Having been a doctor or a scientist or some kind of an academic for much of my life, I have been focused on 'understanding' - and indeed my natural disposition has also pointed that way.
But 'understanding' the world is problematic, because what it really amounts to is making simple models of the world, and using these for prediction and manipulation. All human understanding is inevitably simplified - due to the inevitable constraints and also because that is implicitly the purpose of the whole business... to take the 'infinitely' complex and interconnected world and render it into something simple enough that we can deal with.
This also means that all understanding is wrong - we know it is wrong because we know that most things have been left out, and because to make a model we draw-a-line around a bit of the world and treat it as separate when in reality everything is somewhat connected with everything else.
So understanding the world is - no matter how apparently useful - an exercise in error.
We know that models are false, and we can never know that they are applicable or not - and we can't ever really know except in terms of the model itself - because on major simplification of models is that the outcomes are selective and limited.
And we might know a model worked - in its own terms - up to 'now'; but (as the history of science amply shows) situations may arise in which a previously useful (predictive, manipulative) model breaks-down and fails even to satisfy its own very circumscribed criteria...
The main problem with thinking in terms of models, however, is to believe that they are True. This is what Owen Barfield termed Idolatry, the worshipping of the model as an idol. As when Galileo asserted that his model was really-true - and refused to regard it as merely a more-or-less useful/ better model (hypothesis/ theory).
The modern error has been to assert that Galileo was right, when in fact we know for sure that he was wrong... we just keep on doing this! We assert that the models of science/ technology/ medicine, economics etc are true - when in fact they are never true... and often only last a few months or years before being superseded by something else we 'believe' is true.
It is a shallow and foolish error - a deep metaphysical error; but it is an error that pervades modern life and which is enforced with strong sanctions.
It was an insight of Goethe that models are not knowledge, and that 'knowing' something is more analogous to knowing a person than to modelling a phenomenon. That is, we get to know a friend, we do 'understand' a friend - we do not hypothesis and test models of their behaviour - making and checking predictions, trying to perform manipulations etc. That is what 'managers' do, not friends!
We get to know a friends by... well being with them, thinking about them, being concerned about them... stuff like that. We may know our mother or father in this way, although we cannot and do not want to create a simplified model of them - and if we do, we don't suppose that the model has captured their essence; in fact we know for sure that all such models are wrong.
Through human history we went from knowing, to understanding, and now we should go back to knowing - but this time knowing that we know. Our original knowing (as children, as early Man) was unconscious, was simply taking-for-granted - but now we need consciously to know what we are doing, and to choose it rather than simply taking it for granted.
This is, indeed, the task of tasks which confronts us.