Jeff, it is really great to hear from you again after a long while!!

If his wish is to remain then there is a simple solution. The Braisa states that if he sold himself he can be sold for 6 years or for more than 6 years. Rashi DH veYeser writes that if he specifies a condition that he will be sold for 10 years this is effective.

The Ritva writes that it depends totally on the wishes of the person selling himself. If he sells himself voluntarily he can do this for 6 years or less than 6 years, or if he wants he can sell himself for more than 6 and can work until the Yovel year.

The Mishneh LeMelech Hilchot Avadim 2:3 writes that if he sold himself and did not specify how long for, he will work until Yovel according to Ritva.

Wishing you a Kesivah vaChasimah Tovah.

Dovid Bloom

Follow-up reply:

In the question you wrote that "he sold himself and then had his ear pierced after 6 years". Well, that would depend on the dispute between the Tana Kama and Rabbi Eliezer here. According to Tana Kama if he sold himself he does not have his ear pierced but according to R. Eliezer he does. The Rambam Hilchot Avadim 3:12 rules like Tana Kama that he does not pierce. So according to the Halacha I do not think there would be any siginificance in him piercing his ear because it is unnecessary.

Best wishes

Dovid Bloom