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Like many ambitious people, High School marked the low point of my life. I always HATED school, and my first memories of primary education was of getting literally sick at morning assembly (artefact of Bastardised Confucianism). It was a feeling of entrapment that had to be faced on a daily basis, a particular malaise that even a 7-year-old (as I was) could understand.
That feeling peaked in High School (again, mirroring the experience of others like me). Sure, I had friends, I was good at sports (I was 189cm / 6'2'' by 15 and had been on the Basketball and Track and Field teams), I played in a Band (electric guitar), etc.... But I was future-oriented enough to know that those were shallow trivialities masking the deeper and more sinister creep in the system I was in.
I was not future-oriented enough however, to develop a strategy to combat against that harm like an intellectual and philosopher (I wasn't). Instead, I ended up like many do -- throwing blows at the system whenever I could, and drowning the reactionary pain on whatever mindless stimulation I could find (in my case, lots of Warcraft 3).
Fortunately, time passes, and I was fortunate enough to have the mental soundness to get through that stupidity. Faced with the void of freedom however, people make choices -- most of the time, spontaneous ones without much foresight.
The truly sinister effects of the system now become apparent -- having been bashed so much by an oppressive system, the people who "escape" lack the creativity to invent their own sources of pain. They complain about "not knowing what to do", and box themselves into desperate cycles of half-hearted trial and error. This is the classic version of the elephant tied to the stake.
The fact is that we all need to ask, "How Can I Provide Wealth to the World?", and the escapee from above, having just escaped a very concrete pain, cannot fathom seeking a new, abstract pain -- the Pain of Self-Driven Learning.
The fact is that learning is always painful (if it is not, you're doing something wrong). Any skill that is scarce is almost by definition, unintuitive. More accurately, any combination of skills required to make Wealth is never acquired with ease.
eg: The Genius Mathematician will not realise wealth without being able to put that Math to practical use, say in the form of a Computer Program, and that program will not make anybody happy without being Marketed and Distributed to those who can use it. Even in the confines of Academia, said Mathematician will have to have the social smarts to claw their way up the pecking order to make their ideas (and their egos) known.
Modern life requires a far broader array of skills than any contemporary, formalised system can provide. But the collective, as always, is not fond of change. They'd much prefer the dull ache of shared pain, than try to take a hit and break out into magnificence. "Life is too complicated, and the trying to do something else is not safe", they'd say.
In any case, most formalised systems of work, education, policy-making, etc are still firmly rooted in the industrial (or even agricultural) past. The implication is that they are structured to avoid the evils of that past, and impose upon its members (or hostages) the pains required to do so. ie: Pain that is ultimately for naught in this information age.
The first step is obviously to escape the confines of those institutions (in mind if not in body, preferably both), but for reasons mentioned above, that is not enough either.
The best advice to any escapee: Take a month (literally) to cool off and reflect. Ask the Hard Questions, Plan the next 3 steps, and Seek Your Own Pain. Only you know how to hit yourself where it hurts most.
However, don't hurt yourself in ways that you know you will heal -- bruise, but don't cut. Of course, life is complicated, and many times, you'll find that you'll cut yourself, perhaps a little deeper than you'd imagine.
Randomness is a part of life, and accidents can happen. Fortunately, the body is hardy and the soul even more so. Watch your downside, and be bold when there is nothing to lose, and everything to gain -- it's bound to leave pain.