How a Classic Children's Book Motivates an Entrepreneur to Chug Through Challenges

For one entrepreneur, 'The Little Engine That Could' takes on a whole new meaning.
How a Classic Children's Book Motivates an Entrepreneur to Chug Through Challenges
Image credit: Scot Lerner
Magazine Contributor
3 min read

This story appears in the June 2018 issue of Entrepreneur. Subscribe »

Since I was little, I’ve always had an entrepreneurial spirit. I used to take a wagon around the neighborhood and do roving garage sales. I always had this desire to do something.

Related: The Early Entrepreneurial Spirit of Warren Buffett, Jeff Bezos and Other Icons (Infographic)

As an adult, I tried lots of things, but nothing clicked. I taught. I worked at State Farm. I even went to law school. I met my husband there, but otherwise it was torture. I hated it.

When I became pregnant with our first child, we decided I’d stay home with the baby. But the deal was that I had to make up some sort of income. After doing some research, I had an idea.

I’d been in a sorority in college, and back then most of the sorority gear available was pretty crappy. So I found a company that sold jewelry that they’d engrave with sorority letters. I had no background in computers or tech, but as I nursed the baby, I set up an online shop to sell this jewelry. I called it JennaBenna, and had this grand illusion that I’d start this business and -- boom! -- everyone would start buying. They didn’t. I kept trying different things. Nothing worked. I struggled. I maxed out our credit card.

Related: Low on Motivation? 7 Psychological Hacks to Get Going

That’s where the book comes in. When I was little, my parents read me The Little Engine That Could. A lot. You know -- “I think I can, I think I can…” My mom was a successful entrepreneur, and that little engine was her: I’m gonna do this. People may not believe I can. But I’m gonna do this.

Now I was a mother, and I thought about that book a lot.

One day, out of the blue, a woman approached me. She made those lettered shirts they sell to sororities and asked if I’d buy them wholesale to sell on my site. I did. It went well, but I didn’t like someone else dealing with the end product. I wanted to make it myself. But I had no idea how. 

So I sent my husband to Louisiana to get a used embroidery machine. He drove it back, and we sat in my parents’ garage one Sunday and figured out -- without a manual -- how to cut the letters and sew them on the shirt. We pushed and we pushed and we did it. That shirt was the most hideous-looking thing, but we did it. 

Related: 5 Productivity Truth Bombs From Millennial Powerhouses

Now I make and sell those shirts, we have seven full-time staffers, and we’re on target to hit a million in revenue this year. And I still have my tattered copy of The Little Engine That Could. I’ve read it to my three kids so many times that it’s become a family mantra. It’s funny -- sometimes someone will say, “I can’t do it,” and my kids are like, “No! You need to be like the little train! You need to say, I think I can!” It’s so nice to be able to pass it along.

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