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If I know I will be unable to do a positive time-bound commandment, may I sell myself to another Jew until the obligation passes?

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    You could also become a chassan ;-)
    – MTL
    Dec 18, 2014 at 18:10

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You could not circumvent the obligation, as an Eved Ivri remains obligated in positive time-bound commandments. (An Eved Kena'ani is not, but to make your plan work you'd have to first become a Kena'ani.)

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