Brave Enough To Try: When Failure Gets Fun

The other night, Mike said this superbly profound thing. He said that maybe, sometimes the bravest thing we can do is simply be content.


Mind. Blown.

I’m horrible at being content. It is both my strength and my Achilles Heal. My constant discontentment is my drive that keeps me moving forward, constantly reaching for more. But it’s also what keeps me from enjoying the right here, right now. And what’s the point of moving from point A to point B if you can’t enjoy the scenery along the way?

What’s more, though, it’s what keeps me from experiencing things that I have an interest level that doesn’t match my ability (read: I don’t got the skillz).

I’ve been thinking about this little conundrum: How do you stay content yet motivated?

Maybe the answer lies in how I view failure. I’ve been thinking about failure a lot lately. Like, a lot. Motherhood makes me think about failure, oh, I’d say every other minute. But so does growing up. Because what I’m starting to learn is that you can’t move forward, you can’t grow, you can’t experience life, without embracing failure. Sure, you can micromanage  every millisecond of life to ensure that you don’t fail, but that also means you aren’t doing, well, anything.

Failure is just part of life. Why do we fear it so much? Why are kids in school not allowed to fail? Why are employees not allowed to fail? Why are moms not allowed to fail? And by “allowed,” I mean “not socially acceptable.” We all fail. But when we do, how do we view those failures? Do we view them as a sign of weakness, or of strength?

In her book, Daring Greatly, Brené Brown said that “when failure is not an option, we can forget about learning, creativity, and innovation.”

Failure is often “not an option” when we’ve linked our identity to an outcome: if you do well, you feel good about yourself, if you mess up, you feel crummy about yourself. What does this look like? Let me quote Brown again, because she says it so dang well:

Once you realize that your self-worth is hitched to what you’ve produced or created, it’s unlikely that you’ll share it, or if you do, you’ll strip away a layer or two of the juiciest creativity and innovation to make the revealing less risky.There’s too much on the line to just put your wildest creations out there. If you do share it in its most creative form and the reception doesn’t meet your expectations, you’re crushed.

Brown talks a lot about separating our sense of worthiness from what we do. She said when you do that, you can expect to try and try again at things and not feel a sense of shame or failure.

I’m starting to wonder about this whole Type A and Type B categorization of people. What if it’s not about who has the drive and who doesn’t, but really, about who seeks perfect outcomes above all else, but sacrifices experience, and those who seek experiences for the simple goal of…experiencing, learning, growing, be-ing, regardless of outcomes?

I’ve always been Type A person. A go-getter. An achiever. I’ve mentioned here before that I don’t typically attempt things that I won’t be good amazing at. I don’t like trying something that I can’t instantly master because WHAT DOES THAT SAY ABOUT ME??? The old me would instantly say it meant I couldn’t hack it. That I was incapable. That I wasn’t smart enough, tough enough, pretty enough, creative enough…you get the picture. So I’d quit.

What’s the trade off? The trade off, I’m starting to see, is that this thinking keeps my world small. I can create the illusion that I’m very good at a few things, but even then that’s a full time production of smoke and mirrors. That also means I’m not allowing room for things that I’m interested in, regardless of my ability.

I watched this amazing documentary the other day about the Barkley Marathon. It’s this crazy trail race, which some have called the world’s most difficult, that takes place each year in Tennessee. The founder is this guy who just cracks me up to watch, with more than the average person’s share of wry humor. He said something though, that stuck with me. He said, “You can’t accomplish anything without the possibility of failure.”


I’ve always cared a whole heck of a lot about accomplishing things. I live and die for to-do lists, good grief. But I think he is right. I could have a 100 page to-do list of things I know I can check off without really accomplishing something. Or, I could have a single item list, with one thing that I know I’m probably going to fail at, that you bet your sweet life will feel like an accomplishment.

I’m going to be thinking about this, and I’m going to come up with that thing. That thing that will make me feel like I’ve really done something, just because I tried it. Something that will have been worth the experience, regardless of the outcome.

It’s not so much that I’m asking myself what I’d do if I knew failure wasn’t an option. But rather, what am I going to do, knowing full well that I’m going to fail, but in the failing, I will truly find success?

I’d love to hear from you on this, readers. I know WordPress makes it a real drag to reply, but I promise, just fill out your email address (which only I see, and I’m honestly not a scary person), and then the hard part is over and you can comment here for ever and ever. I’d love to hear what this makes you think about. What do you want to try, regardless of your ability or the outcome? What’s that thing that you’ll probably fail at, but you’re going to try anyway? What are you going to fail at, but fail at so beautifully because it will be a life giving, story making, awe inspiring experience? Please, dear reader, lets be brave enough to try and fail…together.

2 thoughts on “Brave Enough To Try: When Failure Gets Fun

  1. Ok, so I’ll take a stab at this. Last summer I so enjoyed making bouquets from my flower beds and bringing them inside to enjoy. I also enjoyed stopping by the road during walks with the kids and picking flowers, ok weeds, to add to my arrangements. It made me so happy to do something simple and creative. I was just thinking how I need to plant more things so I can keep doing this. This will taking planning and a bit of research (bleh). I’m not a natural gardener so I will have to do some digging (pun!) to pick the right things to plant. I would also like to be able to have enough to give out to friends and family as simple “I love you gifts” or “thank yous”. Stuff may not grow, I may kill some plants in the process, but much like everything in life there will be a chance for great beauty amidst the “dirt”.

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