Are your Attributes and Skills good enough?
To become a Mastermind you need your Agility and Personality to be at least
34, and you also need one favored Skill at least
80 and two favored Skills at least
30The favored Skills for the Thieves are Acrobatics, Light Armor, Marksman, Security, Short Blade, and Sneak
You can check all this info in your stats Menu, and by hovering the pointer over your Factions (listed in your Menu also)