What Would You Do if You Couldn’t Fail?

Here’s a provocative question, thanks to my new friend Al Pittampalli:

What would you do if you couldn’t fail?

It reveals what is often really holding us back from living out our dreams: Fear.

Fear is holding us back. It’s causing us to bide our time. To wait and wonder what we’re supposed to do with our lives.

Al’s challenge is powerful, poignant, and timely. He shares more in this video (if you can’t see it in email or RSS, click here to watch it:

So, what about you?

What would you do if failure wasn’t an option?

Would you join the Peace Corps? Go skydiving or paint for a living? Spend more time with your spouse, being a little more lavish on date nights?

If nothing could stop you, what would you do? Chances are your life would look drastically different.

Couldn't Fail
Photo credit: Oran Viriyincy

It’s not as bad as you fear

Of course, the answer to this question is quite telling. Because more often than not, we don‘t fail. The things we fear will happen don’t.

Sure, failure happens. We all want to be like that guy in that movie Limitless — take a pill and change your life overnight.

But it doesn’t work like that. Fear is overcome like any enemy — inch by inch, one small victory at a time. As this happens, we learn that it’s rarely as bad as we think it might be. And we slowly begin to believe in ourselves.

We fear never being able to ride a bicycle, but eventually we don’t fall.

We doubt anyone will ever find us attractive. And yet, somehow, this beautiful woman (or handsome man) says “yes” to a date. (And one day, to marriage.)

We worry we’ll never get a job, but if we keep asking, eventually we find something great. Therein lies the rub: if we keep asking.

You have to try

We tend to blame the evasion of our dreams on external circumstances — not enough time, terrible economy, lack of marketability, yadda yadda.

In other words, we shift the blame.

Then, when we find ourselves living lives we never signed up for, we condemn ourselves, which only further immobilizes us. We say that we’re just too lazy or afraid to do such things.

And eventually, we grow careless and eventually jaded towards dreams in general. We lose faith. It’s a terrible, vicious cycle, and it all begins with this fear of failure.

Enough is enough

I’m tired. You’re tired. We all want out. There has to be another way of doing life.

There has to be a secret to why some people work through fear and others do not, why some constantly risk failure and many don’t. There has to be a way to be free.

Guess what? There is.

It begins with a question

The question, actually. What would happen if today, there was no possibility of failure? What if there only good and perfect things planned for you? But only today? It would be like winning the lottery, right?

You’d be more courageous, friendly, and imaginative. You wouldn’t have to think about people hating your ideas or turning you down. And this is where it gets fun.

Try living like this today. Just for a day, as an experiment. Take more risks. Dream bigger. Go for broke.

Nothing is holding you back now. You have permission. You can go back to being safe tomorrow. Right now, I want you to try something different. Do something with your dream that you’d otherwise be afraid to do.

This is how people who are changing the world live their lives every day. So it’s not too much to ask you to try it on for a single day. Is it?

I’d love to hear from you:

What’s holding you back? What would you do with your life… if you couldn’t fail? Let’s discuss in the comments.

83 thoughts on “What Would You Do if You Couldn’t Fail?

  1. Thanks for sharing that video.  As I sat listening to it I was thinking of New Year’s resolutions and goals.  I used to hate setting goals for the same reason he said…I was afraid if I didn’t achieve those goals it would be one more thing to beat myself up about.  I used to have “beating myself up” down to art.    One of my favorite quotes is “falling down doesn’t make you a failure, staying down does.”    Thanks for the encouragement to keep stepping out and to keep getting back up. 

  2. Honestly? I would start over. I have a reached a point where I think the next season of life for my family is going to look very different than where we are now. If I knew I couldn’t fail, I might just hit restart and remove everything that is currently there and just worship God and allow myself to hear Him speak.

  3. You know…I’d do exactly what I’m doing now–I’d keep writing and blogging and improving my art. 

    I take that back, there is one thing I haven’t done yet that I’d do. I have this little idea in the back of my mind that I haven’t acted on yet that I keep waffling over. But I’d go for it. 100%. 

  4. If I couldn’t possibly fail or be rejected or admonished or slighted, then I’d write a novel and have it published.  I’m actually in the process of one as it is, and hope to finish it.  This was a great post- pretty inspirational.  I may refer to this later, Jeff =)

  5. If I couldn’t fail I’d start a writing and speaking ministry aimed at helping people who have been marginalized by the modern church and try to heal the wounded who’ve been shot by God’s army rather than helped to a hospital (a.k.a. the church.)  

  6. I’d like to have debt free rental houses and own a hardware store.  I enjoy giving a great deal.  I just don’t have much to give at this point. 

    Thanks for sharing this Jeff.

  7. I have always firmly believed that fear of success is very real. At first, it didn’t make any sense: who wouldn’t want to succeed? Doesn’t everyone? But it was after attempting to start a business with a buddy – and having him passively sabatoge it over and over again, despite the fact that we were getting investors on board and excited – that I realzed that human beings, in general, are terrified of success.

    I think it has to do with a general fear of chance and the American attitude of “we must work for someone else in a big, huge corporation and accept our two weeks of vacation a year (that our bosses won’t let us take).”

  8. I love this question!  The first thing that popped into my head: become a rock star.  But honestly, I have so many dreams.  If I couldn’t fail, I’d do lots of traveling, work for a non-profit, and write and write and write until I had something fairly publishable.  I’d say this is the type of question we need to ask ourselves on a daily basis to keep our priorities straight.  Thanks.

  9. Good advice, but why do I keep seeing pictures of Seattle on your blog?  I live here and recognize the Public Market and King Street Station and Paul Allen’s leaning tower.  You live three thousand miles from here.  Who is taking the pictures?

  10. Wow Jeff, great question! Today I don’t really believe in failure. I believe we all have times things don’t live up to where we want them to be, but it’s not failure. Failure or success is based on different interpretations by different people, so who determines if I fail? You, me, my family, my friends…..God? If I learn from the outcome is it truly failure?

    Of course I haven’t always believed that, and if you were to ask me the question, “What would I do if I knew I couldn’t fail”, I would have given you a different answer depending on how old I was. When I was five, I wanted to be a Pro Bowler. Between the ages of nine and twenty, I wanted to be a Missionary in a foreign land. From the age of 35 to 50 I wanted to be a Pro Golfer. Funny how life changes.

    Today God has me in a job that 7 months ago I would have laughed if anyone told me I would have. No way, in no instance, would I ever be a reporter/writer/editor for a newspaper. God has a great sense of humor because writing is not a gift that He gave me. I’m not good at it and in fact I hate doing it. I only like it after it’s done. Unfortunately, in the newspaper business, there is always another article to write. I hate it because it scares me to death. It literally terrifies me, knowing that someone will be reading what I write. If I have any fear of failing at all, it would have to do with writing, so I guess if I knew I couldn’t fail, I would want to be able to offer people something that they needed through my writing. That I could bring something to them that would enhance their lives. Encourage them, make them smile, or just give them a reason to want to keep being who they are.

    A close second would be losing weight, but that’s a whole other story!

  11. ” if we keep asking.”

    And here lies the antidote to fear. It’s that sliver of faith that keep us going, one step at a time, instead of being paralyzed by fear.

    Beautiful post.

  12. Okay, I promise to read this post later, but the image of the metro bus caught my eye because… that’s in Seattle and only a few blocks from where I work! Sweetness.

  13. Love this, J! Honestly, I can’t say what I’d do if fear wasn’t holding me back. I’m 18, I’ve got my entire life ahead of me, and I am living towards the future I want. My decisions wouldn’t be something big, but instead sharing the gospel, which tends to be one of the scariest things I know to do. 

  14. Totally excellent! I do believe, however, that it is important to have failure as a possibility. For me, the question is more like, “What do you want to do more than anything else,  and are willing to detach completely from the outcome?”

    (Mine is: write a novel)

    In other words, if you knew exactly how things were going to turn out, where is the thrill in that?

    Thanks, as always, Jeff!


  15. I love your point that fear must be faced and challenged, otherwise we don’t grow.  Likewise, it’s been said that you’re only as good as the opponents you overcome; therefore, we need to view fear as that opponent and whittle away at it every day. I’m trying. Thanks for the reminder, bro. 

  16. Man, fear of failure has long been a struggle. Particularly with relationships and how other people view me. Can get crippling. I’m actually trying out a new church small group tonight and have had reservations about it. But I love the question you posed: what if there was zero chance at failure today? Would I still have reservations? What would I be afraid of?

    Gonna try to live life today with no fear; we’ll see what happens.

  17. “A life spent making mistakes is not only more honourable, but more useful than a life spent doing nothing” – GB Shaw

    “I can’t understand why people are frightened of new ideas. I’m frightened of the old ones”
     – John Cage

    “Our greatest glory is not in never falling, but in rising every time we fall.”

        1. yep. and I don’t care. it’s not about the money. the value of exposure far outweighs any money i could make on it. i charged a buck on Amazon for it, because they wouldn’t let me give it away.

  18. I write songs. All the time. As much as my brain can stand to churn them out. By this definition, I’m a songwriter. But not exactly by my definition. In a fail-free world, someone out there would be singing my songs–with the CD label track title described as “Words and Music by Mandy Thompson” or whatever. That’s “it” in my mind. But that hasn’t happened. But I’m still writing. Does writing make me a success? Or does publishing make me a success? I’m just not sure. Sooo… I keep writing. I don’t know what else to do.

    1. Well there are plenty of musicians who can play and sing but don’t have the words. Start hanging around coffee shops/practice spaces/record stores and you’ll probably find some artists/bands to collaborate with 🙂

  19. If I couldn’t fail I would cut my own hair, sell the little bit of things I still own, and give all my money to help others. 

  20. My husband and I are in the middle of doing something totally different..he changed jobs from one that was secure, to working for a new nonprofit organization not in our home country. Fear has been at our door POUNDING daily since we’ve made this move, and some days I think we’ve let it slip in and caused us to be paralyzed. Thanks for the challenge to not open the door, or maybe to open the door and to stick my tongue out at the big ugly monster. =)  Sharing this with my husband, cause I think he’ll appreciate your words as well. 

  21. Jeff – thank you for the encouragement and challenge. I think I’m discovering pieces of my dream. I just need to put the puzzle together.

    If I could not fail I would…
    – Write a book about being a stepdad
    – Speak at marriage conferences
    – Teach people in office settings how to be productive, stop killing each other with PowerPoint and stop wasting time in senseless meetings (I’m a big fan of @google-252048fa6edcf65007b4a93a46291727:disqus ‘s book).

  22. This is a very timely post, as I’ve been going over this same thing in my life and relationships right now. I do get scared and want to quit at times, to just live in a little shell where there won’t be any pain. But that isn’t realistic and life is meant to be lived (to the fullest). 

    I didn’t want to comment when you posted this a few days ago, I wanted to really think about the question. What would I do if I couldn’t fail?! It’s surprising and liberating actually. I would be more open to love and to people in general. With my job and career I’ll take chances but with life and relationships I shy away (from fear of loss or being hurt). Thank you for inspiring my reflective thought process, it’s been very eye opening.

  23. I’d go to Argentina for a few months. For me, it’s not really fear that’s keeping me from it though…it’s those danged student loan payments I have to keep making every month that mean I can’t throw caution to the wind and embrace making little and just getting by as I go (also, extremely complicated personal life circumstances, but who wants to talk about/hear about those?).

    Ah well, I’m working towards a lifestyle that will allow for both regular income and ability to travel for months at a time…the dream will happen one way or another.

  24. If I could not fail, I would write. I would write short stories, novels and essays. I love the act of writing. I love the magic of writing and the wonder of reading what others have written. I only discovered your blog yesterday but could not wait to spend more time with it.

    The timeliness of this post takes on a personal urgency. I was very recently terminated from a 15-year position. A position which was no longer fulfilling nor having a positive impact upon my life but necessary for the income security. After a week of fitful contemplation I gave thanks to my former employer and decided to embrace the completely uncertain future and chase my dream.

    Thank you for the encouraging blog.

  25. Great post, Jeff. I just finished a week of pushing myself past my fears. I have been afraid to travel by myself – but I did. I was afraid to go to a museum’s library for book research because I wasn’t ‘credentialed’ – but I did. The terrible things I imagined might happen never materialized. Sometimes you have to ‘do it afraid’ and on the other side is freedom and realizing YOU are the one who gave your fears their power over you. I’m inspired to write about this on my own blog now. And in answer to the question, if I could not fail, I’d write, and do the things I need to do to get better and better at what I love. Which is what I’m doing. Thanks for the encouraging words.

  26. The 23rd of this month marks 100 days to the end of the year (phew) and my resolutions are looking pretty weak if I’m honest. I’m considering trying to force these two ideas into a 100 day challenge to wring the most out of what’s left of the year. USE my time, rather than, more often than not, letting it use me.

    Thanks for the post. I MUST get off my butt. I WILL write more, dance more and do more. No more wasted days!

  27. I think I would go living in America or Canada, applied for great Computer Graphics Studios or Designers toys companies and work as a visual artist. I would go talking with that girl I recently see on Monday this week and ask her for a date.

  28. There are many things I would love to go do, but most of the “risky” ones would involve my going alone, or going selfishly to pursue my own dream at the expense of my family members who need me to be present and focused.  The only “fear” I have is of doing something that would hurt them.  I give up some of my personal dreams in order to fulfill the biggest dream of having a healthy, happy family (something I never had growing up).  One day, all too soon, my children will grow up and move on, and then I can go try some of those adventures.

    That said, I think the premise behind the sentiment of your post is a good one.  Too many of us are hindered by fear of failure.  We need to recapture that childlike confidence we once had that caused us all to raise our hands and say, “Me!  I can!” when asked if we could sing/dance/draw/jump/etc. 

    Heck, I might try flying (sans any aviation devices).

    1. Making money doesn’t mean being selfish. Would you steal it? Or defraud someone? If they give you their money, you have done something to better their lives. Both of you gain something.  

  29. I think the expression for me is that I am totally paralysed. I know there is a way out but can’t get there.  Thanks for the blog….maybe I will actually act on it this time – one can dream.  Made lots of sense – trouble is you have to know what you would do and I am so afraid of making the wrong decision.  But maybe if I had one day where I couldn’t fail then I would like to write maybe. I am scared that I won’t enjoy it/be good at it but with your ‘no fail’ guarantee for a day then that’s okay!

  30. we have to take risks, I guess that’s the way life goes! how could we know wheither we’re gonna make it or not if we have never give it a try! perso, I’m used to get straight to the point even if I’m aware of the consequences. It’s all about that little hope…”when there’s a will there’s way” ! that “will” comes from that little “hope”

  31. I would have a baby with donor egg (I’m 44 and my partner and I tragically lost our only child, a baby, two years ago and haven’t been able to get pregnant since) and somehow combine this with doing a nutrition degree.

    On “crazy” days I actually think I might be able to achieve both of these dreams, but most of the time I struggle to believe I could even achieve one of these things and am emotionally upset because I don’t know which to choose.

    My question is how do you know whether your dream is unrealistic? I used to have confidence in my ability to achieve things such as doing a degree, but have repeatedly failed to see that through.

  32. What would i do if i knew i wouldn’t fail today?
    I guess i would have done what I’ve always wanted to do most!
    Starting to take my Dreams & Goals seriously!
    I would make a difference 🙂

  33. I spent much of last year recovering from a broken leg after I decided to travel abroad to live my dream and learn skydiving (I am 60). I’m highly motivated and have few fears or phobias but recently I was asked the ‘can’t fail’ question in an NLP class and I replied “I would ruthlessly crush all those who have bullied or betrayed me throughout my life”. Does this reveal my fear? You bet it does; I don’t want to go to prison or otherwise lose my freedom so the question I would prefer to ask is “what would you do if there wasn’t a price to pay?”.

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