Why You Should Fail Fearlessly

wedgieIt’s in that moment you propose an idea that you know is going to be met with blank stares if not looks of outright contempt. It’s when you’re about to hit send on that email that shares your hopes and dreams with another. It’s that point in time where it seems like your idea or task or project just isn’t going to work. You may even project a confident image (and there’s nothing wrong with that), but underneath it, you’re afraid your idea isn’t good enough and may even be a disaster. Sometimes you’ll be led to believe — by yourself and/or others — that you’re not good enough.

royalguardfailThink of the biggest professional failure of your life. The biggest one. The one you almost can’t help but laugh at because it went so terribly wrong. Or the one that still puts that sinking feeling in your stomach when it comes to mind.

Now do that thing where you put two fingers on your neck or wrist and check your pulse. Still got one? Good. That means that failure didn’t kill you. You blew it big time, yet here you are.

The natural thing for us to do when faced with fear is to shrink back, thinking that if we but reinforce our current position and keep our head down, all will be well.

But all will not be well. Because if everyone does that very thing, how and why should we expect progress and forward momentum? If the fear of screwing up paralyzes us and/or dominates our thoughts, we need to press into that a little and see what’s really going on there.

And then keep pushing forward, knowing you’re going to fail along the way.

mjFailure, you see, is an essential element of learning, growing, innovating, and leading. If you’re not failing, you’re not trying enough stuff. It’s like that one of my favorite Michael Jordan commercials from back in the day. Point is, if not messing up occasionally, it’s almost certain that you’re not being as innovative as you could be. You’re not taking risks you could be taking. You’re playing it really safe, which is exactly what “they” want.

So try things. In spite of what well-intentioned adults told you when you were little, I think you should let your mind wander. Think of possibilities. Think of what could be. Challenge your own assumptions and presuppositions.

Have original ideas. But further still, and more importantly, share them. Talk about them. Rally others around them. Don’t be afraid of rejection. Who really cares if someone doesn’t like your idea? It’s only after working through scores of bad ideas that you’re going to reach that one really, really great one. And it’s only through failures that you’re going to learn, improve, grow, and stretch yourself.

What am I saying? Here it is — fail. Fail often. And fail fearlessly.



  1. Peter Holewinski says:

    Some real good stuff here. The only way that good ideas surface to the top is by getting worked, commented on, critiqued and adjusted, changed, refined and adopted. By attaching so much attention to the “success” or “failure” of an individual contributor’s ideas, we should be encouraging the ideas and encouraging teams to work on them together to push the value to their limit. Thanks for telling us what we hopefully all hope for.

  2. […] recent Workplace Mojo blog post got me to thinking about the fearlessness of failure. What if we were to fail. Big time. […]

  3. Andy Johnson says:

    Great post, Matt. I’m totally with you on the points you make about generating ideas – we shouldn’t be afraid to explore and talk about them, in fact we should encourage it. Always makes me think of a saying I heard in a training event last year:

    “A bad idea never hurt anyone, but the execution of one could”

  4. absolutely agreed! fail, fail again, fail better :-)
    and after you succeeded with that, do less to do more and stop the glorification of busy –

    combined, these 2 should lead to a very happy relationship with your work 😉

  5. […] additional thoughts on failing fearlessly, I encourage you to visit this blog post written by my friend Matt Monge, and I encourage you to read the work of Brene […]

  6. ava says:

    Just shared it; this is beautiful! As of now I don’t know who wrote this (new reader here) but yay, thank you for sharing your fearless thoughts on failure.

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