You're standing in synagogue on Yom Kippur, hungry because you're fasting and bored because you've heard the whole thing dozens of times before. Your mind wanders a bit as you basically recite from memory. Only three prayers ever really stand out for me and I'm putting aside Unetanah Tokef because I'm only ever moved by how many tragedies (9/11, Katrina) seem to strike close to the holidays. The other two are Al Chet and Ashamnu, confessional prayers that list our sins. This is the time for reflection, which I suppose is the whole point. It's your last chance to look back over the year and think about the horrible things you've done so you can repent and start with a clean slate. Well, folks, I'm here to tell you that it's BS. If you're waiting until then to repent, you may have snuck on board the Halachah bus, but you've missed the life one.
We sin. We transgress. It's what we do. Nobody's perfect. Hopefully, we have the presence of mind to apologize to whomever we've hurt, but that gets done almost immediately. If you're waiting a year to apologize for something and the person is still angry at you, whatever you did is probably too big to be brushed aside with a "sorry" anyways. But, of course, teshuvah has nothing to do with other people. We repent so that we can feel good about ourselves. It's the secret behind that scary guilt that Jewish mothers wield so skillfully. Are we being the best person that we can be? And you're going to wait until the next Tishrei to answer that question?
Maimonides wrote about teshuvah in the late 1100s, when life was much simpler. If he wanted a tish with his boys after Ma'ariv, then they'd have a standing agreement or maybe they'd send him a letter. He wasn't getting texts at 5PM asking if he wanted to meet up last-minute at the new shtetl hotspot. He thinks he was perplexed? He wasn't sitting in Panera with a laptop on wi-fi, a cell, and a BlackBerry. Some would say that the speed of our society means that we have to take these ten days between Rosh Hashannah and Yom Kippur and cherish them as a chance to look back and take stock in ourselves. No way.
It's not easy to walk backwards. It's a little disconcerting to stand backwards against the flow of foot traffic on a busy sidewalk. Go hop on the Metro and watch how many people hate even sitting backwards. We need to see where we're going. Sure, we must have an intrinsic knowledge of where we've been, but we can't let it slow us down. We need to be able to access our life lessons like Wikipedia -- a brief summary of something we've learned that may or may not be true depending on how we've interpreted it or how we've taken liberties with our memories. We need to make adjustments to ourselves on the fly. We can't wait because every opportunity that we might have taken if we had been more self-aware will have passed us by.
Self-reflection is a perpetual necessity. Practice it enough and it won't even take any time. You'll know when you're doing something that hurts your self-image. You'll be able to quickly apologize to other people and, more importantly, to yourself. Without the burden of guilt or doubt, you'll be looking ever forward, ready to see what's coming down the road. It'll be easier to dodge any obstacles or to seize upon any opportunities. Even better, when you're in synagogue on Yom Kippur, chanting the Viddui, the confessional prayers, you'll be able to think about how happy you are that you've already come to terms with your sins throughout the year and your mind can wander on to more important stuff like, "Will they have anything better than bagels at the break fast?!?"