Relationship
There may be a sense of loss or lack that you're experiencing lately, perhaps due to a loved one passing or a lover leaving. Grief and mourning are both called for when we lose someone but it is important to move through these processes and at a certain point you need to move forward. All the time you spend in a state of regret or guilt is obfuscating the people that currently surround you. Be grateful for those who remain and consider your time with them precious.
Financial
The Five of Cups symbolizes a loss of sorts. Perhaps you made a bad trade or have lost assets in some way. Remember that along the journey to mastery, many mistakes will be made and losses realized. Occupying a state of anger and regret will only make you end up losing the most precious asset of all: time. Lick your wounds and learn from your mistakes, as this is the only way to recover what you have lost.
Self
You may find yourself struck with pessimism at the moment. If you're always expecting things to go south then the letdown if they actually do will be more manageable, but this is not a healthy mechanism. Focus on the positive forces that exist in your life and be grateful for them.