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.


Cynicism to the Rescue


Optimistically expecting that everything we say will be perfectly understood and the responses we get can be taken as the gospel, will only get us into trouble or at least leave us sadly disappointed. Once we dispel this naïve notion (or have this dispelled for us), we learn to approach all of our communication quite differently. Now armed with the cynical knowledge that what we say and do will not be well understood by our recipients, we can begin to behave differently.


Here are some hard-learned lessons that cynicism has taught me about communication.


Assume your communication is flawed. Don’t expect everyone will understand the words and intentions of your communication. Ask them questions to uncover what they understood and what they didn’t. Repeat as necessary. It is never acceptable to assume that just because you told someone, they owned the responsibility to act. Unless the recipient understands what it is you have been attempting to communicate, and you confirm that with them (see confirmation below) the only one who is at fault is YOU!


Expect that people won’t tell you the difficult truth. No matter how well intentioned, when you raise a touchy issue, it is unlikely that your audience will tell you how they really feel. Probe for objections. Try to understand which part is distasteful to them. Make it easy for people to express disagreement and acknowledge the inevitability of differences of opinion. During your conversations, ask the hard questions. You know what these are. These are the questions you are afraid to ask for fear of getting turned down. Answers that might indicate what you said was not as good as it sounded. Better to get a quick NO, then to maintain a false hope of a YES.


Anticipate problems that you have not yet identified. Confirmation bias blinds us to the flaws in our own logic. Try to put yourself in your communication recipient’s shoes. Think about how this affects them, not about how you see it. Approach your communication by considering what might be wrong with your logic rather than why it is right. There are a thousand reasons you can use to confirm you are right. Instead, focus on the weak link so you can shore it up.


Always have a backup plan. No strategy survives encounter with the enemy. Whatever plan you come up will likely need to change once it is put into action. Navy Seals assume that their best laid plans will not work. Their approach of: “Two is one and one is none,” refers to always having at least one back up plan ready once the first approach fails.


Post communication solicit a confirmation. There is only one way to find out if the recipient of your communication understands what you were trying to say. Ask! When you do, there are three possible outcomes. The worst outcome is no response. This is what happens when our communication or plan has crashed and burned. No response is a good indication that your request will go unheeded or that it was never received. Try again, perhaps using a different medium (a call rather than an email or vice versa).

The second to worst (or for you optimists, second best) outcome is an overwhelming positive response. While this may seem odd that I rate this second, sometimes this happens because the recipient is trying to please you, rather than agreeing wholeheartedly. You may hear things like: “That sounds fine,” even though it may not. Take this response with a measure of cynicism.


The best confirmation is one that suggests adjustments or corrections to your original plan or communication. When someone takes the initiative to make changes, it is pretty clear that they both understand what you were trying to communicate and are well on their way to agreement (with the adjustments they suggest). I have worked for years with a sales trainer who I believe purposefully made mistakes in his confirmation just to solicit these types of corrections.


Outright optimism may be pleasant and extend your life expectancy, but is not as productive as optimism tempered with a healthy dose of cynicism. Unbridled cynicism may be received as offensive and disenfranchising. When you find an entrepreneur with a mix of the two, you can bet she is capable of changing the world (for the better)! You might even consider making an investment in her company.

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