If you want to join the Thieves Guild in Skyrim, you're in luck. The guild's main missions revolve around stealth, but joining the thieves are among Skyrim's more lenient groups and let you join even if you don't quite pass their test with flying colors. The rewards for taking the plunge into Skyrim's seedy, thieving underside make it worth the effort too.
How to Join the Thieves Guild in Skyrim
Travel to Riften, and seek out Brynjolf, a red-haired Nord. He's in the marketplace during the day and at the Bee and Barn after 8 p.m. Sometimes, Brynjolf approaches you automatically during the day.
Either way, speak with him to start the "A Chance Arrangement" quest. You're tasked with stealing a ring from Brynjolf's strongbox and placing it in another NPC's pocket. Should you fail, Brynjolf says he still believes in you and lets you join the Thieves Guild anyway, though some of the existing members are less than friendly toward you if you fail.
Thieves Guild Perks
You'll receive mastery level training in thieving-related skills, such as lockpicking, and the option to bribe guards and take on as many radiant thieves quests as you want. However, that's just a small part of what makes this guild worthwhile.
Rising through the ranks and completing the guild's quests eventually gets you the Nightingale armor set and sword. Each piece of the armor has perks, such as increasing stealth or stamina, and the Nightingale Sword's special enchantment restores health and stamina when you damage an enemy.
You'll also get to undertake "jobs," a series of small quests revolving around stealing items. There's gold as a reward, but completing available jobs also unlocks city influence quests where you restore the guild's reputation in a given city and unlock new stores if successful.
This is just one of Skyrim's many guilds to spend time with, though. The Mage's Guild might be worth your time if you prefer the spellcaster's life, though the Dark Brotherhood has its own share of special appeals as well.