Die Wortstellung in meinem vorgeschlagenem Satz ist natürlich falsch.

He wars chaaring up the hole time.
wäre besser oder?

my 2 cents:
He stayed strong the entire time.
He kept a stiff upper lip the entire time.

im song dear mr. president von pink wird dies auf eine ähliche weise verwendet...
"how can you walk with your head up high" mit dem Kopf hoch eben...
ich glaube das trifft deinen Kontext ganz gut...

btw, hole = Loch
the whole time

I'd say

danke

He carried his head head high all the time.

He carried his head high all the time.

I take this to mean that he was assured of his accomplishments and had a pride in his affairs , such as his work and his place in the community. Or for "he" you can also read "she"