I've always had really high expectations for myself since I was young. I thought I would either own my own business, travel all over the world, have tons of friends, bang LA 10's etc. I'm a hard worker and like to do things differently so I thought I could make it happen fairly easily. As we all know life is not that simple and sometimes you can only do so much.
Fast forward to the present day. I'm 28 and I have a solid job, rent my own place, have a pretty nice car, produce rap/hip hop music, own lots of cool stuff etc. I know I'm doing better than others and I should be thankful for what I have but I always feel like it's not good enough. That voice in my head tells me I need to do more and I should be more successful, have more friends, more sex partners etc.
Sometimes my high expectations for myself push me to work harder and try new things to be successful but other times it just makes me depressed that I'm not where I think I should be. So how do you guys deal with it?
TLDR: How do you deal with not living up to your own expectations?
First of all, success is relative and you should be proud of what you have accomplished. You are still a baby (relatively speaking) and have the rest of your adult life to make good on the expectations you had of yourself.
As for me, the hardest thing to accept is that pursuing one dream/goal ultimately came at the expense of another. When I was younger, I thought you could have it all (successful career, happy family etc.), but I realized in my late 20s and early 30s that in order to be really good at what I do professionally (professor/researcher), it would make it really difficult to maintain a healthy and fulfilling relationship. I'm now 37, single and childless - the closest thing I have to a relationship is that I am involved with a married woman, but that's a whole other story. I don't necessarily regret this outcome, but there are people who can have it all... I'm just not one of them. I tend towards extremes, and over time, I accepted that balance probably isn't in the cards for me.
With all of that being said, I personally don't want to be happy (in the sense of accomplishments). I have always felt that happiness habituates contentment, contentment habituates complacency, and complacency habituates laziness. The moral of the story being that the moment that you are happy with your station in life, is the moment you stop trying to improve - you should constantly strive and be better, but what "better" is can mean different things to different people (money, material things, friendships etc.).
Also, be kinder to yourself. There are going to be times in everyone's life where we didn't live up to expectations (either our own, or what others have of us), and that's okay. Beating yourself up over it does nothing but undermine your growth with guilt/resentment.