Preparing for Rosh Hashanah and Yom Kippur - Practical Issues

How do you prepare for Rosh Hashanah and Yom Kippur? Obviously, the holidays are what we make of them. And they are a great opportunity for self improvement and to right some lingering wrongs. But all this takes some preparation.

At one extreme, people can simply do nothing to prepare for the holidays. They get to synagogue, find themselves a little bored, and get very little out of the holidays.

At the other extreme, people can approach the holidays at a very high level of generality: repenting for mistakes, seeking forgiveness, starting a new year. The obvious problem is that these lofty ideals are too lofty to do much practical good. One needs to be specific: repent for specific mistakes and seek forgiveness from specific people. Start a new year by doing specific things in a different way.

Here are a few things that I have done and that others have suggested to me. Feel free to offer additional ideas in the comments.

Realistic Resolutions. In some years, I have thought about one or two general things I would like to do better the following year. It might involve personal traits, relationships with others, or plans for specific goals. I then try to think of specific and concrete ways of accomplishing these things. I try to limit myself to things that I probably can do. Reaching a little is OK; reaching too much is likely to produce failure.

I then check in with myself at the (secular) New Year and at Passover (or roughly a third and a half of the way through the year) and try to make mid-year corrections. Am I on track? If so, great. If not, why not?

Similarly, I think about one or two general things that I have done well the past year, perhaps with some difficulty, and think about how I can keep on track. These are sometimes last year's goals.

Meetings. A friend noted that he tries to set up meetings with anyone he has an ongoing problem with and tries to resolve the problem one way or the other.

Going Through the Prayerbook Ahead of Time. Another friend noted that one of her friends goes through the prayerbook before the holidays. Specifically, she focuses on the V'dui and Al Chait, thinks about sins or mistakes that she has made that fall into these categories, and actually takes notes in a personal siddur. (Note: if you do this, its probably a good idea to keep it is a secret locked place.) This process helps her use the structure and content of the prayers to help her become a better person. And obviously the prayers have more meaning to her in synagogue once she has "personalized" them ahead of time.

Any other thoughts?

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UPDATE: a link with a few more suggestions. Aish HaTorah's website has an article on this topic called Three Steps to Genuine Change. (It really discusses three separate methods to implementing positive character changes rather than three separate sequential steps.) Aish is particularly good at these types of practical character issues.