I've been reading and listening to lectures to prepare some writing exercises for Elul, but it really a tall order! I'm going to give some quotes from some of the articles I've read. You can use these to help you get focused in your writing on the z'man we've started: Days of Repentance and Tshuva.
This is an outtake from an article by Rav Nosson Weisz of Aish HaTorah on Parshat Shoftim:
At the very beginning of the Days of Awe we are summoned to take ourselves in hand and appoint internal judges and officers over our characters and behavior and prepare ourselves to face judgment. We are urged to do this in order to avoid having to face God's judgment. By weighing and judging our characters and actions on our own, repenting any wrongdoing and instituting the changes that are needed to correct our faults we can avoid the harsh scrutiny of the heavenly Court. God always prefers to leave matters to human initiative and only people who fail to judge themselves are submitted to the jurisdiction of the Divine Court.
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TESHUVA ON DEMAND
But coming to grips with the "days of teshuva" can be problematic. It is one thing to command people to execute actions on demand, but it is quite another matter to ask people to experience feelings on demand. God designed us with the requisite circuitry to be able to direct ourselves to perform actions that are at variance with our feelings. Such self-control has its limits but the ability to discipline ourselves regardless of how we feel is definitely part of the human repertoire. But God did not supply us with the requisite switch to turn our feelings off or on. To experience a feeling on demand is difficult indeed.
Maimonides devotes the entire first chapter of his Hilchot Deot, the Laws of Character Development to the topic of changing one's character and developing the ability to experience certain feelings; the basic strategy presented there is based on behavior control. Through the execution of a controlled course of behavior that goes against the grain it is possible to affect character change over the course of time. For example, a tendency to stinginess can be overcome by deliberately behaving in the manner of a spendthrift over a period of time.
The point is clear: human beings simply do not have the spiritual equipment to effect immediate changes in their attitudes, feelings or characters. Understanding that you are on the wrong track does not in itself suffice to put you back on the right one. Maimonedes knew this a thousand years ago; psychiatrists have finally arrived at the same conclusion only recently. Knowledge does not alter character, feelings do. This phenomenon of human nature creates a very special problem when it comes to repentance.
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A MATTER OF THE HEART
For repentance must come from the heart. True repentance requires the recognition and acknowledgement of character faults and the resolution to correct them in one's heart. As Maimonides explains:
What is teshuva? The sinner has to stop doing the sin, he must put it out of his mind and resolve in his heart never to go back to doing it again... to the extent that The One who Knows the Secrets of the Heart (i.e. God) can testify that he will never return to this sin again. (Maimonides, Laws of Repentance 2:2)As such, repentance does not seem to be a phenomenon that can be squeezed into a particular time slot or season. It is a process that requires constant focus and attention; it can only be attained gradually, over a long period of time, whose duration is bound to vary from person to person.
How can God order all Jews to begin to repent on command at the start of the month of Elul and complete the process by Yom Kippur in light of the fact that He failed to supply us with the necessary equipment to carry out instantaneous character changes?
To acquire the tools we shall require to approach this problem, let us begin by examining the historic origins of these 40 days of teshuva that begin with Rosh Chodesh Elul and end with Yom Kippur.
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You can read the rest here.