We live in an age with a curiously cheerful relationship to failure.  But that optimism was built for a world that no longer quite exists. For three generations now, doing everything right– getting an education,  holding down a full-time job, following the sensible plan–  has stopped reliably buying a house or a secure retirement. When a single failure can be genuinely ruinous, the advice to dust yourself off and “fail fast, fail forward, fail better”  starts to sound like a privilege reserved for those who can already afford it.

So what actually is failure? Who who sets that standard?  Is failure really as generative as we like to tell ourselves,  or is that a comforting story that only holds up when the stakes are low?

Can a person fail at life, or only in it? And if our failures have become so devastating that no one dares risk them, is the fix a better attitude toward failing, or a world that stops punishing people so severely for it?

This week, we take seriously the possibility that our growing dread of failure is  a rational response to a world that has made failing unaffordable. The real answer, we suggest, may be less about how to fail better and more about how to build a world where other people’s failures aren’t so ruinous.

Grab a drink and join us as we fail our way through Beckett, Nietzsche, Kierkegaard, and Camus toward some clearer sense of what it means to fall short — and toward imagining Sisyphus, if not happy, then at least clear-eyed.

In this episode, we discuss the following thinkers, texts, ideas, etc.:

• Samuel Beckett — source of the episode’s unofficial motto, “fail again, fail better” (from the 1983 prose piece Worstward Ho)
• Stoicism 
• Gottlob Frege 
• Edmund Husserl — whose early Philosophy of Arithmetic, stung by Frege’s critique, gave way to the Logical Investigations and eventually phenomenology)
• Phenomenology 
• Bernard Williams 
• Moral luck 
• René Descartes, Discourse on the Method 
• Immanuel Kant, Critique of Pure Reason 
• Friedrich Nietzsche, On the Genealogy of Morals 
• Kobayashi Maru 
• Socrates 
• Aristotle, Nicomachean Ethics and his doctrine of the mean 
• Søren Kierkegaard, The Sickness unto Death 
• Buddhist philosophy — 
• Albert Camus , The Myth of Sisyphus