When I look at the Five of Pentacles, I'm reminded of Tiny Tim and his family in a Christmas Carol. Marching about in the cold, Tim on crutches, the family thought that the young boy would not last the winter without medical help. Winter is hard on families that fall below the financial state of others – many of them simply have to grit their teeth and bear the cold, even at home. You'll see those who are less fortunate bundle up in layers upon layer of their clothing, simply because that's all they can do. We can all land ourselves in that position, and most of us have already been there before. This hard situation is what the Five of Pentacles embodies.
On this card, it's the dead of winter in the middle of the night. We see a large stained-glass window, the kind that a church would have. The window depicts five pentacles, leaves and flowers entwined around them. Below this window, out in the cold night air, are two poor souls. The one to the left has something wrong with his leg/foot, and walks using crutches. The woman to his right looks financial destitute – her torn clothing is barely enough to keep her warm. The man looks up to the window with a pained expression. Perhaps he is asking God for pity. Maybe he is simply be dreaming of how warm and comfortable it might be inside the building. There is no luck for these two individuals, however – they seem hell-bent on finding a warm place out of the snow, and traipse forward at a fast speed.
This is the card that points to a lack of physical security, safety, and/or comfort. As humans, we run into periods in our lives where we simply don't have the resources in order to feel the comfort we desire. We become sick, we get injured, we run out of money, we lose our jobs, our cars, and even our homes. We like to believe that it can't happen to us – that we prepare too well, that we are too smart, or at least too clever to allow ourselves to fall into a situation like that. We say that... until we end up there. This card is saying that you or someone close to you has, in face, ended up there. The Five of Pentacles can mean that you are going through a rough period, especially physically.
This card can also point to lacking the physical means to do something. For instance, if you're sick but lack medical insurance or money to go to the hospital. It can also mean that you can't physically get some place that you need to go – and example would be that your girlfriend has moved to the other side of the state, but you lack the funds and vehicle to visit her. This could even refer to the age-old cycle of not owning a car, so you can't go to job interviews, so you can't get a job, so you can't get a car... on and on it goes.
Here are some things to ask yourself when you see this card in your readings. What physical struggle are you facing right now? Does it have to do with your resources? Your health? Your surroundings? If you can't change your physical situation, what can you do to improve your mindset about it? How can you be happy even when facing times of hardship?
Two cards that have a lot in common with the Five of Pentacles are the Three of Swords and the Ten of Wands. The Three of Swords can express the emotional side of the physical downturn that is the Five of Pentacles – you may feel a real heartbreak when the material world has you struggling. The Ten of Wands has perhaps the closest meaning to the five of Pentacles, as both cards have to do with burdens and struggles that must be fought and overcome somehow.