carelessly cautious/cautiously careless

One of the most difficult things for me is to control my worrying. It's not that I worry a lot, it's just that I don't know how to find the correct dosage. I've realized that it's a very fine line between not worrying and not caring -- I've found myself constantly O.D.'ing on the medicine.

This is, for me at least, the one of the hardest things to do. To let go of myself completely while still holding on. It's an essential paradox of life. As my homie Gilbert Keith put it, a soldier fighting in battle needs to have a certain modicum of carelessness towards his own life if he wishes to save it; otherwise, he'll cling so dearly to life so as to avoid battle and will probably lose his life doing so. Put much more eloquently, "whoever desires to save his life will lose it."

It's helpful to pause and apply this basic Christian principle to more applicable situations -- friendships, marriages, jobs, anything. Whatever it is you're so afraid of losing is likely already lost. The best relationships in life are those where the people involved are simply careless and free. Free to criticize, to praise, to yell at and to whisper to -- having no fear of losing the other person for speaking your mind. Knowing that no matter what happens, you won't lose me as a friend or spouse or brother, and thus we can live freely, without being enslaved to worry about how a comment could be taken. And this is how life should be -- absolute carelessness meshed with absolute caring. No one said Christianity was an easy thing.

On the other end of the spectrum, cautiousness can be a good thing, but a deadly thing if the dosage is too high:

He who observes the wind will not sow,
And he who regards the clouds will not reap.
--Ecclesiastes 11:4

And here is where "waiting for the right moment" falls flat. Now obviously, if there's a blizzard outside, it's a good idea to wait a little before trying to sow. But after that, we are to do our job as best as we can, at all times:

[Continued]
As you do not know what is the way of the wind,
Or how the bones grow in the womb of her who is with child,
So you do not know the works of God who makes everything.
In the morning sow your seed,
And in the evening do not withhold your hand;
For you do not know which will prosper,
Either this or that,
Or whether both alike will be good.

So be cautious. Be careless. Be caring. Don't worry.

Easier said than done.