Would this be considered overworking yourself.

2 full-time IT Help Desk jobs.

1 will be Monday through Friday

1 will be Saturday through Wednesday

3 days out of the week. You are working back to back jobs

4 days out of the week. You will be working just 1 job

Nah, as a slave you aren't supposed to have time where you can think about freedom, self-realization, recreation or other non-slave stuff. Judging by your inquisitive mind i also assume that a high chance of early degradation of your capabilities due to harsh punishments - so better get as much work done as quick as possible before you end up at the quarry, your last owner.