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You wrote, “Having lived with myself since the age of the dinosaur, I do know that I am Virgo Asc for sure as I’ve read a lot around this. Similarly, I am Jupiter in the 9th (definitely not the 8th) which is the Placidus system.”
First, I was born May 25, 1945, so had finished my freshman year at college when you hatched (dinosaurs were egg-borne and egg-born).
Second, Mars’ transit of the 9th may bring forms of “higher” education which take you beyond the confines of mind.
In Hindu/Vedic astrology, Jupiter is called Guru. The word Guru is made from two words which mean “darkness” and “dispel.” Jupiter/Guru signifies the wisdom which comes when the darkness of ignorance is dispelled.
Third, Jupiter/Guru is at 28°10'22" Aries is western tropical chart. Some say that from 28° of one sign to 2° degrees of the next sign, a planet straddles two energies. In this case, Jupiter/Aries/Mars blending with Jupiter/Taurus/Venus.
The mystic astrologer Ellias Lonsdale gives the following interpretation of the 28-29th degree for any sign:
“Neptune manifesting in a Virgoan way.
“I don’t belong to this world. I’m transcendent, infinite, sacred, magical, devoid of characteristics. Metamorphosis is me. Nothing to me is terribly tragic or irrevocable. I’m not invested in anything because I float freely. I have no ambition, goals, plans, programs, because everything already is. I am completely ineffable, beyond comprehension. The irrational to me is wonderfully expansive.
“I like to go to extremes as a means of creative experimentation. I simultaneously break down things and reconstitute them in unique, original, and startling patterns.”
In his unpublished manuscript, Star Sparks, Lonsdale writes the following about Aries 28-29."
Symbol: “Dr. Jekyll drinks the potion.”
Interpretation:
“Going against the self with a determined and fierce edge. Doing whatever it takes to throw the self off its flow and consistency. Undermining, sabotaging, subverting the ego-mind and its patterns, its needs, its world view.
“Candor determined to hunt down the enemy, which is the unexamined self. Unwilling to let anybody in here get away with anything. Always ready to die, to charge the life radically, to do whatever it takes. Crazed with the desire to be done with illusion and pretense, to be free of the burden of lies, deception of the ego-self pursuing its surface goal to the determent of all of life.
“An honesty, a gutsiness, an ability to follow through on the impulse to find another way, to live in a different manner altogether. The stark combination of shadow inflation with shadow remuneration. The simultaneous state of seeking to be free of self and in the process becoming hung up on self massively.
“A very good and strange idea carried to the ultimate point. We know here that what we allow ourselves to take up as a controlled and self-willed outer pathway will easily become much more of a monster than a fulfillment.And we are well-aware, deeply in touch with the root system that supports and perpetuates our surface motives, and turns them into worlds of everything reinforcing and substantiating the self’s most naïve and useless assumptions, made into a life.
“But what we have a hard time with is doing anything other then cutting away at the patterns. We end up being the shadow, being the one who stops the self from folly untold and moving into those values which are there when we are once again part of the whole.
“A very necessary undertaking which perhaps never lets up and fails to realize that letting be is the center point of wisdom.”
With sincere best wishes