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Yom Kippur
Different people observe Yom Kippur in different ways. What you can and cannot do is affected by what form of judaism you practice (or if you are like me and don't practice judaism but recognize certain holidays as a way of respect for your heritage.)
You are supposed to deprive yourself, disrupt your habits, change your life for the day in such a way that you recognize what you have the rest of the time, and also, appreciate what God gives us. Most especially what you are to appreciate is the Divine Guidance of God and His awesome mercy and love for His creations. And you are to reflect on your behavior and (some say) the behavior of the community around you, and repent either as an individual or as the community (depending on your beliefs) for sins over the past year. You are to let God into your heart, to recognize that you have a mission here on earth, and that mission though it will vary based on God's will, overall is to live such a life that you are judged worthy of admission to His realm in your death. It is assumed you are worthy on Yom Kippur (judgment took place during Rosh Hashana,) this is God's mercy.
On Yom Kippur the God of the afterlife, who is reflected differently in our every day lives than He is in the afterlife, reveals more of Himself to us through our reflection. In this realm we have free will, we can make choices, and we often do make choices that take us in the wrong direction. We focus on wealth and beauty perhaps instead of the mission God created for us. In the afterlife none of this is necessary, because there God shows His complete glory and there is no question in your heart about Him. But in this realm He chooses to show us less and allow us our choices.
One of the most oft told tales today is about Jonah and how he spent time on self reflection and repentance while in the whale, and how he learned that no matter how he tried to avoid it he had to obey God's orders. It was through his failure to obey God that he ended up in such dire straights. And it is through our failure to obey Him that we suffer indecision and angst.
Through this time in the whale and the time after he had followed his mission and convinced the citizens of Ninevah to change their ways, Jonah realized, that God rules with forgiveness and mercy, and that while we all have flaws, we are still His creation and He loves us.
This is an extremely basic explanation. It's both a complex and simple holiday. And its meaning is frequently very personal.
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