YOU SAID:
It's hard to say that I'd rather stay awake when I'm asleep.
INTO JAPANESE
私が眠っているとき、私はむしろ目が覚めていると言うのは難しいです。
BACK INTO ENGLISH
It's hard to say that I am rather awake while I am sleeping.
INTO JAPANESE
私が眠っている間、私はむしろ目が覚めていると言うのは難しいです。
BACK INTO ENGLISH
It is difficult to say that I am rather awake while I sleep.
INTO JAPANESE
私が眠っている間、私はむしろ目が覚めていると言うのは難しいです。
BACK INTO ENGLISH
It is difficult to say that I am rather awake while I sleep.
That didn't even make that much sense in English.