Dealing with Doubt as an Entrepreneur

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Kenny working
doubt as an entrepreneur

It doesn’t matter if you are trying to create a website that focuses on craft beer, a photography business, or educational children’s music curriculum. All of these ideas and more are coming from the minds of creative entrepreneurs; everyday-people trying to create a living doing what they love on their schedule. It’s not easy. The “I’d rather be’s” come into play quite often, along with doubt, frustration, and the “it’s easier to work 9 to 5” mantra. But we all know that if it was easy, everyone would be doing it, and the rewards of entrepreneurship far outweigh the risks and the doubts.

We are excited to share our first guest post. While they do not live in an RV, they do love to travel, and they are definitely fearless. We met fellow entrepreneurs, Jeff and Paige, many years ago when I used to work in the outdoor education arena. They were yet to be married, yet to have kids, and yet to start their own business.

Jeff and Paige
doubt as an entrepreneur

Fast forward years later, Jeff and Paige are now married with kids and running their own children’s entertainment business. Working hard at being innovative entrepreneurs and nourishing parents, but doubting themselves along the way. Was all this effort put forth for their business worth it?

Regardless of where our creativity lies, as entrepreneurs, we all run into doubts and the “I’d rather be’s”. (Click here to read a similar story that I wrote about our entrepreneur struggles.) But if we persevere and work smart, while our doubts won’t disappear, we will gain more confidence, and with that, even more crazy ideas.

We are, after all, searching for the less-than-ordinary!


It’s 9pm. I emerge groggy-eyed from our son, Wolf’s, bedroom.

“Flubbsies?” Jeff asks.
”Mmmmhmm.” I reply. Flubbsies is our word for this moment of coming out of a darkened bedroom, bleary-eyed, squinting at the light, after falling asleep putting the kid to bed.
”So you want to rehearse that new song for Sunday?” Jeff asks.
A moment of annoyance passes through. Not at all! I want to say. I’m tired and the last thing I want to think about is how we’re going to perform Density. Right now I don’t care about the performance, or social media posts, or selling the new album. I’m tired and…

Jeff and Paige
doubt as an entrepreneur
Jeff & Paige Rehearsing “Density” in their PJs at home.

But actually I do care. I care very much about the performance, and selling our new CD, and raising enough money to reach our crowd funding goal to donate the curriculum we’ve created to classrooms. I care about so much of it that sometimes it’s hard to know where to start. For now it’s with this rehearsal of a new song. And this cold dark winter night, after the kid is asleep, is the time we have to rehearse and prepare without interruption. So I swallow the thoughts, and the urge to yell this at my husband, and the temptation of putting off the work for another time. I’ll enjoy the process if I can shake the tired off long enough to say…

“Yes, let me just make a cup of tea.”

Jeff and I are working parents, same as any others, though the content is slightly different from spread sheets and long hours at a computer (trust me there are plenty of those too). Running a kid’s music and entertainment business together is more work and more joy than either of us ever could have imagined. It’s long weird hours, it’s long weird fights about the dumbest things—where to place the stuffed animal onstage, how to say a line of dialogue— it’s also so much joy, fun, and hilarity when we don’t take ourselves too seriously.

Yet, taking things “too lightly,” hasn’t worked either. For every show that we put on there are hours of cumulative rehearsal involved. For every album we’ve released there are days and nights of memorization, creation, recording, production, and workshopping. For every event that we put on there are marketing budgets, social media campaigns, e-mail newsletter blasts, tickets to sell. There is a temptation to always feel like you are missing something, to always wonder… if I had just posted one more time to Facebook, or followed up with one of our community partners to get the word out could we have had more people there, could we have sold an extra album or t-shirt, if I asked differently for someone to sign up on our email list would we have more… But those doubt-filled thoughts, we have learned, lead us no where. Nowhere except a spiral of uncertainty and fear that can be paralyzing. So the work of being small-business owners, entrepreneurs of the educational music kind, is often to focus on the next most important thing, take a deep breath, and trust that if we continue to follow the creativity, love of the earth and human beings, and urge to share that love with others, we’re heading in the right direction.

I don’t have a perfect conclusion for this blog entry. Running our business (or moving out of the way to let it run us), performing for kids and their parents, creating new interesting and relevant content, and constantly promoting ourselves and our brand so that we can continue to support our family and show up fully in our work, is a constant work in progress.

Thanks for reading and if you’re in Boulder, CO. We’ll perform that new Density song at The Rayback Collective Sunday Jan. 13th, 10am. And many more times after that!

Visit our calendar for info about all our upcoming events.

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Blog post originally written for Click here to read more about them. They are quite extraordinary!


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