“Yeah, that didn’t work out so well but it’s ok, I didn’t care that much.”

Whaaaat? The “not caring” crutch is corrosive. Once you learn how to “not care” it’s a hard habit to break. Instead try living your life caring intensely. You’ll find there’s satisfaction in the very act of committing. And putting yourself out there will result in a whole bunch of good things: more energy, more momentum, increased probability of accomplishing your goals.