I have been an observant Jew for more than 27 years, and before that I actually attended synagogue three times a year - twice on Rosh HaShana and once on Yom Kippur. That said, I still haven't really "figured out" this period of time - the ten days of Repentance.
I just have some personal observations - and I would love to hear other's thoughts on the subject.
One thing that I have noticed, is that people have different ideas about their relationship to G-d - and they usually correspond to what type of relationship they have had with their parents. Observant Jews are taught that we must both love and fear G-d. Those people who have had wonderful parenting can usually get the love part, and have a harder time with the fear. Those who unfortunately have had bad parenting, have the opposite reaction - fear is easy, love is hard.
Since we have to do both - we all have work to do, especially during this time of year. Another contradiction in observant Judaism is the idea of how we think about ourselves. We are told that we have to imagine having two scraps of paper - one in each pocket. One says, "We are but dust and ashes (compared to the eternity of G-d)". The other says, "G-d created the entire world just for me (we each have a unique place in this world and a job to fulfill)". So, am I supposed to feel guilty now, in order to do better in the coming year? Or should I feel encouraged, knowing that I still have a special role in life? The answer of course is both - but I always have a hard time with this.
Another problem to throw into this mix is the unavoidable comparisons to others. I know I am supposed to be thinking only of my personal journey up the ladder, but I can't help peeking around at others (which is silly, because you can't tell from outward appearances what is really going on in someone's life - G-d is the only one who really knows).
The only thing I can say for sure is that being religious doesn't mean we have all of the answers - which I used to think back when I wasn't observant. Now the only thing I know for sure is that I still have a lot of questions!
Your input is welcome.
For some great posts on this same topic, check out Beyondbt.