Once you complete your carriage ride, choose Khajiit Race (they have the highest base sneak in the game). After seeing a stormcloaks head get lopped off and running through Helgen, go into the keep with Ralof and chop him (but dont kill) with whatever one handed weapon you can find to boost one handed weapons skill (it's free real estate). After getting out of the keep make sure NOT TO HIT HIM. You will get a bounty.

Once you have finished the aforementioned steps, head to the carriage in front of the Whiterun stables and tell him to go to Riften. This is where the thieves guild resides. Once there, tell the guard outdoors to piss off, and walk through the gates where you will be greeted by another happy soul named Maul. Don't pay him squat, just do one of the other speech options and move right along into the town square where Brynjolf should be waiting for you, and will come up to you asking if you are in need of coin. Just speed through the dialogue until you get to the part where he mentions him making a distraction in the square.

Once receiving the quest (A Chance Arrangement) from Brynjolf to meet him in the town square, wait until daytime and tell him you are ready. Once he starts distracting, go over to Medisi's stand (Jewerly type Stand) and crack the door to the strongbox as well as crack the strongbox open. Once you do so and steal all the items from the box, just stand up and go over to Brynjolf, cause you dont really need to plant the ring (so you can finesse him for a free ring, basically). Once done and it says: QUEST COMPLETED: A CHANCE ARRANGEMENT go down to the ratway and find your way to the ragged flaggon, the thieves guild "hq" of sorts.

*Be careful of the enemies in the ratway if you are low level though, you will get the ♥♥♥♥ beaten out of you if you dont play smartly and consume cheese wheels responsibly

Taking care of business is literally just a fetch quest. Go to Brynjolf, ask him if he has any extra tips on how to get them to pay up, find the people (DO HAELGA LAST so you dont need to steal the dibella statue which wastes time), talk to them and do their individual prompts (its super easy), go back to the guild and you are done. Tell Brynjolf everything is set and you took care of business. Congrats, you are now part of the Thieves Guild! Happy Heisting, and make sure you speak to Tonilia to get your Thieves Guild armor.



Any typos? Let me know in the comments! Please feel free to let me know how I did as well, as this was my first guide after 6 years on steam!

Yes, the "thumbnail" for this guide is vex's head in a bucket.