Tooth Fairy Tales and Why Imagination is KEY (For Kids and Entrepreneurs)


This post is inspired by companies that continue to imagine what’s possible, like my friends at Casper who not only created an incredible mattress (yes I sleep on it) but continued to dream and created their next level pillow! This pillow is an excellent balance between support and softness- perfect for this tired mompreneur and her loose tooth son! 

My son is five and recently lost his first tooth. It wasn’t a moment I was prepared for, not in the way I was for sleep training or first visits to the toilet. Parents spend lots of time discussing those rites of passage, but the first wiggly tooth, the discomfort that goes with it, and it’s ultimate loss? Not even a peep!

My very dramatic son began to worry when his first loose tooth got in the way of chewing hard foods and when it got very wiggly and blood became visible, emotions followed behind. I had to ask him a few questions to understand the root of his anxiety. What I learned was that he was actually afraid of the tooth itself falling out of his gum and what it would feel like without it- how odd for something IN his body to fall out! He wondered how he would eat a chicken drumstick or an apple and what would happen if the tooth fell out when he was at school (what will I do with my tooth? What if I misplace it?). And the biggest confusion of all was with this strange character that everyone mentioned when the loose tooth subject came up in conversation: The Tooth Fairy. Who the heck is she and why should I trust her, his worried eyes expressed.

I hadn’t done my research on the tooth fairy- how people were describing her nowadays, what her going rate was, and how exactly she knew what apartment to come to. So I had to rely upon the thing that I realize now has made me not only a good mom but also a confident entrepreneur…my imagination. Let me explain further.

Again, unrehearsed, the evening came when my son’s anxiety built around this tooth literally hanging by a thread from his gum. It was time to give him something to be excited about. And so I let my imagination guide his. It went something like this:

My son: Where does the tooth fairy live?

Me: Upstate…in the forest, the one down by the river (we have a home in the Hudson Valley so this was a concept he could connect with).

My son: How does she know my tooth is going to fall out?

Me: Well, she has a special ability. When a kid’s tooth is loose, her body starts to vibrate and she knows it’s time to start making her way to where that child lives. (I was kind of amazed how this response flowed without hesitation….a good imagination at work, I must say)

My son: You mean she has a “sense?”

Me: Yes, she senses it…and follows it.

My son: But how does she get to where the child is?

Me: Well, she’s very tiny with wings like a hummingbird. If she has time, she can start to fly towards the kid with the loose tooth. If she’s running out of time, she hops on the back of a car driving down the highway and gets where she needs to go. But she always makes it in time…somehow she’s always ready when that tooth falls out.

My son: Does she always leave money? Can she leave me a little robot instead if I want it?

Me: Don’t forget! She’s very tiny and she’s flying- money is easier for her to carry. So it’s usually just money.

And the conversation went on like that…him darting off questions like bullets, me in my imaginative flow and without hesitation, capturing them and running with them, building his excitement more and more. And it felt so natural to me. Why I wondered? And then I realized something: Because I’m an entrepreneur; I do this imagination dance every single day. Why is our imagination imperative as we build, create and lead? I’ll tell you why:

Imagination is what keeps our dream alive.

Let’s face it, starting something from the ground up is not easy so we need to have an active imagination (literally a concept of the dream we are building, something not yet real that only we can see) to get us through the discomfort, the unknown, and more. Just like when our first tooth is loose and only the concept of the tooth fairy can ease our worry.

Imagination keeps us positive.

Even if you have a concept of what you’re building and you believe it could be profitable, it’s still easy to feel bummed, worried, and even pessimistic at times. Our imagination comes from the part of our brain that is not weighted down by what if’s, guilt, and the stories that people love to tell about their cousin who went bankrupt. Our imagination keeps us happy, driven and excited. It was pretty cool how quickly my son went from worrying about the hole in his mouth to invigorated by the thought of the little tooth fairy hightailing to the city on the tail pipe of an SUV.

Imagination has a reputation for being only for spaced out artist types (no offense).

But that’s so untrue. Imagination keeps the type A’s like myself just dreamy enough. We simply must have something that keeps it light, something special enough so we don’t succumb to the intensity that comes along with entrepreneurship.

If you’re a Mompreneur like I am, I have some great news for you: imagination is right at your fingertips. In fact, you probably have some of the greatest vision wizards a few steps from you, right at this very moment. Kids as you’ve probably figured out live just outside of reality, which is why the tooth fairy, Santa Claus and a slew of other characters seem like dear friends. When your imagination is alive, you don’t have to see it to believe it. And from that space of trust and excitement, really great ideas are born.

Most adults ultimately realize that we spend massive amounts of time, effort and probably money to return to the simple, open, imaginative spirit of a child.

Whether you have kids or you don’t, whether you’re starting a business or you’re not, I guarantee you that you need more time telling stories, dreaming up possibilities, and for once, telling yourself that anything is possible.

Thanks Mademoiselle Tooth Fairy (and my five year old son) for reminding this mom and entrepreneur to dream a little bit bigger and a little more often.