Leaving my job to found a tech startup felt less like flying and more like jumping out of perfectly good airplane.

By Libby Roin (Founder, Polk Street Press)

I went on my first airplane flight when I was nine years old. My generous and brave grandmother took each of her grandchildren on individual trips to a destination of our choice. She said she wanted us to experience someplace other than Oklahoma. I think she might have been secretly afraid we’d end up as bumpkins.

I selected Philadelphia because I desperately wanted to go to the children’s museum there. It seems like an odd choice (my sister chose Disneyland), but I must have seen a really compelling show about it on television.

Looking back, I don’t recall the museum much, but I do remember the feel of exhilaration I felt taking off from my hometown of Tulsa and heading east. I wasn’t scared or nervous, just excited to experience flying and thrilled to be going somewhere new.

At 33, I faced starting a company with very different emotions. Leaving my job to found a tech startup felt less like flying and more like jumping out of perfectly good airplane. My undergraduate degree in English and MBA didn’t seem to prepare me much for entering the world of iOS programmers and web applications. Somewhere along the way, I had developed a fear of flying – going into the unknown, headed somewhere I’d never been before.

After a year of working on my startup, Polk Street Press, there are still a lot of unknowns and to be honest, a little fear, but there are also a few things that I have rediscovered along the way:

  • Learning new things is fun. That little girl who was so excited to go to a museum is still in there. In the first few months of Polk Street everything was new – incorporating a company, hiring a developer, submitting an app to iTunes. A year later, I am still challenged every day to learn or do something for the first time and I love it. Which leads to #2…
  • Making mistakes is still okay. On our trip, I locked myself and my grandmother out of our hotel room. I had been practicing using the hotel room key card and she came out to show me how – just when it stopped working. I had to go down to the lobby with her in my socks. I was mortified! I remember trying to hide behind her in the elevator so no one would notice. She never scolded me. When you’re learning, you make lots of mistakes. Doing a startup means that you have to embrace a little humiliation and move on.
  • Taking risks can be scary but do it anyway. That trip to Philadelphia was also the first time I saw the ocean. I remember thinking it was much larger and colder than the small lakes back home. I entered the water with trepidation and immediately ran back out after being pinched by a crab. But I went back in again and again. I’ve had lots of setbacks and pain in the last year, but I go back in again. The experience is worth it.

Our trip to Philadelphia so many years ago was incredibly special. It truly broadened my view of the world and started a relationship with my grandmother that I still cherish. Inspired by that experience, I looked for new horizons and opportunities to push myself to grow. Launching a company is in many ways the next leg of that journey.

At 84, my grandmother still travels every year and she remains an inspiration to me. A few years ago, I had the opportunity to go to Greece with her – just the two of us. Driving around the country, we made new memories and reminisced about our first trip together. She couldn’t recall the Philadelphia children’s museum much either, but she did remember me doggedly eating my way through an entire bowl of shrimp bigger than my head. I guess I still like a challenge.

Women 2.0 members: How do you deal with uncertainty of starting a startup? Let us know in the comments!

About the guest blogger: Libby Roin is Founder of Polk Street Press, creating fun and educational children’s content that parents can feel good about after seven years at a traditional children’s book publisher. Her first interactive storybook app, Goodnight Safari was released in January 2012 and has built a following of over a million parents and children since then. Her newest app Spatter & Spark will be released in January 2013. Follow her on Twitter at @polkastreetpress