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The Monk and the Riddle: The Art of Creating a Life While Making a Life

3.87  ·  Rating details ·  2,574 ratings  ·  172 reviews
What would you be willing to do for the rest of your life?

It's a question most of us consider only hypothetically, opting instead to "do what we have to do" to earn a living. But in the critically acclaimed bestseller The Monk and the Riddle, entrepreneurial sage Randy Komisar asks us to answer it for real. The book's timeless advice - to make work pay not just in cas

Paperback, 181 pages
Published September 1st 2001 by Harvard Business Review Press (first published March 1st 2000)
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Jessie Young
Apr 07, 2013 rated it really liked it  ·  review of another edition
What I enjoyed most about this book is that its point is simple, yet important: people succeed in Silicon Valley / Tech because they are committed to a goal above and beyond making money.

I work in the tech industry and we're always hearing about people we know or loosely know making big money by having their companies acquired. But I always ask myself: is that really the end goal? Would you really have sacrificed all of those nights, weekends, blood, sweat, tears, relationships to this company i
Matthew Trinetti
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 int
If you’re a first-time entrepreneur looking for ways to fund your business but are unsure how to approach potential Venture Capitalists successfully, this book would have to be on your reading list. Its key “Do’s and Don’ts before, during and after pitching to VCs” are practical and illustrated in entertaining detail through Lenny’s story – an entrepreneur in his twenties who’s got some solid lessons to learn before he’s able to generate the much-needed funds to get his business idea off the gro ...more
David Hornik
Jan 03, 2013 rated it really liked it  ·  review of another edition
I teach an entrepreneurship class to law students and assign The Monk and The Riddle to the class. It is a great book for law students to read because it forces them to think about why they are going to law school, what they are hoping to get out of it, what will ultimately make them happy. While that is arguably a sub-theme of the book, I find it the most interesting piece of the conversation with my students.

On the other hand, the bulk of the book is focused on an entrepreneur's quest to get
Mikko Eerola
Jun 29, 2008 rated it it was amazing  ·  review of another edition
Recommended to Mikko by: Antti Vilpponen
Shelves: on-loan, i-own
A good, quick, enjoyable read.

A word of warning: this is a potentially dangerous book. It may make you rethink your priorities in life.
Lisa Marie O'Connor
Enjoyable read although it didn't tell me anything new, having studied online entrepreneurship, worked in tech start-ups and watched many of the Silicon Valley tech founders on Ted Talks, You Tube etc as part of college study. Maybe I'm too immersed in it but it just seemed to confirm the message any startup founder knows, that there are no 'get rich quick' ideas and if you're in it for the money, get out and find a new idea that you love. Find the 'why' - any start-up that isn't 'love' is a was ...more
Garret Macko
If you get the chance, I'd recommend reading this in one sitting—rather than, as I did, in many short bursts—it's compact enough to do so, and I feel as if doing so would help give the reader a more holistic picture of the tale the author is trying to tell. On that note, I was pleasantly surprised with this work; I normally try to steer clear of books falling within the genre 'self-help', but picked this up on a whim at the recommendation of an entrepreneur I was reading a biography on (if I'm n ...more
Michael Huang
To be fair, Komisar had a good message: “spend your life doing something you are passionate about”, rather than “do something to get rich and then ...”

The story he made up/adapted from real life to convey the message is a D- in creative writing. Way too boring.
Oct 05, 2011 rated it liked it  ·  review of another edition
Unlike all other business books I've read, this one is mercifully short, focused on one big idea, and told as a story. Aside from that, I could not put the book down because it really appeared in my life at the right time to ask the question what I am passionate about my passion in life. Now I am a almost a full believer in abandoning the "Deferred Life Plan" -- do nonsense now to make money, live later -- except that I don't know what I am deferring. I do also like how subtly the benchmarks for ...more
Dec 22, 2017 rated it really liked it
The book is a bit dated as it written before the 2001 dot com implosion. But it really isn't about that era or Silicon Valley even as the story follows a start-up wannabe being guided by the author. It really is about finding a life worth living in the moment and not deferring it until you're too old, tired or sick to enjoy it. There's a great discussion of the difference between passion and drive and which one should be the priority. It's a quick read that should confirm our new found bias towa ...more
Yvette Bowlin
A little misleading, the title and the actual content in the book. A story about a silicon valley ex-VC and how he helps entrepreneurs stay true to themselves as they pursue success. I don't particularly get excited about the premise, but I do like the setting. The low rating is because I wasn't thrilled at the plot and I didn't really believe Komisar. His stories seemed far-fetched and too "perfect." Just seemed contrived and too heavy-handed on the "spiritualism." ...more
Jul 31, 2010 rated it really liked it  ·  review of another edition
If you are an entrepreneur or wish to be or even just looking for financial meaning in your life this book is a must read. It is about, as Joseph Campbell said, following your bliss. We all have hopes and dreams and ideas about success: this book is about staying the course.
Denny Troncoso
Feb 16, 2021 rated it it was amazing  ·  review of another edition
Fantastic book about pursuing ones passion and growing a successful technology company. I enjoyed the authors writing style of the story being told from the eyes of the narrator/mentor. It was so valuable I listened to it twice back to back. Here are my notes:

The experience itself is the end

Business is tough tenacity and endurance are the main requirements. Money cannot be overwhelming objective or endurance will wane.

The things that matter to us personally
Passions and values family relationshi
Feb 03, 2020 rated it liked it  ·  review of another edition
The Monk and the Riddle is a business leadership book by American entrepreneur Randy Komisar. Drawing its arguments from Komisar’s (often humorous) lived experience, rather than didactic lists and frameworks, the book seeks to teach its audience how high-stakes business dealings, particularly those of Silicon Valley, actually go down. The book is structured as a series of dialogues between Komisar and two aspiring entrepreneurs whom he names Allison and Lenny. The dialogue touches on many topics ...more
Oct 30, 2019 rated it it was amazing  ·  review of another edition
What would you be willing to do for the rest of your life...? It's a question most of us consider only hypothetically-opting instead to "do what we have to do" to earn a living. But in the critically acclaimed bestseller "The Monk and the Riddle", entrepreneurial sage Randy Komisar asks us to answer it for real. The book's timeless advice - to make work pay not just in cash, but in experience, satisfaction, and joy - will be embraced by anyone who wants success to come not just from what they do ...more
Juliette Weiss
Jan 15, 2018 rated it it was amazing  ·  review of another edition
“Don’t confuse drive and passion. Drive pushes you forward. It’s a duty, an obligation. Passion pulls you. It’s the sense of connection you feel when the work you do expresses who you are. Only passion will get you through the tough times.”

Bought this book years ago for Danny Warshay’s Entrepreneurship class and finally got a chance to read it. And wow, it could of have been at a better time!

The big picture advice, like the difference between leadership + management or drive + passion, made me r
Feb 06, 2021 rated it liked it  ·  review of another edition
I heard of this book from one of the Harvard Business Review Ideacast episodes. I tracked it down and began to read first it paints Silicon Valley as this place of Milk and Honey. Where only the strong (and extremely smart) survive and the cast of characters are VC’s with pleated pants investing in tomorrow’s technology (TiVo). I grew weary of his storytelling midway through the book. But towards the end one page (As he stands atop a mountain while riding his bike) Randy Komisar puts ever ...more
Sep 24, 2017 rated it it was amazing  ·  review of another edition
What an outstanding book, well worth revisiting and deserving of sufficient time to digest its contents. It took me some time to be swept up by the main parable, the central pillar around which Komisar crafted his narrative, but once that had happened, I found myself relating it - as well as the highly pertinent asides selected from Komisar's own life - to other readings (e.g. The ideas of the stoics, as well as some that were later echoed by Cal Newport). This book isn't just about what's neede ...more
Tom Lambotte
Feb 23, 2018 rated it really liked it  ·  review of another edition
A solid, easy read with some great ideas and questions to make you think. This book was read by the author of Traction many years ago and it inspired him to becoming a business coach and doing what he does now.

Big takeaway idea:
“What are you willing to do for the rest of your life? It does not mean, literally, what will you do for the rest of your life? ...that would be absurd...what it really asks is, if your life were to end suddenly and unexpectedly tomorrow, would you truly be able to say y
Sally Duros
This book inspired me to interview Randy Komisar for a column I was writing at the time.

Passion – it’s on the ceiling!
Posted on April 5, 2003
First Published in Sally’s World, April 2003


In the 80s, we worked hard. In the early 90s, we worked smart. In the late 90s, we worked fast. But now, firmly established in the new millennium, we are working all three, but most of all we are working passion.

Today many of us have switched careers or spun o
Dilip Massand
While the description appealed to me, I found the book a little too light and simplistic.. But then again the message is light, simplistic, and yet true. Be passionate about your work, pursue something you believe in, and enjoy the journey - for that is it's own reward... Find your purpose and make it your work... Rather than work and keep your dreams and purpose on hold, as part of a "deferred life plan"... the book was a light sojourn, with a positive message, but somehow felt lacking in depth ...more
Jul 08, 2021 rated it liked it  ·  review of another edition
I found this book fascinating. I enjoyed how the story was presented and learned a lot from it. I didn't give it a higher eating because I felt like while it gave a lot of entrepreneurial lessons, it didn't provide me with actions, a thought process, nor allow new to learn any new insights about myself. Based on the first chapter, I thought that the last item would really be the case, but that never happened. I wish the book had circled back to the introductory story before ending, that really w ...more
Jul 26, 2017 rated it really liked it  ·  review of another edition
This is a good narrative for those professionals who subscribe to the notion that "you only go around once..." while also asking themselves the question "what should I really be using my 'superpowers' for?"

Although one could argue the author is traveling downhill a bit with a couple of explosive successes behind him, the counterpoint should argue does that really matter, or did that just give him the bandwidth to have the epiphany?

Happy to have stumbled upon it. A quick read.
Paul Fisher
Jul 16, 2018 rated it it was amazing  ·  review of another edition
I really enjoyed this book. It was a quick read, and easy to follow. At first, I thought that the story was going to have characters that were over-developed and too typecast, and if it was a 300 page book it probably would have. But the short, concise nature of the story got to a point, and did so in a way that left the reader feeling that the length was just right. Short, but it did not need to be longer.
Chetan Chothani
The strange intersection of a business book with a Fantasy Series (Stormlight Archives)! In his fantasy series, Brandon Sanderson emphasizes Journey before Destination as part of the immortal words of the Knights Radiants. Similarly, in this book, Randy Komisar, in a round about way teaches entrepreneurs that it is not about the destination, but rather its about the journey.

Thoroughly enjoyable book. Brings perspective!
Monya De
Not sure why MBA faculty are so into this. The artificial central conceit is Komisar stringing a poor founder along and imparting some blather about how his idea is not fundable because it is just an e commerce site. I'm sure Bezos would beg to differ and say you do not need a fancy story or emotional connection to your startup. Then he sort of meanders through his autobiography in between torturing the founder. ...more
Feb 05, 2018 rated it it was ok  ·  review of another edition
This book can be summed up in one line—"Working with purpose is > working for money"

It was entertaining, but ultimately it's use of a fictional narrative to recount the author's experience felt shallow and left me wanting more.

Author could have done a better job at tying this lesson *directly* to his own life experiences and provide *real* examples in support of his philosophy.

Sebastian Patron
A fantastic read that makes one think about where their passion and their drive comes from, and how to intersect the two. Komisar also introduces the concept of the deferred life plan, where one lives life doing what they have to do (step 1) in order to do what they want to do (step 2). Komisar warns against this, stating that it will lead to unhappiness and being unfulfilled. Short, easy read.
Cassidy DeAngelis
Feb 20, 2019 rated it really liked it  ·  review of another edition
A book bought on complete impulse and purely based on the title, I have to say it was quite an eye opening read. Komisar takes a dive in to what it means to have a successful life, based on not just what you do but who you are at your core. He challenges the mainstream thinking that we should sacrifice our lives in order to make a living.
Charles Dalton
Nov 01, 2020 rated it really liked it  ·  review of another edition
Entertaining, brief read with a few core messages. My takeaways:

1) Reinforcing my belief that for companies, people are everything. You need to hire excellent ones, inspire them with a phenomenal mission, and actually execute on that vision.

2) Drive is push, passion is pull.

3) Leadership is what holds companies together long-term, management is just a tool to execute.
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Randy Komisar joined Kleiner Perkins in 2005 and focuses on early-stage investing.

Previously, he was a co-founder of Claris Corp., served as CEO for LucasArts Entertainment and Crystal Dynamics, and acted as “virtual CEO” for such companies as WebTV and GlobalGiving. Randy also served as CFO of GO Corp. and as senior counsel for Apple Computer, following a private practice in technology law.


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“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.” 136 likes
“In theory, the risk of business failure can be reduced to a number, the probability of failure multiplied by the cost of failure. Sure, this turns out to be a subjective analysis, but in the process your own attitudes toward financial risk and reward are revealed.

By contrast, personal risk usually defies quantification. It's a matter of values and priorities, an expression of who you are. "Playing it safe" may simply mean you do not weigh heavily the compromises inherent in the status quo. The financial rewards of the moment may fully compensate you for the loss of time and fulfillment. Or maybe you just don't think about it. On the other hand, if time and satisfaction are precious, truly priceless, you will find the cost of business failure, so long as it does not put in peril the well-being of you or your family, pales in comparison with the personal risks of no trying to live the life you want today.

Considering personal risk forces us to define personal success. We may well discover that the business failure we avoid and the business success we strive for do not lead us to personal success at all. Most of us have inherited notions of "success" from someone else or have arrived at these notions by facing a seemingly endless line of hurdles extending from grade school through college and into our careers. We constantly judge ourselves against criteria that others have set and rank ourselves against others in their game. Personal goals, on the other hand, leave us on our own, without this habit of useless measurement and comparison.

Only the Whole Life Plan leads to personal success. It has the greatest chance of providing satisfaction and contentment that one can take to the grave, tomorrow. In the Deferred Life Plan there will always be another prize to covet, another distraction, a new hunger to sate. You will forever come up short.”
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