The “fail small” advice is becoming more and more widespread. It’s meant to get people who make things out of planning mode and into execution by giving them the comforting notion that it’s safer to actually produce something than to plan it all out in advance. It’s good advice, but most formulation of it leave out a key detail.
The “fail small often” ideal makes sense: Don’t bet on a single outcome, but make small errors and keeping adjusting. It’s good and lovable advice. But what’s often missing in its common formulations is the part that makes it work. The part that happens after a failure is comparison. You have to be able to compare the results of failure to your objective. Merely failing a lot is not the point.
To do this you have to have two things. First, an objective. Second, a reliable way to compare results with the objective. Of course, I’m sure the advice dispensers imply you should do this, and those who successfully use “fail small” do indeed do it. But the point needs to be explicit if the advice is ever going to be useful for those who aren’t already good at using it.