Sometimes, it's important not to care.
Obviously, you shouldn't be indifferent to everything, but in a way, not giving a fuck helped me get out of my comfort zone.
When I was in elementary school, I was a very shy child. Mainly because I was afraid of what other people would think of me if I did muster up the courage to say something. I would only speak when the teacher called on me, and would rarely talk to other kids in my class. I cared too much. If I spoke in class, people would be surprised that I did, and if I didn't, I would be asked why I didn't.
It wasn't until the end of high-school and especially the beginning of college, I simply got too tired to care about anything. Now this could have been a pretty bad thing, but it also leads to some pretty good things too.
For one, my confidence boosted. I started being less self-conscious about my appearance and focused on myself and what I actually did care about. I started speaking up more and getting more involved.
Most importantly, my attitude made me less afraid to do things that were out of my comfort zone. I literally took every opportunity that I saw. If the opportunity works out, great, if it doesn't, who cares. Move on.
I started applying to and getting involved in anything that I saw. I would think "just do it, who gives a shit." This allowed me to get my job that I absolutely love now, and have taken up some leadership positions school. I have taken classes I was not interested in, and ended up liking. I entered in the UIC Art Fest and ended up winning, and am participating in it this semester again as well. I applied for a leadership position last minute (a why not? moment) for an association at UIC that I was a part of, and got it. I realized that the reason I wasn't achieving certain things in life wasn't because I wasn't good enough, but because I cared too much. I cared to the point that I was too afraid to try anything. I was constantly doubting myself and would psych myself out of doing anything I was interested in. It wasn't until I got to my lowest that I realized what I was doing wrong.
When you stop caring so much and just allow things to happen without overthinking, things will come to you. But you have to go out and snatch those things up. Do things that make you uncomfortable, because, at the end of the day, no one will give a shit about your stupid mistakes or "embarrassing moments", and neither will you.