We uphold courage as a virtue of which we probably all wish we had more. Why we wish we had more, and don’t just decide to have more is that courageousness is a difficult attitude to sustain. It requires us to push our convictions forward in the absence of a guarantee, to shed our defensiveness when faced with the always unknowable future. This can feel dangerous, risky, maybe even irresponsible in certain contexts. But I want to play the other side for a moment. When faced with that same unknowable future – what options do we have besides being courageous? And are they really safer? 

    Thus emerges the figure of the pragmatist. The one who is risk-averse; the foil to the heads-in-the-cloud idealist whose aspirations most likely outstrip the reality of the world. We laud the pragmatist for different reasons: for being grounded, maybe even wary. Safe. A pragmatist, in the way we currently conceive of one, is someone who knows how to grease the wheels of the present, to keep us in check and maybe even to keep us safe. 

     I’m going to show my hand perhaps too early here, but I think this is a false dichotomy. I think we have lost the sense of what pragmatism was originally supposed to mean, which has caused us to lose the sense of what it means to be both pragmatic, and on what grounds we allow ourselves to be courageous. In recovering some of the original spirit from where pragmatism came from, my goal is to challenge the assumption that there exists such a thing as a “risk averse” option when faced with an unknown and unknowable future. Pragmatism was never about finding the safest path forward, but as a way of reasoning that led us, ideally, to face uncertainty with less teeth-chattering and apprehensiveness. 

    Pragmatism as a school of thought is an essentially American contribution to philosophy (yes, we might not have invented democracy like the Greeks, or metaphysics like early Islamic philosophers, or smoking cigarettes outside of cafes like the French, but we did do something). Pragmatism emerged around the late 19th century and early 20th century with figures like Charles Sanders Peirce, William James, John Dewey and W.E.B. Du Bois. At the risk of over-generalization, pragmatism was a way of thinking that sought to deal with pluralism in a way that could accommodate multiple different perspectives and ways of looking at the truth. It grounds our discussions about our ideas and beliefs not so much in abstract terms, but to be evaluated on the real-world actions and utility they provide for our lives. What William James called their “cash value,” in a very American way of phrasing it.

     It was a way to loosen up our ideas – take a step back from our absolutes, the things from which we’d never budge, and to bridge the gap between how we think and how we act. Crucially, this was a different way to think about truth. Something being true, in a philosophical sense, for the pragmatist, was when the idea becomes useful, leads to an increase in human flourishing. 

    My own interest in pragmatism is tied up closely with my interest in William James, for whom the efficacy of pragmatism was a life-or-death issue. James, “the father of American psychology,” published three extraordinarily influential books: The Principles of Psychology, Essays in Radical Empiricism, and The Varieties of Religious Experiences, along with a ton of essays that ranged from super academic pieces on psychological concepts, to larger, more accessible meditations on what it means to believe in something without infallible evidence. 

    The latter – what it means to believe without evidence – is something he correlated closely with pragmatism, and with bravery. He wrote an essay somewhat dramatically titled “Is Life Worth Living?,” which, for my money, is one of the more profound explorations about what it means to be courageous. In it, he takes the eponymous question as both our most deeply felt and one in which we cannot remain neutral. So, when tackling this question James appeals to the same sort of reasoning he lays out in another one of his most popular essays, “The Will to Believe,” where he writes

To preach scepticism to us as a duty until 'sufficient evidence… is to yield to our fear of its being error is wiser and better than to yield to our hope that it may be true. It is not intellect against all passions, then; it is only intellect with one passion laying down its law. And by what, forsooth, is the supreme wisdom of this passion warranted? Dupery for dupery, what proof is there that dupery through hope is so much worse than dupery through fear.

     We live in a world of maybes. This is what James stresses time and time again. And so when we are faced with the question of what makes life worth it for us – there is no guarantee we will be right, that our beliefs about what sustains us might turn out to be true. When faced with a dilemma like this, we might be tempted to punt the question altogether – to be an irascible skeptic, to try and remain on the fence until certainty can be obtained. But here again, James has a response.

If a thinker had no stake in the unknown, no vital needs, to live or languish according to what the unseen world contained, a philosophic neutrality and refusal to believe either one way or the other would be his wisest cue. But, unfortunately, neutrality is not only inwardly difficult, it is also outwardly unrealizable, where our relations to an alternative are practical and vital. This is because, as the psychologists tell us, belief and doubt are living attitudes, and involve conduct on our part.

Living attitudes.

‍We inhabit not just the mental landscape of our attitudes, but the real life consequences of them. “If, for instance, we refuse to believe that the room is getting cold, we must leave the windows open and light no fire just as if it still were warm. If I refuse to believe that you are worthy of my confidence, I must keep you uninformed of all my secrets just as if you were unworthy of the same.”

     The pragmatic approach to this world of maybes is, to James, to stake one’s life on a possibility. That our belief in something actually might bring it to fruition. That belief helps create the fact. There is no certainty that you’ll be right, but the pragmatic approach to courage is to acknowledge that making no decision – that to play it safe – though it may feel passive, is just as much a decision as making a leap towards an unknown future. That the most dangerous, risky move one might make is not to move at all. Courage, too, is a living attitude, and perhaps the most classically pragmatic of all. For if pragmatism ultimately means willing to judge our beliefs on the behaviors and actions they produce, knowing in advance there is no pre-set truth or path to follow that will lead us to a foregone conclusion, then the best we can do is to take a less defensive posture towards the unknown. In his essays, James literalizes the popular “leap of faith” dictum by posing the following scenario: you’re climbing a snowy mountain and suddenly the ice cracks, leaving an abyss over which you need to jump. This is a decision you have no choice but to make. There is no “retreat.” Believing you will make it to the other side will much more likely lead you to actually making it to the other side than being overcome with doubt when it’s time to make the jump. A living attitude, indeed. 

     I say this all because I often introduce myself as “Andy”, a person at IDEO who “helps our clients navigate critical junctures in their business life cycles.” This is, broadly speaking, true. My first conversation with our clients usually revolves around their most critical business needs. How to stay ahead of the curve, how not to fall prey to stagnation, how to create something genuinely new and exciting. But this often can come at a tension with the broad landscape of risk aversion in corporate America. A fear to deviate away from what’s working, or what’s worked in the past. In this sense, though we may laud courage as an enviable virtue, we rarely are allowed to bring it to the workplace. If only due to that same existential dilemma James so eloquently detailed: inertia, fence-sitting, indecision, defensiveness. These are all our reflexive responses to an unknown future. They feel safe. 

     But what we learn from James is that no-decision – the “safe” option, is the most dangerous decision we can make. To my mind, this is incontestably, empirically true. Technology changes fast, culture changes faster and as much as we wish we could occupy the role of the oracular, infallible trendspotter, no one can predict the future. One day you’re Blockbuster and you shoo away some company called Netflix who wants you to buy them for $50M, the next day you have one last remaining store in Bend, Oregon. One day disco sales are up 400%, the next day the Chicago White Sox are hosting Disco Demolition Night (a cultural outrage that should’ve never been allowed to happen).  

     So here’s my New Year's challenge: reframe “continuing business as usual” as an active choice, not just a passive acquiescence to a future that seems safer because it looks so much like the past. A world of maybes. “We stand on a mountain pass in the midst of whirling snow and blinding mist through which we get glimpses now and then of paths which may be deceptive. If we stand still we shall be frozen to death. If we take the wrong road we shall be dashed to pieces. We do not certainly know whether there is any right one. What must we do?” 

     We really only have one choice: have the courage to build the path as you walk along it. It’ll certainly be better constructed than the one made out of teeth chattering and indecisiveness. After all, how did Henry IV greet the tardy Crillon after a victory had been gained? “Hang yourself, brave Crillon! we fought at Arques, and you were not there.” Fighting words, for sure. But then again, what it means to be both pragmatic and courageous is to refuse to be a bystander in your own life. Don’t be tardy. Don’t let the world pass you by. More courage!