Why Failure Must Be On The Table

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There’s so much glory built around the potential for failure in the world of entrepreneurship.

At least in VC-backed tech, you’re not really an entrepreneur (not my assessment) until you’ve lived through at least one big flame-out. The lack of this experience, some even say, might be a barrier to funding because the smart money wants to know you know how to weather a storm before entrusting you with another tranche of other peoples’ money.

VC’s and angels know 5 out of 10 investments will evaporate. Three in 10 will break even. One will do okay. One more will do really well. And one in a hundred or a thousand will be the next twitter. Founders know this, too. Everyone’s betting on the monster hit that will make up for the dogs 1,000 times over. In that world, failure is an accepted and even mandatory part of the path to success. Just part of the game.

But what about the world of everyday mortals?

Bootstrap entrepreneurs and artists where what’s on the line is what’s in your bank account, your credit card or line of credit? Where it’s not so easy to walk away from a big mistake? Is the potential for failure still an important, even mandatory part of the equation?

Answer. Much as we wish it wasn’t so. Still, yes.

Entrepreneurship–or any process that seeks to evolve the status quo–requires you to regularly test commonly held limits and beliefs. The natural outcome of this is that sometimes you’re right, other times you’re wrong. Either way, you never know until you get out of your head and take action in the world.

The potential not just for failure, but failure that matters, failure you feel, must be on the table. If it’s not, then what you’re setting out to do is either so safe or so devoid of the the potential for impact that success might allow you to check a box on a piece of paper, but beyond that, nobody’ll care. Including you.

Sure, there are ways to chunk both risk. To create many more smaller, more incremental opportunities for failure and success. Lean methodology and it’s Japanese forefather, Kaizen, are examples. But there is no way to completely eliminate it. Because…

The same circumstance that presents the potential to fail also serves as a gateway to the opportunity to succeed. You cannot close the door on the former, without also closing the door on the latter.

So, yes, living, acting and deciding to move forward in the face of potential failure isn’t easy. Especially when it requires you to go all in. And especially later in your lifecycle when you’ve got more on the line. To risk success in art, in business, in love, in life is, indeed, a bit terrifying.

But really, what’s the alternative?


+++Quick Notes+++

  • Good Life Project Application Deadline is Sunday – The response to the launch of Good Life Project on Tuesday has blown me away. We’ve already received many applications for the program and have been reviewing them as they come in. If you haven’t gotten your application in yet, don’t wait until the last minute. The deadline is Sunday at midnight Eastern time. And if you have no idea what Good Life Project is, click here now to find out.
  • Guided Mindfulness Resource – UCLA’s Mindful Awareness Resource Center has a wonderful set of downloadable guided mindfulness mp3s available. They don’t cost anything. Check them out if you need a bit of help staying with your practice.


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29 responses

29 responses to “Why Failure Must Be On The Table”

  1. Owen Marcus says:

    Right on Jonathan, it’s not so much we have to fail, but we need to be willing to fail if we are to truly succeed.
    My best clients are entrepreneurs not because they don’t fail. Because they are smart about failure, they do their due diligence, use the gut sense – then take the risk. What they also do better than many is admit sooner when something isn’t working.

    The problem with failure is not failure – it’s allowing it to continue.

    • Keith says:

      Could not agree more, if you are so worried about failure that you never execute, how does that work to your advantage. the 1/100 being the “next big thing” means in theory you could fail 99 times in a row before finding success. Few people can fail once, twice or even 5 times without questioning themselves.

  2. Giovanna says:

    Great posts… thinking here about beeing a entrepreneur regarding life (self) transformations and the presence of failure in that process aswell…

    I was talking to my husband earlier today about being bold towards the will to change (doing what it takes to do it) and improve oneself and how it´s a rare trait (this boldness) (we weree talking about compassion too). And now you got me thinking that that sometimes is fear of failure too (many other possible reasons, but I didn´t thought of this one yet).

  3. Giovanna says:

    just saw a bunch of typos in my comment… sorry…

  4. Cindy Paden says:

    Jonathan, I really like your quote:

    “The same circumstance that presents the potential to fail also serves as a gateway to the opportunity to succeed. You cannot close the door on the former, without also closing the door on the latter.”

    I would like to use it in my email signature line. I work with a group of entrepreneurial engineers in a technology incubator.

  5. Gayle Arnold says:

    At this point, today, I’m very near the bottom–some naysayers would say I’ve failed–but each time I speak with someone about my vision, I hear the strength in my voice and I feel the passion in my heart and I know I’m just in the rebuilding phase, learning more about myself and how to build the business and life of my dreams. Thanks again, Jonathan.

    • Sophia Wisdom says:

      Great sharing from everyone..I agree that failure happens in everything as it leads to success, failures keep me humble and I love the feeling of it. We ( humans create money ) so I suppose failure is an expected action of human beings, without it we won’t feel human. Thanks!

  6. Dave Doolin says:

    “Bootstrap entrepreneurs and artists where what’s on the line is what’s in your bank account, your credit card or line of credit? Where it’s not so easy to walk away from a big mistake? Is the potential for failure still an important, even mandatory part of the equation?”

    Agreed, and probably even more so than when failing on someone else’s money. Possibly even *far* more important than when failing with someone else’s money.

    For one, it’s your own money. But I think the greater risk is higher emotional involvement when risking one’s own money. It’s harder to quit when it’s not working!

    How to chunk down the risk is an incredibly valuable skill to learn. While I’m finding it difficult to chunk down on my current less-than-successful main project, that experience has made me *ruthless* on side projects. And it’s working. Part of the success of the side projects is making a successful exit… when the project hasn’t met its goals. In other words, not making goals is a sort of success in itself.

    The alternative is mediocrity working for someone or some company who doesn’t have your best interest in mind.

  7. Christopher says:

    I love hanging around people who fail and are willing to fail. Those are the people who really believe in something, and the ones I want in my life.

    Thank you Jonathan.

  8. You put forth a compelling argument here, Jonathan. “Skin in the game” is the only game in town, so to speak.

    I am thinking it might just be true. And I am OK with that. If it’s easy, it probably won’t give you much in the long term.

    Well wrought essay!

  9. Molly Gordon says:

    One key to making failure generative is to be wide open to feedback from the world around you. This means paying attention to positive reinforcement as well as negative feedback, and not letting yourself be inflated by one or deflated by the other.

  10. I’ve been exploring failure from many different perspectives lately, both inside my head and out in the world. The more I dare, the more I risk failure and the worse it feels, yikes! But at this point I’m also finding a peculiar kind of grace in it, I’m starting to sense where there is flow and where there isn’t.

    Thank you Jonathan, your words made my day.

  11. Joe Flood says:

    I was reading a book on writer’s block which said that the condition comes from a fear of the imperfect. Your book looks perfect in your head. But in bringing it to life, it’s not going to be perfect, because it’s a part of our imperfect world. So writers procrastinate. The same is true for lots of other projects. Everyone has some great idea but most people don’t act on it. But real satisfaction only comes from getting your project into the world.

  12. Edna Wilson says:

    For many years failure was a nasty word for me and then I was afraid more of succeeding, go figure. As someone with their own business, failure seems like a necessary part of the equation. And I’m learning over and over that when I lose a client or they decide not to use my services, it’s often a blessing and not a failure at all.
    Thanks for the reminder, great inspirational piece.

  13. Curt Finch says:

    The day you fail isn’t the most significant day in your entrepreneurial life. It’s the day after that’s truly important. Keeping a backlog of successes AND failures, whether they reflect the activities of one company or multiple, is incredibly important. Cliche as it may sound, it is nevertheless true that the only true failures are the ones we do not learn from.

  14. Kristen says:

    Thanks for this post Jonathan. I think it’s important to remember that failure is needed… even though it really stings when you’re failing with your personal funds, personal vision, and your own time. In growing my business I’ve made some good choices and I’ve had some total flops. It’s pretty hard to walk away from the flops, but I’m coming to realize that I need to move on to successful ventures and not sweat those that failed. Learn from them and go on 🙂

  15. Fadi El-Eter says:

    The main problem with Entrepreneurship is cash flow. You need to ensure that you still have cashflow.

    As entrepreneurs (in our first years of entrepreneurship ) are almost always tight on cash (if not heavily in debt), and that dictates all our decisions. It’s sometimes hard for us to push the limits when we don’t know what’s waiting for us. We’ve already pushed it once when we quit our jobs and created our own business. A wait is good.

    The nice thing about being an entrepreneur is that, with time, you slowly, but surely, build a sense or resilience in your cash flow strategies…

  16. John Mulry says:

    You know that old saying “Failure is like compost, use it to grow.” It’s definietly true, I’m just starting out with my finess business and I’ll be first to admit it’s pretty scary but the act of getting out of our comfort zone is both scary and exhilirating, wouldn’t you agree?

    We’re gonna fail, make mistakes along the way, foul up all that but if we learn from them and come back tronger wer’re better for it!!

  17. AJ Leon says:

    Could not agree more, bud. Right on.

  18. Jon says:

    Maybe it is just the same drive to succeed that leads to failure or glory? To fail big time you have to be so totally convinced that your idea is going to work that you piles everything into it. Half hearted ideas never register on the failure scale (whatever that is!), it is the big projects that suddenly fall dead that get noticed. But, without that same conviction, the successful projects will never develop.

  19. Stuart says:

    Hi Jonathan,

    I prefer to look at failure a little differently – to me, failure is not so much something that must be experienced, like an ill-tasting medicine to make us feel better. Rather, I believe failure goes hand-in-hand with success. The two are the same as they both move us forward on the path of life.

    Bill Gates had companies before he began Microsoft, but I bet when he originally started out, he had no idea his initial business was going to ‘fail’. I reckon he thought he was going to make it big with the first attempt. Even those it didn’t work out, he still learned a valuable amount and gained vital experience. Without that experience and knowledge, Microsoft wouldn’t be what it is today.

    Like beauty, failure is in the eye of the beholder. It needs to be put on the table with success, where both can be viewed as equally important to happiness.

    Interesting read Jonathan, take care 🙂

  20. I was looking for a quote about creativity for my own blog and I found here on your site. Well, after I used the quote (I mentioned where I found it) I came back to look around. I really liked what I saw. This post is exactly where I am in my mind. It said what I needed to hear. I should actually print it and hang it above my workspace. Thank you for a great site and inspirational post. I am signed up for your newsletter and I will be back. Don’t let that scare you lol.

  21. JP Reynolds says:

    I’m a self-described “recovering perfectionist.” That overwhelming need to be perfect at all I do has often prevented me from either undertaking or completing a project. I’ve had to learn how to “successfully” fail. Recently, I was asked to give a talk on “how to prepare for college” to juniors at a private prep school here in Los Angeles. I presented the idea that the best way to prepare for the future is to learn how to see opportunity wherever opportunity may appear––even in those places we want to avoid. I think there are three ways in which we can condition ourselves to recognize opportunity: by being resourceful; by being curious about other people; and by not being afraid to fail. I’m not sure what kind of response I was expecting; however, the students surprised me with their thanks for my talking about “failure.” They seemed relieved and grateful. . .

  22. I love this post. I just wrote a post on the need to fail quickly in order to succeed, and then came across this today.

    Thank you!

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