Oshikarade kanashiki mono wa mi narikeri ukiyo somukan kata o shiraneba - Gosen Wakashu(English Translation & Meaning)

惜しからでかなしきものは身なりけり
憂き世背かん方を知らねば

Roma-ji: Oshikarade kanashiki mono wa mi narikeri ukiyo somukan kata o shiraneba
English Translation: Not worth regretting,
yet the thing I grieve for most
is this self of mine,
since I do not know the way
to turn my back on this sad world
Meaning: It is not dear to me, and yet what I find most sorrowful is this self of mine, for I do not know how to turn my back on this weary world.
Commentary: Book Sixteen Miscellaneous Poems II 1189

Headnote: "On the occasion of speaking about how the world does not go as I wish."
The poet says that what he finds sorrowful, though not precious, is his own self, since he does not know how to renounce this weary world. Wishing to leave a world that will not go his way yet not knowing the path to renunciation, he laments the self he can neither keep nor cast away.
According to the headnote, he composed it while speaking of how the world did not go as he wished.
The poet, "Tsurayuki," is Ki no Tsurayuki. A son of Ki no Mochiyuki, he was the leading compiler of the Kokinshu and wrote its kana preface. He is also known as the author of the Tosa Diary.

The first line, "Oshikarade," means "not regretting it," with "de" a negative conjunctive particle.
The second line, "kanashiki mono wa," means "what is sorrowful," holding both tenderness and grief.
The third line, "mi narikeri," means "is my own self, I find," with "keri" the exclamation of realization. The poem pauses here.
The fourth line, "ukiyo somukan," means "to turn my back on the weary world," that is, to leave secular life by taking orders.
The last line, "kata o shiraneba," means "since I do not know the way," supplying the reason for the third line in inverted order. It has the same form as "hate o shiraneba" in the last line of the next poem, so the endings of the two poems echo each other.
Author: Ki no Tsurayuki
Source: Gosen Wakashu
Prev Poem: Ureshiki mo uki mo kokoro wa hitotsu nite wakarenu mono wa namida narikeri
Next Poem: Omoiizuru toki zo kanashiki yo no naka wa sora yuku kumo no hate o shiraneba