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How to Think Differently to Succeed in a Complex World

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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.

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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.

Still not convinced? If that's because what I'm telling you challenges some deep-seeded beliefs, then maybe you should look at them more critically. If, on the other hand, you're not willing to accept my premise because you haven't seen enough evidence, then pat yourself on the back. That, my friend, is a good thing.

Here are a couple of examples of black-and-white thinking I come across all the time:

The common wisdom of the entrepreneurial collective is that you either slave away for the man in a 9-to-5 job you hate or take matters into your own hands and become an entrepreneur. In reality, you have so many more choices than that it isn't funny.

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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. Neither was wildly successful, but, when he saw the opportunity to turn around that startup, he jumped on it. Needless to say, that was a very smart and nuanced decision. And now he's doing the same thing again.

The truth is, all the successful entrepreneurs I know got there the same way: by entering a growth industry, enjoying their work, gaining experience, networking, and, finally, when the opportunity to run their own show arose, they took the bull by the horns and did it. That may not be the only way, but I bet it's a way you've never thought about.

Likewise, the current entrepreneurial drumbeat is to do what feels good, fill your head with inspirational quotes, be happy, and everything will work out great. Focus on your strengths and ignore your weaknesses. If it sounds positive, then it must be good. If it sounds negative, then it must be bad.

Like it or not, that's nothing but a bunch of utopian fluff.

All that glitters is not gold. Seeking instant gratification is never the path to long-term happiness and fulfillment. And in all likelihood, you'll never achieve great things without facing tough obstacles, crashing and burning, and finally rising up from the ashes.

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 be a multidimensional thinker.

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