, not just how to achieve it.

“The Monk and the Riddle” is a call to pursue meaningful work, reject empty careerism, and find fulfilment in the journey, not just the destination. It’s about creating a life with purpose while still being entrepreneurial, strategic, and ambitious.

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