It's one of the most exemplary pieces of new age advice.
Like any exemplary piece of advice, it fails (no pun intended) to acknowledge that context varies. Case in point, when we hear about "failing often" we might forget that there are at least two different types of failure.
Failing to act, and failing despite action.
I assume the "fail often" gurus refer to failing despite action when they spread their holy words. After all, you don't get to the "move fast, break things" mindset without actually moving (and fast). In short, yes you might fail. But you fail because you tried something different enough to actually risk losing something else.
However, not trying counts as failure to. Here, you fail not because you acted, but rather because you didn't. For example, you might have frozen in the heat of the moment. Or failed to realize that the moment demanded you to act in the first place. Or maybe the system in which you realized the need for action wasn't set up for action (i.e. "this is not in the protocol" or "that's not my department").
All things considered, I get what the "fail often" gurus are trying to achieve. But we have enough half-assed advice on the internet to not acknowledge the context in which we tell other people what to do.