On the utility of being radically non-naïve
At the intersection of optimism and pessimism is a realism that helps one pursue creative ambitions, build successful organizations, and face calamity bravely
Pessimists sound smart, optimists make money - someone on Twitter.
This resonated with me. I am often a pessimist. The underlying reason often is a desire to sound smart. Having worked at companies where “seeing around corners” and chiming in with the one overlooked insight is highly valued, I have spent a lot of time in my career identifying what could go wrong in order to help mitigate that risk. I also often feel like there may be many people in the room that already see what can go right, so what’s needed is a balancing view.
But I am also often an optimist. Whether it’s the belief that “It will be great!” when my partner and I have departed on a trip for which we have planned very little and everything could go wrong, or the hope in dark hours in my lifetime.
I have found that optimism and pessimism are not so much uncontrollable, pre-ordained features of our identity we are required to live, and more like skills that we can activate when the moment or the team requires either to succeed.
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As a startup founder, there is a constant balance between irrational optimism and cold, hard pessimism. One has to believe that the improbable combination of skill and luck will work out and the company will succeed in order to make such a significant personal sacrifice let alone recruit a world-class team and raise capital. But one also has to be able to identify what is likely to be an obstacle so that the team can ruthlessly remove those obstacles to succeed, and have a backup plan if the original strategy doesn’t prove to be as effective as one may have imagined. It is my belief that a healthy balance of optimism and pessimism is necessary for accomplishment even if in tension. That tension between the two, both within an individual, and politely within a team, can be productive conflict.
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On September 30th, 1888, Nietzsche began his preface to The Twilight of Idols as follows:
To maintain a cheerful attitude of mind in the midst of a gloomy and exceedingly responsible task, is no slight artistic feat. And yet, what could be more necessary than cheerfulness? Nothing ever succeeds which exuberant spirits have not helped to produce.
So, is Nietzsche suggesting we all act cheerful even - and especially - when things are hard? It’s as if Nietzsche knew this tweet was coming in 2020 and provided the philosophical foundation for Internet wit 132 years earlier…
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I almost ended this essay there but then something nagged at me. I doubt that Nietzsche meant ‘cheerful’ in the contemporary sense of the word, and I feared that I was oversimplifying. Sure enough, Anderson and Cristy suggest that ‘cheerful’ to Nietzsche is more complex than a mere happy-go-lucky and positive attitude. Specifically, “For [Nietzsche], the right kind of cheerfulness is radically non‐naïve; it expresses the overcoming of justified revulsion at calamitous aspects of life through a reflective, higher‐order affirmative attitude.” Full abstract is here:
Robert Pippin has recently raised what he calls ‘the Montaigne problem’ for Nietzsche's philosophy: although Nietzsche advocates a ‘cheerful’ mode of philosophizing for which Montaigne is an exemplar, he signally fails to write with the obvious cheerfulness attained by Montaigne. We explore the moral psychological structure of the cheerfulness Nietzsche values, revealing unexpected complexity in his conception of the attitude. For him, the right kind of cheerfulness is radically non‐naïve; it expresses the overcoming of justified revulsion at calamitous aspects of life through a reflective, higher‐order affirmative attitude. This complex notion of cheerfulness turns out to have roots in Montaigne himself, and it must (according to both philosophers) be thought of as a kind of second nature cultivated through practice, as a kind of second nature. Understanding the meaning of cheerfulness thereby sheds light on the conception of philosophy as a way of life in both Nietzsche and Montaigne.
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And that is the unlock. Optimism as defined as a positive outlook is useful. Pessimism as defined as a critical outlook is useful. Just as the world is not simply good or evil, we as people must be more than just an optimist or a pessimist, and one approach as noted here is this concept of being radically non-naïve particularly when faced with calamity.
And what Nietzsche helps us realize, is that cheerfulness as naive optimism is not alone what is required for success. But rather, it is about confronting “calamitous aspects of life” and then “overcoming” through “reflective” and cultivated practice that is cheerful. It is not because of the blind acceptance of the unknown with a smile on our faces, but rather the transformation of the unknown to the manageable through practice that defines effective cheerfulness.
This same notion of overcoming underlies Nietzsche’s definition of ‘ubermensch’ (translation: Superman). But that story is for another essay another day.