Is it possible to be too comfortable with complexity?

No.  Being comfortable with complexity is a strength.  The world is a complicated place.  There are many moving pieces all moving simultaneously.  People are complicated animals and trying to maintain relationships of any type with other people requires an understanding and comfort level with complex situations.  The larger the business, the more complex it is.  There are more people within it to learn to work with, more systems, more layers and more projects underway at any given time.  We are currently working projects that affect us now, planning for future development, strategizing our next projects and casting a vision for the future.  Not only is life a complicated blend of scenarios, it is a blend of time horizons as well.  So having a greater comfort level with complexity the better off you will be in both business and life.

Yes.  Since I am comfortable with complexity, I tend to make everything complicated.  Some things need to be complicated, but most things probably need to be simpler.  We are more stressed by crazy situations than we are by calm.  We seek calm to relax.  Complex scenarios are more stressful than simple scenarios.  More often than not I tend towards taking scenarios and seeing the complexity in them, feeling comfortable with it and voicing it.  I probably don’t articulate clearly enough when I am simply discussing the multiple facets of the situations and when I trying to dig deep to analyze a situation.  There are times I am sharing for awareness and times I am sharing for them to understand the intricacies.  If I continually throw out complexity, I’m adding stress.  If I were uncomfortable with complexity, I would continually seek to simplify, so yes, I can be too comfortable with complexity.