Take Risks to Open Options

Posted February 15, 2007

I was reading a blog post earlier by Ross Mayfield. He was asked what were his best decision and worst mistake as an entrepreneur.

All his answers were good but I was especially struck by what he calls his biggest mistake:

Biggest Mistake — Not taking bigger risks earlier

Maybe because in hindsight all risks are clear, but I always find myself regretting not taking bigger risks earlier. For example, open sourcing the Socialtext code was something we waited on until the company had strong footing. Partially because we thought there would be cannibalization, partially because we were understaffed to really engage with the community. But I believe if we bought this bullet earlier in the history of the company we would be reaping better rewards. As a planning exercise, now I always try to ask two questions: “How could we take more risk?” and “What risk can we take that creates the greatest amount of options?” I find there is always a way to do a little more, in particular by getting past instinct to control prevalent in so many entrepreneurs.

I was so struck because I’m in the middle of taking a big risk.

I am passionate about web development. I want to build web applications that enable people to connect, collaborate, and get more done in their lives. But at my current and soon to be past job, I’m not learning how to build these beautiful web applications.

So I decided to quit and employee myself. I decided that as no one is going to pay me to learn how to do web development, I’ll just have to pay myself.

And now my mom, older sister, and I are going into business together. In a few months, we’ll unveil, the newest and greatest baby card announcement e-retailer. And in the months leading up the our launch, I will be learning web development.

Ross Mayfield learned it was a mistake to not take risks but that taking (calculated) risks opens up options where caution and control can never go. I’m trying to learn this same lesson. By taking this risk, the options I want to have will open to me.

Tagged with entrepreneurship | learning

Subscribe to get updated on new posts!

Kyle's profile picKyle Mathews lives and works in Seattle building useful things. You should follow him on Twitter. Currently exploring what's next and open to consulting.