One of the biggest problems I see is a growing tendency to think in black-and-white terms when the real world exists entirely in shades of gray. Simplicity has its limits. In reality, things are almost never as they seem.

Virtually all the successful people I’ve known over the years are multidimensional or critical 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 the real world can be. “Keep it simple” may be a great mantra, but you often have to consider all sorts of factors and look at things from lots of different angles to arrive at what, in hindsight, might seem like the obvious answer.

While trying to puzzle our way through a tough turnaround of a struggling startup, my CEO once 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 right; that’s exactly how long it took. 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 call 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.

Still not convinced? If that’s because what I’m telling you challenges some deep-seated beliefs, then maybe you should look at them more critically. If, on the other hand, you’re not willing to accept the premise because you haven’t seen enough evidence, that’s a good sign.

Another example of black-and-white thinking is the popular meme that you have two career choices: either slave away for the man in a 9-to-5 job you despise or take matters into your own hands and become an entrepreneur. You actually have so many more choices than that it isn’t funny.

Take my former CEO, for example. He worked for years before developing the skills and making the right contacts to start his first two companies. One flopped and the other was a minor success, but deciding to come in and try to turn around that company was a smart and nuanced decision that paid off big time … for both of us.

Every successful executive and business leader I know got there the same way: by working hard in a growth industry, gaining experience, building their network, and when the opportunity arose, delivering the goods. That may not be the only way, but it’s certainly not the way everyone talks about these days.

The current entrepreneurial drumbeat is to do what feels good, fill your head with inspirational quotes, be happy, and everything will work out fine. Focus on your strengths and ignore your weaknesses. If it sounds positive, then it must be good. Sweep those negative thoughts under the rug.

That sort of utopian thinking isn’t just nonsense; it’s destructive.

If you want to be successful, learn to challenge conventional wisdom and question your own beliefs. If it sounds too good to be true, it probably is. And when it comes to making important decisions, learn to look at things from different perspectives. If you want to make it in a complex world, you have to think critically.

A version of this first appeared on

Image credit Shutterstock.