An effective transgressional act is not an uncompassionate or cruel act. It simply asks whether a rule or a convention or a habit imposed by society or by others serves your own inner purpose. Of course, knowing one's own purpose helps but sometimes we only know that we don't know what we want.
In that situation of not knowing what we want or who we are and it is clear there are no answers to those questions in conforming to social expectations and rules, then the logjam may have to be broken - an instinctual transgression may be the only means to do this.
To break an irrational taboo (irrational in terms of one's own rational needs) is a liberatory act although this begs the question of the rational and the irrational since the social definition of rational or reasonable may be in direct contradiction to what is rational or reasonable for self expression ... for self-becoming.
Much of social life is, in any case, not strictly rational. It can be an imposition from the past, habit, from power, convenience to others and so forth. The central point to remember is this difference between what is reasonable for society and what is reasonable for oneself.
Ideally, rationalities converge in a free society but social conditions are rarely and only contingently free. Either the 'self' must reconsider its position or it must liberate itself from social rationality. This may not be just a liberatory stance but a revolutionary one.
All permanent change in oneself must be (ultimately) sub-consciously willed - to become the creature of an external substance, however, (addiction) is to lose will. The dionysiac qualities of external substances must serve the person and the person should not become slave to or creature of the substance.
A formal exercise in exploring transgression (or an opportunity to transgress norms) might be to list as many things as possible that might be regarded as transgressive within the culture of the day, and then note alongside each:
- whether the transgression or opportunity would be a 'desire' for you, all things being equal - is it what you actually want in itself or as a means to something else unknown?
- what the costs and gains to the self would be in acting out the transgression (even a marginal gain would still be gain);
- what the costs to the self in society might be and then lay out the material and social risks to be set against the personal gains.
If the answer lies in fear or anxiety or shame and not in financial cost or lack of fundamental interest, then you cannot be liberated as a person unless the actually desired transgression (say, being gay in a faith-based community) has been faced head on. But a transgression is still not a stupidity.
A transgression that damages one's own mental or physical health or safety or one's own property or risks the full weight of the law may, indeed, be a transgression but it is also a stupidity. If the law is stupid, change the law, learn secrecy or take the consequences but never be stupid in order to posture as 'free'.
The gay example is perfect in this respect. A gay person in most of the modern West has no need to transgress because homosexuality is an accepted new norm within the norm of tolerance and diversity but it was not always thus. Campaigning, secrecy and punishment were the 'norms' for the abnormal.
For tens of thousands of males (more!), a brutal choice was given - to conform because of the sheer weight of social pressure or to take phenomenal risks in order to express your sexual nature. Nor were homosexual people (of both sexes) the only oppressed people in society - the list is endless.
Today, polyamorous personalities may not be punished and may wonder precisely what they are campaigning for - and campaigning itself is an aberration from 'being' - but they still live under conditions where secrecy (aka 'discretion') is required and the social structure is biased against them.
But transgression is not merely a revisiting and revision of social reality. It is also a revisiting and revision of personal reality - the habits and conventions of the self and the construction of oneself by others for the sake of others (without needing to unravel the beneficent construction of oneself through the love of others).
The irony of this in the gay example is that a homosexual may find themselves obligated to become 'gay' with a new set of oppressive behavioural norms when all they really want to be is a 'normal' person who just likes sexual attachments to their own sex. Identity politics can oppressively construct people because it is 'social'.
A transgression can even be against harmful habits, routine or those personal rituals that act as barriers to desire or to becoming what one wishes to be. Perhaps there is an act of apparent private 'sin' that you want to undertake but do not know that you want because it is buried deep within you out of fear.
The problem here is, of course, with the idiot inherited notion of 'sin' but let that pass. But if this 'sin' is there, bring it out into the open, study it closely, imagine it, decide whether it is a desire that requires action. The desire may evaporate in the light of honest consideration but the 'sin' may also evaporate into an action.
If the 'sin' does no material harm to you or others (so let us be explicit in condemning non-consensual sex, paedophilia and bestiality where harms may be reasonably presumed as default), then why not make this transgression happen, savour it, make it part of yourself - or just return it to its box without guilt or shame as having been studied, felt and rejected after all - for oneself and not for the social or some imagined being watching your every step.
Or it may be transgression in favour of a secret desire that only you could ever know was desired and which only you think of as 'wrong'. Why on earth, under such conditions, would you not transgress against oneself for the sake of oneself?
Transgression can also be something with a ritual quality between two or more - though be careful that the breaking apart of an old convention does not create a new and equally enslaving one. We are back to the identity politics of turning homosexual feeling into gay culture.
To become lost in a cult or culture is no liberation, especially if it is the replacement of one ideological rigidity with another. To be merely rebellious for the sake of rebellion (I am 'against' not 'for' in such cases) is also not to be truly liberatory nor revolutionary.
Transgression is not a matter of thought in itself but of the necessity of unblocking life energy. Transgression for the sake of transgression becomes just an absurd waste of energy, a bad habit. Every revolutionary act must be focused precisely on the unblocking of energy and only on that purpose.
Finally, transgression for one person is different from transgression for another. A woman is different from a man in this respect. The risks are different. All must respect the material risks taken by the other.
Each must try and enter into the mind of the other in order to understand that transgressions must be proportionate and intelligent. This is not the imagined empathy of new age loons for trees and rocks but a really existing empathy between persons. And transgress against trangression if you must ...