Is your boss a disgruntled optimist?

Farrell Evans looked unhappy, and I was concerned. Big Duck was knee-deep helping Farrell and his team at the Bridge Golf Foundation (a nonprofit startup leveraging the power of golf to create opportunities for young men of color) launch a signature program. As the organization’s cofounder and Executive Director, Farrell’s vision must be brought to life and expressed clearly, so I asked him if he was feeling ok.

“Me? Don’t worry: I’m always disgruntled,” Farrell replied casually, wth a smile, while his colleague nodded rigorously in agreement. A journalist by training, Farrell believes it’s imperative to be a little skeptical of even the most well-intentioned people and situations.

As a business founder myself, I realized I’m regularly disgruntled, too. Big changes or subtle tweaks that would bring the vision more effectively to life, and the gap that represents “room for improvement,” is often the first thing I see.  

But I’m also an optimist, and so is Farrell. If I, or the people I work with, try hard but occasionally fail, I’m fine with that—and I’ll forget most failures fast. That’s undoubtedly the best way to learn.

Perhaps all founders are disgruntled optimists?