What Are You Willing To Do For The Rest of Your Life?

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It’s a question asked in Randy Komisar’s extraordinary book, The Monk and the Riddle: The Education of a Silicon Valley Entrepreneur.

Coming from someone in the lifestyle or personal development field, the question might not be so odd. But, that’s not Randy. At least, that’s not his overt M.O.

Randy has a long history in Silicon Valley as a tech CEO, virtual CEO shadowing and mentoring start-up teams, a Stanford professor and most recently, a partner at the legendary Sand Hill Road VC firm, Kleiner Perkins Caufield & Byers.

With that background, you’d figure it’d be all about building companies in the name of the biggest possible exit.

Because VCs make bank not so much on their portfolio companies’ annual revenues, but on their liquidation events. So, why would Komisar ask the hard-driving protagonist with an idea for an online venture, most of which boast notoriously short life-cycles, if he’d be willing to do it for the rest of his life?

Two reasons. One, because, in Randy’s words, he’s not actually asking…

“literally, what will you do for the rest of your life? That question would be absurd given the inevitability of change. No, what the question really asks is, 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? What would you be willing to do for the rest of your life? What would it take to do it right now?

Because how you experience your life today matters. But also, because it’s better business.

The ideas that come out of the exploration of that question are far more likely to be the true game-changers than the ones birthed of the quest for biggest pile of Benjamins in the valley.

Also because Randy knows that launching, growing and making a company succeed is insanely hard and you’ll be presented with a litany of uncertainty, barriers and challenges along the way:

Tenacity and endurance are key to business success. But tenacity is seldom sustained simply by the drive for riches. Endurance most often wanes in the face of persistent obstacles if money is the overwhelming objective.

There’s got to be a deeper motivator. In fact, a recent Harrison Group survery of the richest 1% in the U.S. revealed a staggering number of pentamillionaires and…

  • 80% started their own businesses or worked for a small-business that exploded.
  • Most did not accumulate the bulk of their fortunes over time, but rather in a fairly short burst after years of hard work.
  • Most of this new money is generated by risk-takers for whom “wealth is a byproduct of pursuing their passion.”
  • For most, money was not much of a motivator. Solving a problem or improving on something that existed was.

Ventures driven by something deeper are more likely to live long enough to not only succeed, but thrive and possibly even dominate. And, for someone like Komisar, who’s got his own and his company’s skin in the game, that’s big.

Leading with passion isn’t just good for life, it’s good for business. And, if what you strive to create has a genuine impact on peoples’ lives, it’s good for the world.

So, now I’ll turn Randy’s questions out to you…

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

What would it take to do it right now?

Share your thoughts and answers in the comments below…

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54 responses

54 responses to “What Are You Willing To Do For The Rest of Your Life?”

  1. Tim Brownson says:

    I’m lucky in so much as I am doing what I’ll do for the rest of my life.

    When they are hammering the lid down on me I’ll probably be asking the guy if he really enjoys hammering lids down on dead people, or whether he has other hopes and dreams?

    It should freak him out if nothing else.

    • Excellent points, great post!

      I do agree that it is not about the money in terms of how we think from the end. If we are setting financial goals, we need to think about how we will put that money into action when it comes to us. The income will be created while we are in timeless awareness.

      For example, if we like to drive, we’ll need to buy a car and fill it up with gas and have repairs made on occasion, so money will help us there, and if we’re pursuing our passion WHILE making the world a more enjoyable place for those around us, and, in turn, everybody around them, we are living a creative life in the truest sense.

      Thanks as always, Jonathan!


  2. David says:

    No, I have to confess I’m selling today for a better tomorrow. If I died tomorrow I’d be pretty annoyed about the way I’ve spent the last 9 months of my life.

    The thing is, it wouldn’t take much of a change in my circumstances to turn that on its head.

  3. I like how you mention that, “Ventures driven by something deeper are more likely to live long enough to not only succeed, but thrive and possibly even dominate.”

    I like what David Logan from Tribal Leadership mentions about organizations driven by the “groups” highest values. They have the deepest and most cohesive bond within the organization. Since our highest values are driven by what we perceive is missing the most this “void” drives our highest values.

    “Solving a problem or improving on something that existed.”

    Identify the void, discover the value and create the solution.

  4. David Wang says:

    Wow Jonathan, this is powerful! To answer your questions: I want to help people lead better lives by realizing that wealth does not mean having a large bank balance. There are more important things in life like discovering yourself, family and faith. I’m lucky enough that I’ve started on it already with my newly-launched website 🙂

  5. …And what the rest of you (real) life is willing to be for you :).
    Quite an important question, even though it leaves a lot of room to admit that majority of the things in life are out of our control.

    • Natalie says:

      Irina that’s a great question to ask back. You should definitely know what you want to achieve in life, my mission is to get women to court bolder dreams and turn them into reality by going into business for themselves – creating freedom and adventure along the way.

      But I can also ask life, and the universe what it would like to offer me, teach me and tell me in order to make this a reality.


  6. […] This post was mentioned on Twitter by Jonathan Fields, Grant Griffiths, Judy Martin, David Wang, Tony Teegarden and others. Tony Teegarden said: RT @jonathanfields What Are You Willing To Do For The Rest of Your Life? http://bit.ly/ccVv7n (pls RT) […]

  7. Anne Wayman says:

    I’m mostly doing what I want… except there are always changes within me… so I’m working to fund what isn’t happening yet.

  8. Faith McGown says:

    As I transition from a successful career in real estate to building a business around my passion for health and wellness, I have been warned time and again that my new gig won’t be as lucrative as real estate. Some have suggested I continue the course in real estate to financially support my passion. I say 1) it’s not about the money; it’s about doing what speaks to me and what I believe is my best contribution to others; and 2) I believe money follows passion. Thank you Randy and thanks you Jonathan for encouraging us to pursue our passion!

  9. Nate says:

    I want to help people live a more mindful life….thus helping people create more meaning in life and shed the pervasive stress and anxiety that they live with.

    So, to be more mindful of their actions, thoughts, relationships and most importantly, work. And your question gets right to the heart of this. How many people actually take a mindful approach to work?

    You bring up a powerful point here:

    “For most, money was not much of a motivator. Solving a problem or improving on something that existed was.”

    This is where people need to start looking and this is where flow and order can be brought into consciousness and work. How can you take a problem that you’ve encountered in your life and solved for yourself and help others solve for themselves?

  10. caitlyn says:

    Here’s the thing – and I was just blogging about it the other day ( http://imaginingbetter.com/?p=1465&cpage=1#comment-619 ) – I LOVE what I do every day. That it gives me a pay cheque is, most days, miraculous to me. The “problem” is, I have a JOB. I love my job, but that pay cheque is capped. After 11 years and some more letters behind my name I am at the top of the grid.

    There is some time in my day to do a bit more – hence the blogging and a few other things – but if I want some balance there isn’t a lot more time to add entrepreneurial ventures to the day.

    I have followed my passion, money has come – AND I’m ready to win big at the money game. Advice?

  11. I’d be willing to build things, ideas and systems that add enormous, life changing value to other people’s lives. Do stuff that has an exponential result in that it impacts the lives of people so positively that they go on to create positive impact themselves.

    I think I’m partly there… but examples like Randy show me how far I’ve got to go still 🙂

    • Chris says:


      You’ve got to turn those abstract ideas into specifics. You’re on the path, but you’ve got to get out of the big picture and focus on the details. I think you would be amazed at the results.

  12. Being in my mid-20’s I think it’s really difficult to answer Randy’s questions. I feel so unsatisfied and unfulfilled in my current position (for 3+ years), then again most of my friends are in the same boat. I know what I love to do, but understanding how to make a living based on these desires seems impossible and like “cloud chasing,” as my dad would say. It’s easy to hush those longing dreams, but reading this post today has inspired me to look further. Thanks for the insight.

  13. Theron K. Cal says:

    Real Brother here.

    Nice enlightening article.The issue for me is not what am I willing to do for the rest of my life,which I do everyday and am doing now which is participating in the debate,but the question is how in the HELL do you make enough money to survive so that you can do what you’re willing to do for the rest of your life?For me I’ll write for free and have but I need to find a way do to it and get paid.But good article.

  14. Marie Z says:

    Turning our passions into a meaningful life is most challenging. Everyone has bills to pay and the transition from hobby to career can be long. That said, the journey of 3000 miles starts with one step so the most imortant step is the first one!

    The hardest part of all is to understand what it is that motivates you, tickles your curiosity, gets you moving…. then owning that piece of yourself and nourishing it.

  15. I’m pursuing my higher degrees (MSCJ and then PhD in CJ) in what has been a passion of mine for many years. I put them off until my sons were grown and then went all out. I also have a passion for creating. I’ve been doing that (trying to grow that business while pursuing my degrees) and am a contributing artist to a site whose profits go help victims of domestic violence. Using my passions to help people in any way I can – even if it’s by imparting a smile – is what drives me. Am I willing to do this the rest of my life? Heck yeah!

  16. Sharon says:

    Ok, this is the question I am currently asking myself.
    Last month I had a sudden heart attack and was DEAD! Talk about a wake-up call to the lifesyle I was living and how far away from my passions I have strayed.

    I thought, given what has happened, this would be an easy question to answer. I was wrong. I am wrestling with it everyday…getting back to where I got off track in the first place.

    I didn’t smoke or drink or eat right or exercise. I was a multiple business owner, stressed out (apparently to the max)and running through my life. At 50 and not particularly overweight, the whole heart-stopping thing is hard to understand. But understand it I must and will.

    Please answer this question for you and your life. Start living your dreams and following your passions.

    I, luckily, have been granted a second chance and will not take it for granted. I am urging all of you to do the same.


  17. John Sherry says:

    I’m priviliged to say after 40 plus years I’m doing what I would happily do for the rest of my life through blogging. Some things take time but that’s Ok as you get there in the end. And that’s it! Too many today want quick fixes or get rich schemes without wanting to put in the effort and time investment. I’m not yet earning a living from my blogging butI’ve earnt the living I enjoy through years of doing other work. I guess if I’d die today I would have at least been alive in what I did when my maker came. Can’t ask more than that!

  18. I want to be able to communicate the benefits of sustainable living through my writing. I have been doing this through my blog for a long time and have recently moved over to taking this up as a full time career. Granted, I have not got everything I wanted but I think I am on that road.

    So if the world were to face a comet tomorrow I won’t really have a general regret about my career path. I would regret not being able to travel to Brazil, though.

  19. Dana Shino says:

    Question —

    What if you are most definately doing something of meaning, something that contributes, something you love, something that is in total alignment with the soul and path, something that improves others lives . . . and yet the monetary, the financial support is not directly flowing to support it? What then? Isn’t that the real question? Doing what you love and being supported in it?

  20. I started my career in the design business as a self-employed person from day one out of college… I didn’t have a plan at all. I just knew I loved the idea of being a great designer. ..getting paid to be a great designer was another matter… but I figured that out rather quickly and enjoyed enough growth and success in my business to raise my family in comfortable surroundings and even explore other creative passions along the way. During those years, I believed that I was doing what I was meant to do, and would be doing it for the rest of my life… then one day (several years ago) I just couldn’t do it anymore! It was a shocking, disorienting truth… my time as a “great designer” was over. I had invested my whole adult life in that identity… I wandered about in the dark forest for several years trying to re-discover what had so suddenly become lost. I lost my passion ( and the money stopped too).

    Many people in the “lifestyle / personal development movement/business” fail to be honest with themselves and others that life (and everything else in the universe) is in a constant state of change. These kinds of questions become trite, over-simplifications to living a life well-lived.

    Life mastery is not as simple as the warmed-over cliche of “doing what you love and the money will follow”. But it does sell books and boost the online status of gurus who will have you believe all you have to do is find your passion and live it.
    I have come to learn and believe that life mastery or leadership is nothing more than “the quality of your presence” while you are here!

    Passions, interests, occupations, relationships will come and go–all in a constant state of change. Embrace the changes in life like a lover and wear a helmet!

    to your inspired success,

    • Danette Vernon says:

      Dear Thomas,

      I hope you don’t mind, but I passed on your letter to friends, as I felt your letter had such value. The idea of the “quality of your presense” making up your life, in a daily life is very livable, yet gives power to every moment.

      I am 50, work with teen moms, just got back from a month in Australia visiting friends and doing all of the stuff you might do in AU; I have great friends and family, yet what to do with the rest of my life has put me on the road as a seeker…so thanks for your words, they will do till I find the “next thing”…and even then they will give larger meaning to that phase of my life.


      Danette Vernon

  21. Hugh says:

    I loved reading this book. Randy is a cool thinker. I think I’m going to go home tonight and dust off that book and give it another glance.

    I’m not doing what I want to do, but I am working on it. I’m working hard every day to make my dream a reality. Thanks for the continued inspiration!

  22. Always loved the book… one of my favorites. So real in a world of flash and glam…

    Thanks for reminding me of it.


  23. Phil Miller says:

    I love the two questions posed and personally respond to questions like that. But as my wife likes to point out, I’m not like most people.

    I have come to asking a simpler, less intimidating question that I tfind most people can think about. “What do you do when you’re not getting paid?” It can lead you to the others, but i find most people aren’t ready to start at the “meaning of life level”. At least not here in the midwest 🙂

    Another thought reflected in some of the comments above is that it can be naive to just jump and believe “the money will follow.’

    Maybe/maybe not. Depending on life stage you may need a more substantive revenue model than “belief”. Belief doesn’t pay mortgages in the short term. That’s why I coach crawl/walk/run strategies on testing or piloting ideas rather than diving in. If you can sustain passion and show success, then you begin to have a credible financial model for living your dream long term.

  24. Evan says:

    Connecting deeply with people.

    One quibble. Beware of the ideology of risk. It may be necessary to take some risk but it is also wise to reduce it as much as possible. Just because something is risky doesn’t mean that it is worthwhile or will be successful.

    The Millionaire Mind is a study of millionaires in the US and is quite useful at disspelling the myths about entrepreneurship.

  25. Audrey Kral says:

    I have asked the question of, “If I die now, will I be OK with that?” since I was about 15 (well over 2 decades ago)when I realized it would be ok to die, meaning that there really was not anything that HAD to be done other than living.
    That said, I have often battled the question of How to Make a Living doing what I love? I bring in money doing one of the things I love, oil painting, but not enough to live where I do. I keep expanding my mind and using others ideas. Thanks Jonathan for the inspiration and everyone for the thoughtful comments.

  26. Chris says:

    What would it take to do it right now?

    3 Words ….

    Clarity of Focus

    (Clarity is hard to come by in the age of information overload).

  27. Jonathan Fields says:

    Hey gang,

    Fantastic answers, as always. I noticed one theme that kept coming up in the comments was the challenge of turning what makes you come alive into enough money to live well in the world.

    I’m also not a believer that if you do what you love the money will automatically follow. But, I do believe there are so many ways to approach what you love that people don’t consider, unconventional paths, that can help mine your passion for substantially more income than most people make.

    In fact, doing that was the primary focus of my last book, Career Renegade.

    So, if that’s your question, go borrow a copy from your local library (no need to buy it, especially if money’s tight), you may find a lot of the answers you’re looking for, or at least have many more options stimulated.

  28. Scott says:

    Jonathan, Thanks for the soul searching question from Randy’s book. I guess I’d have to say, I am doing a job that pays the bills. I enjoy it fine but it’s not really what I care about. It was a means to the same income I could have if I chose to enter the management field my degrees are in. Since my dad had his first heart attack early in the game, I decided that the stress was not worth it.

    Next stage, caught the entrepreneurial bug late, still acquiring the required skill sets. Started the attached website with the thought of working from home with more freedom. Mistake; it still is not what I care about. Although since following folks like you, I find myself drawn to reading much in similar niches.

    What I really care about is the niche of a new blog I’ve slowly been preparing and thinking more deeply about because it is something I really care about. Our health.
    Thanks again,

  29. I love the essence of this but it is something I struggle with for people who don’t understand it. People often say “you can’t just pursue a pie in the sky dream” and I tend to agree with them. So I think you’ve got to have a financial foundation first and foremost which from there you can leap off from to pursue your dreams. Thoughts?

    • Evan says:

      Hi Nick, my thought (perhaps annoyingly) is ‘it depends’.

      Bricks and mortar things probably do require a chunk of money in advance. On line things are (compared to bricks and mortar) breathtakingly cheap. So you can try out stuff and learn as you go.

      In a complex situation (like online business) predictability is pretty scarce, so you just try stuff and keep what works. There are some guidelines but that’s about it. You might discover that nobody cares about what you do – in which case you haven’t got a business. Usually it’s a case of modifying and tweaking and getting better as you go.

  30. I think that it is important to be realistic along the way. I support the idea of dream big, but live in the real world.

    You need to have an idea of where you want to go and accept that there are going to be challenges along the way. You also need to deal with the consequences of past decisions you made. I’m having to move slowing forward where I want to do based past decisions. In Maslow terms, my self-actualization efforts (top of the pyramid) are struggling with the bottom – the food and housing. I need to deal with the current mortgage – to keep the roof over our heads and food on the table for the family while I make an effort.

    It is so much easier to pursue these types of changes if you begin doing so earlier in your life – before you have established spending patterns and are locked into monthly payments (cars, mortgage, et al).

    This portion “Most did not accumulate the bulk of their fortunes over time, but rather in a fairly short burst after years of hard work.” is also very important and should not be overlooked. After years of hard work…

  31. Bastian says:

    I heard alot of good things about the book “The Monk and the Riddle”. After reading your post I finally dicided to read it myself. Also it looks like many of the bloggers in here enjoyed his book.

  32. […] question of what I’d be willing to do for the rest of my life would usually bug me, because it’s too abstract to be useful. But then Jonathan Fields […]

  33. Gwen Bell says:

    Here via @the99percent.

    I’m willing to help people extract the truth from their stories (through practice/self-reflection) and recognize that potency in all aspects of their lives, on and off the web/mat. It’s a joy to live at the crossroads of passion and financial wellness. And, as Komisar mentions, it’s years of work in the making.

    Enjoying it for me is both pre-requisite and by-product.

  34. Daniel Oates says:

    I would gladly spend the rest of my life coaching individuals in physical movement, nutritional awareness, meditative practices, and bodywork. This is of course, so long as the business is structured in a way where I am able to live in the manner that I am endorsing.

  35. I think what I enjoy most is learning. I like finding a problem, then learning ways to solve it, and then trying each one until the problem is solved.

    I would love to do this the rest of my life.

  36. […] Comments View full post on Hacker News […]

  37. Eddie says:

    Nice review and summation here. This book seems like it would be a good read for a career driven individual.

  38. […] This post was mentioned on Twitter by Gwen Bell, Karen Caterson. Karen Caterson said: RT @gwenbell Jonathan Fields asks: what are you willing to do for the rest of your life? http://bit.ly/9iZWJF < thanks 4 this, i'm pondering […]

  39. […] Wealth is a by-product of pursuing a passion. […]

  40. […] question would be absurd given the inevitability of change. No, what the question really asks is, if your life were to end suddenly and unexpectedly tomorrow, would you be able to say you’ve been… What would you be willing to do for the rest of your life? What would it take to do it right […]

  41. […] What Are You Willing To Do For The Rest of Your Life? (jonathanfields.com) […]

  42. Kris says:

    Hi, “What Are You Willing To Do For The Rest of Your Life?” this question is very interesting..I have a lot to do for the rest of my life like finishing my study and have a good job in the future and be happy everyday..that’s it..

  43. David John Hall says:

    Great post.

    I think an equally important question, or perhaps different perspective, is asking: What are you willing to FEEL for the rest of your life? Gratitude. Love. Success. They are states and can be achieved no matter where you are — and they are not job/vocation/business specific. I have come to understand that we want life experiences because of the accompanying feelings. And I can give myself those feelings any time I choose.

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