Why The Best Entrepreneurs are Cynical Optimists


I admit that I’m cynical. I come by it naturally, a product of my life experiences. Cynicism is generally not admired. My wife hates my cynicism. She says that it often comes across as contemptuous and irritating. Some of my business colleagues feel I am overly fixated on problems. But I am also an optimist.


I try to reconcile the two. If I wasn’t a cynic I wouldn’t find problems to fix. My cynicism helps me spot opportunities and the improvements they need. If I wasn’t an optimist, I wouldn’t have the guts to tackle these opportunities. My cynicism plots the path, my optimism causes me to act.


Psychologists tell us that being cynical is not healthy. Critics warn that cynicism will cause you to miss out on forming deep friendships and love. Neither is true for me. People say that cynical people are often depressed and have high rates of diseases. I’m far from depressed and as for diseases, so far so good. Those same critics say that cynical people are just not nice. But nice is relative. If status quo is nice then certainly I am not.


I believe it is too easy to dismiss cynicism as bad. Studies tell us that by age forty-four our cynicism starts to grow. Mine started earlier. My first bout of true cynicism arose in graduate school (more about that later). It seems pretty easy to see why the older we get the more cynical we become. Life is hard. Sometimes it is not fair. Not all people are honest. The older you get the more experience you have with people who disappoint you.


According to the Oxford English Dictionary being cynical is:


Believing that people are motivated purely by self-interest; distrustful of human sincerity or integrity.

This doesn’t adequately describe my feelings. I don’t think that everyone is dishonest or insincere. I just know that those type of people exist… everywhere. I have run into my fare share.


The Oxford Dictionary also defines optimism as the opposite of cynicism. Being optimistic is usually thought of as good; cynicism bad. But for me there is room for both. And without both most entrepreneurs would fail.


Entrepreneurship is based on being cynical of the status quo while being optimistic of your potential for success — sometimes naively overly optimistic. (I think I am going to use this to define entrepreneurship in the future.) Entrepreneurship is about fixing problems, improving things, finding better approaches, creating change and making life better. Optimists don’t pursue great, they are happy to settle for good.


In business, as in life, cynicism has its place and wielded appropriately can improve almost everything you do, from forming relationships (even romantic ones) to managing your company. You just have to understand when and how to use it for your benefit rather than have it negatively weigh down your optimistic attitude. Most of our interpersonal relationships could use a bit of cynicism.


Using Cynicism to Communicate


Most of us fall prey to confirmation bias. That is the process of interpreting evidence that reinforces your existing opinions, thoughts, ideas or decisions, while ignoring any evidence to the contrary. We all do it. From our love-struck first meeting with the partner of our dreams who we believe to be perfect, to business decisions about which markets to attack. We put on blinders or at least rose-colored glasses that filter out the negatives of whatever decision we are making.


Unfortunately, that bias interferes with our objectiveness. We expect that everyone will see the accuracy of our opinions. This same confirmation bias is what is causing the conflicts that we are seeing in our world today. We get fixated on what we think is right and can’t accept evidence or opinions that don’t agree with our point of view. We often use social networks to screen out people who don’t think the same as us.


Our written and verbal communication follows this same pattern. Human communication is flawed. Remember the game of telephone you played as a child. Despite your best intentions to communicate precisely, often what was said was not what was heard. More often than not, the message given to one person changes as he or she passes it along to the next person in line. By the time this has been passed down the line the message told doesn’t resemble the one we originally set in motion. Our bias is that we know the message was clear and we expect it will be communicated accordingly. But we are wrong.


Most interpersonal communication, one on one, is even worse. Optimistically assuming the person you are communicating with is even listening (cynics know this is usually not the case) is the start of our failure. Even when we do listen to what people are trying to tell us, the response we give is often superficial and insincere. We spend most of our listening time, thinking about our retort rather than concentrating on the message received.


Our response to the communication we receive is generally not intended to be completely honest. For example, Venture Capitalists, when they are checked out on a deal you are pitching will often respond about how interesting your proposal is. It’s only after you leave that they shred your pitch deck.


Sales prospects respond to your sales pitch by telling you how interested they are and that all that stands between you and the sale is approval from their manager or their board. But you never hear back from them and wonder what went wrong.

Dates tell us how much fun they had on their first date with us. Yet, they never return our next call.


Are all humans liars?


Most humans don’t like to offend people, at least not directly to their faces. We call these white lies – small inoffensive untruths, not intended to hurt anyone. Sure, there are some people who get their jollies telling people how stupid they are. I had a professor like that in graduate school. He relished the opportunity to slay his unsuspecting students. His approach was refreshingly honest. Only problem was this is what fed my fledgling cynicism. Other than someone like this professor, most people can’t handle the complete honesty that authentic communication entails.


When a friend asks you how the new outfit they just paid a lot of money for looks, would you ever say it makes you look fat? Not and still remain friends. To some degree, we all can identify with the Hans Christian Andersen fairy tale about the Emperor’s new clothes. Naked or not, we generally won’t respond genuinely.


In sales we call optimism happy ears. Sales people spend most of their time getting turned down or ignored by their prospects. When they finally get someone willing to listen to their pitch, they get understandably excited. Even a lukewarm response may sound to them like a resounding YES!


Managers encounter this problem as well. Their communication with their teams seems clear to them. But their staff did not hear it as well as they may expect. Employees smile and accept a direction they don’t prefer. It is highly unlikely they will express their disdain to their manager out loud.


Like all children, when my daughter was younger, she used to ask for outrageous things. (Come to think of it, she still does.) Rather than respond with a resounding NO, my wife and I would often retreat to: We’ll think about it. I believe they tell you in child rearing 101 that abrupt NOs are not preferred parent-child communication. Unfortunately, our unwillingness to be direct was received as a clear and committed YES, and was treated as if it were our promise.


The Heath Brothers in their best-selling book, Made to Stick, referred to a study done in 1990 by Elizabeth Newton. She used a simple game where the players would sing a song in their heads and rather than sing out loud, they would instead tap the out the rhythm. Most members of the study expected their “listeners” would identify the song they were tapping. But only one in forty did. What happened? The expectation was that the tapper was clearly communicating. Only problem was, she wasn’t.