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We’re taught from a young age to play it safe. In high school, our friends warned that asking the most popular girl to prom would only result in rejection and humiliation. In college, our parents pleaded with us to major in a “guaranteed” subject like engineering or finance, so we wouldn’t move back into their basements. At work, our former bosses convinced us that letting them take credit for our work was the surest way to a promotion.

We’ve been handed a raw deal. Let’s face it: Our friends were afraid their prom dates would be outshone, our parents wanted us to pay off our college debt ourselves, and our bosses were looking to get their work done without working 80-hour weeks. Where was the benefit for us?

My greatest initial business mistake wasn’t drilled into my head with bribes, but I absorbed the lesson, anyway. I started out working for an entrepreneur who often changed course, diving into new fads at every turn. The results were often quite costly: our resources were spread thin, we had little focus, and our team was constantly confused.

When I launched my own business, I vowed I wouldn’t make the same mistake. I went to the other extreme, developing a business model that was so tightly focused on my niche — eBooks — that little else could ever fight its way in. I didn’t want to adjust any of our core fundamentals and I resisted adding new services or products, regardless of how closely they aligned with our mission.

I was a disaster waiting to happen because I was limiting myself to what seemed safe. Various members of my team sensed how crushing the limitations were becoming — for both me and my business — and they started nagging me to reconsider several of the endeavors they’d proposed. After enough of these reminders, I started researching the options and realized that it really does take money to make money. Some risks are appropriate to take.

The payoff was huge. I had been hesitant to offer a paid VIP membership to for fear that people would reject anything from us that wasn’t free. We added a membership package that now accounts for half our revenue. I also stifled my concern about embracing new technologies: I green-lighted a mobile app, which has now been installed 230,000 times, and also launched a Facebook Page that grows by 10,000 fans per month. I had, very clearly, been wrong.

A lot of the credit goes to my team for constantly looking for new possibilities, and doggedly pursuing the ones they believed in. But my old tendencies have also served us well. Our forays into new venues have worked, in part, because of my cautious nature. I learned to evaluate opportunities properly, plan accordingly, and allocate the right amount of resources to each.

I haven’t reached the level of eagerness for new ventures that my former boss exhibited, but my newfound openness to change has made me a better businessman and a better manager. I’m more considerate of my team members’ suggestions, and I feel less caged-in than before. I learned that while people may not be able to get a prom do-over, they can always start again where they are.