Perhaps the biggest problem I see with a lot of young entrepreneurs I meet is a tendency to think in black-and-white terms when the real world is almost entirely made up of shades of gray.

Virtually all the successful people I've known over the years are multidimensional thinkers who ask a lot of questions and look at things from many points of view before arriving at what is usually the right decision. That said, they didn't all start out that way.

Experience has a way of teaching us just how complex things can be in the real world. And while "keep it simple" is a great mantra, you often have to consider all sorts of factors and look at things from many angles to arrive at what, in hindsight, seems like the obvious answer.

It reminds me of a time when my CEO and I were trying to puzzle our way through the myriad issues at a struggling startup we were trying to turn around.

After I admitted to feeling a little discouraged, he looked at me and said, "When you take over a company, it takes three months to figure out what's really going on," then he grinned and added, "And another three months to figure out how to fix it."

He was so right. Things are almost never as they seem. And while we did eventually take that company public with nearly a billion-dollar valuation, it took quite bit of creative problem solving and some relatively complex strategies to accomplish what our predecessors couldn't.

What we sometimes describe as out-of-the-box thinking is actually a process of questioning conventional wisdom, challenging the status quo, and looking at problems differently to arrive at unique solutions. Preconceived notions and strongly held beliefs, (aka black-and-white thinking) is an impediment to that process.