Meanings according to Rider-Waite:
ASTROLOGICAL SIGNIFICANCE: Saturn in the 2nd house as an indicator of crisis and decline.
FIVE OF PENTACLES The Five of Pentacles is a card of crisis, deprivation, and worry. It signifies decline, failure in affairs, when we feel pitiful, miserable, abandoned, and at times indeed find ourselves in straitened circumstances. At the same time, the Five of Pentacles rarely heralds truly serious losses, sorrows, or ruin, but merely points to the uncertainty of one's position and to our subjective sense of fear at losing the ground beneath our feet. Such periods of decline are characteristic of every crisis of growth, when a person leaves a sphere that has become familiar and stable, and crosses over into a new one, still unfamiliar, and possibly dangerous.
From the book: Hajo Banzhaf. THE TAROT HANDBOOK. Translation from German by E. Kolesov. Publisher: Center for Astrological Research, 1999.
FIVE OF PENTACLES Worry. The first decan of Taurus, from April 21 to April 30. Astrological equivalents: Leo, Aquarius, the Sun, the Fifth and Eleventh Houses.
The sign of Taurus symbolizes the capacity for creative labor. But true creation is the harmonious union of the material and the spiritual into a single whole. While the actions of Capricorn are grounded in its own inner core, and its "I" is capable of leading it toward its goal because for this sign that "I" proves more significant than anything else, for Taurus the "I" dissolves into feeling and desire. If a person's "I" is satisfied and nothing else compels him to act, then in order to take up a task, there must arise a desire to do "something" for which the surrounding world will be grateful. Therefore, the principal task of the first decan of Taurus is to become aware of one's feelings, to understand the desires that have crept into the soul, and to respond to them. This decan is endowed with enterprise in everything that pertains to the sensual sphere — and for this reason it is distinguished by successful functioning and administrative activity in the sphere of art. It is also characterized by emotional receptiveness, with which it is endowed by the searching Mercury — its ruler, although Taurus is also marked by a slowness of perception. Feeling assimilates information not at the speed of the mind, but firmly so: in comprehending, it lays the foundation of the edifice of the future. Sensual experience becomes the basis of life's wisdom. And wisdom traditionally speaks of the transience of all that is perishable. The TAROT card depicts beggars beneath the windows of a temple. The pitiful figures of two cripples show how powerless man is over the earthly. Free will often only cripples a person: he is frequently incapable of walking his life's path without errors. But the windows of the temple are illumined: spiritual force helps to overcome life's miscalculations and becomes the natural inner support of a person in his material activity. True feeling possesses this force and gives a person the possibility, having risen above circumstances, of governing the course of life's phenomena. The trap. To grow rigid in the habitual and in eternal dissatisfaction (including with oneself). Stupefied by the blissful state of the FOUR OF PENTACLES, a person breaks out to the level of the FIVE, which acts like a stone cast into a swamp. No other card so precisely reflects the state of Leo, longing amid routine for something extraordinary, as the FIVE OF PENTACLES. The theme of this card resounds with Uranus, in its detriment in Leo. Uranus acting on the material level and at times taking on materialized forms. Where Aquarius will be "absorbed" by a new idea, Leo will take a mistress, and therefore the FIVE OF PENTACLES often signifies erotic adventures, infatuation, flirtation, love games. The situation of the rake, the carouser, often follows the FIVE OF PENTACLES. The shattering of the calm atmosphere of the FOUR is, of course, not given freely. It is often accompanied by financial losses, breakdowns, failures, disappointments, unhappy love, ambiguous situations. Sometimes the disruption of the FOUR's tranquility proves to be a mistake, and the person thinks only of how to return back (the devil led him astray). At the same time, it should be noted that the FIVE OF PENTACLES symbolizes karmic situations — that is, those set from the very beginning — and therefore easily finding their support in the horoscope.
UPRIGHT POSITION In the upright position, the FIVE OF PENTACLES usually signifies the loss of something material and, in exchange, the acquisition of life experience, the drawing of a lesson. As a symbol of the collapse of the balanced scheme of the FOUR, it may manifest itself in the form of anarchism, of the clash of group interests. In a spread, it generally signifies complexities, difficulties, leading you either to success and to consolidation at a new level, or driving you back to the level of the FOUR. Either way, the memory of the experience lived through remains, regardless of whether it was positive or negative.
REVERSED POSITION In the reversed position, the FIVE OF PENTACLES signifies the overexpenditure of energy, the squandering of reserves, vulnerability, fear; it signals that you have turned onto a bad road; it symbolizes disharmony in love relationships. Here the afflicted sign of Leo, or the Fifth House, plays itself out. The card may also indicate stagnation in affairs, worldly cares, dissatisfaction. It may happen that you see great possibilities for yourself, but they are not yet fully attainable. The higher goal is already in sight, but at the present moment is not yet within reach.