The more I live this entrepreneurial life the more I realize how much of a psychological game it is.

I was reminded of it the other day as I watched this interview between Jason Calacanis and Jerry Colonna, a very well known CEO coach in the technology industry.  The 90 minute interview is incredible, they  cover many aspects of how he works with CEO’s and the issues they (we) deal with during the entrepreneurial journey.

There are so many things in this interview I want write about but one of the biggest things that stuck out to me was the idea of “chasing demons” with entrepreneurship.  Jerry and Jason both reveal how their Dad’s lost their jobs when they were young, and how greatly it impacted them, and still does to this day.   For both of them, they committed to never be dependent on a large company, since it could all be gone one day if you are fired.  Deeper, it was the feelings of inadequacy (or the fear of) which drove both to become successful in their pursuits.  It’s amazing and touching to hear them talk about their fears and doubts, and how they are rooted simply from watching their father’s struggles as they were young men.

I think this is something very important to understand.

Why are you so driven?

What demons are you chasing?

Jerry bravely mentions chasing demons is not necessarily bad – not knowing you are chasing demons is.  Not fully understanding who you are and why you are doing things is a scary place to be.

Another thing he points to is how ALL of us feel inadequate, regardless of financial stature and prominence.  He works with over 60 clients (many billionaires) and without fail he see’s highly successful individuals tearing themselves apart, comparing themselves to other founders who – quite frankly – got incredibly lucky with their outcomes.

He emphasizes how much random luck has to do with success in business.

His point: figure yourself out.  Determine who you are outside of your company, your family, and your city.  Once you get to the core of who you are you can fully embrace the life of entrepreneurship without the feeling of insecurity and doubt.

The lesson to take here is although it might be scary to face these demons, once you do you will open yourself up to a much happier entrepreneurial journey.