Having one of those moments of gaming where I suppose the writing equivalent is writers block.

Every time I start the game with one character, I want to reroll and do something else.

I sometimes draw inspiration from what other people have done, but also feel much more immersed when I'm reminding of all the things I havent personally done or even want to do.

Sooo, what race are you, what are your motivations, what skills do you specialise in or mostly use etc.

As an aside to this, my particular problem is that I always have difficulty roleplaying a rogue that joins either the thieves or the assassins. I find it very hard to do those quests on one hand, and then do anything remotely helpful on the other. I.e., why does my thief even bother asking "so is there any work around here?", when the whole point of a thief is that they dont really do an honest day's work.
Why do I care about Mr X's missing valuable faily heirloom? I mean, I like the very useful tip of some loot, but in reality it just leaves me with a quest item I cant get rid of and a journal entry that wont go away either.

I guess what I'm saying is, that if I wanted to play your standard sword and board warrior, it's so easy to do as so many of the quests are "go off and be the strong hero" type, and there are much, much less of "go and spy on this person" or "go and retrieve this by any means necessary".
I also find it hard to justify doing the main quest with any thief or assassin. I've got some RP reasons in my head that I've come up with over the days, but nothing really that doesnt feel like I'm making an excuse to be honest.

I want to be able to play a rogue type, without being the typical hero. I tried playing as a stealthy hero type, and not joining the thieves or assassins, but it doesnt 'feel' right.

Am I making sense lol?

Part of being a successful thief or assassin is blending in with the rest of society.
If you always act like a thief.... you wouldn't be very successful at it.
Sometimes an assassin has to act like a normal guy.... do the mundane jobs... just so the entire town doesn't know he's an assassin.... or to get closer to the target.
It's all about playing the role. Fill in the blanks with something you make up.... then act it out.

my favorite character ATM for role-playing is my High Elf I'm a thalmor supporter and will not join either of the civil war thoug i left helgen with Hadvar. My character came to Skyrim to train at the Mages College and is on his way to becoming Archmage. I plan to become a vampire as soon as I become archmage then continue with the main quest. I attack both imperials and stormcloaks when the opportunity presents itself.

Well, good or bad, everyone has an urge to live. If you knew the world was going to be obliterated and everyone - including you - would die and only you could save it by fulfilling your destiny...well, you would wouldn't you, regardless of your moral inclination. Methinks you'd be swept along by the 'Oh crap' factor. Theres your MQ motivation right there.

My character is an Orc who pokes his nose into everywhere and does whatever he wants. Usually he does good but he's not averse to shady dealings either. Especially as his long stint as a goody-two-shoes earned him minimal thanks and continued abuse from kids.

So what about the rogues out there? Anyone an out and out thief?
I find that one hard actually, because to get the most benefit from a tomb robber for example, and otherwise thief, you want the lockpicking, stealth and pickpocketing perks.

How have people got on with that? I assume that I will have to be pretty much non-combat at all as I wont be very good at it with perks in those other skills.

i'm roll playing a Alik'r Asassin, that was trying to get out of Skyrim after killing his target.

he was cougth by the Imperials when he was just about to excape Skyrim, he hates the Imperials cuse they are mupets of the Thalmor so he joins Ralof on his excape and persues his new found Dovakin identity cuse he has litle choise in the subject (instinct of survival)

and so on.....