Dear Jack,
I have recently come to a sort of crisis that has left me questioning the very direction I've set myself in. I keep trying to scrape up enough money to escape my surroundings for a less familiar Surrounding, but each time I try some catastrophe results in my utter failure. My dilemma comes not from new ways to succeed but I'm more wondering: How might I keep up this fight in which I seem to be pitted against fate itself and avoid growing weary of exhausting my time and energy on fruitless attempts? To put it in more concise terms: How does one keep up their motivation in the face of a cycle of failure?
As someone who was relieved almost to tears that none of my long time friends asked at my 35th birthday "Gosh Jack, you've been playing in bands for 20 years now- how does that feel?"  I can tell you that Winston Churchill was spot on when he said, "Success is going from failure to failure without a loss of enthusiasm."  I am now 37, thanks.
dear Mr. cloth,
I occasionally experience a sense of paralysis right at the time of waking up from sleep. I cant tell if I’m dreaming or not and its scary. have you ever heard of such a thing?
Sure, this is a pretty common condition which occurs when the brain wakes from a deep REM sleep before the body does and is called "hypnopompic paralysis".  As you probably know during dreaming our nervous system paralysis itself to avoid thrashing about and annoying our girlfriends.  Hypnopompic paralysis can also be accompanied by a sense of falling into one's body (that happens to me a lot) and sometimes feelings of great joy!  If it's bothering you try not sleeping on your back, don't nap during the day and keep regular hours.  There are some pharmaceuticals for it but I’m not that kind of Doctor and to tell you the truth I like those kind of dreams.
Jack,
I come to you with my problem. I am a young writer/musician growing up in a town enthralled by corporations like Target. Independent businesses are smashed a month after opening. Local music is floundering. I find myself with nothing to do, and therefore nothing to base my writing on. I experience the same thing everyday. World/Inferno's music and lyrics have always been an inspiration to me, what do you suggest as a remedy?
Bust out man, no one's going to do it for you.  get out there and make some bad decisions, foolish romantic choices, put yourself through some cruel and unusual punishment and then you will find your question as naive as I find it endearing.
Dear Jack,
Why waltz?
  1. because jogging is bad for the knees
  2. because it's a dance which allows you to talk to your partner
  3. it encourages posture
  4. it freaks out the squares
  5. it confuses police when they arrive to break up the punk rock show
  6. it is a gateway dance to syncopation!
  7. holding hands battles anxiety
  8. it is how lovers dance in dreams
  9. because you have a heart
  10. and I would like to dance with you!
Dear Jack, Some time ago I became convinced I'd never see the state come crumblin' down, and gave up days of marching and congressman-calling for nights of Bacchanalian debauch. Still, I can't fight the lingering feeling that I'm running away. Is real freedom found within, or is all this drinking and smoking and window-smashing just turning a blind eye to oppression?
no, no, no- kissing is the most effective tool we have in fighting fascism, don't doubt it and don't stop it.
Jack, has the Jersey underground always been as cliquey as a high school from some television teen drama, or was I just blind to it for the past many years?
it has always been some kind of punk rock survival trait that we don't talk to each other except to maybe nod passing in the street before muttering "poseur".    the curse of our age is that we yearn for companionship yet prefer to fight alone.  pride is a sin and we confuse pride with dignity.  we got a lot on our minds and don't want to bother anybody with the weight of our particular world on our particular slouching shoulders. But it's the same world and most of us have the same tattoos.  yeah it has always been like that but there has also always been moments, been parties, when factions come together and that is what makes a scene.  kids who survive more than a couple of years will always end up holding hands; they will be the only ones who understand what each other are talking about.
I think I may just bother you again, to tell you to hurry up and come to Australia. I'd really like that. You guys could even stay at my house, regardless of what my parents might say, its not as if though they could do much if you're already here. I promise that there will be much to drink, and I hear i'm a pretty good cook.

Anyway, I do have just a bit of a problem. I'm currently in my last year of school, I used to have nice dreams and ambitions and such, but i've recently stopped caring about pretty much everything 'cept for my friends and music. I no longer care that i'll probably not be "successful" in life, and i'm usually more respectful toward my parents and my most annoying older sister, but lately I’ve been quite blunt with them. It's not bothering me too much, just that a friend of mine said that they're not very happy with this "new" me. What would you say, I should do?
I think a person who is dedicated only to their friends and to music is some one I would like to hang out with.  Anyone who could find fault with that would probably kill a party when they walk into a room. can't wait to get antipodean with 'ya.
Paul Robeson, definitely. But what about Ginsberg?
Maybe I am biased because I knew Allen and never hung out with Mr. Robeson but their struggles are not in the same league.  Disaffected intellectual versus son of a former slave?  It's a hard old life for all of us but let's keep things in perspective.  Paul lost everything he had ever gained against odds you and I can actually not even picture for his beliefs, for his people, while Allen smiled offhandedly and fondled young rocker boys until the very moment of his death.  It is the difference between a hero and a personality-and who is the more famous today?  Nice work on that Clash song though.
dear jack,
I think it is unfair to capitalize certain letters and words and not others. what do you think?
all letters were created equal but some are more equal than others. And how about those letters that didn't even make it into the dictionary?  How do you think they feel?
Dear Jack,
Recently, I have been getting into fights with my family and friends. They're mostly about things of some importance, but its starting to wear on me. I'm afraid that I've lost the will to stand up for myself because I don't want to fight anymore. What do you think would be the proper course of action?
The master Sun Tzu teaches us that the best way to win a battle is to not to engage in one.  Smile, say "yes, sure."  then do whatever you were going to do in the first place.  No wear, no tear.  or if you don't like me paraphrasing (which I've noticed seems to annoy people while I am in the middle of winning an argument) here's the original:  
是故百戰百勝，非善之善者也；不戰而屈人之兵，善之善者也。
"Therefore one hundred victories in one hundred battles is not the most skillful. Seizing the enemy without fighting is the most skillful." confuse and conquer.
Dear Mr. Terricloth, recently I am told that I'll be involuntarily committed to a "behavioral health center". what can I do to get out but not lose the passion of teenaged anarchy?
run. away. from. home. do not return until your parents have gotten over this skinner box control thing. you might want to say good bye to any aging family pets.
So I've been thinking about the almost straight-edge lifestyle I've been leading. I know anyone who does drugs on a regular basis would tell me that it's the greatest thing ever, but I don't know whether I should give in or not. I'm still in high school, and I thought maybe I could stay drug free. But maybe that's not the best thing...?
I can't believe I’m saying this but if you don't want to do drugs don't do them.  They are supposed to be fun, not something to stress about.  Also your phrase ". . .give in or not." I find disturbing.  Hope you are ok.
What would it take to seduce you dear Jack?
proximity, money and drugs.