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One of the benefits of getting older is that you allow yourself to shed the trappings of what you thought you ought to be, and just be yourself. You don't seem to really want to devote the time and energy into being a hipster, which after all is younger people in pursuit of fleeting fashion. Like you said, what is hip today is not hip tomorrow. The flip side of that is: there's nothing more ridiculous than an older person trying to be hip.
That said, you will also learn to separate the wheat from the chaff. Some of what is considered hip is also actually quality stuff, be it music or fashion or some other thing. Most stuff is crap, however, and that goes double for what is hip at any one time. Learn to appreciate what is truly good: it's stuff that was hip once upon a time but no longer is, like Charlie Parker's jazz or Mozart, or stuff that was never hip but was good anyway. Then you'll learn the truth: true hipness is knowing and appreciating the good things in life, whatever they are and whenever they came from.
I.e., my friend, 'tis time to grow up.
Channel your desire into some artform and just define yourself as being hip and keep your dull bland life as it is except for your art, you don;'t need talent - you have a computer and you are smart enough to use the internet so just make some art or musc or video. Don't worry about talent - most people don't have it and it doesn't matter. It is play for your mind and your spirit.
Most hipsters have boring dull crap jobs too. After work they shine. Nerds are the hipsters and hipsters are the nerds. The only difference is one does bad fashion with intent and the other doesn't.
Ever watch youtube? Anyone can be hip. There is something you can do to satisfy your urges. You just have to do it or something until you find it.
... when I was a young thing, I wanted to be a real hippie, yet no matter how long my hair and how flared my pants, and how much hash was smoked, I never quite felt that I was a real hippie, and although my friends all had the paraphenalia of hippiedom, I still felt that they were all bourgeois under the surface.
Of course, decades later I learned that even incredibly hip people like Mick Jagger just wanted to make a lot of money and get laid a lot. This was a great disappointment to me, because had I not been a hippie, I probably could have made more money and gotten laid more too.
Over time lot of my hippie friends became heroin addicts, and my wife, who was really cool, decided that life with me was not hip enough, left me, moved to a hipper location, and found another hipper man and filed for divorce. However, before the divorce was completed, she managed to kill herself with a heroin overdose. A few weeks later the hip boyfriend who had turned her on to the joys of heroin topped himself too.
All this was long ago, and now everyone perceives me as straighter than straight and I play Frank Sinatra and Ella Fitzgerald and read Jane Austen, and I am perfectly happy and keep my hair short so the baldness is less obvious, and get all my clothes at WalMart and am still better dressed than 90% of people, and bake bread and make jam and have a wonderful girlfriend who thinks I am really cool. Silly girl!
This kind of reminds me of a joke I made once - now that hipsters have adopted the nerd look, how are you going to tell the actual nerds apart?
I've always been one of the latter. In middle school I had a big head, glasses, secondhand clothes, straight A's, the whole deal. Being an immigrant also meant that I was always behind socially and culturally. I discovered Nirvana in 7th grade (3 years after they had stopped existing). That was my entry point into 'rock music' and what I perceived as a way out of nerddom. I hoped that going into a new high school would give me a chance to reinvent myself, but in high school I turned out to still be a nerd, just a nerd with contact lenses and an ill-fitting Metallica t-shirt. In college it was a Thursday t-shirt and a goatee. Now it's hair that covers half my face and a Blood Brothers t-shirt over a collared button-down shirt. But a nerd nonetheless.
One may very reasonably ask the question: if you dress like a hipster, listen to hipster music, appreciate hipster irony, and watch Adult Swim, what makes you a nerd rather than a hipster? But you know the answer to that as well as I do, don't you? The 'real hipsters', they're different somehow from mere mortals like you and I, just like I thought the real metalheads were in high school and the real punk kids were in college. They all lived and breathed their subculture with such ease, such perfect fit that it was impossible to imagine them ever not having been members of it. All of their friends were other, equally cool memebers of the same subculture, they had a seemingly endless supply of subculture-appropriate girlfriends, and you would never see them at a show alone, fidgeting and trying to look busy between bands. The hipster in-crowd really seem like they came out of the womb sporting an ironic smirk and a miniature-sized Sonic Youth t-shirt.
The horrifying truth that people like us know is that being a nerd has nothing to do with how you look, dress, talk, or act, but how you think - the very core of your being that you can never change. You may very well be able to fool others with your impeccable wardrobe and tastes, but only after you have carefully calculated and agonized over every single detail of how exactly to present yourself. And what's worse is, you are completely aware of this, and hate yourself for being so 'fake', but at the same time, you have not the faintest idea of how one would go about being 'real'. And so you go on, every step you take feeling indeed like a fashion show, because you have no idea how to stop. And that, my friend, is the nerddom that you will never escape.
I would love to be Dr. Phil (or my mom) right now and comfort you with some trite crap about how everyone actually feels this way inside, and all the confident, fully adjusted hipsters you see smirking ironically at shows and at record stores are actually going through the same existential acrobatics deep down. From my experience, however, I highly doubt it, or at least that it's as acute for them. But the upshot is that hipster culture's absorption of and friendliness towards nerddom will have inspired a good number of actual nerds to at least superficially join the movement. So don't assume that you're the only impostor in the ranks. Look hard enough, and you'll find plenty of people like yourself (and like me).
My point is that, as your unhappiness after your attempt to live a hipster-free life shows, you will feel uncomfortable and self-conscious wherever you go, whatever lifestyle you try to lead. And if you're going to feel like an impostor anywhere you go, you may as well be among people who listen to better music than Coldplay :-)
Disclaimer: The link below is a perfect example of a carefully contrived attempt at hipsterdom, as is my reading of Salon and posting of this letter.