THE ELDER SCROLLS V: SKYRIM
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11.5 Additional Jobs
Ready for some extra work? Once Brynjolf instructs you to speak with Vex and Delvin Mallory about additional work they may have for you (after you complete Thieves Guild Quest: Taking Care of Business and you “officially” join the Guild), immediately chat with either of your new brethren.
Aside from offering you training in Lockpicking (Vex) and Sneaking (Delvin), ask them to explain the jobs they have to offer you, and then begin any you wish.
You can have one Additional Job from each of them active at any given time.
The Guild frowns on you quitting jobs you may be finding too difficult, but this is possible too. When you successfully finish a certain number (and variety) of Additional Jobs, Part 3: City Influence Quests become accessible (see below).