How do you deal with not living up to your own expectations?

I use to be super happy getting wasted, bumming around in piss stained pants, stealing whatever I needed. Didn't have no rent to worry about. No spirit sucking job to go to. Just selfish pleasures 24/7. Then I read a Jordan Peterson book and it ruined my life. I lapped up the fridge magnet platitudes. Yes, I could be a better person today than I was yesterday. I could eat muesli. I quit drugs. Quit fun. Got a job. Made money. Became successful. Got a mortgage. Became respectable. Productive. Now my life is a banal hell. I say things like hang in there to my colleagues. I mow my lawn. Pay insurance. Set goals. It's truly disgusting.
You would have fit right in here in Portland.
 
You would have fit right in here in Portland.

Portland? Nah Portland’s no good. I hitched through there when I got out of Nam. I was walking along the highway being like all super serious n shit, when this fat sheriff started bullying me. So I put on a carpet and jumped off a cliff. Then I shot up the town and had a little cry about all the gross Nam stuff I’d seen. They like, totally banned me from all off Portland. Said I was too rambunctious
 
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I drink and wonder off, pacing from here to there, and to there from here, I drink some coffee and eat some food, I listen to scientist youtube videos, and I keep on trucking and working when I get the chance, my bills get paid and the sun goes down.
 
Just live and be merry. You got nothing to lose really, you didn't choose to be born. So make the most of it as best you can possibly make it.
 
Portland? Nah Portland’s no good. I hitched through there when I got out of Nam. I was walking along the highway being like all super serious n shit, when this fat sheriff started bullying me. So I put on a carpet and jumped off a cliff. Then I shot up the town and had a little cry about all the gross Nam stuff I’d seen. Then they banned me for being too rambunctious
Hell of a story but they don't ban anybody around here. You can smoke crack/meth on public transit, shit on the side of buildings, set up camp on any street, assault people while yelling at the top of your lungs and people will just leave you alone.
 
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?

My imperfections are what makes me perfect. Fuck what other people think.
 
At some point i thought as shit area rat in positive case i would ideally get mediocre warehouse job and barely manage to live in mediocre part of the city

I have pretty good job and live easily in one of nicest neighborhood of the city, even saving money while at it

I surpassed realistic expectations

i did'nt surpassed dreams, but if you're adult (i'm 38) who gives a fuck
 
You have ambition and drive. Don’t stop and analyze for too long. Keep driving.
 
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