So you don't have to watch videos, I'll write it out.
When you ask for a job, it will be in a specific one of the big cities(Solitude, Markarth, Whiterun, and Windhelm.) Once you have done four jobs in each city, you'll receive a special job. You must do all four special jobs to become a Thieves Guild Master.
*NOTE: You can do any type of job you want.
Thanks to Rajeanero for the avatar and Xerofox for the awesome signature pic!
Batman: Arkham City; 70/70 (1500G)
Elder Scrolls: Skyrim; 75/75 (1550G)
Borderlands 2; 59/59 (1375G)
Originally Posted by Metabolic x360a
Maybe it's just the universe making up for douchebag's like you.