Instead of waiting for something to go wrong and then conducting a post-mortem, conduct a “pre-mortem” by imagining it went wrong then using the power of hindsight to deduce the likeliest reason it went wrong.
People dramatically under estimate how many decisions one has to make before shipping the v1 of even the simplest product. They all seem obvious in retrospect, but so, so much thinking had to happen to ship something like "press a button, get a ride."
One of the biggest reasons it gets harder to do new things as you get older is that new things are generally undignified at first (indeed, this is an excellent heuristic for discovering them) and the older you get, the more dignified you're expected to be.