I originally saw "fail upwards" in alpinist Mark Twight's writings[1] ten years before that: his sense is to keep going up and over the summit even when things have gone terribly wrong: you may no longer have the option to descend the way you came up.
[1] "Extreme alpinism" (passage can be found on google books)
Urban dictionary (http://www.urbandictionary.com/define.php?term=fail upwards) dates this term 2009.
I originally saw "fail upwards" in alpinist Mark Twight's writings[1] ten years before that: his sense is to keep going up and over the summit even when things have gone terribly wrong: you may no longer have the option to descend the way you came up.
[1] "Extreme alpinism" (passage can be found on google books)