Optimism is a Double-Edged Sword

What would you say is the toughest situation you have faced as a leader? How did you deal with that adversity and what did you learn from it?

Recognizing when things aren't going well, aren't going right, and deciding... At times, I don't think that I've acted quickly enough.

What held you back from acting quickly?

Optimism. Again, it's the sort of double-edged sword of any entrepreneur or any leader, you want to believe, you want to will yourself and your team to success. And if that's how you're wired, nine times out of ten, it's what's going to allow you to succeed. But that tenth time can also be why you failed. You were blinded to the fact that it wasn't working or your colleague wasn't working or your relationships with your superiors weren't working, wasn't working right, and you didn't acknowledge it and do something about it sooner.

But how do you know if optimism, for example, carried you through times one through nine? And you're thinking, well, that same optimism will carry me through to the tenth time.

That's what makes it tough, my friend. It's exactly what makes it tough and why, even as you come to work every day singing the song championing the project and shouting from the rooftops about how great it's all going and how much progress you're making. The leader then needs to go back into their office or go home at night and double check with themselves. Is it as good as I'm making it out to be? And if it's not, come to terms with that and try to do something about that. It's tough. It's really tough because it's not necessarily natural for a leader or entrepreneur to check themselves, in that respect.