The only way to learn some lessons is to have something you care about blow up in your face. That's the cost of the lesson. Sometimes it's not worth the price of admission.

Steve Blank is a celebrity of sorts around here, but who is to say that that experience, as terrible as it was at the time, wasn't responsible for setting him up for his future successes?

I'm somewhat earlier in my career, and undoubtedly have similarly devastating events waiting for me, in addition to the select few behind me. Framing those as "learning experiences" softens the blow considerably when things don't go as they "should".