HeresMyAccount: Well the way that you describe them, I'm not sure I'd call them "successful failures". Maybe I'd say that you've had some successes and other failures, or some successes and other things that you haven't gotten around to trying yet.
Generally a successful failure means you failed at your main aim, but gained a side benefit, that may indeed help you to be more successful in the future. Sometimes things can be looked at too black and white, when usually there are many shades of gray.
We advance through life learning from both our successes and failures in any case. That is what growth is all about.
At some point you have to face the end result of where you are heading, and decide if that's enough for you, or where you need grab some courage and push a few boundaries to improve your lot in life.
Or you can stay safely secure in a padded room, much like they might give you in a mental institution, to abrogate all risk of self harm ... perhaps even in a straight-jacket.
In any case, the choice is yours, and you are the captain of your ship.
I suggest you engage in some bravery and engage with life in a more meaningful manner. Don't succumb to your fears.
There are challenges but also rewards to no longer sitting on the fence.
P.S. Crevurre is a troubled soul, so best we ignore him until he shows consideration for others.