Failing Gracefully

I’m sick of the Internet’s obsession with failing.

I can hardly check Facebook or the few news sites I do read without coming across some entrepreneurial article about the importance of failing big or failing fast or failing often.

What perturbs me about this school of advice is that, at its core, failure is positioned as the goal and should be celebrated.

I don’t know about you, but I hate failing. I never begin a project with failure as the objective or even as an acceptable outcome. My goal is to be successful.

That isn’t to say that I have never failed. In fact, failure is often a natural and unavoidable feature of the creative process.

As an improviser, it is essentially built into the craft. Anyone trying to create comedy in the moment without a plan is bound to occasionally miss the mark.

As a writer, failure is also inevitable. To craft a headline or print ad or blog post that will see the light of day means that my work has to pass through several filters – my creative director, the executive creative director, the account team, the client.

Tim Walsh during Creative Weekend Beta
Tim Walsh, Photo Credit: Steven Harowitz

It’s nearly impossible for something as subjective as creative work (whether it’s improvised comedy, writing or anything) to pass through four different filters and come out the other side unchanged. Everyone has different tastes and competing visions.

If you’re starting (or growing) a creative pursuit – a blog, sketch videos, photography, making jewelry – you’re going to fail at some point. Hell, even if you’re just sitting at home playing video games, you’re going to eventually hit the “game over” screen.

So what do you do when you fail?

For starters, don’t make failure your goal. Don’t celebrate it. Don’t fail big or hard or often. The speed and size are much less important than how you handle it. Here are four steps for failing gracefully.


Have you ever suffered through an improv scene you knew was bombing? Have you ever presented work to a client only to have them say “this ain’t it?” Have you ever gone on a date that was so terrible you had to sneak out the bathroom window to escape?

Despite your best intentions, you are failing. So take a deep breath and accept it for what it is. The initial sting will soon pass.



Rocket science is easy – either the rocket lifts off or it explodes into 1000 pieces. Creative work is hard – it’s all a matter of individual taste. There is no all-powerful being that can say whether or not Moby Dick is a “good book.”

When people give feedback on creative work (or you give yourself feedback), it is not a personal attack or critique of you as human being. I have submitted 10 headline options for approval only to have all of them all rejected. It doesn’t mean I’m a bad writer. I give my students notes on their scene work all the time. It doesn’t make them bad improvisers. It just means that you didn’t hit the mark this time.


Since none of us created something with the goal of failing, we had a reason for doing something the way we did. Sometimes, that reason is flawed – like if our reason for denying our scene partner is because “I thought it would make me look funny.” But sometimes, our reason for doing something is right – like I heightened the game correctly, but the audience just wasn’t laughing.

It shouldn’t be your default assumption that you’re right, but sometimes, if you can explain why you did something a certain way and defend your point of view, you may end up coming out on top.

Treehouse Networkshop's Meeting of the Minds hosted by Wesley Hoffman
Treehouse Networkshop’s Meeting of the Minds; Photo Credit: Treehouse Networkshop


Despite the fact that I think everything I create is perfect, when I accept feedback and try again, the new creation is often better than my original submission. Real feedback (not people being jerks) comes from a place of support. People want to see you succeed. Just give it another shot. Chances are you’ll surprise yourself.

In a way, I do sympathize with all of the “failure” articles on the Internet – those who fear failure never start anything. Fear of failure shouldn’t be the boss of what creative projects we undertake. But we also shouldn’t set out with failure as our goal or an acceptable outcome. We should strive to succeed beyond our wildest imaginations. Only then can we fail gracefully, learn from it, and pump ourselves up to kick ass next time.


What do you think? Is it better to plan for failure or just fail gracefully if it happens?

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