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Elder Scrolls V: Skyrim Leveling Guide

In order to use this guide to quickly level your Skyrim skills you will need understand a few basic game mechanics first. Killing things and completing quests does not give you experience like a typical RPG would. Instead, gaining experience is the result of leveling up your skills. The amount of experience you need to level up increases the higher in level you are, meaning at level 1 let us pretend you need 100 XP to get to level 2. You might then need 120 XP to get to level 3, etc. Also, the higher your skill is, the more XP you get when you level it up, meaning that raising Archery from level 1 to 2 might grant you 50 XP, but leveling Archery from level 2 to 3 might give you 100 XP.

Now, the typical way you increase your skill level in something is by using the related skill. For example, to increase your Archery level you need to hit enemies with arrows, to level Sneak skill you need to successfully sneak by an NPC without them detecting you, to level Lockpicking you need to work on picking locks, etc. There is an alternative though.

Throughout Skyrim you will come across trainers that can raise your level in a particular skill for a fee. The fee to train you goes up with the skill, meaning training to level 2 Archery will cost much less than training to level 100 Archery. Some trainers will only train you after you have done certain quests for them (or for other people). You are limited to 5 skillups through trainers per level. That limit is shared between all skills meaning you can train 5 times total for any combination of skills you want. So if I went to train Archery 3 times and Sneak 2 times, I would be unable to train more until I leveled up. A list of trainers is available here.

Ok, enough with the background information, how do we use this system to our advantage and quickly level up skills? Well, hopefully you have no moral qualms about robbing people because you are going to be doing a lot of it.

Thieves Guild

My guide is based around using the trainers at the Thieves Guild. In order to join the Thieves Guild you will have to travel to the town of Riften and begin the quest A Chance Arrangement. Continue the quests until you become a member of the Thieves Guild (getting your respective achievement or trophy for joining). You should now have access to the trainers. The particular training you are looking for is named Vipir The Fleet and he is located in the The Ragged Flagon – Cistern. He trains Pickpocket which is the essential skill you’ll be using to exploit your way to high skill levels.

Now, a lot of what you do now depends on how patient you are and how high your Pickpocket skill is going into this. I will explain the general idea.

Pickpocketing the Pickpocketer

What you will be doing is training Pickpocket with Vipir The Fleet, then taking your money back by pickpocketing him immediately afterwards. As you do this, you’ll gain skill from him teaching you and from taking your money back. This will not only level your Pickpocket skill a ton, but it will also level up your character very quickly, especially at lower levels.

The problem with this method is for people with a low Pickpocket skill. The amount of gold you are trying to take back depends on how high your Pickpocket skill is. The lower the skill is, the less it will cost to train and the easier it will be to pickpocket because it is more difficult to successfully pickpocket larger amounts of gold. But it is still difficult to pickpocket even a small amount of gold at lower skill levels. That means you should be saving before you attempt to pickpocket every single time because if you fail, you will no longer be able to try to pickpocket that target. When you try to pickpocket, and select Vipir The Fleet’s gold amount, look to the right side of the screen and you will notice the game gives you your chance of successfully stealing the gold.

I will not lie to you. Even a 33% chance to successfully pickpocket the gold will cause you a lot of frustration. In theory, this means you’ll manage to take the gold back 1 out of every 3 times you try. While I was doing this, my success rate at that level was much lower. I had to load my previous save many times at the start. I know this is very frustrating, but as your skill goes up this will get easier, I promise.

There are a few things you can do to increase your chances.

  1. Never attempt to pickpocket Vipir the Fleet unless you are completely hidden. This is somewhat easy to do in the Thieves Guild location because it is fairly dark and easy to hide.
  2. Take a look at the Pickpocket Skill Perks. To make this whole thing much easier, put points into Light Fingers, Night Thief, and Cutpurse.
  3. Try and find Vipir the Fleet at around 3:00 AM game time. I managed to find him asleep at this time which made taking the gold a lot easier.

You will want to get your Pickpocket skill to around 50 before you continue (though this depends on whether you put points into Night Thief and Cutpurse, and how much the training is going to cost for the next skill you will want to train).

The next step is to pick another skill you want to train. For example, say I wanted to level Sneak next. As it happens, there is a Sneak trainer named Delvin Mallory in the Thieves Guild. I would repeat the same thing I was doing with Vipir the Fleet; just train the skill, steal your money back, and repeat.

Some things to keep in mind: the cap of 5 trained skills per level will not matter to you if your character is a low level because you will reach your next level within the 5 trained skills. As you level up though, you will find that you will not level up with just 5 skill increases so choose your skills carefully. Start using this guide on skills you think are the most important.

The real slow down comes when your Pickpocket skill reaches 100. As you take money back from trainers (especially if you are training a skill in the 75 range which will run 2,800 gold per training session) your Pickpocket will level with you granting additional XP and helping you level within the 5 training sessions. After the extra XP from Pickpocket goes away (because you maxed it out), your XP gains drop dramatically and you will be stuck at your character level until you level your skills in more legitimate ways.

To Sum It Up

  1. Get your Pickpocket skill to around 50.
  2. Put points into Pickpocket perks Light Fingers, Night Thief, and Cutpurse.
  3. Go to a trainer for a skill you would like to level up quickly.
  4. Train your skill.
  5. Save your game!
  6. Attempt to take the gold you just paid back.
  7. If successful, go back to step 4. If pickpocketing was unsuccessful, reload your game and then go back to step 6.

If you have any questions, feel free to leave a comment below!

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  1. How do you pickpocket Vipir the fleet?
    Right now my Pickpocket skill is 57, I’ve got One light fingers, Night Thief & Cutpurse perks.
    I’m trying to pickpocket 1500 gold from him at night while he’s asleep, while hidden and I can’t ever get more than 0% change to pickpocket it. The sword and bow gie me 90% chance but the gold is always 0% – why??

    I’ve tried when he has 1500 gold and 10,000 – nothing changes my odds.
    I’ve tried with Pickpocket boosting gloves, amulet and ring – and without – no change to the odds. What’s going on – am I doing something wrong?

    • You should probably be 3/5 Light Fingers, and then 4/5 when you reach 60. If I remember correctly, I put points into Light Fingers as soon as I could. It doesn’t sound like you’re doing anything wrong otherwise. If you don’t have enough spare perks to put more points into it, I would go level something else (something cheaper so you can still pickpocket) until you level up and can fill out Light Fingers.

      Definitely keep on all of the gear you have that boosts Pickpocketing. Even though it doesn’t seem like they’re doing anything, they are.

    • some items cannot be pickpocketed

  2. Chris /

    So, I have a question that ‘sorta’ realates to what your saying here. Once a particular skill gets to 100, let’s say Archery, I should put the Bow away and move to 2-handed as I will no longer gain any XP and therfore not increase my ‘overall’ level by using my bow?

    • If your goal is to increase your character level, then yes. I wouldn’t switch to another weapon just for that purpose though for a few reasons. First, assuming you leveled your Archery exclusively, by the time your skill is at 100 your character level will be so high that trying to level another weapon skill from scratch will be very difficult because enemies will take forever to die. Second, it would probably be better to level a skill like sneaking, blacksmithing, enchanting, alchemy, etc. because the benefits of those other professions are very valuable. Third, since the game (mostly) scales with level, there isn’t a high incentive to level up past 50 or so.

  3. if you train then kill a person you can get your money back(i have pickpocket 100 and a pickpocket set and the highest the chance of pickpocketing after training is 12%, sneak kill is easier)
    warning if they go through a door the money they have drops dramaticly

    • Your chance of pickpocketing gold back after training depends directly on the amount of gold you’re trying to pickpocket. Obviously the more expensive the training, the more difficult it will be to pickpocket the money back. With the proper perks, like Cutpurse which makes pickpocketing gold is 50% easier, as well as Night Thief and Light Fingers, you can increase your chances much higher than 12%.

      The obvious downside to killing the NPC is you cannot use that NPC to train again. I wouldn’t recommend it. Even if your chance of pickpocketing is only 12%, I would much prefer saving the game, trying to pickpocket, and reloading my save game rather than killing the person.

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