I learned a beautiful thing in R' Yitzchak Ginsburg's "Living in Divine Space"
He says how the Baal Shem Tov taught that we mustn't let humility prevent us from serving Hashem. However unworthy we may feel we are, if we approach serving Hashem with such feelings, we'll lack enthusiasm and zest - and these are things we need when serving Hashem. And on the other side - once we've achieved something - we learned, davened, whatever, then we need to have humility, that was all a gift from Hashem.
He connects this to the words שגיאה (to make a mistake) and הגשה (to come close). The root of both words are the two letters ש and ג. In the word for mistake, sh'giah, the shin comes before the gimmel. In the word to come close, hagashah, the gimmel precedes the shin.
He says that the gimmel stands for gaavah, arrogance, and the shin for shiflut, humility. The way to come close to Hashem is to first have arrogance - to approach Him and serve Him despite our faults, but then afterwards to have humility, to know that whatever we achieved is all a gift from Him.
But if we put the shiflut first, so that we don't serve Him with enthusiasm and zest, and then put the gaavah afterwards, taking credit for whatever we did achieve, then we're on a mistaken path.
Then R' Kivak tonight said a very similar thing. Rebbe Nachman teaches us to be 'baki b'ratzo' and 'baki b'shov' - to be experts at moving forward and experts at falling.
When we fall we need to know that Hashem is right there with us, next to us and by our sides. He still loves us and treasures us, and is there for us. There's no despair.
And when things go well and we're moving higher we need to know that we have to keep on striving for Hashem. He's so great that we can never 'arrive'. Maybe we haven't even started yet.
The problem is that we do the opposite. When we're down we get resentful and depressed that things aren't going our way. And as soon as we have a little bit of success, we have a few pennies in the bank, we feel like we're okay and we forget about Hashem. We get proud.
The goal is to strive to be close to Hashem whether we're up or down.
I think these ideas are very important for us in our struggle here. When we're down we need to have the gaavah to know that Hashem is still with us. He still loves us and is there for us. He never tells us that we're beyond hope. Despite whatever we've done, we need to turn to Him and carry on doing what we can to serve Him.
And when things are going well we need to have humility. To recognise that wherever we've got to is a gift, and remember how dependent we still are on Hashem's grace, love and help. And we need to keep striving to foster an ever closer and closer relationship with Him, because לגדולתו אין חקר.