To repent is always a good idea. The best idea is to find books on the subject from the Middle Ages before the concepts of faith and repentance got watered down during the Renaissance. Many ideas of the Renaissance are important, but do not take the place that the Middle Ages had on the importance of Faith with Reason. (That was the unique contribution of the Middle Ages.)

The issue is really like that of Hegel that there is a kind of dialectical process going on in history in which truth gets steadily clarified. [So even though the Renaissance was an improvement on many things from the Middle Ages, still that does not mean to throw out teh good that was unique to the Medieval period.]

I thought about repentance for some time while I was in Uman and came up with the idea that surely most of my mistakes I am unaware of. Just learning the Gates of Repentance  and other books of Musar of the Middle Ages and Rav Israel Salanter is a help but there can be even after learning Musar many issue that remain unclear. So it occurred to me that at least some of my mistakes I am aware of. I can tell by subsequent events and stemmed directly. So the idea I got was to repent on at least what I know I did wrong. Then with help from above hopefully I might be able to get further. This seemed certainly an advantage to just picking out of  a hat what happens to occur to me what repentance might be.