Dina Coopersmith asks a good question at Aish.com, before answering with a story and a longer explanation. First the question:
bq. "Why does Rosh Hashana, the Day of Judgment, come before Yom Kippur, the Day of Forgiveness? Shouldn't we first be forgiven for all the past sins, repent, become a new person on Yom Kippur, and then have a better chance on Rosh Hashana of getting a good judgment and a sweet year?"
Now, the story...
bq. "The Rabbi of Novardok told a story of the man who was riding a train. Someone mentioned to him that the train was headed in the completely opposite direction from his destination. The man, unperturbed, got up and changed to a seat facing in the opposite direction. Now he was facing his destination!"
To understand the relevance of the story to the question, you'll want to read the full article.
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