Madonna has a cluster of planets in the signs of Leo and Virgo (including her Sun and Moon) and coinciding with her move to New York, Saturn was making a very powerful series of conjunctions by transit to these Leo and Virgo planets (see chart). All accounts of this period for Madonna are very Saturnian in nature; it was a time of hardship, frustration, loneliness, isolation, dejection, deflation, paucity, debilitation and challenges—all attributes of Saturn.

The young Madonna, so successful in her attempts at getting her ambitions and needs met in the smaller, less competitive world of high school and college, logically thought that she could parlay this on the larger stage of New York. However, Madonna was about to receive one of Saturn's most powerful qualities—a heaping dose of reality. Madonna was talented and ambitious but so were all the other thousands of New Yorkers hungering for a shot at fame and stardom. At the time, Madonna's ambitions and opportunities were thwarted and limited at nearly every turn, and, in a fashion typical of Saturn, Madonna had to curtail her dreams—albeit momentarily—to settle for far less than she had expected and imagined. This is fundamental for the nature and action of Saturn—to impress hardships and limitations so that our desires and dreams conform to that which is more realistic and to force a more mature acceptance of the world on its own terms.

It is also characteristic of major Saturn transits to give its challenges and life lessons in spades. Not only are Saturn's trainings hard and push us to the brink, but almost all facets of life become frustrating, depressing, bleak, and confining. So all-consuming can major Saturn transits become that during critical points it is often difficult to recall times of joy, excitement, freedom, and openness—as if the experience of these very human and very necessary dimensions of life become completely unavailable to one. Madonna, without money, established friends, and the familiar landscape of home, was left alone in the often austere and embittering backdrop of New York to tackle fame and fortune. After consistently experiencing rejection, Madonna describes her only solace: "I'd go to Lincoln Center, sit by a fountain and just cry. I'd write in my little journal and pray to have even one friend. I had been used to being the big fish in the little pond and all of a sudden I was nobody." (5)

Although some accuse Madonna of over accentuating this period of frustration—of turning the process of rejection and testing normal for any star into an overblown, media-ready Mein Kampf—there is little doubt that these were the years that forged Madonna into a war-hardened woman taking knocks from the greatest of all urban jungles, New York. An individual lacking Madonna's confidence and ambition would have been knocked out from this severe testing from Saturn. On the positive side, because of Madonna's birth chart configuration and because of the relative slowness of Saturn's orbit (29.5 years), she would be able to take the most difficult passage of Saturn in one large dosage. However, of greater value, it was this period that matured Madonna, forcing her to take her ambitions seriously, to adjust her dreams and confidence to the reality of the world, and to thicken her skin.