On Being Boldly Dumb

05/13/2015 04:28 pm ET | Updated May 12, 2016

I've decided being dumb and being bold are two sides of the same coin; you don't know which one it'll land on until the end.

What no one ever told me is that while the coin is still in the air, when you don't know what the outcome will be, you can feel so dumb.

I'd guess that all people perceived today as bold and innovative did things in the beginning that made them feel really dumb or that other people thought was really dumb (or maybe both).

When we often hear success stories all the dumb moves just seem bold, exciting, thrilling, as if the successful person knew all along all those dumb moves were in service of this end where everything paid off.

And while I'm sure there are many confident people out there who act boldy and feel that they know it's all going to work out, I also think there's this other camp, the people who actually feel dumb almost the whole time, but move forward anyway. The people who don't know if what they're trying will work, if their dumb moves will one day be perceived as bold, but they go anyway. They can't not.

I'm of the latter group. I feel dumb all the time. Like, "who do I think I am?"

I've read a lot of wonderful books written by women that have taught me women especially can struggle with this. I'm working on it.

But in the meantime, I also know I can't wait to not feel dumb. I've got to act in spite of it. And here's what I'm learning, what no one has ever told me before so I'm going to be the one to say it out loud:

I feel dumb! I feel stupid!

I pretend that I'm not feeling this way. When I'm traveling interviewing people for my next book I answer the Uber drivers confidently when they ask what I'm doing in their city: "I'm a writer." In those moments, I feel bold. For that entire drive, I really believe it. I sit with it. I let it warm me. I. Am. A. Writer. It feels like truth.

And then not too long after, when I'm back home in Florida with my laptop on my couch, I feel dumb again. What am I doing? Am I bold or am I actually crazy? How long until I know? Why is this so hard? When does The Bachelorette come back on TV? Life's big questions.

But, somehow, I write any way. I keep going. Because, deep down, I think I hope that dumbness can transform into boldness. At the very least, I know I have to know, and that I won't really know if I'm dumb or crazy until I finish, until I've given it absolutely everything I've got.

If it ends up that the coin lands on dumb, if I know I tried everything, I know I'll be okay with that. I decided a while ago that I know I have to go for a thing not when I'm 100 percent sure it will work, but when I'm 100 percent sure I'll regret not trying. If I know I can live with it not working, then I know I'm ready.

I've decided a dream is something worth feeling dumb for. Worth failing for.

Sometimes when you go for a dream, when you put yourself out there, when you try to create something, the journey sounds so beautiful and poetic in hindsight, as if you knew all along. Well, I'm speaking out in the middle of a big project, and I want to tell you the truth -- I don't know how this is all going to end and it's really really scary. But I'm doing it anyway. I haven't gotten to the point where I don't feel dumb yet, but I have gotten to the point where I'm okay with that feeling; I can live with it, I can move with it, I can use it to my advantage.

I remind myself that dumb and bold are two sides of the same coin, and that you can't get one without the other. So if any of my dreams require the kind of boldness that's only recognized in hindsight, then I've got to learn to live with the dumb, with the unknown, with the uncertainty, with the vulnerability, with the OMG WHAT AM I DOING WHY CAN'T I BE NORMAL?!

So, if there's a dream or a project you've been thinking about starting but are afraid because you feel dumb, go ahead -- be dumb. One day someone might look back and say you were bold, but you'll know the truth, the secret of it, and you'll get to smile and say thank you, all the while pondering what dumb thing you can do next.