The people you want to hire should have achieved some measure of convential success, but they should have also engaged in somre desperate lark that made no sense from a career or social status perspective.

안녕하세요. 교수님.

위의 should have achieved 는 '~했었어야 했는데'로 해석하고

그리고 밑에 should have engaged in 은 가정법 결과로 분석했는데

옳게 한 것인지 궁금해서 질문 올립니다.