The repeated pattern in this sonnet is one in which the speaker connects his present suffering with a reliving of what has occurred earlier (perhaps long earlier) in his life. His allusions are to a mostly unspecified series of traumas which, in his recollections of them, have the effect of exacerbating his present unhappiness.
This is paradoxical because the first allusion is to the "sessions of sweet silent thought"—a positive symbol, to say the least. We therefore see a contradiction between that opening line and the later reference, in which it's implied that untold past traumas are multiplying his present sources of discomfort:
I sigh the lack of many a thing I sought,
And with old woes new wail my dear time's waste.
The speaker is obsessing over his current "lack" of things that presumably would make his life different and happier. But at the same time, the phrase "love's long since cancell'd woe" indicates that whatever that previous love was, he has gotten over it (since it was...
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