It's said that we learn best by making mistakes, but how much of it is tolerable?

I'm talking about implementing new technological solutions for professional projects. In the Singapore context, "professional" would mean that it must be either a 100% success or a failure that will never be known. And a 100% success for new technology is definitely too high an expectation. Hence, it's always the second case.

We know that technology takes time to be refined. People come up with good ideas, transform them into projects, discover problems, fix them, new problems come out, fix them again, new problems surface yet again, sweep under the carpet and ta da!!!!!!! New stuffs.........

How long can this last before we blow our own cover???