Omoiizuru toki zo kanashiki yo no naka wa sora yuku kumo no hate o shiraneba - Gosen Wakashu(English Translation & Meaning)

思ひ出づる時ぞかなしき世の中は
空行く雲の果てを知らねば

Roma-ji: Omoiizuru toki zo kanashiki yo no naka wa sora yuku kumo no hate o shiraneba
English Translation: When I recall it,
then it is that I grieve—
for in this world
like clouds that cross the sky
we cannot know where we will end
Meaning: It is when I remember that I grieve, for in this world, like the clouds drifting across the sky, we cannot know where we will come to rest.
Commentary: Book Sixteen Miscellaneous Poems II 1190

Headnote: "Sent to someone at a time when something weighed on my mind."
The poet says that it is when remembering that sorrow comes, for in this world, as with clouds drifting across the sky, no one knows the end. Amid brooding, the poet overlays the uncertain course of the clouds with the fragility of a world whose future cannot be seen.
According to the headnote, it was sent to someone at a time when something weighed on the poet's mind.
The poet is listed as anonymous, and the composer's name has not come down to us.

The first line, "Omoiizuru," means "recalling," with an extra syllable.
The second line, "toki zo kanashiki," means "is when I grieve," with "zo" an emphatic binding particle closed by the attributive "kanashiki." The poem pauses here.
The third line, "yo no naka wa," means "this world."
The fourth line, "sora yuku kumo no," means "of the clouds crossing the sky," a figure for what has no fixed course.
The last line, "hate o shiraneba," means "since we do not know the end," taking the same form as "kata o shiraneba" in the last line of the preceding poem, so the endings of the two correspond.
Author: Unknown Poet
Source: Gosen Wakashu
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