Skyrim was the first ES game I played. I've bought Oblivion too, but to be quite honest I played it for about half an hour and struggled to get into it. I escaped the prison and the sewers, and actually did get out into the world ... but then didn't know what to do. I wandered aimlessly in the direction of Weynon Priory, then turned it off and started a new game of Skyrim.

Now, I sense I'm coming to the natural conclusion for my latest Skyrim character and want to have another try at Oblivion - I've watched YouTube videos of it and read about it, it looks like a fun game. I should be able to enjoy it. I think part of my problem is, I know Skyrim. When I'm planning a character, I know what sort of things there are to do in Skyrim; whilst there are still some surprises, I know roughly what that character is going to do. I've got a lot more in to the roleplaying aspect of the game during my playthroughs of Skyrim, and now the idea of starting a game where I don't know what my character should do is ... well, frankly a bit daunting.

Which is bizarre, because what I first liked about Skyrim is that I could do anything and everything. Made a Dunmer character because they looked cool, didn't go anywhere near magic the first time, just made her a sneak-archer, who somehow still managed to be Harbinger of the Companions and Arch-Mage. She stole everything, even though she wasn't really a thief, and mercilessly assassinated even though she wasn't really a killer.

I tried to spend a lot of time scrutinising the various skill options available in Oblivion, the racial bonuses, the different classes and birthsigns, trying to devise the perfect combination for my character. Didn't help - I had her all set up, but then when you're actually out there in Cyrodiil, it's a different story. Would she go into this cave or do this quest? In Skyrim, I'd know if it made sense or not; in Oblivion, I could end up unwittingly sending my mage-abhorring character into a situation where it's all about magic.

Maybe I should just make a more general character..? Maybe if I made a character where the only 'backstory' was generally evil and morally ambivalent, I'd have more success - just always do the wrong thing..?

I also bought Oblivion after Skyrim, and my first Oblivion character failed horribly, because I didn't understand that I had to repair weapons and armor... so I was stuck with broken weapons and armor inside an Oblivion plane, and had no save outside of that plane.

My second I played for quite a long time. I had only a rough idea of her personality and background in the beginning, but she developed as I played. That might be a solution for you, not going too much into detail but let the character develop as you play. It might also help to pick one or two major questlines to focus on, and to save before starting a new quest, so that if you feel forced to do something out of character ypu can go back to an earlier save and choose not to do that quest.

You may have felt just as lost when you began to play Skyrim too. You probably don't remember it anymore. But I think if you spend enough time in Cyrodiil you'll eventually feel that you know what to do here, too.

I wouldn't worry too much about sending a non-mage into situations where it's all about magic. There are not many of those types of situations in Oblivion. In Oblivion one character can do virtually everything in the game. This was, I understand, one of the major criticisms of Oblivion when it came out. But I think we can also choose to see this as an opportunity. When we can do anything with a character (or all things with one character) we have the freedom to choose what we want to do. We are not locked into an archetype, a style of play or a quest line from the beginning. Our characters can grow and change as our games progress.

I think broder_fisk's advice is very good and I second it: start a generalized character and let her develop naturally. Several of us make "test characters" for our first couple of play-throughs. We don't do much roleplaying with these characters. We use these characters to get a "feel" for the game. Once we know what we're doing we start to roleplay.