so, you've spent time customizing your character (or maybe you picked a preset, not judging) and you've just escaped Helgen. you've already decided what you want your class for your character to be and it just so happens to involve stealth and/or thievery. This guide'll show you how to do just that without spending any money at all, as well as it being quick.

you're gonna need to join the thieves guild before doing all this, as well as get a pretty decent amount of money, like about 1.5 to 2k. so, after you've done al the quests up to the point where you can get into the cistern of the ragged flagon, talk to Vipir the Fleet. he'll be somewhere in there. He's how you learn how to pickpocket. after you've leveled up your pickpocket skill high enough, you might want to get the pickpocket perk that makes it easier to pickpocket gold. after you've got that, start training.


as you can see ive already leveled my pickpocket up so i can't do this anymore so this has limits but it's good for a starter. so when you've leveled your pickpocket up 5 times, you need to wait for him to go to sleep or any time you're undetected and pickpocket him to steal the money back. if you keep repeating this process and leveling up then you can get the skill high quickly. but don't let the money build up too much in his pockets because then it becomes harder to steal.

QUICKSAVING BEFORE YOU DO THIS IS RECOMMENDED BECAUSE INCASE YOU GET CAUGHT AND CAN'T GET YOUR MONEY BACK YOU CAN RELOAD THE SAVE.

when you've leveled up your pickpocketing high enough, go talk to Vex or Delvin or any other person in the theives guild to level up other stealth skills, and do the same thing with them.

this trick works with pretty much any trainer in skyrim so that makes it super easy to level up your stuff fast as long as you have a good amount of gold. hope it helps.