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In a world that equates success with financial security, the loss shown on the Five of Pentacles can be a humbling blow to one's self-esteem. This can be brought about in many ways, but even though an exterior event may seem to be the cause, this card often shows a loss that you bring upon yourself. Even though the Pentacles are a material suit, and Fives usually deal with real-world problems, the theme of poverty is not the true destitution shown on the Five of Pentacles. There is a spiritual loss that often precedes or accompanies loss of material wealth.
But since outer problems must often be resolved before inner conflict can be attended to, the outer meaning of the Five of Pentacles shall be explained first. This card shows the many faces of material misfortune and lack: loss of funds, general poverty, illness, unemployment, solitude. The card also tells you that many of these are caused by your emotions. Greed will lead to loss, anxiety will lead to error, possessiveness will lead to solitude. By focusing on the material, you lose sight of the spiritual development the Ace promised. You may be rich for a while, but all will be lost if you learn nothing.
This leads up to the more spiritual meaning of the Five of Pentacles. This card represents the dark night of the soul, when you must stumble around in the darkness because you can no longer see the light shining within you. Often, during times like this, salvation is not far away, but because you are so preoccupied with your material problems you cannot see it. The two people on the Rider-Waite card walk by a brightly lit church, unable to acknowledge how close a solution to their destitution is. The church is an apt symbol because it provides spiritual comfort while helping those who cannot help themselves.
When the Five of Pentacles appears it is almost always a warning that you are likely to experience some kind of loss, material or otherwise. If this loss has not yet happened you can prevent it or lessen the blow. Worrying about problems like this will do nothing but make them even worse, so stop worrying and start doing something! If you are in a situation where you have lost a great deal, know that you have the ability to get it back. There is always a solution, always a way out, always a church window just around the corner. So either open your eyes and go to it, or close your eyes and let the inner light guide you.