I'm sure the scenery near the cliff is beautiful, and climbing can be a good experience. But then I don't really think failing the first few tries is a lost.
Funny enough, the first few things that I want to learn before a "self-optimize" includes what could happen if I failed (and how to recover from it). The combined knowledge makes the process safer (for your time and effort).
The first time I tried to drive a car, the first thing I asked the teacher even before I started the engine was "what should I do in order to make it stop?", because I expect mess ups, the knowledge on how to react to it might be valuable later.
BTW: Another thing that I've learned in my life so far is don't get too fixated on something. Life is short, putting your effort on one thing removes it from another. Not all optimization is required, which is true in software development as well as in life.
The city where I live got a few cliffs from mining operations, almost 90 degrees up down and very tall. I lived under one of them when I was little, but I never developed any passion for it. If I try to climb it base on my none-existing skills, I'll probably end up as a missing-person record and food for mountain rats. But I never feel any lost in my life for not able to climb those cliffs.
There are so many struggles we can commit our lives to fight against, the act of picking a good one is equally important as the fight itself.