Rosh Hashana is the 'Yom Din', the Day of Judgment. It is also the day in which Abraham brought Isaac to Mt. Moriah to be sacrificed. The day in which Isaac experienced yirat shamayim, awe or fear of heaven, like, I venture to say, nobody else in the history of mankind ever has. The Bnei Yissachar writes that the root of yirah (awe/fear) and din (judgement) comes from the strength of the original tzimtzum, the original constriction of G-d's light in order to create the world. What is the connection between these ideas and what does it mean for us? Let's see.
When a baby is born, it comes through the extremely constricted birth canal only to eventually be born into the world, to be released from its constriction. It is said that this is one of the most traumatic events of our lives. The fear must be intense! However, when the baby completes this fearful journey, it is BORN. According to one tradition, the Creation of the world took place on the 25th day of the month of Elul, thereby placing man's creation date on Rosh Hoshana. So to speak, the Universe went through a tzimzum of which the 'end' product was the birth of man. In other words, at the end of tzimtzum is creation. How does this connect to yirah? On the day of the birthday of mankind, we stand at the end of line of the constriction and stand in fear, in awe, of He that caused this event to take place. Hashem is the One who 'decided' to restrict Himself, so to speak, and begin this wonderful act of creation. We stand at this tiny little space at the end of it all looking out saying, "Wow, where does it all go, where does it all come from?"
Have you ever really looked at a Shofar? You know, the one we blow on Rosh Hashana. It is extremely constricted on one end and wide open on the other. There is a similar idea here. We blow the shofar to cry out to Hashem. As it says in psalms 118, "From the narrow place I called G-d, and He answered me from His expansiveness." Why do we blow a Shofar on Rosh Hashana? We blow it because Isaac's life was spared and a ram was sacrificed instead. The Shofar, the ram's horn is a symbol of the binding of Isaac and his being spared.
Isaac was on the altar; he was prepared to be sacrificed to G-d. What more could you ask for in regards to yirah? He was there on the altar with a knife over his head! The interesting thing is that Isaac's name means laughter. Paradoxical? Maybe; however, it makes a lot of sense. Isaac saw that place, that place where it all came from. He was ready to go there and yet he returned. From the restricted, awesome, fearful place he was able to see the great intangible vastness of Hashem's greatness. When you can bring that awareness down to this world, there is nothing else to do but be joyful and happy and laugh, knowing where this whole limited, restricted existence comes from, and that it's going to be allright no matter how limited it seems.
No matter what you've done, there is teshuvah, there is returning. But you must be willing to experience the din, the judgment of Hashem, to ask Him for mercy and forgiveness. When you realize before who you stand and from where it all comes, then you can realize that on Rosh Hashana it is a day of birth, a day of new beginnings and maybe even laugh at the great grandeur of Hashem's design. May everybody have a Shana Tova and be written and sealed for a good year!