Zen & the art of startup advice

A dirty secret of “startup advice” blogposts is that, aside of the placebo effect, the advice is not terribly useful. Why? Well, if you tried to synthesize all of the available advice into a single coherent framework, you would quickly realize that the aggregate “advice framework” is deeply self-contradictory.

Self-contradictory advice is fascinating. If you aren’t familiar with the cold-reading techniques that “mind-readers” use, I highly suggest taking the time to study them. One technique, known as “The Rainbow Ruse” is especially relevant to the discussion:

The rainbow ruse is a crafted statement which simultaneously awards the subject with a specific personality trait, as well as the opposite of that trait. With such a phrase, a cold reader can “cover all possibilities” and appear to have made an accurate deduction in the mind of the subject, despite the fact that a rainbow ruse statement is vague and contradictory. This technique is used since personality traits are not quantifiable, and also because nearly everybody has experienced both sides of a particular emotion at some time in their lives.

ie: “I would say that you are mostly shy and quiet, but when the mood strikes you, you can easily become the center of attention.”

Using these techniques I could easily make all sort of statements about entrepreneurship, hiring, fundraising, big companies, etc. and sound believable/sensible.

Let me be clear though, I don’t think that anyone writing this sort of advice is intentionally using these techniques to manipulate the audience. Rather, I think that it uncovers one real truth of startups, and life in general: nothing is black-and-white, and in fact, much of succeeding in life consists of being comfortable sitting with contradictory information.

The discomfort caused by holding conflicting information about something has a name: Cognitive Dissonance. Some psychologists would argue that most personality disorders are essentially symptoms of the various strategies people take attempting to cope with Cognitive Dissonance. If you are a highly-functioning person, you likely don’t have a personality disorder, rather you are trying to resolve your Cognitive Dissonance in a constructive way: acquiring knowledge and experience with the expectation that in a fair world you will be rewarded for your hard work. (Alternately, you could be a highly-functioning psychopath )

To resolve our anxiety in the most productive way we can, we stare at our glowing screens looking for Truth, for Meaning, for some sort of concrete resolution. We want to stamp out the gripping fear lurking in the back of our minds, the Fear that we aren’t exactly sure what we are doing, and that things all seem shinier and easier when other people do them. We create linear narratives that make us feel comfortable knowing: 1) There is a reason things happened the way they did. 2) The reason things happened is both knowable and easily understandable. 3) We can digest all of those learnings from reading a 1000-word blogpost. The Success that we read about is easily attainable, you just need follow these 5 simple rules, or find a co-founder, or raise an angel round, and then everything will get way easier, right? Anxious people eat this stuff up… anything to cure the squishy uncertainty in the pit of their stomachs.

Ben Horowitz did a great job of capturing his conflicted internal monologue as a CEO in his recent post, The Struggle. Additionally, this amazing installment of Peter Thiel’s Stanford class notes is focused on the extreme and contradictory traits that founders exhibit.

So how can we keep our “advice filter” in good operating condition? Beware of black-and-white thinkers. Beware of people that present very simple narratives as the explanation of incredibly complex events. Don’t take anything you read too literally. Be comfortable with the fact that much of what you feel will be squishy and complicated. Realize that everyone feels this way, it’s just that some work harder than others to cover it up.

There is a self-contracting mantra that I keep in the back of my mind. The goal is to remind myself of the shades of grey, of the inherent contradictions in any situation, and to smooth out the roller-coaster of emotions, emotions which are just as dangerous when things are going well as they are when things are going poorly. The mantra goes something like this:

Things are much worse than they seem, also, things are much better than they seem.


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