Pickpocketing actually worth leveling or should I just save-scum?

[RiftenWanderer]

I'm on my second playthrough (level 18, playing on Switch) and I keep dumping perks into pickpocketing because I feel like I'm supposed to, but honestly it feels like I'm wasting time. Even with a couple perks, I still get caught constantly trying to steal anything valuable, and the stuff that actually succeeds isn't worth the risk. Am I just bad at it or is there a threshold where it actually clicks? Should I just reload if I fail or is there a smarter way to use this skill?

 

[TamrielTactician]

You're not bad at it—the skill just has a weird power curve that makes early levels feel pointless. The catch is that pickpocketing's success chance depends way more on your Pickpocket skill and the target's level than on perks alone, so at level 18 you're basically fighting an uphill battle against anything worth stealing.

Here's the thing though: you don't actually need to level it if you don't want to. Save-scumming works fine, but there's a smarter path. Get the perk that boosts success chance on high-value items (I think it's called something like "Wax Hand"? Not 100% sure on the name), and more importantly, just pickpocket everything that's not valuable for like an hour. Lockpicks, potions, common gear. Your skill will climb fast and suddenly those valuable steals actually land. It's boring but it works.

Alternatively—and this is what I did on my Switch run—just don't pickpocket at all until you've hit like level 40 through other means, then blast through the early perks. Or join the Thieves Guild (the questline where you do some burglaries for Brynjolf and the crew) and do their radiant jobs, which level the skill and make the failures feel less wasteful since you're getting paid anyway.

Honestly if you're not having fun with it, just dump the perks into something else. There's no "must-have" build that requires pickpocketing.

 

[WhiterunModder]

Yeah, that advice is solid. I'd add that on Switch you're basically stuck with vanilla, so you don't have mods that rebalance the skill curve (stuff like Ordinator on PC changes how pickpocketing scales, makes it way less tedious), which means you're grinding the "intended" experience and it genuinely sucks early on.

The radiant jobs thing is the real move though. You're getting paid and leveling, so even when you fail a pickpocket check during a job, you're not just eating the loss—you're already compensated. Plus the Thieves Guild questline itself has some actual story moments, so it doesn't feel like pure grind. Way better than standing in Whiterun stealing iron daggers for two hours.

Fwiw if you really hate it, pickpocketing is one of the few skills where you can just... not engage. Unlike, say, Destruction magic where you kinda need it to be a mage, or Smithing where it's almost mandatory for endgame gear, pickpocketing is pure flavor. You can steal stuff the boring way (kill everyone, loot bodies) or just buy what you need. Not optimal, but it works.