Why I hate the question, what would you do if you knew you couldn’t fail?

Uncategorized May 11, 2020

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I cringe each time I hear this question, “what would you do if you couldn’t fail?”


Yup...I hate this question. It’s also a question I used to ask people.

So for the longest time I didn’t want to admit I hated it, because I didn’t want to be called out for changing my mind.

But it’s okay to outgrow how we used to do things. As we evolve it’s normal to shift and change our own perspectives. 

It doesn’t make you inauthentic, or fake. It makes you REAL. The same person we are right now doesn’t have to be the same person we were two years ago.

So the reason I started to hate this question is because I don’t believe our journey on earth is void of failure.

I actually believe failure is part of the process. But asking someone, “what would they do if they couldn’t fail?” seems like an unattainable goal, but more importantly, a goal I don’t want to encourage people to strive for.


Because failure is inevitable. And all the failures I’ve faced thus far have been my greatest lessons learned. 

Maybe not in the moment, I get it.

And yes, failing doesn’t always ‘feel’ good, but it’s not the failure itself that feels shitty, it’s the meanings we attach to it. So failing is something I encourage my clients to embrace. 

Instead of asking my clients what would they do if they couldn’t fail, I opt to ask them this instead, “what are you willing to do knowing you’re going to fail?”

Seems like a gut punch...but it’s real life!!

Preparing people for failure instead of painting an idyllic picture of a journey that doesn’t exist is one of the most beautiful things you can offer your people. 

And one of the most gracious things you can offer yourself. 

Sometimes we set the bar so damn high it doesn’t even exist. And while I love dreaming BIG, I equally love promoting real life.

So dear friend, failure is something to embrace, it’s also part of this beautiful journey of achieving success. 

I’d love to hear your failure stories and what you’ve learned from them.


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