It was a [my] privilege to work with him.
彼と一緒に働けるということは光栄であった
It was a question of sink or swim.
いちかばちかだった
It was a severe test for him.
彼にはつらい試練だった
It was a significant [substantial, considerable] improvement on [over] its predecessor.
それは以前のものと比べてかなり進歩していた
It was a silly thing to do.
ばかなことをしたものだ
It was a struggle for her to make (both) ends meet.
収支を合わせるのに彼女はさんざん苦労した
It was a stupid thing to do.
ばかなことをした
It was a very sad affair.
非常に悲しいことだった
It was a wicked blow to his pride.
それは彼のプライドをいたく傷つけた
It was a wound to his pride.
それは彼の自尊心についた傷だった