How many million times are we told to, or do we tell others (or ourselves) to “do your best”? This doesn’t seem like bad advice. Rather, it seems like very *good* advice. After all, when is slacking ever a good thing?

But then we come to overthinkers. (Like me)

I’ve been stymied by the “do your best” admonishment on countless occasions. The problem is in the retrospective. That insidious little voice, while looking backwards, says, “…but was that really your best? Or could you have done better?”* The automatic answer, if you’re honest with yourself, is that, of course, you could have done better. But this is a trap.

Let’s follow this to its logical conclusion. If you can say, with honesty, that you have *never* done your best, EVER, when you should have, then what kind of person does that make you? Does this, for example, make you a terrible parent if you have never done your best to raise your children? Right. But what’s the answer?

There are two problems here. The first is that we are not supposed to be looking backwards all the time. I’m not talking about memories (mostly), but about Monday morning quarterbacking. The past is in the past. What’s done is done. Did we screw up? Yes, almost certainly. But it’s in the past. We are not saved in the past, or the future (another discussion), but in the present. All we have to work with is today, the day God has given us.

So what now? Do we agonize over it, replay every sordid detail, regret we didn’t choose differently, castigate ourselves until the end of time..? No, we accept we failed, because we are fallen human beings, we go to confession (if appropriate), and we move on, perhaps taking a lesson with us. What is gained by infinite regret? This is how the demons lead us into despair, by putting up our worst moments in front of us, “This is Your Life” style.

The second problem is that we are not supposed to be judging our own spiritual progress. We are usually terrible judges of ourselves, either because we are over-lenient due to blind spots (we all have them) or because we are hyper-critical. How can we possibly know the state of our own souls? Great saints have said that they are the worst of sinners. Looking at this superficially you would think that either they are ridiculously hard on themselves or lying out of false humility. The truth is neither. The more the soul aligns itself with God, the more it is able to see. A pitch dark room doesn’t look too messy at first glance but it may be filled with filth. Bring in a candle and you can see rubbish everywhere. That candle may reveal the next room to be quite clean, until you turn on the overhead light and see an inch of dust. The progression goes on. The greater the light, the more easily you see even tiny specks of lint. The difference is the amount of light you let in the room. In the uncreated light of God none of us looks good. This is how you can feel like a pretty decent person on the day of your (adult) baptism and a year later wonder why you’ve grown so terrible. You haven’t, but you’ve let more light in the room and see things you never were able to see before with that flickering votive candle.

I want to point out that it is a great blessing to be able to see our sins. This is not a cause for despair! On the contrary, this is by the Grace of God because we can’t fix/clean what we can’t see. Only by seeing the filth can we begin to clean it up. Because the demons hate us and want to destroy us they want to (1) keep us ignorant of our sins and/or (2) paralyze us with despair so we can’t make progress.

I was told by my spiritual father a story many years ago about an incident at an American men’s monastery when one of the novices accidentally caused heavy damage to a brick wall when using a piece of heavy equipment. The spot had to be demolished and rebuilt. There were pilgrims there at the time who were expressing sympathy to the novice and said something like, “I bet you feel just terrible about this, making such a mess” The novice simply looked at them and replied, “but that’s what I do. I make messes.” He wasn’t self-recriminating, nor brushing it off. He was dispassionate about it, acknowledging that it was a mistake, and only to be expected since he was human and made mistakes. This was a good lesson that I, sadly, have yet to internalize.

Father is aware of my problems with “just do your best” and says something closer to, “make a good, reasonable effort with God’s help.”

*There is a similar mental conversation detailed in C. S. Lewis’s Surprised by Joy, in which he got in his head as a child that his prayers only had worth if he meant them. So he would finish his bedtime prayers, then listen to that little voice which queried, but did you really mean them?? upon which he would begin all over again, over and over, until falling asleep, exhausted, in the wee hours of the morning.