As entrepreneurs we all experience plenty of rejection. When I think about the most impactful rejection I ever received, I can vividly remember my first investor meeting nearly 15 years ago.  I was 20 years old, palms sweaty and pitching an online rebate idea that I came up with.

Half way thru my pitch I noticed the investor beginning to wonder off into his own thoughts. He formed this sort of smile grin thing while continuing to stare right through me.  I continued through my presentation until I began to feel like my whole vision was amusing to this man!

 What he said at that moment would take me several years to fully un-pack.

“you know…I’m not going to invest, but you may actually pull this thing off because you don’t know any better.”

Needless to say, I took offense to his words and immediately fired back with this “who are you to tell me” type of attitude. Looking back on it, I also realize how arrogant I was in those days.

So…where’s wisdom in these words?  

Well, it wasn’t until several years later in a cocktail party conversation with this investor, that I actually understood what he meant by this.

This was not meant to convey that I was incompetent or that my presentation was lacking.  It was an accurate observation that because I had yet to experience the windy road of entrepreneurship (like this man had) I probably didn’t know enough reasons why I couldn’t succeed and therefore, I had the advantage of being less likely to get bogged down with details and biases that might stall most people.  

Sometimes when we know too much about something we can’t help but to see all the twists and turns in the road ahead.  This can lead to asking the wrong kinds of questions.

Another way to look at this, think about going to the gym in the morning. Some mornings you wake up and begin to think about all the steps involved like getting out of bed, finding your socks, sneakers and heading to the gym all before the actual work out begins!  
Now think about a morning when you just sprung out of bed and went to the gym without thinking about it.

Same task but it felt different… why?  

Maybe that day you were thinking about something else, something exciting you needed to do at work for example.

As humans, we have a mind that can make things seem over-complicated to a point where we risk stalling our own momentum.  There’s a steep upside to understanding how this works because you can literally hack your own mind to gain advantages in almost any situation.

I’m not suggesting that entrepreneurs ought to ignore reality and hard lessons from the past to better evaluate opportunities. However, I have observed that it can be beneficial to try and balance complex thinking with simple thinking.