Hello people of the forum. I'm relatively new to Elder Scrolls, so I'm not high level yet (level 9), and I do a lot of messing around in the game just to see what's gonna happen. And most recently, I did some crime-- I already forgot what it was-- and chose the 'send me to jail' option or whatever. Once I got there I was like, "Oh sweet I can bust outta here the fun way." So I'm in the whiterun prison and go down through the dungeon, and come across the chest full of my stuff. Now this is the problem: My lock-picking skills are low a this point. I think have the first perk which makes Novice locks easy. The chest with my stuff in it is an "Adept" difficulty lock. I only have one lock pick and I saved right before trying to open this chest. Most of the time it breaks. I guess my question is, is it possible to pick an adept lock at my skill level? Is it worth sitting through however many loading screens it will take to get my stuff back? The other option I am thinking about it going outside and getting new stuff, working on leveling up my lock picking and then just go back to the chest later. In this case, will my stuff still be in there way later? I know how video games have a way of forgetting this sort of stuff. Skyrim seems to be pretty good about that though. Any comments or advice would help me out. Thanks.

Yes it is possible. If you had enough lock picks and patience you could pick a Master lock.

You don't have to pick your way out. Easiest thing would be to serve your time.
Note when you break out that is considered a crime.

http://images.uesp.net/c/c4/Fishystick.jpg

Yes it is possible - there's no in-game mechanic preventing you from opening a lock at a higher level than your skill, you just need to be patient and keep trying. You could also see if the local alchemist or general shopkeeper in town has a potion of lockpicking (locks 20% easier to open for 30 seconds!) for sale and go straight back to the chest that is giving you trouble. Or get some lockpicks, it's easier to retry without reloading because on a reload the position of the spot the pick has to be in is reset to a different place so you have to start from scratch.

Some players find lockpicking very easy to do, I struggle with it sometimes, but I've on occasion opened Master level locks with only around 20 skill in lockpicking - usually requires several broken picks before I find the sweet spot though!

I have picked Expert and Master locks at an early level. Just use a VERY fine touch