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February 13th, 2020


Are you a pessimist or an optimist?


Despite people’s likelihood to answer this binary question, it’s a ridiculous and potentially damaging question for the very reason that it is binary.


Can we not be somewhat optimistic and pessimistic?


Is it possible to be a pessimistic optimist?


Or an optimistic pessimist?


These might sound like an attempt to combine words in superficially pedantic ways, but the intention is a bit more genuine.


For one, there’s that old adage:


Hope for the best, expect the worst.


Does that not sound somewhat like an optimistic pessimist?


In the realm of business, startups and well, generally trying anything, being an optimist is touted as the superior perspective in this binary, and for one core reason:


The optimist is more likely to try something, and keep trying when things don’t work out. 


In this case, even if the optimist never actually learns, they can still succeed by sheer luck of just trying random things.


In comparison, the pessimist is less likely to take action because the pessimist does not believe that action will accomplish what it aims do to.  Pessimists might disagree with this by claiming that the action they do take is with the belief that it will result in the desired effect.  But an optimist might say the same thing.  But given the two perspectives, the optimist is far more likely to add the caveat that something unexpectedly good might also happen, and therefore make it worth doing.  The truly diehard optimist will claim that every action, no matter how ill-formed the result has some sort of silver lining.  And as impractical as this might be when it results in recklessness, it’s certainly a better mentality from a subjective point because the optimist –if true to their belief- can’t really get beat down in the way a pessimist believes by implication of their lack of action.


But, we can combine these two perspectives.


An optimist can strive to accomplish some good achievement, but also maintain a pessimism about the effectiveness of the plans that have been laid out to get there.  It might seem more even-keeled to balance optimism with skepticism that one’s plans will work, but examine the difference in the result when a plan actually does work.


The skeptical optimist is going to be pleasantly surprised,


whereas the pessimistic optimist who takes the action anyway, will prove themselves wrong when the action succeeds.


Now which is a more useful experience from an emotional point of view that seeks to move forward?


Being pleasantly surprised?


Or being proven wrong?


In the short term, being pleasantly surprised sounds like a better deal, for the superficial reason that it sounds like a nice experience, but that’s not the question.  Which experience is actually more useful?


Proving one’s self wrong is undoubtedly more useful because it allows a person to become more comfortable with being wrong.  This is important because all of our inability stems from flaws in our assumptions and our perspective of the world.  It’s only by rooting out those flaws and correcting them that we gain a clearer understanding of the reality that we’re dealing with and thereby gain greater agency.


While the skeptical optimist might passively assume their thinking is wrong in some ways, the pessimistic optimist knows their thinking is wrong in some ways and actively seeks them out as opposed to waiting for the pleasant surprise of something going the way we want.


The pessimistic optimist holds an idea in their mind and then tries to prove themselves that it’s not possible by taking all potential action that might make it happen.  This method is far more robust than the wishy-washy hope of the skeptical optimist.


Our outlook is a double-edged sword, and the pessimistic optimist remembers to use both sides.


  1. An optimistic pessimist is impossible. You simply… can’t really Hope for the worst and expect the Best. That’s simply a contradiction, because if you are hoping for anything, then that’s going to be some sort of ideal, which would also be the best.


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