Pickpocketing is secretly the fastest way to level Pickpocket early

[WhiterunModder]

So I just realized something stupid on my current playthrough. Everyone talks about pickpocketing the Thieves Guild people for easy XP, but that's actually slow as hell if you're doing it legit (getting caught, reloading, etc). But if you just... pickpocket literally everyone in Whiterun for like 20 minutes while they sleep, you can hit 50+ Pickpocket before you even finish the main quest intro stuff.

I'm talking just stealing iron daggers, food, literally anything. The XP gain is based on item value, not difficulty, so pickpocketing a 2-gold fork 50 times levels you just as fast as pickpocketing a 500-gold ring once. And since everyone's asleep and you're not getting caught, there's zero consequences.

I don't know why the guides all recommend grinding on the Thieves Guild members when you could just become a ghost in your own town for an evening and come out with 50+ Pickpocket and a criminal record nobody cares about. The Thieves Guild questline doesn't even start until you pickpocket the right person anyway, so you're not locking yourself out of anything.

Am I missing something or is this just the most obvious optimization nobody mentions?

 

[DragonbornVet]

You're not wrong that it works, but you're kind of glossing over why people don't do this. Yeah, the XP is based on item value, but pickpocketing low-value stuff is still tedious as hell - you're clicking the same animations over and over for 20 minutes straight. The Thieves Guild grind at least gives you something to do between attempts, and honestly most people just quicksave before each attempt instead of reloading on failure, so it's not that much slower in practice.

Also, the "zero consequences" thing is technically true but only if you're cool with being a wanted criminal in Whiterun from level 1. Your bounty doesn't reset when you leave town, and guards will recognize you. It's not a game-breaker, but it's annoying to deal with early on if you're not planning a full criminal playthrough. Some people actually want to roleplay as a normal person for the first few hours.

That said, if you're just min-maxing and don't care about the roleplay angle, yeah, sleep-pickpocketing the entire hold is faster in terms of pure time-to-level. It's just boring as hell and most guides probably don't mention it because the audience isn't looking for "exploit the AI for 20 minutes" advice - they want something that feels like actual gameplay. But you found a legit optimization, so fair play.