When you remove “fail better” from this context, the first thing it loses is its rhythmic frame. “Fail better” is meant to resonate with the many other curt phrases that make up the passage, which together create a kind of vibration in Beckett’s text. This vibration, rather than any plot (“Worstward Ho” doesn’t seem to have one), the way these phrases respond to one another, creates the text’s main through line. There is an important thematic element to the original context of “fail better” as well: the singsongy cadence of Beckett’s prose makes it clear that failing better isn’t supposed to usher one on to eventual success. Ever trying and ever failing are all there is. In fact, the entire text is about the way in which failure leads not to eventual salvation but inescapably toward frustration. (The narrative, such as it is, of “Worstward Ho” concerns a visit to a graveyard.)
Does the quote’s provenance matter? In the context of an investigation into what tech calls thinking, yes. Firstly, because the way it is quoted is deeply revealing of how Silicon Valley quotes ideas in general. There’s a whole register and context you have to un-hear in order to end up feeling cheered by “fail better.” Secondly, the particular way in which Beckett’s quote gets misappropriated suggests certain ideas he was very interested in and that the tech industry has trouble talking about. The very thing Beckett was after—failure as a condition of life, failure removed from the retrospective halo of eventual success—is something that the new tolerance for failure has, paradoxically enough, all but eradicated. By taking away failure’s sting, the tech-mantra version of “fail better” has eliminated things only that particular sting could tell us.
Mark Zuckerberg may have encapsulated Silicon Valley’s gospel of failure better than anyone in his address to the Harvard class of 2017: “J. K. Rowling got rejected twelve times before publishing Harry Potter. Even Beyoncé had to make hundreds of songs to get ‘Halo.’” Those kinds of lists are everywhere in Silicon Valley, and they are perfectly meaningless. After all, the fact of rejection is no more a testament to the fact that one should keep going than it is to the fact that one should not.
The numbers cited are impressive only to people outside the fields these numbers come from. Anyone who’s written a novel will tell you that just twelve rejections is a sign of some pretty smooth literary agenting. And writing a hundred songs to score a hit would likely be an excellent ratio for most people in the music industry. Narratives like this repackage the way trial and error already work across our culture into a kind of salvation narrative. Which ironically removes the “better” part from “fail better.” Cass Phillipps found that as FailCon grew, “sharing your postmortems became cool,” but “only really after you’d become successful some other way.” There were lessons to be gleaned from the event, but those lessons became less and less about failure and more and more about success. The original vision that had made FailCon, and other events like it, so interesting was that it wanted to linger on how it feels to be in the middle of failure, on how to have an honest conversation about failure while one is failing or at least has not yet succeeded. But this was something FailCon wasn’t able to provide.
Somewhat ironically, then, FailCon became a victim of its own success. In 2014, Phillipps canceled FailCon San Francisco, telling The New York Times that “it’s in the lexicon that you’re going to fail.” An event that had been conceived as an antidote to hagiographic developers’ conferences and tech booster-fests like TechCrunch Disrupt had become an extension of these events. It was emblematic of the way failure got co-opted by the top, by those eager to show that, yes, they too had some hard times, before they drive away to Atherton in their Model X. Open talk about failure had started out as an important corrective, but it had been swallowed by the system.
Around the time Phillipps decided to shutter FailCon SF, Elizabeth Holmes put up a Michael Jordan quote in the Theranos headquarters in Palo Alto that said, “I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.” The company made a fetish of the failure discourse: its main product, the blood-testing machine called Edison, was named after a famous (and probably misattributed) quote from Thomas Alva Edison—“I have not failed 10,000 times. I have found 10,000 ways that won’t work.” As with almost any artifact associated with Theranos, this obsession with getting it wrong now seems almost cosmically ironic—not because Theranos ultimately failed, but because Theranos wasn’t actually playing. What shots was Theranos even taking that it could have missed? What ways did it find that didn’t work? Thanks to the startup’s incredible secrecy and its legal war machine, we still don’t know. Now it is up to the U.S. District Court in San Jose to figure it out.
One thing the misappropriation of Beckett’s “fail better” has in common with the Jordan and Edison quotes is its mode of address: they are exhortations to self-optimize, addressed to a single individual. They seem out of place in the lobby of a large company and more appropriate in a freshman dorm room, where one single person can look up at them through tears of frustration from time to time. Silicon Valley founders, inventors, and moneymen routinely embrace the first-person plural when they’re really talking about themselves—although they
