"The only safe thing is to take a chance" - Elaine May

March 19th, 2012

On Doubt and Optimism for Entrepreneurs

When I was a 35 year old CEO, I knew everything. Now I’m a 58 year old CEO and there’s rafts of things I don’t know.
- Howard Diamond

If you have attended an event where entrepreneurs are bound to be lurking, you will undoubtedly notice they are the most optimistic people ever. It’s their job to be right? They have to exude confidence in what they are doing because they are always selling, even when they aren’t.

However what you probably might not know and rarely see are the moments when the most confident and even the most successful entrepreneurs doubt themselves. The reason you don’t see it often is because they are masters at hiding it. In fact, I doubt myself quite often but you wouldn’t notice it because I never show it. I’ll explain in moment how I deal with doubt and uncertainty.