What would you do if you knew you couldn’t fail?

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Three simple questions…

  1. If you knew you could not fail and those around you would not only suspend judgment, but wholeheartedly support you…what would you do?
  2. Are you doing it?
  3. If not…why?

Oh, one final question…

  1. If your reason for not doing something is that you’re afraid of failing or being judged…how much worse would that be than never having tried?

Ponder it over the weekend.

And share your thoughts below…

if you dare…

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42 responses

42 responses to “What would you do if you knew you couldn’t fail?”

  1. loveandsalt says:

    I dare!

    I can’t WAIT to get started on this one. See ya Monday…

  2. Great questions. I’ll get back to you with what I discover.

  3. Allison says:

    1. Open a restaurant.
    2. No
    3. I am waiting until I can devote all of my time to it, because I know something like that would take a ridiculous amount of time to be successful at. I don’t have the time because I really need to finish school, and considering that I only have 1.5 quarters left, it’s more worth my time to just finish it already (plus my parents will murder me if I don’t!) Not to mention I have to do A LOT of research about all the things that go into it, so I’d like to be better prepared before I leap into something this big!

    Really great thought exercise though… it definitely made me put some thought into it!

  4. Patrick Badstibner says:

    Get back on the board, though with no balance, that may end up being more suicidal. as far as The overall answer, I am doing it, four years ago I was told i would be bed ridden, one year ago, I was told to give up my working days were over, six months ago I was approved for social security in under two months on the first try. Though I miss the board and my first business, I will do what most said can’t be done. With the mental pursuit of excellence all things are evidently possible. Yet to remind me of the wave, and the tube.

    A quote I love that goes along with your thoughts,
    “The uncommon man doing the uncommon thing will meet with uncommon success at the uncommon hour.”

    Thanks as always for challenging with your blog, it makes life a little easier each day.


  5. Dagnir says:

    For some it takes a long time to fight that demon and it’s a nasty place to be. To start out knowing you can’t fail, then fail…fail…fail and getting more difficult to keep bouncing back. I just can’t give up though, so see you on the other side.

  6. Dan says:

    This is something I ask internally often. Unfortunately (or fortunately…), my answers come up varied every time I ask. So many great things to do in this life. I find the real challenge is part 3, identifying a reason why I’m not doing it…and it comes down to a simple few words; “fear” and “being reasonable”.

  7. michelle says:

    i would audition for a rock band! which is something i plan to do this weekend (sunday evening, to be exact), even though i’ve come so very close to calling the whole thing off…for fear of failure.

  8. Ooh! I’m happy to report I’m doing what I want. I retired from teaching last June and am happily working on projects and traveling, just as I wanted to do. I’m also sharing my experiences by doing inspirational speaking and writing.


  9. I would have done what I do now years ago. 😉

  10. 1. I’d probably be shocked. Full support is something I’ve never had.
    2. Because I’ve never had full support, I always do what I want, so yes is the answer.
    3. Irrelevant question because of 1 and 2.

    Extra question: I have no fear of failure. The only time I’ve feared failure is pointing a horse at a high jump – because failure usually means a bad fall and some pain. Ouch.

  11. Eman says:

    1. Travel the World
    2. Yes, partially
    3. Lack of money…

  12. sharon says:

    1. Travel & Photography
    2. Part of it
    3. Money

  13. sharon says:


    1. Have a bunch of babies
    2. No
    3. Money

  14. Jonathan Fields says:

    @ Allison – wow, a restaurant, that’s very cool. I know quite a bit about that biz, having helped with the marketing and launch for a number of restaurants in NYC. It’s a huge challenge, but a very cool one at that!

    @ Pat – constant inspiration, brother, some day, you’ll have to share more of your story with us!

    @ Dagnir – yeah, the questions are easy, the answers…not so much, and they change all the time, but it’s a great exercise to keep returning to them.

    @ Dan – fear of failure and the need to do the “reasonable” thing are two huge roadblocks for most people. I’ll be writing more about that soon. But, ponder this…conventional wisdom breeds conventional action, which breeds conventional living. For many , that’s fine…for me, I want more

    @ Michelle – so, so, so…how’d it go?!?!?! Did you audition? Hmmm, hmmm, hmmm?

    @ Flora – awesome, glad to hear you’re doing it!

    @ Monika – Just keep looking forward, my friend, it sounds like you’re pointing in the right direction!

    @ James – interesting how you respond to the expectation of no support and fear of failure. Most people would shut down and not pursue many things, while you go the other way and just jump in.

    @ Eman – That’s cool, I never really had the mega-travel bug, but if it’s really burning inside you, yo might want to explore alternative ways to travel. Check out Tim Ferriss’s 4 Hour Workweek. Time and I differ on certain issues, but he’s got some great resources for super-affordable ways to travel around the world.

    @ Sharon – Travel, photography and babies, eh? I’ve seen your work on the second one and I think it’s only a matter of time!

  15. @ Jonathan – One would think no fear and jumping in is a good thing. It can lead to reckless decisions, impulsive action and a heap of messes. Because there is no support, you’re left cleaning it all up on your own.

    Fear is a good thing. And support is invaluable. Trust me.

  16. Jonathan Fields says:

    @ James – Agree that support makes a huge different, it’s far easier to work with it than without it. Though, constructive support, where those who support you also question, advise, challenge and quide your decision, is far more useful than blind allegiance, which can just keep you speeding down the wrong road.

    And, enough fear to bring clarity and consideration is a good thing, too, but so much that it stifles what would be constructive action, not so good.

  17. If I knew I could not fail, I would write, speak, and develop an intensive workshop/retreat for married couples who desire to have more passion, adventure, and pleasure in the relationship. This idea has been rolling around for a while. I think the reason I have not acted on it thus far, fear.

    Well, fear no more, I’m off to create. I’ll keep you posted.

  18. adelaide kontras says:

    i am totally doing what i was intended to do and i so get judged by the selective few…..or many
    i do not care
    i am happy
    and if i fail ill still be happy because i am where i am suppose to be

  19. […] What Would You Do If You Knew You Couldn’t Fail? I like this question better than “what would you do if you had a million dollars?” because it eliminates the easy “do nothing at all” answer that a lot of people give. This one actually nails what you’re passionate about. (@ jonathan fields / awake at the wheel) […]

  20. loveandsalt says:

    I’ve been kicking this one around all week. At first I thought: “Quit my job!” What I always think, but this time I asked myself: why? I don’t hate my job, and there are many things about it that are challenging and rewarding. Just saying “quit my job” has become a dead-end goal for me, asking the universe for more freedom when I’m not even using what freedom I already have.
    So, if I couldn’t fail, what would I DO with the time and space I hope to gain by quitting my job? And, if I can’t fail, why not do those things now? I have rededicated myself to using my energy for my work and awareness, not letting the “job” provide any excuse at all. (Maybe I’ve rewritten the question to read: “what would you do if you knew you still wouldn’t get fired?” Odd: I already KNEW I can’t be fired–I have tenure!)
    This week I sent out manuscripts that have been on my desktop for months, because there was never a perfect time when I could do it all at once. I stepped up the posting on my blog, even though I’m still finding my way with it, and haven’t even got around to posting any pictures. I did a whole lot of “even thoughs” and it feels great.
    I am taking my own maxim to heart: Nourish your freedom to see it increase.

  21. Emmet says:

    Definitely trying to do what I want to be doing, and it’s really really hard. I want to be an entrepreneur and eventually a film director, two of the most difficult careers to be successful in. Thing is I will always know that at least I gave it a shot, even if I fail miserably.

  22. Nigel says:

    I am interested in hearing more about overcoming the failure side of the question.
    I want to become a financial planner because I want to help people have happier, less stressful lives. If I had no fear of failure, I feel this job would be a large part of the purpose of my life and allow me to help others in a very meaningful way. I am a horrible sales person though and not very social, which is a large part of the job.
    So I guess my real question is,”Is fear of failure ever a valid reason for not doing what we want?” and “How do we overcome fear of failure when it is something we are genuinely not good at, but a necessary part of accomplishing something we want?”

  23. When I was a freshman in college I tried out for the baseball team during open tryouts and found myself grossly overmatched. Not only that, I was terrible during the three days. So it was no shock when the coach said he wouldn’t be picking me for the team. Fast forward ten years and it’s one of my proudest achievements. I hear so many people looking back and wishing they had at least tried to do this or that and they look at me like I’m a rock star when I tell this story.

    So I’ve learned my lesson: do what you gotta do and do it hard.

  24. […] a think about where your life is headed… What would you do if you knew you couldn’t fail? by Jonathan Fields | […]

  25. Rick Francis says:

    Nigel wrote:
    ”Is fear of failure ever a valid reason for not doing what we want?”
    “How do we overcome fear of failure when it is something we are genuinely not good at, but a necessary part of accomplishing something we want?”
    The danger is that the fear may prevent you from ever accomplishing your goals. The only time that is a good thing is if your goals are foolish or dangerous. In those cases the fear is very healthy for you!
    However, the example you gave is neither…it is a reasonable and achievable goal. You just don’t have all the skills you need yet.
    To reduce the fear, take small non-threatening steps that progress toward your goal. You could try learning salesmanship before trying to start the business by taking a class, doing some sales work in your current job, reading on the subject, etc. Just be sure to set up a timeline with some goals so that you don’t keep trying to lean for 20 years!
    Try doing financial planning as a side business. If you don’t succeed you still have an income to fall back on. Or look into volunteer opportunities, churches or non-profits may offer some kind of financial counseling. I wouldn’t be surprised if they could use some help too.

    -Rick Francis

  26. loveandsalt says:

    After all is said and done… I would get on a plane and go see him and look once more into his eyes, his face, and ask…

  27. Adfecto says:

    1. Open one or more of the businesses that have been bouncing around in my head for the last 10 years. I’m still like a kid who wants to be a race car driver/fireman/pizza maker. Instead I want to own a Papa Johns franchise, home theater installer, real estate management company, and financial planning firm.

    2. No

    3. Lack start up capital and I’m in a very comfortable good paying job. I make more than I need to get by but not enough to get rich. I have a wife and mortgage to provide for.

    I am afraid of failing in the transition to business owner rather than employee. The results may be financially catastrophic. I’m not prepared to loose my house on the chance that I might “hit it big.” Risk is the double edged sword in that it takes a huge bet to hit it big. It would take a really big and risky bet to materially improve my current life.

    One day I’ll have enough wealth and passive income that I could safely make this transition so I’ll just be patient (maybe 30+ years) until that time comes.

  28. Hope says:

    1.Do art–the pieces I wanted, how I wanted, and submitting them to book publishers, magazines, galleries.

    2. Only (very) part time.

    3. Because a) I like having a roof over my head and something other than ramen on the table. And b) because of the fear of rejection. It is unbelievably, incredibly hard to take your art, things you’ve poured yourself into, made the best that you possibly could, and show it to others–only to get rejected. Again, and again, and again …

    Lots of people talk about living with a life of regret about things they’ve never done. But to play devil’s advocate–if you don’t try, then you still have the illusion that you *could* have succeeded, if you’d really wanted to. It’s not much, but it might be better than looking back on a lifetime of rejection as just another ‘wanna-be’ that never made it.

    That said, I haven’t given up my art yet. I still have a little hope left that I’m not just beating my head against a brick wall, I guess.

  29. Jonathan Fields says:

    @ Everyone – Hmmm, it’s amazing how stifling fear of failure or fear of poverty is. In fact, the fear is often so overpowering, it can shut down a willingness to explore non-traditional ways to earn a really nice living, while integrating much of what you love into how you earn that living. I am not saying it’s easy, I’ve certainly made a lifetime out of exploring the issue, but it’s a lot more doable than most people believe.

    I’ll be writing more on this very soon.

    Thanks so much to everyone for sharing so sincerely

  30. Nicole says:

    I find it isn’t the fear of failure that hinders me. Failing is fine for me, I’ll learn from it, then do better next time, essentially finding that success in it. It’s the endurance of the time it can take to succeed. Busting your ass is a lot more work when it’s long term, especially when you know there might not be a basket of rainbows greeting you in the end.

    But still, for me, it’s oh so worth it.

  31. nataJane says:

    This is a beautiful photo…

  32. simon says:

    1. i will travelling around the world
    2. its done

    thats make my perspective more wisely

  33. Richard Howes says:

    So my first post to any blog was hear a couple of days ago, and now I find I’ve instantly turned into a serial poster!

    I’ll repeat part of what I said on another topic, lack of self esteem/confidence/belief.

    Its self belief that is the key ingredient in whether people let the fear of failure prevent them from taking the plunge so to speak.

    The irony is that often a fear of failure, and the lack of self esteem that drives that fear, creates a paralysis of decision and action that ensures failure. This is particularly true of people who jump half way in (the entrepreneur who takes the plunge into his own business but does not have the courage to take the bold decisions necessary for success).

    Success requires bold action, bold action requires us to overcome the fear of failure, the fear of failure is driven by lack of self esteem.

    A difficult challenge to be sure. I know.

  34. Emma says:


    1- be making art that I am proud of and that is true.
    – be actively involved in creating projects to improve my community.
    – lead a healthy lifestyle

    2- I just started.

    Just a little message to everyone out there… I held myself back from pursuing my first goal for a very long time because in my mind it wasn’t a practical option. As a result, looking back, the rest of my life suffered. Ever since I started going after what I want, I would dare to say my whole life has improved. I have more energy because I’m excited about what I’m doing, I enjoy the small moments of my life more and am more appreciative, and I have a new stronger will-power where I didn’t before. I’ve realized that I can truly do anything I want to. I have a new faith and trust in myself that I will be o.k. and whatever life throws at me I will be able to handle it.

    I would recommend following your dreams to everyone! If you don’t, you’re not really living.


  35. Allison says:

    1.Ask a guy I like out (along with many other things)
    3.I’d rather keep the friendship than lose it because he doesn’t feel the same way

  36. Samantha says:

    1. – Mentor/Executive coach for women in the 20s and 30s…and doing marketing consulting services. Trying to find work that is fulfilling, financially lucrative, flexible and fun (does it exist???)
    2. I do this on a pro-bono basis…but still have a VP Marketing job that kills me…but it’s very lucrative
    3. I’m afraid of being poor, I’m afraid of STILL having a frightening workload – I’m burned out!

  37. Kay says:

    Ladies and Gents. This is a great post. Is it possible for us to have a real time discussion on this?

  38. demcb says:

    234 hour Halo REACH marathon. of i couldnt fail i would win every single game. and i wouldnt be banned because i couldnt fail. if that makes sense

  39. aaishah says:

    1)I’d go to a bank/ Bill gates and say that my friend bet me a grand that I couldn’t get you to give me £1,000,000… and obviously as I cant fail I will gain £999,000… not bad for a days work….
    2)Am I doing it? no!
    3) why? because i would be humiliated !!!!

  40. Mart says:

    1. I would do too many things. I’m at a point where I am supposed to pick a degree in University, but I stagger away from everything I really want to try. I think I have a problem knowing exactly what I want to do in life…

    2. No. None.

    3. Fear. Uncertainty. Unsteadiness.

    I really need to think things over from your perspective.

    I came across your blog at such a depressing day, and it’s bed time, over here, so it did give me even if a hint of hope. Thank you so much:)

  41. Bob Suckalewski says:

    1) If I knew I couldn’t fail, I would kill everyone who got in my way. And I mean kill them with kindness and let them know that they were in my way.
    2) I am not doing this now because I don’t believe people would support me on this.
    3) see (2)
    4) It makes me cry

  42. […] What would you do if you knew you couldn’t fail? -Ohh no, no de nuevo.. – Demasiado tarde.. […]